(1R,3R,4S)-3-hydroxy-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one

Base Information

• Chemical Name: (1R,3R,4S)-3-hydroxy-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one
• CAS No.: 22759-33-7
• Molecular Formula: C₁₀H₁₆O₂
• Molecular Weight: 168.236
• Mol file: 22759-33-7.mol

Synonyms:2-Bornanone,3-hydroxy-, exo- (8CI); Bicyclo[2.2.1]heptan-2-one, 3-hydroxy-1,7,7-trimethyl-,exo-; exo-3-Hydroxy-2-bornanone

Chemical Property of (1R,3R,4S)-3-hydroxy-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one

Chemical Property:

• Vapor Pressure: 0.00334mmHg at 25°C
• Boiling Point: 250.9°Cat760mmHg
• PKA: 13.08±0.60(Predicted)
• Flash Point: 103.4°C
• PSA: 37.30000
• Density: 1.107g/cm³
• LogP: 1.37250

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (1R,3R,4S)-3-hydroxy-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one

There total 28 articles about (1R,3R,4S)-3-hydroxy-1,7,7-trimethylbicyclo[2.2.1]heptan-2-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: 95.0%

Acetic acid (1S,4R)-4,7,7-trimethyl-3-oxo-bicyclo[2.2.1]hept-2-yl ester (15795-31-0,31658-22-7,31658-57-8,83462-15-1,91839-98-4,125409-78-1) → 3-hydroxycamphor (10373-81-6,21488-68-6,22759-33-7,24326-34-9,28357-09-7,28357-11-1,80513-77-5,80513-78-6,82264-38-8)

Guidance literature:

With potassium hydroxide; In methanol;

DOI:10.1016/S0040-4020(01)89491-6

Reference yield: 5.0%

Camphor (76-22-2,68546-28-1) → 5-endo-hydroxycamphor + 8-hydroxycamphor (3751-95-9,10334-06-2,40724-36-5,60966-80-5) + endo hydroxy-6 oxo-2 bornane (1935-16-6,3004-27-1,29050-85-9,75992-92-6,114529-11-2,125638-05-3,141782-91-4) + 3-exo-hydroxycamphor (22759-33-7) + 5-exo-hydroxycamphor (1126-88-1,1607-84-7,4367-83-3,13948-58-8,22285-79-6,107438-74-4) + 6-exo-hydroxycamphor (1935-16-6,3004-27-1,29050-85-9,75992-92-6,114529-11-2,125638-05-3,141782-91-4)

Guidance literature:

With Botryosphaeria sp. CBMAI 1197; In dimethyl sulfoxide; for 120h; Microbiological reaction;

DOI:10.21577/0103-5053.20160262

Reference yield:

(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one (464-49-3,68546-28-1) → 5-endo-hydroxy-1,7,7-trimethylbicyclo<2.2.1>heptan-2-one (107438-74-4,1126-88-1,1607-84-7,4367-83-3,13948-58-8,22285-79-6) + (+)-3R-exo-hydroxycamphor (28357-11-1) + (-)-(3S)-endo-hydroxycamphor (10373-81-6,21488-68-6,22759-33-7,24326-34-9,28357-11-1,80513-77-5,80513-78-6,82264-38-8,28357-09-7)

Guidance literature:

With cindoxin; Escherichia coli flavodoxin reductase; N₂₄₂T mutant; NADPH; catalase; In aq. buffer; at 25 ℃; for 0.5h; Enzymatic reaction;

DOI:10.1016/j.abb.2019.07.025

upstream raw materials:

(R)-camphorquinone

(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one

(1S)-camphor

Acetic acid (1S,4R)-4,7,7-trimethyl-3-oxo-bicyclo[2.2.1]hept-2-yl ester

Downstream raw materials:

2-exo-3-endo camphane-2,3-diol

(R)-camphorquinone

(+)-2-endo-3-exo-camphane-2,3-diol

2-endo-3-endo camphane-2,3-diol