(1S,2R,4R)-1-isopropyl-4-methyl-(2-vinyloxy)cyclohexane

Base Information

• Chemical Name: (1S,2R,4R)-1-isopropyl-4-methyl-(2-vinyloxy)cyclohexane
• CAS No.: 127642-93-7
• Molecular Formula: C₁₂H₂₂O
• Molecular Weight: 182.306
• Mol file: 127642-93-7.mol

Synonyms:

Chemical Property of (1S,2R,4R)-1-isopropyl-4-methyl-(2-vinyloxy)cyclohexane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,4R)-1-isopropyl-4-methyl-(2-vinyloxy)cyclohexane

There total 12 articles about (1S,2R,4R)-1-isopropyl-4-methyl-(2-vinyloxy)cyclohexane 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: 88.0%

rac-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl vinyl ether → menthol (89-78-1) + (1S,2R,4R)-1-isopropyl-4-methyl-(2-vinyloxy)cyclohexane (5989-48-0,7637-09-4,7637-10-7,7637-11-8,23960-73-8,46173-76-6,127642-93-7,3885-03-8) + (1R,2S,4S)-1-isopropyl-4-methyl-2-(vinyloxy)cyclohexane (7637-11-8)

Guidance literature:

With water; C₂H₃O₂^(1-)*C₃₆H₅₃CoN₂O₂⁽¹⁺⁾; In methanol; at -10 ℃; for 2h; Product distribution / selectivity;

Reference yield: 81.0%

vinyl acetate (108-05-4,9003-20-7) + (-)-menthol (2216-51-5) → (1S,2R,4R)-1-isopropyl-4-methyl-(2-vinyloxy)cyclohexane (5989-48-0,7637-09-4,7637-10-7,7637-11-8,23960-73-8,46173-76-6,127642-93-7,3885-03-8)

Guidance literature:

With bis(1,5-cyclooctadiene)diiridium(I) dichloride; sodium carbonate; In toluene; at 100 ℃; for 3h; Inert atmosphere;

DOI:10.1016/j.tet.2012.02.025

Reference yield: 75.0%

acetaldehyde ethyl menthyl acetal (363603-37-6) → (1S,2R,4R)-1-isopropyl-4-methyl-(2-vinyloxy)cyclohexane (5989-48-0,7637-09-4,7637-10-7,7637-11-8,23960-73-8,46173-76-6,127642-93-7,3885-03-8) + (-)-menthol trimethylsilyl ether (18419-38-0,62338-23-2,88390-70-9,122999-13-7,66808-39-7)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; triethylamine; In dichloromethane; at 20 ℃; for 15h; Yields of byproduct given;

DOI:10.1016/0040-4039(95)00087-S

upstream raw materials:

(-)-menthol

acetylene

butan-1-ol

ethyl vinyl ether

Downstream raw materials:

2-menthoxyethanethiol

acetaldehyde

Refernces

• 1、 Guo, Yonghong,He, Chuan,Yang, Bo,Yang, Wu,You, Lijun. "Enantioselective Silylation of Aliphatic C?H Bonds for the Synthesis of Silicon-Stereogenic Dihydrobenzosiloles". . p. 22217 - 22222. Retrieved 2020.
• 2、 Chen, Jia-Rong,Wu, Ya-Li,Xiao, Wen-Jing,Xu, Shuang-Hua,Zhao, Quan-Qing,Zhou, Xue-Song. "Visible-Light-Driven Nitrogen Radical-Catalyzed [3 + 2] Cyclization of Vinylcyclopropanes and N-Tosyl Vinylaziridines with Alkenes". supporting information. . Retrieved 2020/03/13.