4bH-benzo(3,4)cyclobuta(1,2)cyclohepten-4b-ol, 5,6,7,8,9,9a-hexahydro-, cis-

Base Information

• Chemical Name: 4bH-benzo(3,4)cyclobuta(1,2)cyclohepten-4b-ol, 5,6,7,8,9,9a-hexahydro-, cis-
• CAS No.: 54881-57-1
• Molecular Formula: C₁₃H₁₆O
• Molecular Weight: 188.269
• DSSTox Substance ID: DTXSID00203372
• Wikidata: Q76150870
• Mol file: 54881-57-1.mol

Synonyms:4bH-benzo(3,4)cyclobuta(1,2)cyclohepten-4b-ol, 5,6,7,8,9,9a-hexahydro-, cis-;54881-57-1;cis-5,6,7,8,9,9a-Hexahydro-4bh-benzo(3,4)cyclobuta(1,2)cyclohepten-4b-ol;DTXSID00203372;LS-33736

Chemical Property of 4bH-benzo(3,4)cyclobuta(1,2)cyclohepten-4b-ol, 5,6,7,8,9,9a-hexahydro-, cis-

Chemical Property:

• Vapor Pressure: 8.97E-05mmHg at 25°C
• Boiling Point: 326.1°Cat760mmHg
• Flash Point: 122.9°C
• Density: 1.16g/cm³
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 188.120115130
• Heavy Atom Count: 14
• Complexity: 225

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC2C3=CC=CC=C3C2(CC1)O
• Isomeric SMILES: C1CC[C@H]2C3=CC=CC=C3[C@]2(CC1)O

Technology Process of 4bH-benzo(3,4)cyclobuta(1,2)cyclohepten-4b-ol, 5,6,7,8,9,9a-hexahydro-, cis-

There total 8 articles about 4bH-benzo(3,4)cyclobuta(1,2)cyclohepten-4b-ol, 5,6,7,8,9,9a-hexahydro-, cis- 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%

cycloheptanone (502-42-1) → 5,6,7,8,9,9a-hexahydro-4bH-benzo[3,4]cyclobuta[1,2][7]annulen-4b-ol (31274-16-5,54881-57-1)

Guidance literature:

cycloheptanone; With tetramethylpiperidine; tert.-butyl lithium; In tetrahydrofuran; hexane; at -40 ℃;

halobenzene; In tetrahydrofuran; hexane; at -40 ℃; for 5h;

DOI:10.1139/v03-099

Reference yield: 78.0%

allyl (4bRS,9aSR)-5,6,7,8,9,9a-hexahydro-4bH-benzo[3,4]cyclobuta[1,2]cyclohepten-4b-yl carbonate → 2-(2-allylphenyl)cycloheptanone (1397261-72-1) + 5,6,7,8,9,9a-hexahydro-4bH-benzo[3,4]cyclobuta[1,2][7]annulen-4b-ol (31274-16-5,54881-57-1)

Guidance literature:

With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In toluene; at 80 ℃; Inert atmosphere;

DOI:10.1055/s-0031-1290943

Reference yield: 44.0%

iodobenzene (591-50-4) + cycloheptanone (502-42-1) → 5,6,7,8,9,9a-hexahydro-4bH-benzo[3,4]cyclobuta[1,2][7]annulen-4b-ol (31274-16-5,54881-57-1)

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 5h; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.orglett.9b03652

upstream raw materials:

bromobenzene

cycloheptanone

6,7,8,9,10,11-hexahydro-benzocyclononen-5-one

iodobenzene

Downstream raw materials:

2-phenylcycloheptanone

6,7,8,9,10,11-hexahydro-benzocyclononen-5-one

2-(2-methallylphenyl)cycloheptanone