Tag: 100-200

On June 26, 2014, Kobayashi, Kaori; Suzuki, Tamotsu; Okuzumi, Tatsuya published a patent.Synthetic Route of 386704-04-7 The title of the patent was Preparation of N-arylsulfonyl amino acid amide derivatives as transient receptor potential ankyrin 1 (TRPA1) antagonists and medicine containing them. And the patent contained the following:

The title compounds represented by formula [I; Ar = each (un)substituted C6-10 aryl or C1-9 heteroaryl; Y = C(Ry1)(Ry2) or a single bond; Z = C(Rz1)(Rz2), O, S, or a single bond; n, m = 0 or 1 and n+m≤1; ring A = (un)substituted phenylene or 5- or 6-membered divalent heteroaromatic ring; ring B = (un)substituted C6-10 aryl or C1-9 heteroaryl; R1 = H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, halo-C1-6 alkyl, C3-6 cycloalkyl, or C3-6 cycloalkyl-C1-6 alkyl; R2, R3 = H, C1-6 alkyl, C2-6 alkenyl, or C2-6 alkynyl; R4-R8, Ry1, Ry2, Rz1, Rz2 = H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, halo-C1-6 alkyl, C1-6 alkoxy, HO, halo-C1-6 alkoxy, NH2, C1-6 alkyl, mono- or disubstituted amino, or halo; each adjacent R4-R8, Ry1, Ry2, Rz1, or Rz2 together forms a double bond and/or ring; or R5 and R6, R7 and R8, Ry1 and Ry2, or Rz1 and Rz2 on the same carbon atom together form a ring; Rx1, Rx2, Rx2, Rx3, Rx4 = H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, hydroxy-C1-6 alkyl, amino-C1-6 alkyl, or mono- or di(C1-6 alkyl)amino-C1-6 alkyl; or Rx1 and Rx2 or Rx3 and Rx4 on the same carbon together form a ring] or pharmaceutically acceptable salts thereof are prepared These compounds have transient receptor potential ankyrin 1 (TRPA1) antagonistic activity and are useful for the prevention or treatment of diseases associated with a TRPA1 antagonist and TRPA1, in particular pain-related diseases, inflammatory diseases, digestive tract diseases, pulmonary diseases, bladder diseases, skin diseases, or nerve diseases, more specifically chronic pain, acute pain, asthma, chronic obstructive pulmonary disease, functional gastrointestinal disorders, reflux esophagitis, inflammatory bowel disease, or pruritus. Thus, L-proline was condensed with 5-chlorothiophene-2-sulfonyl chloride in the presence of NaOH in aqueous THF solution at room temperature overnight to give 97% (2S)-1-(5-chlorothiophene-2-sulfonyl)pyrrolidine-2-carboxylic acid which was condensed with 4-(aminomethyl)phenol using 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and 1-hydroxy-7-azabenzotriazole (HOAt) in the presence of Et3N in CH2Cl2 at room temperature for a few hours to give 72% (2S)-1-(5-chlorothiophene-2-sulfonyl)-N-[(4-hydroxyphenyl)methyl]pyrrolidine-2-carboxamide (II; R = H). II (R = H) was condensed with phenylboronic acid in the presence of supper acetate, Et3N, and mol. sieve 4Å in CH2Cl2 at room temperature for a few hours to give II (R = Ph). II (R = Ph) and (2S)-1-(3-thienylsulfonyl)-N-[[3-[[4-(trifluoromethyl)phenyl]methoxy]phenyl]methyl]pyrrolidine-2-carboxamide (III) inhibited the allyl isothiocyanate-stimulated increase in cellular calcium concentration in human fetus kidney cell-derived 293T cells expressing human TRPA1 with IC50 of 0.22 and 0.0085 μM, resp. The experimental process involved the reaction of (6-(Trifluoromethyl)pyridin-3-yl)methanol(cas: 386704-04-7).Synthetic Route of 386704-04-7

The Article related to arylsulfonylproline amide preparation transient receptor potential ankyrin 1 antagonist, arylsulfonyl amino acid amide preparation trpa1 antagonist, pain inflammatory disease prevention treatment, digestive tract disease prevention treatment, pulmonary disease prevention treatment, bladder disease skin disease prevention treatment and other aspects.Synthetic Route of 386704-04-7

