(R)-(+)-1-Octyn-3-ol

Base Information

• Chemical Name: (R)-(+)-1-Octyn-3-ol
• CAS No.: 32556-70-0
• Molecular Formula: C8H14O
• Molecular Weight: 126.199
• Hs Code.: 29052990
• European Community (EC) Number: 628-242-8
• UNII: AZ9V2W5SW4
• DSSTox Substance ID: DTXSID10426439
• Nikkaji Number: J264.796F
• Wikidata: Q27274201
• Mol file: 32556-70-0.mol

Synonyms:32556-70-0;(R)-(+)-1-Octyn-3-ol;(r)-oct-1-yn-3-ol;(3R)-oct-1-yn-3-ol;1-Octyn-3-ol, (3R)-;(r)-1-octyn-3-ol;(3R)-1-octyn-3-ol;(+)-1-Octyn-3-ol;1-Octyn-3-ol, (R)-;1-Octyn-3-ol, (+)-;1-Octyn-3-ol, (R)-(+)-;UNII-AZ9V2W5SW4;AZ9V2W5SW4;SCHEMBL235985;DTXSID10426439;VUGRNZHKYVHZSN-QMMMGPOBSA-N;MFCD00192370;AKOS025404386;?(R)-(+)-1-OCTYN-3-OL;(R)-(+)-1-Octyn-3-ol, 99%;AS-35717;CS-0172229;J-018781;Q27274201

Chemical Property of (R)-(+)-1-Octyn-3-ol

Chemical Property:

• Appearance/Colour: clear colorless to light yellow liquid
• Vapor Pressure: 0.496mmHg at 25°C
• Melting Point: -39°C (estimate)
• Refractive Index: n20/D 1.442(lit.)
• Boiling Point: 169.6 °C at 760 mmHg
• Flash Point: 63.9 °C
• PSA: 20.23000
• Density: 0.887 g/cm³
• LogP: 1.56080
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 126.104465066
• Heavy Atom Count: 9
• Complexity: 98.4

Purity/Quality:

98%,99%, ^*data from raw suppliers

(R)-(+)-1-Octyn-3-ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 27-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(C#C)O
• Isomeric SMILES: CCCCC[C@H](C#C)O
• Uses: (R)-(+)-1-Octyn-3-ol is used as a reactant in the stereoselective preparation of cyclooxygenase metabolites of 8,9-epoxyeicosatrienoic acid.

Technology Process of (R)-(+)-1-Octyn-3-ol

There total 51 articles about (R)-(+)-1-Octyn-3-ol 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: 92.0%

(R)-3-(2-Ethoxy-ethoxy)-oct-1-yne (128146-65-6) → (R)-1-octyn-3-ol (32556-70-0,37911-28-7)

Guidance literature:

With pyridinium p-toluenesulfonate; In isopropyl alcohol;

DOI:10.1016/S0040-4039(01)93429-X

Reference yield: 87.0%

oct-1-yn-3-one (27593-19-7) → 1-octyn-3-ol (32556-71-1,37911-28-7) + (R)-1-octyn-3-ol (32556-70-0,37911-28-7)

Guidance literature:

With (-)-(S)-BINAL-H; In tetrahydrofuran; Title compound not separated from byproducts; 1.) -100 deg C, 1 h; 2.) -78 deg C, 2 h;

DOI:10.1021/ja00334a042

Reference yield: 87.0%

5-((tert-butyldimethylsilyl)oxy)pent-3-yn-2-yl diethyl phosphate (133319-86-5) → (R)-1-octyn-3-ol (32556-70-0,37911-28-7)

Guidance literature:

With potassium carbonate; In methanol; at 0 - 25 ℃; for 20h; Inert atmosphere;

DOI:10.3390/molecules22030364

upstream raw materials:

oct-1-yn-3-one

1-Octyn-3-ol

N-(p-toluenesulfonyl)-L-phenylalanyl chloride

3-acetoxy-1-octyne

Downstream raw materials:

1-((R)-1-Ethynyl-hexyloxymethyl)-4-methoxy-benzene

(R)-octa-1,2-dien-1-yl diphenyl phosphine oxide

(R)-1-octene-3-ol

Refernces

• 1、 Yadav, Ashok K.,Manju, Meera,Chhinpa, Pukh Raj. "Enantioselective cathodic reduction of some prochiral ketones in the presence of (-)-N,N′-dimethylquininium tetrafluoroborate at mercury cathode". . p. 1079 - 1081. Retrieved 2003.
• 2、 Kalek, Marcin,Johansson, Tommy,Jezowska, Martina,Stawinski, Jacek. "Palladium-catalyzed propargylic substitution with phosphorus nucleophiles: Efficient, stereoselective synthesis of allenylphosphonates and related compounds". . p. 4702 - 4704. Retrieved 2010.
• 3、 Michelet,Besnier,Tanier,Touzin,Genet,Demoute. "Practical preparation of both optically pure enantiomers of but-1-yn-3-ol, oct-1-yn-3-ol and 6-methylhept-2-yn-4-ol using biocartol as resolving agent". . p. 165 - 167. Retrieved 1995.
• 4、 Xiao, Ling,Kitazume, Tomoya. "Optically active propargylic and allylic alcohols with a difluoromethyl group at the terminal carbon". . p. 3597 - 3601. Retrieved 1997.
• 5、 de Leeuw, Nicolas,Torrelo, Guzman,Bisterfeld, Carolin,Resch, Verena,Mestrom, Luuk,Straulino, Emanuele,van der Weel, Laura,Hanefeld, Ulf. "Ester Synthesis in Water: Mycobacterium smegmatis Acyl Transferase for Kinetic Resolutions". . p. 242 - 249. Retrieved 2017/11/16.
• 6、 Reddy, Ramidi Gopal,Venkateshwarlu, Ravula,Ramakrishna, Kallaganti V. S.,Yadav, Jhillu S.,Mohapatra, Debendra K.. "Asymmetric Total Syntheses of Two Possible Diastereomers of Gliomasolide e and Its Structural Elucidation". . p. 1053 - 1063. Retrieved 2018/06/18.