(1R,2S,4R)-4-phenylcyclohexane-1,2-dicarboxylate

Base Information

• Chemical Name: (1R,2S,4R)-4-phenylcyclohexane-1,2-dicarboxylate
• CAS No.: 36299-64-6
• Molecular Formula: C₁₄H₁₆O₄
• Molecular Weight: 248.279
• DSSTox Substance ID: DTXSID70428111
• Wikidata: Q82240895
• Mol file: 36299-64-6.mol

Synonyms:(1R,2S,4R)-4-phenylcyclohexane-1,2-dicarboxylate;DTXSID70428111

Chemical Property of (1R,2S,4R)-4-phenylcyclohexane-1,2-dicarboxylate

Chemical Property:

• Vapor Pressure: 7.08E-10mmHg at 25°C
• Melting Point: 185 °C
• Refractive Index: 1.5389 (estimate)
• Boiling Point: 476.2°Cat760mmHg
• Flash Point: 255.9°C
• PSA: 74.60000
• Density: g/cm³
• LogP: 2.35570
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 246.08920892
• Heavy Atom Count: 18
• Complexity: 309

Purity/Quality:

99%, ^*data from raw suppliers

4-TRANS-PHENYLCYCLOHEXANE-CIS-1,2-DICARBOXYLIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(C(CC1C2=CC=CC=C2)C(=O)[O-])C(=O)[O-]
• Isomeric SMILES: C1C[C@H]([C@H](C[C@@H]1C2=CC=CC=C2)C(=O)[O-])C(=O)[O-]

Technology Process of (1R,2S,4R)-4-phenylcyclohexane-1,2-dicarboxylate

There total 6 articles about (1R,2S,4R)-4-phenylcyclohexane-1,2-dicarboxylate 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: 82.0%

(1S,2R,4S)-4-Phenyl-cyclohexane-1,2-dicarboxylic acid dimethyl ester → 4-phenyl-1,2-cyclohexanedicarboxylic acid (1444-93-5,36299-64-6,36299-65-7,36299-66-8)

Guidance literature:

With water; lithium hydroxide; In tetrahydrofuran; at 40 ℃; for 10h;

DOI:10.1016/j.tet.2018.05.035

Reference yield: 82.0%

cis-1,2,3,6-tetrahydrophthalic acid (2305-26-2) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1) → (1R*,2S*)-4-phenylcyclohexane-1,2-dicarboxylic acid (1444-93-5,36299-64-6,36299-65-7,36299-66-8)

Guidance literature:

With aluminum (III) chloride; for 5h;

DOI:10.1007/s11172-017-1820-x

Reference yield: 81.0%

cis-1,2,3,6-tetrahydrophthalic acid (2305-26-2) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1) → 4-phenyl-1,2-cyclohexanedicarboxylic acid (1444-93-5,36299-64-6,36299-65-7,36299-66-8)

Guidance literature:

cis-1,2,3,6-tetrahydrophthalic acid; benzene; With aluminum (III) chloride; at 50 ℃; for 24h;

With hydrogenchloride; In water; at 0 - 20 ℃; for 0.666667h;

DOI:10.1016/j.tet.2018.05.035

upstream raw materials:

cis-1,2,3,6-tetrahydrophthalic acid

benzene

cis-1,2,3,6-tetrahydrophthalic anhydride

2-phenyl-1,3-butadiene

Downstream raw materials:

(3aS,5R,7aR)-5-Phenyl-hexahydro-isobenzofuran-1,3-dione

Refernces

• 1、 Firstova,Kofanov,Krasovskaya,Danilova. "Simple and efficient synthesis of new tricarboxylic acids bearing cyclohexane and norbornane fragments". . p. 867 - 869. Retrieved 2017/09/29.
• 2、 Bernath, G.. "FUSED-SKELETON SATURATED SIX-MEMBERED 1,3-N,O, N,N AND N,S HETEROCYCLES, FUSED-SKELETON ARYL-SUBSTITUTED SATURATED ISOINDOLONES". . p. 509 - 530. Retrieved 2007/10/02.