(1R,2S,5S)-2-((R)-hydroxy(phenyl)methyl)-7-methylenebicyclo[3.3.1]nonan-3-one

Base Information

• Chemical Name: (1R,2S,5S)-2-((R)-hydroxy(phenyl)methyl)-7-methylenebicyclo[3.3.1]nonan-3-one
• CAS No.: 473828-52-3
• Molecular Formula: C₁₇H₂₀O₂
• Molecular Weight: 256.345
• Mol file: 473828-52-3.mol

Synonyms:(1R,2S,5S)-2-((R)-hydroxy(phenyl)methyl)-7-methylenebicyclo[3.3.1]nonan-3-one

Chemical Property of (1R,2S,5S)-2-((R)-hydroxy(phenyl)methyl)-7-methylenebicyclo[3.3.1]nonan-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,5S)-2-((R)-hydroxy(phenyl)methyl)-7-methylenebicyclo[3.3.1]nonan-3-one

There total 2 articles about (1R,2S,5S)-2-((R)-hydroxy(phenyl)methyl)-7-methylenebicyclo[3.3.1]nonan-3-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: 90.0%

benzaldehyde (100-52-7) + 3-methylenebicyclo<3.3.1>nonan-7-one → (1R,2S,5S)-2-((R)-hydroxy(phenyl)methyl)-7-methylenebicyclo[3.3.1]nonan-3-one (473828-52-3)

Guidance literature:

3-methylenebicyclo<3.3.1>nonan-7-one; With n-butyllithium; (R,R)-N,N-bis-(1-phenylethyl)amine; lithium chloride; In tetrahydrofuran; hexane; at -78 ℃; for 3h; Inert atmosphere;

benzaldehyde; In tetrahydrofuran; hexane; at -78 ℃; for 3h; enantioselective reaction; Further stages; Inert atmosphere;

DOI:10.1021/ol502543r

Reference yield:

7-methylenebicyclo[3.3.1]nonan-3-one (17933-29-8) + benzaldehyde (100-52-7) → (1R,2S,5S)-2-((R)-hydroxy(phenyl)methyl)-7-methylenebicyclo[3.3.1]nonan-3-one (473828-52-3)

Guidance literature:

7-methylenebicyclo[3.3.1]nonan-3-one; With n-butyllithium; (R,R)-N,N-bis-(1-phenylethyl)amine; lithium chloride; In tetrahydrofuran; hexane; at -78 ℃; for 3h; Inert atmosphere;

benzaldehyde; In tetrahydrofuran; hexane; at -78 ℃; for 3h; Inert atmosphere;

With water; acetic acid; In tetrahydrofuran; hexane; optical yield given as %ee; Inert atmosphere;

DOI:10.1021/ol900441f

Reference yield: 100.0%

4-chlorobenzoyl chloride (586-75-4) + (1R,2S,5S)-2-((R)-hydroxy(phenyl)methyl)-7-methylenebicyclo[3.3.1]nonan-3-one (473828-52-3) → (R)-((1R,2S,5S)-7-methylene-3-oxobicyclo[3.3.1]nonan-2-yl)(phenyl)methyl-4-bromobenzoate (1146974-75-5)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1021/ja509766f

upstream raw materials:

benzaldehyde

7-methylenebicyclo[3.3.1]nonan-3-one

Downstream raw materials:

(1R,5S)-2-((E)-benzylidene)-7-methylenebicyclo[3.3.1]nonan-3-one

(1R,2R,5S)-7-Methylene-2-((S)-1-phenyl-ethyl)-bicyclo[3.3.1]nonan-3-one

(R)-((1R,2S,5S)-7-methylene-3-oxobicyclo[3.3.1]nonan-2-yl)(phenyl)methyl-4-bromobenzoate

(1R,2S,5S)-2-benzyl-7-methylbicyclo[3.3.1]non-7-en-3-one