(1S,2S,5S)-(-)-2-Hydroxy-3-pinanone

Base Information

• Chemical Name: (1S,2S,5S)-(-)-2-Hydroxy-3-pinanone
• CAS No.: 1845-25-6
• Molecular Formula: C10H16 O2
• Molecular Weight: 168.236
• Hs Code.: 2914400090
• UNII: P3X9755FQK
• DSSTox Substance ID: DTXSID70456111
• Nikkaji Number: J303.620K
• Wikidata: Q72481206
• Mol file: 1845-25-6.mol

Synonyms:1845-25-6;(1S,2S,5S)-(-)-2-Hydroxy-3-pinanone;(1S,2S,5S)-2-Hydroxy-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one;(-)-2-hydroxy-3-pinanone;P3X9755FQK;(-)-(1S,2S,5S)-2-Hydroxy-3-pinanone;(1S,2S,5S)-2-Hydroxypinan-3-one;Oxypinocamphone, (1S,2S,5S)-(-)-;2-Hydroxypinocamphone, (1S,2S,5S)-(-)-;Bicyclo(3.1.1)heptan-3-one, 2-hydroxy-2,6,6-trimethyl-, (1S,2S,5S)-;(1S,2S,5S)-2-hydroxy-3-pinanone;UNII-P3X9755FQK;SCHEMBL5935443;(-)-2alpha-Hydroxypinocamphone;1R_2R_5R_hydroxy_3_pinanone;DTXSID70456111;AMY14837;AC-514;MFCD00040556;(1s,2s,5s)-2-hydroxy-pinan-3-one;AKOS015855324;AKOS015900077;CS-W017794;(-)-2.ALPHA.-HYDROXYPINOCAMPHONE;AS-71357;H0863;D90966;A880769;(1S,2S,5S)-(-)-2-Hydroxy-3-pinanone, 99%;(1S,2S,5S)-(-)-2-Hydroxy-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one;(1S,2S,5S)-2-HYDROXY-2,6,6-TRIMETHYL-BICYCLO[3.1.1]HEPTAN-3-ONE;Bicyclo(3.1.1)heptan-3-one, 2-hydroxy-2,6,6-trimethyl-, (1S-(1alpha,2alpha,5alpha))-;BICYCLO(3.1.1)HEPTAN-3-ONE, 2-HYDROXY-2,6,6-TRIMETHYL-, (1S-(1.ALPHA.,2.ALPHA.,5.ALPHA.))-

Chemical Property of (1S,2S,5S)-(-)-2-Hydroxy-3-pinanone

Chemical Property:

• Vapor Pressure: 0.00491mmHg at 25°C
• Melting Point: 36-38 °C(lit.)
• Refractive Index: -33 ° (C=0.5, CHCl3)
• Boiling Point: 245 °C(lit.)
• PKA: 12.93±0.40(Predicted)
• Flash Point: 104.5°C
• PSA: 37.30000
• Density: 1.081g/cm³
• LogP: 1.37250
• Storage Temp.: Refrigerator
• Solubility.: Chloroform, Ethyl Acetate, Methanol
• 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:

98% ^*data from raw suppliers

(-)-(1S,2S,5S)-2-Hydroxy-3-pinanone ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

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
• Uses: A useful chiral auxillary for synthesis (1S,2S,5S)-(-)-2-Hydroxy-3-pinanone is an essential oil from Hyssopus officinalis L. and Cymbopogon jwarancusa (Jones) Schult. An essential oil from Hyssopus officinalis L. and Cymbopogon jwarancusa (Jones) Schult. It is used in cosmetics.

Technology Process of (1S,2S,5S)-(-)-2-Hydroxy-3-pinanone

There total 40 articles about (1S,2S,5S)-(-)-2-Hydroxy-3-pinanone 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

2α-hydroxy-2,6,6-trimethybicyclo<3.1.1>heptan-3-one oxime

pinanediol

Downstream raw materials:

[(1S,2S,5S)-2-Hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-(3E)-ylideneamino]-acetic acid cyclohexyl ester

(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

(1R,2R,5R)-ethyl-((2-hydroxypinan-3-ylene)amino)acetate

Refernces

• 1、 Carlson et al.. "". . p. 5941. Retrieved 1968.
• 2、 Curci, Ruggero,D'Accolti, Lucia,Detomaso, Antonia,Fusco, Caterina,Takeuchi, Ken'ichi,Ohga, Yasushi,Eaton, Philip E.,Yip, Yu Chi. "Selective oxidation of tertiary-secondary vic-diols to α-hydroxyketones by dioxiranes". . p. 4559 - 4562. Retrieved 1993.
• 3、 Gur'eva, Yana A.,Alekseev, Igor N.,Dvornikova, Irina A.,Zalevskaya, Olga A.,Kuchin, Aleksandr V.. "Synthesis and characterization of new palladium complexes based on polydentate chiral Schiff base and amines ligands derived from (+)-2-hydroxypinan-3-one". . p. 300 - 305. Retrieved 2018/11/21.
• 4、 Frensch, Gustavo,Labes, Ricardo,Wosch, Celso Luiz,Munaretto, Laieli Dos Santos,Salomé, Kahlil Schwanka,Guerrero, Palimécio G.,Marques, Francisco A.. "New chiral ligands derived from (+) and (-)-α-pinene for the enantioselective addition of diethylzinc to aldehydes". . p. 420 - 422. Retrieved 2016/01/12.