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On March 5, 2022, Fang, Yuying; Tan, Qingyun; Zhou, Huihao; Gu, Qiong; Xu, Jun published an article.Application In Synthesis of 3-Hydroxyphenylacetic acid The title of the article was Discovery of novel diphenylbutene derivative ferroptosis inhibitors as neuroprotective agents. And the article contained the following:

Herein, with phenotypic assays, a new diphenylbutene derivative ferroptosis inhibitor, DPT was discovered. Based on this hit, new diphenylbutene derivatives I [R1 = H, 2-OMe, 3-OH, etc.; R2 = H, 3-OH, 4-OH, etc.] synthesized via condensation of (piperazinyl)pyrimidine and (phenyl)-phenylpentadienoic acids II and evaluated their ferroptosis inhibitory activities in HT22 mouse hippocampal neuronal cells and found that three compounds exhibited improved inhibitory activities compared with DPT. Among these active compounds, compound I [R1 = 3-OMe-4-HOC6H4, R2 = H] displayed the most potent anti-ferroptosis activity (EC50 = 1.7μM). Further studies demonstrated that compound I [R1 = 3-OMe-4-HOC6H4, R2 = H] was a specific ferroptosis inhibitor. It was revealed that different than the classic ferroptosis inhibitors, compound I [R1 = 3-OMe-4-HOC6H4, R2 = H] blocked ferroptosis by increasing FSP1 protein level. Compound I [R1 = 3-OMe-4-HOC6H4, R2 = H] could penetrate blood-brain barrier (BBB). In a rat model of ischemic stroke, compound I [R1 = 3-OMe-4-HOC6H4, R2 = H] effectively mitigated cerebral ischemic injury. Therefore, it was confirmed that compound I [R1 = 3-OMe-4-HOC6H4, R2 = H] as a novel ferroptosis inhibitor with a new scaffold, was promising for further development as an agent against neurol. diseases. The experimental process involved the reaction of 3-Hydroxyphenylacetic acid(cas: 621-37-4).Application In Synthesis of 3-Hydroxyphenylacetic acid

The Article related to phenyl pyrimidinyl piperazinyl pentadienone diastereoselective preparation ferroptosis inhibitor dpt, piperazinyl pentadienone phenyl pyrimidinyl diastereoselective preparation adme human, phenylpentadienoic phenyl acid preparation piperazinyl pyrimidine condensation, cinnamaldehyde phenylacetic acid perkin, diphenylbutene, fsp1 and other aspects.Application In Synthesis of 3-Hydroxyphenylacetic acid

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Flinker, Mathias; Yin, Hongfei; Juhl, Rene W.; Eikeland, Espen Z.; Overgaard, Jacob; Nielsen, Dennis U.; Skrydstrup, Troels published an article in 2017, the title of the article was Efficient Water Reduction with sp3-sp3 Diboron(4) Compounds: Application to Hydrogenations, H-D Exchange Reactions, and Carbonyl Reductions.Recommanded Product: 2160-93-2 And the article contains the following content:

Diboron complexes with aminodiols and aminotriols such as I were prepared or generated in situ from (HO)2BB(OH)2; the diboron compounds reduced H2O or D2O to yield H2 or D2 which was used for chemoselective alkene and stereoselective diaryl alkyne hydrogenation, deuterium exchanges, and aldehyde and ketone reductions to alcs. in a two-chamber reactor. The experimental process involved the reaction of 2,2′-(tert-Butylazanediyl)diethanol(cas: 2160-93-2).Recommanded Product: 2160-93-2

The Article related to chemoselective hydrogenation deuterium exchange carbonyl reduction diboron diethanolamine complex, diboron aminodiol aminotriol complex preparation reductant hydrogen generation, reduction water hydrogen diboron aminodiol aminotriol complex reductant, alkene alkyne chemoselective hydrogenation water hydrogen source diboron and other aspects.Recommanded Product: 2160-93-2

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On June 19, 1990, Kuehne, Martin published a patent.Safety of Isochroman-3-ol The title of the patent was Preparation of cycloalkyl and aromatic moieties-containing vinblastines and vincristines as antitumors. And the patent contained the following:

