In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 106-28-5, name is (2E,6E)-3,7,11-Trimethyldodeca-2,6,10-trien-1-ol, the common compound, a new synthetic route is introduced below. 106-28-5
L-(+)-Diethyltartrate (428 muL, 2.5 mmol, 12.5 mol %) and 4A molecular sieves(2g, 0.1g/mmol) were placed in a 50 mL round bottom flask under a stream of argon.CH2Cl2 (20 mL) was added at room temperature, followed by Ti(Oi-Pr)4 (600 muL, 2mmol, 10 mol %). The mixture was stirred vigorously at room temperature for 20 min.tert-Butylhydroperoxide (4.54 mL, ~25 mmol, 125 mol%, 5-6 M in decane) was addedand the mixture was stirred 5 min at room temperature. The mixture was cooled in aCH3CN / dry ice bath. The temperature was maintained below -40 C. Farnesol (5.06mL, 20 mmol, 100 mol %) was added and stirred in the CH3CN / dry ice bath for 10 h.The mixture was placed in the freezer overnight. The next day citric acid monohydrate(420 mg, 2 mmol, 10 mol%) was dissolved in 1:1 acetone / diethylether (~5 mL) and thesolution was added to the reaction mixture. The mixture was stirred vigorously for 20min at room temperature. Celite was added to the mixture and stirred vigorously for 1min. The slurry was filtered through a thick pad of celite and the celite was washed withEt2O. The clear filtrate was washed with saturated Na2S2O3 and then dried with MgSO4.Column chromatography isolated 4.53 g of S1 (95% yield). The enantiomeric excess wasdetermined by HPLC of the benzoate to be 87%. 1H NMR (400 MHz, CDCl3):delta 5.10 (m, 2H), 3.84 (ddd, J = 4.3, 7.5, 12.0 Hz, 1H), 3.70 (ddd, J = 4.9, 6.7, 11.8 Hz,1H), 2.99 (dd, J = 4.3, 6.7 Hz, 1H), 2.16-1.94 (m, 6H), 1.71 (m, 1H), 1.69 (s, 3H), 1.614(s, 3H), 1.608 (s, 3H), 1.48 (m, 1H), 1.32 (s, 3H).13C NMR (125 MHz, CDCl3):delta 136.0, 131.6, 124.4, 123.3, 63.2, 61.6, 61.4, 39.8, 38.7, 26.8, 25.9, 23.8, 17.9, 17.0,16.2.IR (NaCl, thin film): 3422, 2919, 1456, 1384, 1033 cm-1.HR-MS (ESI) m/z calcd for C15H26O2 [M+Na]+: 261.1825, found 261.1830.[alpha]20D = -4.2 (c = 1.9, CHCl3). Chiral HPLC analysis: Analysis was performed on the corresponding benzoate (BzCl,Et3N, DMAP, CH2Cl2): (Chiralcel AD-H, hexanes:2-propanol, 99:1, 1.0 mL/min):tR(2S,3S) = 7.3 min; tR(2R,3R) = 8.1 min. The enantiomeric excess was determined to be87%.
Statistics shows that 106-28-5 is playing an increasingly important role. we look forward to future research findings about (2E,6E)-3,7,11-Trimethyldodeca-2,6,10-trien-1-ol.
Reference:
Article; Underwood, Brian S.; Tanuwidjaja, Jessica; Ng, Sze-Sze; Jamison, Timothy F.; Tetrahedron; vol. 69; 25; (2013); p. 5205 – 5220;,
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