dibenzyl 2-[(1R)-3-oxocyclohexyl]propanedioate

Base Information

• Chemical Name: dibenzyl 2-[(1R)-3-oxocyclohexyl]propanedioate
• CAS No.: 164931-75-3
• Molecular Formula: C23H24O5
• Molecular Weight: 380.441
• DSSTox Substance ID: DTXSID20452365
• Nikkaji Number: J688.464D
• Wikidata: Q82272949
• ChEMBL ID: CHEMBL1319626
• Mol file: 164931-75-3.mol

Synonyms:dibenzyl 2-[(1R)-3-oxocyclohexyl]propanedioate;164931-75-3;SCHEMBL6638662;CHEMBL1319626;DTXSID20452365;NCGC00017821-01;[(R)-3-Oxocyclohexyl]malonic acid dibenzyl ester

Chemical Property of dibenzyl 2-[(1R)-3-oxocyclohexyl]propanedioate

Chemical Property:

• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 380.16237386
• Heavy Atom Count: 28
• Complexity: 497

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(CC(=O)C1)C(C(=O)OCC2=CC=CC=C2)C(=O)OCC3=CC=CC=C3
• Isomeric SMILES: C1C[C@H](CC(=O)C1)C(C(=O)OCC2=CC=CC=C2)C(=O)OCC3=CC=CC=C3

Technology Process of dibenzyl 2-[(1R)-3-oxocyclohexyl]propanedioate

There total 6 articles about dibenzyl 2-[(1R)-3-oxocyclohexyl]propanedioate 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: 98.0%

cyclohexenone (930-68-7) + malonic acid dibenzyl ester (15014-25-2) → (R)-3-[bis(benzyloxycarbonyl)methyl]cyclohexanone (164931-75-3)

Guidance literature:

With (R,R)-La-linked-BINOL Complex; In 1,2-dimethoxyethane; at 4 ℃; for 85h;

DOI:10.1021/ja001036u

Reference yield:

cyclohexenone (930-68-7) + malonic acid dibenzyl ester (15014-25-2) → (R)-3-[bis(benzyloxycarbonyl)methyl]cyclohexanone (164931-75-3) + dibenzyl 2-((S)-3-oxocyclohexyl)malonate

Guidance literature:

Al-Li-(R,R')-2,2'-dihydroxy-1,1'-binaphthyl; In tetrahydrofuran; for 72h; Product distribution; various time, catalysts;

Reference yield:

cyclohexenone (930-68-7) + malonic acid dibenzyl ester (15014-25-2) → (S)-3-[bis(ethoxycarbonyl)methyl]cyclohexenone (151600-50-9) + (R)-3-[bis(benzyloxycarbonyl)methyl]cyclohexanone (164931-75-3)

Guidance literature:

With piperidine; 5-[(2S)-pyrrolidine-2-yl]-1H-tetrazole; In chloroform; at 20 ℃; for 72h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1002/chem.200800673

upstream raw materials:

cyclohexenone

malonic acid dibenzyl ester

Downstream raw materials:

dimethyl 2-((R)-3-oxocyclohexyl)malonate

2-((1R,3R)-3-Hydroxycyclohexyl)malonic acid dibenzyl ester

(R)-3-methoxycarbonylmethylcyclohexanone