The title compounds [I; R1R2 = alkylene, benzo; R10 = HCO, Me; R11 = alkoxy, trialkylammoniumyl; R12 = alkanoyloxy, OH; R13 = alkyl] were prepared Vindoline-HCl was condensed with Me (3aRS,4RS,11bSR)]-3-benzyl-4-[2-(tert-butyldimethylsilyloxymethyl)phenyl]-1,2,3,3a,4,5-hexahydro-7H-pyrrolo[2,3-d]carbazole-6-carboxylate to give, after desilylation, a 1:1 mixture of (5R,7S)-3-benzyl-5-[2-(hydroxymethyl)phenyl]-1,2,3,4,5,6,7,8-octahydroazonino[5,4-b]indole-7-(15-vindolinyl)-7-carboxylate (II) and its 5R,7R-diastereomer. II was then cyclized in CH2Cl2 containing Et3N and p-toluenesulfonic anhydride to give, after hydrogenolysis, (9R,11S)-15-[1,2,4,9,10,11,12,17-octahydro-11-(methoxycarbonyl)indolo[2′,3′:6,7]azonino[1,2,3:bc]isoquinolin-11-yl]vindoline (III). III had an ED50 comparable to that of vinblastine against P388 leukemia cells resistant to adriamycin. The experimental process involved the reaction of Isochroman-3-ol(cas: 42900-89-0).Safety of Isochroman-3-ol

The Article related to vinblastine cycloalkyl aryl preparation antitumor, cycloalkylvinblastine preparation antitumor, vincristine cycloalkyl aryl preparation antitumor, cycloalkylvincristine preparation antitumor, antitumor vinblastine vincristine cycloalkyl aryl, arylvinblastine preparation antitumor, arylvincristine preparation antitumor and other aspects.Safety of Isochroman-3-ol

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On May 28, 2020, Zhong, Wenge published a patent.Category: alcohols-buliding-blocks The title of the patent was Preparation of 1H-benzimidazole-6-carboxylic acid derivatives as glucagon-like peptide-1 receptor (GLP-1R) agonists and uses thereof. And the patent contained the following:

