[(1R,6S,7R,8R)-8-((2E,4E)-5-Phenyl-penta-2,4-dienyl)-bicyclo[4.2.0]octa-2,4-dien-7-yl]-acetonitrile

Base Information

• Chemical Name: [(1R,6S,7R,8R)-8-((2E,4E)-5-Phenyl-penta-2,4-dienyl)-bicyclo[4.2.0]octa-2,4-dien-7-yl]-acetonitrile
• CAS No.: 82808-53-5
• Molecular Formula: C₂₁H₂₁N
• Molecular Weight: 287.404
• Mol file: 82808-53-5.mol

Synonyms:[(1R,6S,7R,8R)-8-((2E,4E)-5-Phenyl-penta-2,4-dienyl)-bicyclo[4.2.0]octa-2,4-dien-7-yl]-acetonitrile

Chemical Property of [(1R,6S,7R,8R)-8-((2E,4E)-5-Phenyl-penta-2,4-dienyl)-bicyclo[4.2.0]octa-2,4-dien-7-yl]-acetonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(1R,6S,7R,8R)-8-((2E,4E)-5-Phenyl-penta-2,4-dienyl)-bicyclo[4.2.0]octa-2,4-dien-7-yl]-acetonitrile

There total 3 articles about [(1R,6S,7R,8R)-8-((2E,4E)-5-Phenyl-penta-2,4-dienyl)-bicyclo[4.2.0]octa-2,4-dien-7-yl]-acetonitrile 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:

[(1S,6S,7S,8R)-8-((2E,4E)-5-Phenyl-penta-2,4-dienyl)-bicyclo[4.2.0]octa-2,4-dien-7-yl]-methanol (82808-51-3) → [(1R,6S,7R,8R)-8-((2E,4E)-5-Phenyl-penta-2,4-dienyl)-bicyclo[4.2.0]octa-2,4-dien-7-yl]-acetonitrile (82808-53-5)

Guidance literature:

Multi-step reaction with 2 steps

1: CBr₄, PPh₃ / CH₂Cl₂ / -10 °C

2: hexamethylphosphoric acid triamide / 25 °C

With carbon tetrabromide; triphenylphosphine; In N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane;

DOI:10.1021/ja00384a078

Reference yield:

tert-Butyl-diphenyl-[(1R,6R,7R,8S)-8-((2E,4E)-5-phenyl-penta-2,4-dienyl)-bicyclo[4.2.0]octa-2,4-dien-7-ylmethoxy]-silane (82679-76-3) → [(1R,6S,7R,8R)-8-((2E,4E)-5-Phenyl-penta-2,4-dienyl)-bicyclo[4.2.0]octa-2,4-dien-7-yl]-acetonitrile (82808-53-5)

Guidance literature:

Multi-step reaction with 3 steps

1: n-Bu₄NF / tetrahydrofuran / 0 deg C -> 25 deg C

2: CBr₄, PPh₃ / CH₂Cl₂ / -10 °C

3: hexamethylphosphoric acid triamide / 25 °C

With carbon tetrabromide; tetrabutyl ammonium fluoride; triphenylphosphine; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane;

DOI:10.1021/ja00384a078

Reference yield:

sodium cyanide (143-33-9,25596-52-5) + (1S,6S,7S,8R)-7-Bromomethyl-8-((2E,4E)-5-phenyl-penta-2,4-dienyl)-bicyclo[4.2.0]octa-2,4-diene (82808-52-4) → [(1R,6S,7R,8R)-8-((2E,4E)-5-Phenyl-penta-2,4-dienyl)-bicyclo[4.2.0]octa-2,4-dien-7-yl]-acetonitrile (82808-53-5)

Guidance literature:

In N,N,N,N,N,N-hexamethylphosphoric triamide; at 25 ℃;

DOI:10.1021/ja00384a078

upstream raw materials:

sodium cyanide

(1S,6S,7S,8R)-7-Bromomethyl-8-((2E,4E)-5-phenyl-penta-2,4-dienyl)-bicyclo[4.2.0]octa-2,4-diene

[(1S,6S,7S,8R)-8-((2E,4E)-5-Phenyl-penta-2,4-dienyl)-bicyclo[4.2.0]octa-2,4-dien-7-yl]-methanol

tert-Butyl-diphenyl-[(1R,6R,7R,8S)-8-((2E,4E)-5-phenyl-penta-2,4-dienyl)-bicyclo[4.2.0]octa-2,4-dien-7-ylmethoxy]-silane

Downstream raw materials:

endiandric acid F methyl ester

endiandric acid E ethyl ester

endiandric acid F

endiandric acid E