(7R*,9S*)-2-(diphenylphosphinoyl)-5,5-dimethyltricyclo<7.3.0.0^3,7>dodeca-1,3-diene

Base Information

• Chemical Name: (7R*,9S*)-2-(diphenylphosphinoyl)-5,5-dimethyltricyclo<7.3.0.0^3,7>dodeca-1,3-diene
• CAS No.: 129031-69-2
• Molecular Formula: C₂₆H₂₉OP
• Molecular Weight: 388.489

Synonyms:(7R*,9S*)-2-(diphenylphosphinoyl)-5,5-dimethyltricyclo<7.3.0.0^3,7>dodeca-1,3-diene

Chemical Property of (7R*,9S*)-2-(diphenylphosphinoyl)-5,5-dimethyltricyclo<7.3.0.0^3,7>dodeca-1,3-diene

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Technology Process of (7R*,9S*)-2-(diphenylphosphinoyl)-5,5-dimethyltricyclo<7.3.0.0^3,7>dodeca-1,3-diene

There total 5 articles about (7R*,9S*)-2-(diphenylphosphinoyl)-5,5-dimethyltricyclo<7.3.0.0^3,7>dodeca-1,3-diene 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: 71.3%

1-(Cyclopent-1'-en-1'-yl)-4,4-dimethyl-6-hepten-1-yn-3-ol (119795-77-6) + chloro-diphenylphosphine (1079-66-9,74391-44-9) → (7R*,9S*)-2-(diphenylphosphinoyl)-5,5-dimethyltricyclo<7.3.0.03,7>dodeca-1,3-diene (129031-69-2)

Guidance literature:

With dmap; In diethyl ether; Ambient temperature;

DOI:10.1021/jo00305a025

Reference yield:

1-(Cyclopent-1'-en-1'-yl)-4,4-dimethyl-6-hepten-1-yn-3-ol (119795-77-6) + chloro-diphenylphosphine (1079-66-9,74391-44-9) → 1-(1'-cyclopenten-1'-yl)-1-(diphenylphosphinoyl)-4,4-dimethyl-1,2,6-heptatriene (129063-45-2) + (7R*,9S*)-2-(diphenylphosphinoyl)-5,5-dimethyltricyclo<7.3.0.03,7>dodeca-1,3-diene (129031-69-2)

Guidance literature:

With dmap; In diethyl ether; at 25 ℃; for 0.5h; Title compound not separated from byproducts;

DOI:10.1021/jo00305a025

Reference yield:

2,2-dimethyl-4-pentenal (5497-67-6) → (7R*,9S*)-2-(diphenylphosphinoyl)-5,5-dimethyltricyclo<7.3.0.03,7>dodeca-1,3-diene (129031-69-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) n-BuLi / 1.) Et₂O, hexane, 0 deg C, 30 min, 2.) 0 deg C to room temperature, 2 h

2: 4-(N,N-dimethylamino)pyridine (DMAP) / diethyl ether / 0.5 h / 25 °C

With dmap; n-butyllithium; In diethyl ether;

DOI:10.1021/jo00305a025

upstream raw materials:

1-(1'-cyclopenten-1'-yl)-1-(diphenylphosphinoyl)-4,4-dimethyl-1,2,6-heptatriene

1-(Cyclopent-1'-en-1'-yl)-4,4-dimethyl-6-hepten-1-yn-3-ol

chloro-diphenylphosphine

ethynylcyclopentene

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