The title compounds represented by formula I (X1-X5, Y1-Y5, Z1-Z4, T2-T4, T6-T8, Ra, Rb, Rc, Rd, R1-R3, m, n, and o are defined below) or pharmaceutically acceptable salts, stereoisomers, solvates, or hydrates thereof are prepared for use in, e.g. treating type 2 diabetes mellitus, pre-diabetes, obesity, non-alc. fatty liver disease, non-alc. steatohepatitis, and cardiovascular disease. X1-X5, Y1-Y5, Z1-Z4, T2-T4, and T6-T8 are defined as [the dashed line with a solid line = a single bond or a double bond; X1, X2, X3, X4, X5 = each independently N or CH, wherein no more than three of X1-X5 are N and ring A does not contain 3-nitrogen ring atoms at 3 contiguous positions; W = O, S, or each (un)substituted CH2 or NH; Y1, Y3, Y4, Y5 = each independently N, NH, CH, or CH2; Y2, Y6 = each independently N, C, or CH, wherein there is no more than 3-nitrogen ring atoms in ring B and ring B does not contain 3-nitrogen ring atoms at 3 contiguous positions; Z1, Z2 = each independently N, C, or CH, wherein at least one of Z1 and Z2 is N; Z3, Z4 = each independently a bond, CH, CH2, CH:CH, CH2CH2, CH2CH, or CHCH2, wherein ring C contains no more than two double bonds; provided that when ring B = (un)substituted pyridine-2,6-diyl, then (1) W is not O, and/or (2) ring C is not (un)substituted piperazine-1,4-diyl and/or (3) ring C is not (un)substituted piperidine-1,4-diyl; wherein Z1 is N, and/or (4) ring A is not phenyl; T2, T3, T4 = each independently N, O, S, C, or each (un)substituted NH or CH ; T6, T6, T8 = each independently selected N or (un)substituted CH; wherein no more than 4 of T2, T3, T4, T6, T7, and T8 are selected from N, O, and S; EE = CO2H or a carboxylic group surrogate (e.g. C(O)CF3, CH(F)CF3, C(O)NHCN, C(O)NHOH, C(O)NHOMe, 2H-tetrazol-2-yl, etc.)]. Ra, Rb, Rc, and Rd are defined as [Ra = hydrogen, deuterium, halogen, cyano, or each (un)substituted C1-6 alkyl, C1-6 alkoxy, NH2, 6-10 membered aryl, 5-8 membered heteroaryl, 3-8 membered saturated or partially saturated cycloalkyl, 3-8 membered saturated or partially saturated heterocyclyl; Rb = hydrogen, deuterium, halogen, cyano, or each (un)substituted C1-6 alkyl, C1-6 alkoxy, NH2, 6-10 membered aryl, 5-8 membered heteroaryl, 3-8 membered saturated or partially saturated cycloalkyl, or 3-8 membered saturated or partially saturated heterocyclyl; Rc = hydrogen, deuterium, halogen, cyano, or each (un)substituted C1-6 alkyl, C1-6 alkoxy, NH2, 6-10 membered aryl, 5-8 membered heteroaryl, 3-8 membered saturated or partially saturated cycloalkyl, or 3-8 membered saturated or partially saturated heterocyclyl; Rd = hydrogen, deuterium, halogen, cyano, or each (un)substituted C1-6 alkyl, C1-6 alkoxy, NH2, 6-10 membered aryl, 5-8 membered heteroaryl, 3-8 membered saturated or partially saturated cycloalkyl, or 3-8 membered saturated or partially saturated heterocyclyl]. R1-R3, m, n, and o are defined as [R1 = independently halogen, cyano, OH, or each (un)substituted C1-6 alkyl, C1-6 alkoxy, C2-6 alkenyl, C2-6 alkynyl, NH2, 6-10 membered aryl, 5-8 membered heteroaryl, 3-8 membered saturated or partially saturated cycloalkyl, or 3-8 membered saturated or partially saturated heterocyclyl; R2 = independently halogen, cyano, OH, oxo, or each (un)substituted C1-6 alkyl, C1-6 alkoxy, NH2, 6-10 membered aryl, 5-8 membered heteroaryl, 3-8 membered saturated or partially saturated cycloalkyl, or 3-8 membered saturated or partially saturated heterocyclyl; R3 = independently halogen, cyano, OH, oxo, or each (un)substituted C1-6 alkyl, C1-6 alkoxy, NH2, 6-10 membered aryl, 5-8 membered heteroaryl, 3-8 membered saturated or partially saturated cycloalkyl, or 3-8 membered saturated or partially saturated heterocyclyl; m = an integer of 0-4; n, o = each independently an integer of 0-5]. Thus, sequential amination of 2,6-dichloropyridine with tert-Bu piperazine-1-carboxylate in DMSO at 110° for 12 h and (4-chloro-2-fluorophenyl)methanamine in the presence of BINAP, Pd2(dba)2, sodium tert-butoxide in toluene at 100° for 12 h gave tert-Bu 4-[6-(4-chloro-2-fluorobenzylamino)pyridin-2-yl]piperazine-1-carboxylate which was treated with CF3CO2H in CH2Cl2 and underwent alkylation with tert-Bu (S)-2-(chloromethyl)-1-(oxetan-2-ylmethyl)-1H-benzimidazole-6-carboxylate in the presence of K2CO3 in DMF at 90° for 5 h and deprotection by treatment with CF3CO2H to give (S)-2-[[4-[6-(4-chloro-2-fluorobenzylamino)pyridin-2-yl]piperazin-1-yl]methyl]-1-(oxetan-2-ylmethyl)-1H-benzimidazole-6-carboxylic acid (II). II in vitro showed EC50 of ≤0.015μM for production of cAMP in HEK293T cells expressing human GLP-1R. The experimental process involved the reaction of (6-(Trifluoromethyl)pyridin-3-yl)methanol(cas: 386704-04-7).Category: alcohols-buliding-blocks

The Article related to benzimidazolecarboxylic acid preparation glp 1r agonist, oxetanylmethylbenzimidazolecarboxylic acid preparation glp 1r agonist, piperazinylmethyloxetanylmethylbenzimidazolecarboxylic acid preparation glp 1r agonist, glucagon peptide 1 receptor glp 1r agonist, type 2 diabetes mellitus prediabetes obesity treatment and other aspects.Category: alcohols-buliding-blocks

