1-Phenylcyclopentane-1,2-diol

Base Information

• Chemical Name: 1-Phenylcyclopentane-1,2-diol
• CAS No.: 131221-80-2
• Molecular Formula: C11H14O2
• Molecular Weight: 178.231
• DSSTox Substance ID: DTXSID401307390
• Nikkaji Number: J1.981.907H

Synonyms:1-phenylcyclopentane-1,2-diol;1-Phenylcyclopentane-cis-1,2-diol;131221-80-2;1-Phenyl-1,2-cyclopentanediol;SCHEMBL1866342;DTXSID401307390

Chemical Property of 1-Phenylcyclopentane-1,2-diol

Chemical Property:

• XLogP3: 1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 178.099379685
• Heavy Atom Count: 13
• Complexity: 175

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CC(C(C1)(C2=CC=CC=C2)O)O

Technology Process of 1-Phenylcyclopentane-1,2-diol

There total 8 articles about 1-Phenylcyclopentane-1,2-diol 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: 48.0%

5-oxo-5-phenylpentanal (75424-63-4) + (-)-8-phenylmenthol (65253-04-5) → 1-phenyl-1,2-dihydroxycyclopentane (131221-80-2) + (6S) 6-phenyltetrahydro-2H-pyran-2-one (112607-34-8) + (1'R,2'S,5'R,5SR)-5-hydroxy-5-phenylpentanoic acid 2-(2-phenylprop-2-yl)-5-methylcyclohexyl ester + 5-(5-hydroxy-5-phenyl-pentanoyloxy)-5-phenyl-pentanoic acid 5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

Guidance literature:

With samarium diiodide; In tetrahydrofuran; at 25 ℃; Further byproducts given;

DOI:10.1021/jo016058t

Reference yield: 48.0%

5-oxo-5-phenylpentanal (75424-63-4) + (-)-8-phenylmenthol (65253-04-5) → (S)-5-(5-Hydroxy-5-phenyl-pentanoyloxy)-5-phenyl-pentanoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester + 1-phenyl-1,2-dihydroxycyclopentane (131221-80-2) + (6S) 6-phenyltetrahydro-2H-pyran-2-one (112607-34-8) + (1'R,2'S,5'R,5SR)-5-hydroxy-5-phenylpentanoic acid 2-(2-phenylprop-2-yl)-5-methylcyclohexyl ester

Guidance literature:

With samarium diiodide; In tetrahydrofuran; at 25 ℃; Further byproducts given;

DOI:10.1021/jo016058t

Reference yield: 7.0%

cyclopent-1-en-1-ylbenzene (825-54-7) → (rac)-syn-1-phenylcyclopentane-1,2-diol (81155-86-4,131221-80-2)

Guidance literature:

With MnO₄(-);

DOI:10.1002/anie.201204469

upstream raw materials:

Neomenthol

5-oxo-5-phenylpentanal

(-)-8-phenylmenthol

isopropyl alcohol

Downstream raw materials:

2-Phenylcyclopentanone

pinanediol

Toluene-4-sulfonic acid (1S,2S)-2-hydroxy-2-phenyl-cyclopentyl ester

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