Delta3,2-Hydroxylbakuchiol

Base Information

• Chemical Name: Delta3,2-Hydroxylbakuchiol
• CAS No.: 178765-49-6
• Molecular Formula: C₁₈H₂₄O₂
• Molecular Weight: 272.387
• Mol file: 178765-49-6.mol

Synonyms:

Chemical Property of Delta3,2-Hydroxylbakuchiol

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

13-Hydroxyisobakuchiol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Delta3,2-Hydroxylbakuchiol

There total 20 articles about Delta3,2-Hydroxylbakuchiol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

(S,3E,7E)-8-(4-((tert-butyldiphenylsilyl)oxy)phenyl)-2,6-dimethyl-6-vinylocta-3,7-dien-2-ol (1492056-98-0) → 4-((S,1E,5E)-7-hydroxy-3,7-dimethyl-3-vinylocta-1,5-dien-1-yl)phenol (178765-49-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1016/j.tet.2013.10.064

Reference yield: 77.8%

(3E,7E)-8-{4-{[(tert-butyl)diphenylsilyl]oxy}phenyl}-6-ethenyl-2,6-dimethylocta-3,7-dien-2-ol (1226876-76-1) → (+/-)-Δ3-2-hydroxybakuchiol (178765-49-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;

DOI:10.1002/hlca.200900243

Reference yield: 75.0%

4-((3S,E)-3-(2-(3,3-dimethyloxiran-2-yl)ethyl)-3-methylpenta-1,4-dien-1-yl) phenol → 2-hydroxy-Δ3-bakuchiol (178765-49-6)

Guidance literature:

4-((3S,E)-3-(2-(3,3-dimethyloxiran-2-yl)ethyl)-3-methylpenta-1,4-dien-1-yl) phenol; With sodium tetrahydroborate; diphenyl diselenide; In ethanol; for 2h; Inert atmosphere; Reflux;

With dihydrogen peroxide; In tetrahydrofuran; at 0 - 20 ℃; for 2h;

DOI:10.5012/bkcs.2012.33.7.2378

upstream raw materials:

(3E,7E)-8-{4-{[(tert-butyl)diphenylsilyl]oxy}phenyl}-6-ethenyl-2,6-dimethylocta-3,7-dien-2-ol

(E)-2-methylbut-2-enoyl chloride

(S)-tert-butyl 3-((R)-4-isopropyl-2-oxooxazolidine-3-carbonyl)-3-methylpent-4-enoate

(S)-tert-butyl 3-(hydroxymethyl)-3-methylpent-4-enoate

Refernces

• 1、 Xu, Qian-Qian,Zhao, Qun,Shan, Guang-Sheng,Yang, Xi-Cheng,Shi, Qi-Yuan,Lei, Xinsheng. "A facile asymmetric synthesis of Δ3-2-Hydroxybakuchiol, Bakuchiol and ent-Bakuchiol". . p. 10739 - 10746. Retrieved 2013/12/04.
• 2、 Shi, Lei,Lei, Xinsheng,Zhang, Jiange,Lin, Guoqiang. "Synthesis of racemic Δ3-2-hydroxybakuchiol and its analogues". experimental part. p. 555 - 564. Retrieved 2010/06/14.