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On June 21, 2003, Kuehne, Martin E.; Bornmann, William G.; Marko, Istvan; Qin, Yong; LeBoulluec, Karen L.; Frasier, Deborah A.; Xu, Feng; Mulamba, Tshilundu; Ensinger, Carol L.; Borman, Linda S.; Huot, Anne E.; Exon, Christopher; Bizzarro, Fred T.; Cheung, Julia B.; Bane, Susan L. published an article.Related Products of 42900-89-0 The title of the article was Syntheses and biological evaluation of vinblastine congeners. And the article contained the following:

Sixty-two congeners of vinblastine (VLB), e.g. I, , primarily with modifications of the piperidine ring in the carbomethoxycleavamine moiety of the binary alkaloid, were synthesized. For example, I was prepared starting from δ-valerolactone (II). Methylation of II at the 3-position followed by ring opening gave MeO2CCH(Me)CH2CH2CHO which was reacted with indoloazepine III. The resulting bridged indoloazepine was N-benzylated to give pyrrolocarbazolecarboxylate IV. IV then went through a series of reactions, including addition to vindoline to give I in 81% yield. These compounds were evaluated for cytotoxicity against murine L1210 leukemia and RCC-2 rat colon cancer cells, and for their ability to inhibit polymerization of microtubular protein at <10-6 M, and for induction of spiralization of microtubular protein, and for microtubular disassembly at 10-4 M concentrations An ID50 range of >107 M concentrations was found for L1210 inhibition by these compounds, with the most active 1000× as potent as vinblastine. The experimental process involved the reaction of Isochroman-3-ol(cas: 42900-89-0).Related Products of 42900-89-0

The Article related to vinblastine congener preparation antitumor, microtubular disassembly spiralization induction polymerization inhibition vinblastine congener, spiralization induction microtubular vinblastine congener, polymerization inhibition microtubular vinblastine congener, colon adenocarcinoma inhibition vinblastine congener and other aspects.Related Products of 42900-89-0

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Category: alcohols-buliding-blocksIn 2020 ,《Selective oxidation of alcohols by porphyrin-based porous polymer-supported manganese heterogeneous catalysts》 appeared in Applied Organometallic Chemistry. The author of the article were Chen, Jian; Zhang, Yan; Zhu, Dajian; Li, Tao. The article conveys some information:

A series of porphyrin-based porous polymers to support Mn heterogeneous catalysts (Mn/TFP-DPM, Mn/TFP-DPM-2, Mn/TFP-DPM-3, and Mn/TFP-DPM-4) (TFP-DPM is a copolymer of 1,3,5-triformylphloroglucinol and 2,2′-dipyrrolylmethane) in the selective oxidation of alcs. was designed and synthesized. TFP-DPM and TFP-DPM-2 demonstrated micro/nanoscale spherical morphol., whereas TFP-DPM-3 and TFP-DPM-4 exhibited nanosheets structure. According to surface area and porosity anal. results, the sp. surface areas of these catalysts were less than 300 m2 g-1. Thermogravimetric anal. indicated that the synthesized catalysts maintain their stability even at 300°C. Catalysts Mn/TFP-DPM and Mn/TFP-DPM-3, which had the smallest and largest sp. surface area among the four catalysts, resp., were used to perform selective oxidation reaction of alcs., with exptl. results indicating that both have excellent catalytic performance. These catalysts possess good catalytic performance despite their low sp. surface area, suggesting that porphyrin-based porous polymer-supported Mn heterogeneous catalysts are promising materials for selective oxidation of alcs. The results came from multiple reactions, including the reaction of 3-Pyridinemethanol(cas: 100-55-0Category: alcohols-buliding-blocks)

3-Pyridinemethanol(cas: 100-55-0) belongs to pyridine. Pyridine derivatives lend themselves to many roles in the spirited field of supramolecular chemistry – whether as the ligand backbone of metal-organic polymers or presiding over the key electronic stations of nanodevices. In biochemistry, pyridine-containing cofactors are necessary nutrients on which our lives depend. Category: alcohols-buliding-blocks

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Song, Geyang; Nong, Ding-Zhan; Li, Jing-Sheng; Li, Gang; Zhang, Wei; Cao, Rui; Wang, Chao; Xiao, Jianliang; Xue, Dong published an article in 2022. The article was titled 《General Method for the Amination of Aryl Halides with Primary and Secondary Alkyl Amines via Nickel Photocatalysis》, and you may find the article in Journal of Organic Chemistry.Formula: C6H13NO The information in the text is summarized as follows:

