Phenol, 4-[5-ethenyl-5-methyl-2-(1-methylethenyl)cyclohexyl]-

Base Information

• Chemical Name: Phenol, 4-[5-ethenyl-5-methyl-2-(1-methylethenyl)cyclohexyl]-
• CAS No.: 138568-27-1
• Molecular Formula: C18H24O
• Molecular Weight: 256.388
• Mol file: 138568-27-1.mol

Synonyms:

Chemical Property of Phenol, 4-[5-ethenyl-5-methyl-2-(1-methylethenyl)cyclohexyl]-

Chemical Property:

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Phenol, 4-[5-ethenyl-5-methyl-2-(1-methylethenyl)cyclohexyl]-

There total 20 articles about Phenol, 4-[5-ethenyl-5-methyl-2-(1-methylethenyl)cyclohexyl]- 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: 93.0%

1-methoxy-4-((1R,2R,5R)-5-methyl-2-(prop-1-en-2-yl)-5-vinylcyclohexyl)benzene (54154-44-8) → cyclobackuchiol B (138568-27-1)

Guidance literature:

With potassium carbonate; thiophenol; In 1-methyl-pyrrolidin-2-one; at 220 ℃; for 13h;

DOI:10.1002/chem.201303538

Reference yield: 42.0%

bakuchiol (17015-60-0,93998-10-8,10309-37-2) → cyclobackuchiol B (138568-27-1) + cyclobakuchiol A

Guidance literature:

With hydrogenchloride; In dichloromethane; water; at 20 ℃; Overall yield = 56 percent; Optical yield = 50 percent de;

DOI:10.1371/journal.pone.0248960

Reference yield:

(1R,5S)-(+)-nopinone (38651-65-9) → cyclobackuchiol B (138568-27-1)

Guidance literature:

Multi-step reaction with 14 steps

1.1: selenium(IV) oxide; sulfuric acid / methanol / 5 h / 20 °C / Cooling with ice

2.1: dihydrogen peroxide; pyridine / dichloromethane / 20 °C / Cooling with ice

3.1: copper(l) iodide / tetrahydrofuran / 0.5 h / -78 °C

3.2: 2 h / -78 - -50 °C

4.1: boron trifluoride diethyl etherate / acetic anhydride / 20 °C / Cooling with ice

5.1: sodium hydride; methanol / mineral oil / 0.5 h / 20 °C

6.1: potassium tert-butylate / tetrahydrofuran / 0.17 h / 0 °C

6.2: 1 h / Reflux

7.1: potassium hydroxide / propan-1-ol / 1 h / 20 °C / Reflux

8.1: ethyl acetate; diethyl ether / 0.08 h / 0 °C

9.1: lithium diisopropyl amide / tetrahydrofuran / -78 °C

9.2: 0.5 h / -78 °C

10.1: sodium hydrogencarbonate / para-xylene / 12 h / Reflux

11.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 °C

12.1: triethylamine; dmap / dichloromethane / 17 h / Reflux

13.1: sodium tetrahydroborate / N,N-dimethyl-formamide / 12 h / 80 °C / Cooling with ice

14.1: thiophenol; potassium carbonate / 1-methyl-pyrrolidin-2-one / 13 h / 220 °C

With pyridine; methanol; dmap; selenium(IV) oxide; sodium tetrahydroborate; copper(l) iodide; lithium aluminium tetrahydride; sulfuric acid; boron trifluoride diethyl etherate; potassium tert-butylate; dihydrogen peroxide; sodium hydride; sodium hydrogencarbonate; potassium carbonate; thiophenol; triethylamine; potassium hydroxide; lithium diisopropyl amide; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; propan-1-ol; diethyl ether; dichloromethane; para-xylene; acetic anhydride; ethyl acetate; N,N-dimethyl-formamide; mineral oil;

DOI:10.1002/chem.201303538

upstream raw materials:

beta-pinene

(1R,5S)-(+)-nopinone

(1R,3S,5R)-6,6-dimethyl-3-(phenylselanyl)bicyclo[3.1.1]heptan-2-one

(+)-apoverbenone

Refernces

• 1、 Kawashima, Hidehisa,Kaneko, Yuki,Sakai, Masahiro,Kobayashi, Yuichi. "Synthesis of cyclobakuchiols A, B, and C by using conformation-controlled stereoselective reactions". . p. 272 - 278. Retrieved 2014/01/17.