(1S,2R,3S,5R)-2-[(dicyclohexylphosphinoyl)methyl]-6,6-dimethylbicyclo[3.1.1]heptan-3-ol

Base Information

Chemical Name:(1S,2R,3S,5R)-2-[(dicyclohexylphosphinoyl)methyl]-6,6-dimethylbicyclo[3.1.1]heptan-3-ol
CAS No.:768402-63-7
Molecular Formula:C₂₂H₃₉O₂P
Molecular Weight:366.524
Hs Code.:

Synonyms:(1S,2R,3S,5R)-2-[(dicyclohexylphosphinoyl)methyl]-6,6-dimethylbicyclo[3.1.1]heptan-3-ol

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Chemical Property of (1S,2R,3S,5R)-2-[(dicyclohexylphosphinoyl)methyl]-6,6-dimethylbicyclo[3.1.1]heptan-3-ol

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Technology Process of (1S,2R,3S,5R)-2-[(dicyclohexylphosphinoyl)methyl]-6,6-dimethylbicyclo[3.1.1]heptan-3-ol

There total 2 articles about (1S,2R,3S,5R)-2-[(dicyclohexylphosphinoyl)methyl]-6,6-dimethylbicyclo[3.1.1]heptan-3-ol 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: 97.0%

: 768402-54-6
(1S,2R,3S,5R)-2-[(diphenylphosphinoyl)methyl]-6,6-dimethylbicyclo[3.1.1]heptan-3-ol

: 768402-63-7
(1S,2R,3S,5R)-2-[(dicyclohexylphosphinoyl)methyl]-6,6-dimethylbicyclo[3.1.1]heptan-3-ol

Guidance literature:: With hydrogen; nickel; In methanol; at 50 ℃; for 48h; high pressure;
DOI:10.1016/j.tetasy.2004.05.045

Reference yield:

: 869290-47-1
[[(1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]methyl]diphenylphosphine oxide

: 768402-63-7
(1S,2R,3S,5R)-2-[(dicyclohexylphosphinoyl)methyl]-6,6-dimethylbicyclo[3.1.1]heptan-3-ol

Guidance literature:: Multi-step reaction with 2 steps

1.1: borane-dimethyl sulfide complex / toluene / 6 h / 50 °C

1.2: 18.4 g / meta-chloroperbenzoic acid / CH₂Cl₂ / 10 - 15 °C

2.1: 97 percent / hydrogen / Raney Ni / methanol / 48 h / 50 °C / high pressure

With dimethylsulfide borane complex; hydrogen; nickel; In methanol; toluene;
DOI:10.1016/j.tetasy.2004.05.045

Reference yield:

: 768402-63-7
(1S,2R,3S,5R)-2-[(dicyclohexylphosphinoyl)methyl]-6,6-dimethylbicyclo[3.1.1]heptan-3-ol

: dicyclohexyl[[(1S,2R,3R,5R)-3-(diphenylphosphino)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl]phosphine

Guidance literature:: Multi-step reaction with 3 steps

1.1: polymethylhydrosiloxane; titanium(IV) isopropoxide / toluene / 2 h / 100 °C

1.2: 93 percent / borane-dimethyl sulfide complex / toluene / 0.08 h

2.1: methanesulfonyl chloride; triethylamine / CH₂Cl₂ / 2 h / -20 °C

2.2: t-BuOK / tetrahydrofuran / 18 h / 50 °C

2.3: 44 percent / borane-dimethyl sulfide complex / tetrahydrofuran

3.1: 96 percent / N,N'-bis(3-aminopropyl)piperazine / toluene / 12 h / 100 °C

With titanium(IV) isopropylate; 1,4-bis(3-aminopropyl)piperazine; polymethylhydrosiloxane; methanesulfonyl chloride; triethylamine; In dichloromethane; toluene;
DOI:10.1016/j.tetasy.2004.05.045