(1S,2S,3R,5S)-(+)-2,3-Pinanediol

Base Information

• Chemical Name: (1S,2S,3R,5S)-(+)-2,3-Pinanediol
• CAS No.: 18680-27-8
• Molecular Formula: C10H18O2
• Molecular Weight: 170.252
• Hs Code.: 29051990
• European Community (EC) Number: 606-096-6
• UNII: Y6ZCV4AVRA
• DSSTox Substance ID: DTXSID00171941
• Nikkaji Number: J551.231J
• Wikidata: Q27294324
• ChEMBL ID: CHEMBL4303429
• Mol file: 18680-27-8.mol

Synonyms:Pinanediol;(1S,2S,3R,5S)-2,3-Pinanediol;(1S, 2S, 3R, 5S)-(+)Pinanediol;(1S,2S,3R,5S)-(+)Pinanediol;(+)-2,3-Pinanediol;(+)-Pinanediol;

Chemical Property of (1S,2S,3R,5S)-(+)-2,3-Pinanediol

Chemical Property:

• Appearance/Colour: white to light beige crystalline powder, crystals
• Vapor Pressure: 0.001mmHg at 25°C
• Melting Point: 57-59 °C(lit.)
• Refractive Index: 1.52
• Boiling Point: 263.738 °C at 760 mmHg
• PKA: 14.68±0.60(Predicted)
• Flash Point: 120.838 °C
• PSA: 40.46000
• Density: 1.091 g/cm³
• LogP: 1.16430
• Storage Temp.: 2-8°C
• Solubility.: Chloroform, Methanol (Slightly), Toluene (Slightly)
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 170.130679813
• Heavy Atom Count: 12
• Complexity: 212

Purity/Quality:

99%min ^*data from raw suppliers

(1S,2S,3R,5S)-(+)-2,3-Pinanediol ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C2CC1C(C(C2)O)(C)O)C
• Isomeric SMILES: C[C@@]1([C@H]2C[C@H](C2(C)C)C[C@H]1O)O
• Uses: (1S,2S,3R,5S)-(+)-2,3-Pinanediol is a bicyclic monoterpene diols that has been shown to induce differentiation of S91 melanoma and PC12 pheochromocytoma cells and thus provide possible therapeutic and sunless tanning use. It is also used in the transformation of isopinocampheol and caryophyllene oxide. (1S,2S,3R,5S)-(+)-2,3-Pinanediol is a bicyclic monoterpene diols that has been shown to induce differentiation of S91 melanoma and PC12 pheochromocytoma cells and thus provide possible therapeutic and sunless tanning use. It is also used in the transformation of isopinocampheol and caryophyllene oxide. (1S,2S,3R,5S)-(+)-Pinanediol can be used as a chiral reagent in the synthesis of homochiral α-hydroxyketones and in the resolution of prolineboronate esters.

Technology Process of (1S,2S,3R,5S)-(+)-2,3-Pinanediol

There total 41 articles about (1S,2S,3R,5S)-(+)-2,3-Pinanediol 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: 96.5%

(+)-α-pinene (7785-70-8,25766-18-1) → pinanediol (18680-27-8)

Guidance literature:

With osmium(VIII) oxide; trimethylamine-N-oxide; In pyridine; water; tert-butyl alcohol; for 96h; Heating;

Reference yield: 96.0%

(s)-sodium bis(pinanediol)borate → pinanediol (18680-27-8)

Guidance literature:

With hydrogen fluoride; In diethyl ether; at 25 ℃; for 0.5h;

DOI:10.1016/0022-328X(88)87067-0

Reference yield: 92.9%

3,6,6-trimethyl-bicyclo[3.1.1]hept-2-ene (4889-83-2,23978-81-6) → pinanediol (18680-27-8)

Guidance literature:

With pyridine; osmium(VIII) oxide; trimethylamine-N-oxide; In water; tert-butyl alcohol; for 15h; Inert atmosphere; Reflux;

upstream raw materials:

(+)-α-pinene

(+)-2α-hydroxy-3α-tosyloxypinane

methyl magnesium iodide

Acetic acid (1S,3R,5S)-6,6-dimethyl-2-oxo-bicyclo[3.1.1]hept-3-yl ester

Downstream raw materials:

(1S,2S,5S)-(-)-2-hydroxypinan-3-one

pinanediol vinylboronic ester

(+)-pinanediol-4-bromo-butane-1-boronate

(3aS,4S,6S,7aR)-3a,5,5-trimethyl-2-phenylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole

Refernces

• 1、 Bhunia, Anup,Bergander, Klaus,Daniliuc, Constantin Gabriel,Studer, Armido. "Fe-Catalyzed Anaerobic Mukaiyama-Type Hydration of Alkenes using Nitroarenes". supporting information. p. 8313 - 8320. Retrieved 2021/03/08.
• 2、 -. "Boric acid compounds, and preparation method and use thereof". Paragraph 0164; 0165; 0166. . Retrieved 2017/09/21.