trans-2-Hydroxypinocamphone

Base Information

• Chemical Name: trans-2-Hydroxypinocamphone
• CAS No.: 20536-50-9
• Molecular Formula: C₁₀H₁₆O₂
• Molecular Weight: 168.236
• UNII: PTP4C2GHL7
• Mol file: 20536-50-9.mol

Synonyms:PTP4C2GHL7;trans-2-Hydroxypinocamphone;2-Hydroxypinocamphone, (+)-trans-;UNII-PTP4C2GHL7;Oxypinocamphone, (1R,2S,5R)-(+)-;2-Hydroxypinocamphone, (1R,2S,5R)-(+)-;3-Pinanone, 2-hydroxy-, (1R,2S,5R)-(+)-;20536-50-9;Bicyclo(3.1.1)heptan-3-one, 2-hydroxy-2,6,6-trimethyl-, (1R,2S,5R)-;Bicyclo(3.1.1)heptan-3-one, 2-hydroxy-2,6,6-trimethyl-, (1R-(1alpha,2beta,5alpha))-;SCHEMBL20721720;BICYCLO(3.1.1)HEPTAN-3-ONE, 2-HYDROXY-2,6,6-TRIMETHYL-, (1R-(1.ALPHA.,2.BETA.,5.ALPHA.))-

Chemical Property of trans-2-Hydroxypinocamphone

Chemical Property:

• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 168.115029749
• Heavy Atom Count: 12
• Complexity: 244

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(C2CC1C(C(=O)C2)(C)O)C
• Isomeric SMILES: C[C@@]1([C@@H]2C[C@@H](C2(C)C)CC1=O)O

Technology Process of trans-2-Hydroxypinocamphone

There total 25 articles about trans-2-Hydroxypinocamphone 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: 98.0%

(2S,4S)-2-[(1R,2R,5R)-2-Hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-(3E)-ylideneamino]-4-trimethylsilanyloxy-pentanoic acid tert-butyl ester → (-)-(2R,3R,5R)-2-hydroxy-3-pinanone (1845-25-6,10136-65-9,20536-50-9,73466-08-7,84236-04-4,125073-44-1,24047-72-1) + (2S,4S)-2-Amino-4-hydroxy-pentanoic acid tert-butyl ester

Guidance literature:

With citric acid; In tetrahydrofuran; for 96h; Ambient temperature;

DOI:10.1055/s-1997-3246

Reference yield: 72.0%

(-)-α-pinene (7785-26-4,25766-18-1) → (-)-(2R,3R,5R)-2-hydroxy-3-pinanone (1845-25-6,10136-65-9,20536-50-9,73466-08-7,84236-04-4,125073-44-1,24047-72-1)

Guidance literature:

With potassium permanganate; water; In acetone; at -10 ℃;

DOI:10.1016/j.tetlet.2015.12.042

Reference yield: 62.0%

tert-butyl 2-[(E)-((1R,2R,5R)-2-hydroxy-2,6,6-trimethylbicyclo-[3.1.1]heptan-3-ylidene)amino]acetate (276253-82-8) + 2-(trifluoromethoxy)ethyl trifluoromethanesulphonate (329710-76-1) → (S)-tert-butyl 2-[(E)-((1R,2R,5R)-2-hydroxy-2,6,6-trimethylbicyclo[3.1.1]-heptan-3-ylidene)amino]-4-(trifluoromethoxy)butanoate + (-)-(2R,3R,5R)-2-hydroxy-3-pinanone (1845-25-6,10136-65-9,20536-50-9,73466-08-7,84236-04-4,125073-44-1,24047-72-1)

Guidance literature:

tert-butyl 2-[(E)-((1R,2R,5R)-2-hydroxy-2,6,6-trimethylbicyclo-[3.1.1]heptan-3-ylidene)amino]acetate; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 1.5h; Inert atmosphere;

2-(trifluoromethoxy)ethyl trifluoromethanesulphonate; In tetrahydrofuran; at -78 - 20 ℃; Overall yield = 1.34 g; diastereoselective reaction; Inert atmosphere;

DOI:10.1039/c6ob02436j

upstream raw materials:

rac-α-pinene

(-)-α-pinene

(1S,5R)-2,6,6-Trimethyl-bicyclo[3.1.1]heptan-3-one

isopinocamphone

Downstream raw materials:

(2S)-2,6,6-trimethyl-3-(pyridin-3-ylmethylimino)bicyclo[3.1.1]heptan-2-ol

(2R)-2,6,6-trimethyl-3-(pyridin-3-ylmethylimino)bicyclo[3.1.1]heptan-2-ol

carvacrol

eucarvone