It was reported that Ni(II)-bipyridine complex catalyzed efficient C-N coupling of aryl chlorides and bromides with various primary and secondary alkyl amines under direct excitation with light. Intramol. C-N coupling was also demonstrated. The feasibility and applicability of the protocol in organic synthesis was attested by more than 200 examples. In the part of experimental materials, we found many familiar compounds, such as trans-4-Aminocyclohexanol(cas: 27489-62-9Formula: C6H13NO)

trans-4-Aminocyclohexanol(cas: 27489-62-9) belongs to anime. Reduction of nitro compounds, RNO2, by hydrogen or other reducing agents produces primary amines cleanly (i.e., without a mixture of products), but the method is mostly used for aromatic amines because of the limited availability of aliphatic nitro compounds. Reduction of nitriles and oximes (R2C=NOH) also yields primary amines.Formula: C6H13NO

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Zhao, Fengqian; Ai, Han-Jun; Wu, Xiao-Feng published an article in 2021. The article was titled 《Radical Carbonylation under Low CO Pressure: Synthesis of Esters from Activated Alkylamines at Transition Metal-Free Conditions》, and you may find the article in Chinese Journal of Chemistry.Product Details of 100-55-0 The information in the text is summarized as follows:

High CO pressure (> 40 bar) is usually needed in radical carbonylation reactions in the absence of metal catalyst. In this communication, a transition-metal-free radical carbonylation of activated alkylamines with phenols and alcs. under low CO pressure (1-6 bar) was developed. Various esters were obtained in moderate to excellent yields under simple reaction conditions with good functional group compatibility. After reading the article, we found that the author used 3-Pyridinemethanol(cas: 100-55-0Product Details of 100-55-0)

3-Pyridinemethanol(cas: 100-55-0) belongs to pyridine. Pyridine is very deactivated towards electrophilic substitution with respect to benzene. For this reason classical formylation, using methods such as the Gattermann or Vilsmeier reactions, are not generally successful. Product Details of 100-55-0

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Jonsson, Helgi Freyr; Orthaber, Andreas; Fiksdahl, Anne published their research in Dalton Transactions in 2021. The article was titled 《Studies on gold(I) and gold(III) alcohol functionalised NHC complexes》.Recommanded Product: 126456-43-7 The article contains the following contents:

Five pairs of novel chiral alc. functionalized gold(I) and gold(III) NHC complexes derived from chiral amino alcs., were synthesized and characterized (NMR, IR, HRMS). Single crystal x-ray diffraction data of gold(I) and gold(III) complexes are reported and discussed. The chiral imidazolium preligands were readily synthesized via the oxalamides, subsequent reduction and final orthoformate condensation. An improved method was used for generation of gold(I) NHC complexes (up to 92%) and further oxidation afforded the corresponding gold(III) NHC complexes (up to 99%). All the Au(I) and Au(III) NHC complexes proved far more catalytically active in a 1,6-enyne alkoxycyclization test reaction than our previously tested N,N- and P,N-ligated Au(III) complexes. Comparative gold(I) and gold(III) catalytic studies demonstrated different catalytic ability, depending on the NHC ligand flexibility and bulkiness. Excellent yields (92-99%) of target alkoxycyclization product were obtained with both gold(I) and gold(III) complexes with the bulky N1-Mes-N2-ethanol based NHC ligand. In the experimental materials used by the author, we found (1S,2R)-1-Amino-2,3-dihydro-1H-inden-2-ol(cas: 126456-43-7Recommanded Product: 126456-43-7)

(1S,2R)-1-Amino-2,3-dihydro-1H-inden-2-ol(cas: 126456-43-7) belongs to anime. Reaction with nitrous acid (HNO2), which functions as an acylating agent that is a source of the nitrosyl group (―NO), converts aliphatic primary amines to nitrogen and mixtures of alkenes and alcohols corresponding to the alkyl group in a complex process. This reaction has been used for analytical determination of primary amino groups in a procedure known as the Van Slyke method.Recommanded Product: 126456-43-7

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