[(1R,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] 2-chloroacetate

Base Information

• Chemical Name: [(1R,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] 2-chloroacetate
• CAS No.: 71804-27-8
• Molecular Formula: C18H25 Cl O2
• Molecular Weight: 308.848
• European Community (EC) Number: 622-085-9
• Mol file: 71804-27-8.mol

Synonyms:(1R,2S,5R)-(+)-5-Methyl-2-(1-methyl-1-phenylethyl)cyclohexyl chloroacetate;71804-27-8

Chemical Property of [(1R,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] 2-chloroacetate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 82-84 °C(lit.)
• Refractive Index: 1.522
• Boiling Point: 385.281°C at 760 mmHg
• Flash Point: 188.265°C
• PSA: 26.30000
• Density: 1.084g/cm³
• LogP: 4.55100
• XLogP3: 5.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 308.1543077
• Heavy Atom Count: 21
• Complexity: 347

Purity/Quality:

98%,99%, ^*data from raw suppliers

(1R,2S,5R)-(+)-5-Methyl-2-(1-methyl-1-phenylethyl)cyclohexyl chloroacetate 99% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC(C(C1)OC(=O)CCl)C(C)(C)C2=CC=CC=C2
• Isomeric SMILES: C[C@@H]1CCC([C@@H](C1)OC(=O)CCl)C(C)(C)C2=CC=CC=C2
• Uses: (1R,2S,5R)-(+)-5-Methyl-2-(1-methyl-1-phenylethyl)cyclohexyl chloroacetate may be used in the synthesis of (-)-8-phenyl-menthol, (+)-8-phenylmenthyl isocyanoacetate and (+)-cularine.

Technology Process of [(1R,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] 2-chloroacetate

There total 8 articles about [(1R,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] 2-chloroacetate 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: 85.0%

8-phenylmenthol + chloroacetyl chloride (79-04-9) → (1R,2S,5R)-(+)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl chloroacetate (71804-27-8)

Guidance literature:

In diethyl ether; N,N-dimethyl-aniline; at -5 - 45 ℃; for 13h; Schlenk technique; Inert atmosphere;

DOI:10.1021/jacs.5b01517

Reference yield: 71.0%

(1R,2S,5R)-(+)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl dichloroacetate (152481-90-8) → (1R,2S,5R)-(+)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl chloroacetate (71804-27-8)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; samarium diiodide; In tetrahydrofuran; at 0 ℃; for 0.5h;

DOI:10.1021/jo9803838

Reference yield: 67.0%

(-)-8-phenylmenthol (65253-04-5) + chloroacetyl chloride (79-04-9) → (1R,2S,5R)-(+)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl chloroacetate (71804-27-8)

Guidance literature:

With N,N-dimethyl-aniline; In diethyl ether; 1.) 0 deg C, 3 h, 2.) reflux, 3 h;

DOI:10.1039/a707310k

upstream raw materials:

5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexanol

chloroacetic acid

(-)-8-phenylmenthol

chloroacetyl chloride

Downstream raw materials:

(-)-8-phenylmenthol

(+)-8-phenylmenthyl azidoacetate

(-)-8-phenylmenthan-3-yl glycinate

(+)-Enneaphylline