1-{3-Phenylbicyclo[1.1.1]pentan-1-yl}ethan-1-one

Base Information

• Chemical Name: 1-{3-Phenylbicyclo[1.1.1]pentan-1-yl}ethan-1-one
• CAS No.: 83249-05-2
• Molecular Formula: C13H14O
• Molecular Weight: 186.254
• DSSTox Substance ID: DTXSID701261886
• Mol file: 83249-05-2.mol

Synonyms:83249-05-2;1-{3-phenylbicyclo[1.1.1]pentan-1-yl}ethan-1-one;1-(3-Phenylbicyclo[1.1.1]pentan-1-yl)ethan-1-one;DTXSID701261886;1-(3-Phenylbicyclo[1.1.1]pent-1-yl)ethanone;EN300-36348493;EN300-37374206

Chemical Property of 1-{3-Phenylbicyclo[1.1.1]pentan-1-yl}ethan-1-one

Chemical Property:

• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 186.104465066
• Heavy Atom Count: 14
• Complexity: 253

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)C12CC(C1)(C2)C3=CC=CC=C3

Technology Process of 1-{3-Phenylbicyclo[1.1.1]pentan-1-yl}ethan-1-one

There total 3 articles about 1-{3-Phenylbicyclo[1.1.1]pentan-1-yl}ethan-1-one 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: 89.0%

methyllithium (917-54-4) + 3-phenylbicyclo<1.1.1>pentane-1-carboxylic acid (83249-04-1) → 3-acetyl-1-phenylbicyclo<1.1.1>pentane (83249-05-2)

Guidance literature:

In diethyl ether; for 3.15h; Ambient temperature;

DOI:10.1021/jo00146a031

Reference yield:

methyl 3-phenyl-2,2-dichlorobicyclo<1.1.1>pentanecarboxylate (65862-03-5) → 3-acetyl-1-phenylbicyclo<1.1.1>pentane (83249-05-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) tri-n-butyltin hydride, azobis(isobutyronitrile), 2.) NaOH / 1.) 130 deg C, 76 h, 2.) H₂O, heating, 2 h

2: 89 percent / diethyl ether / 3.15 h / Ambient temperature

With sodium hydroxide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In diethyl ether;

DOI:10.1021/jo00146a031

Reference yield:

iodobenzene (591-50-4) + [1.1.1]propellane (35634-10-7) + dimethylglyoxal (431-03-8) → 3-acetyl-1-phenylbicyclo<1.1.1>pentane (83249-05-2) + 3-acetyl-3'-phenyl<2>staffane (137335-42-3) + 3-acetyl-3''-phenyl<3>staffane (137335-43-4) + 3-acetyl-3'''-phenyl<4>staffane (137335-44-5)

Guidance literature:

With tri-n-butyl-tin hydride; Multistep reaction; 1.) pentane, 8 h, irrad., 2.) benzene, 6 h, irrad.;

DOI:10.1021/ja00028a029

upstream raw materials:

methyllithium

3-phenylbicyclo<1.1.1>pentane-1-carboxylic acid

iodobenzene

[1.1.1]propellane

Downstream raw materials:

3-phenyl-1-(2-hydroxy-2-propyl)bicyclo<1.1.1>pentane

3-acetoxy-1-phenylbicyclo<1.1.1>pentane

4-Nitro-benzoic acid 1-methyl-1-(3-phenyl-bicyclo[1.1.1]pent-1-yl)-ethyl ester