(S)-1-Octen-3-ol

Base Information

• Chemical Name: (S)-1-Octen-3-ol
• CAS No.: 24587-53-9
• Molecular Formula: C₈H₁₆O
• Molecular Weight: 128.214
• Hs Code.: 29052990
• European Community (EC) Number: 624-352-5
• UNII: 07D31239FH
• Nikkaji Number: J66.869I
• Wikidata: Q27093997
• Metabolomics Workbench ID: 1488
• Mol file: 24587-53-9.mol

Synonyms:(S)-1-Octen-3-ol;24587-53-9;(S)-oct-1-en-3-ol;(3S)-oct-1-en-3-ol;1-Octen-3-ol, (3S)-;(S)-(+)-1-Octen-3-ol;(+)-1-Octen-3-ol;oct-1-en-3S-ol;(S)-Matsutake alcohol;1-Octen-3-ol, (S)-;1-Octen-3-ol, (+)-;UNII-07D31239FH;07D31239FH;3(S)-hydroxy-1-octene;(3S)-1-Octene-3-ol;1-Octen-3-ol,(3S)-;S-(+)-1-Octen-3-ol;SCHEMBL5804837;CHEBI:46735;LMFA01050367;MFCD04972323;DB03025;J-015582;Q27093997;(S)-1-Octen-3-ol, >=95% (sum of enantiomers, GC)

Chemical Property of (S)-1-Octen-3-ol

Chemical Property:

• Boiling Point: 168.4 °C at 760 mmHg
• PKA: 14.63±0.20(Predicted)
• Flash Point: 61.1 °C
• PSA: 20.23000
• Density: 0.834 g/cm³
• LogP: 2.11360
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 128.120115130
• Heavy Atom Count: 9
• Complexity: 69

Purity/Quality:

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

(S)-1-Octen-3-ol ≥95% (sum of enantiomers, GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(C=C)O
• Isomeric SMILES: CCCCC[C@@H](C=C)O
• Uses: (S)-1-Octen-3-ol can be used:As an odorant in the study of an olfactory sensory map of the?Anopheles gambiae?maxillary palp.As an intermediate in the synthesis of natural product polyporolide and a prostaglandin named 8-aza-prostaglandin E1.As a substrate in the preparation of trienols by reacting with 1-iodo-1,3-dienes using Pd(OAc)2/AgOAc.

Technology Process of (S)-1-Octen-3-ol

There total 125 articles about (S)-1-Octen-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: 95.0%

Toluene-4-sulfonic acid (2R,3R)-3-pentyl-oxiranylmethyl ester (111321-48-3) → (R)-1-octene-3-ol (3391-86-4,3687-48-7,24587-53-9,50999-79-6)

Guidance literature:

With sodium hydroxide; tellurium; sodium formaldehyde sulfoxylate; In tetrahydrofuran; for 6h; Ambient temperature;

DOI:10.1021/jo00055a029

Reference yield: 91.0%

(2R,3R)-2-<(R)-p-tolylsulfinyl>-1-(trimethylsilyl)-3-octanol (155394-02-8) → (R)-1-octene-3-ol (3391-86-4,3687-48-7,24587-53-9,50999-79-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 0.75h; Ambient temperature;

DOI:10.1016/S0040-4020(01)80816-4

Reference yield: 90.0%

1-pentyl-2-propenyl acetate → (R)-1-octene-3-ol (3391-86-4,3687-48-7,24587-53-9,50999-79-6)

Guidance literature:

1-pentyl-2-propenyl acetate; With potassium carbonate; In methanol; at 20 ℃; for 2h; Inert atmosphere;

With di-isopropyl azodicarboxylate; acetic acid; triphenylphosphine; In methanol; at 20 ℃; for 8h; Inert atmosphere;

DOI:10.1002/ejoc.201301365

upstream raw materials:

1-octen-3-ol

oct-1-en-3-one

oct-1-en-3-yl acetate

C₂₂H₂₆O

Downstream raw materials:

(R)-octan-3-ol

(S)-2-hydroxyheptanal

(S)-octan-3-ol

2-hydroxy-heptanal-(1)

Refernces

• 1、 Patil, Pradnya H.,Fernandes, Rodney A.. "A stereoselective synthesis of the reported structure of polyporolide". . p. 49189 - 49194. Retrieved 2015.
• 2、 Wang, Xiao-Gang,Wang, Ai-E,Hao, Yi,Ruan, Yuan-Ping,Huang, Pei-Qiang. "Modular enantioselective synthesis of 8-aza-prostaglandin E1". . p. 9488 - 9493. Retrieved 2013.
• 3、 Zhang, Fuhao,Zeng, Jingwen,Gao, Mohan,Wang, Linzhou,Chen, Gen-Qiang,Lu, Yixin,Zhang, Xumu. "Concise, scalable and enantioselective total synthesis of prostaglandins". . p. 692 - 697. Retrieved 2021/06/01.
• 4、 Kim, Taehyeong,Lee, Sung Il,Kim, Sejin,Shim, Su Yong,Ryu, Do Hyun. "Total synthesis of PGF2α and 6,15-diketo-PGF1α and formal synthesis of 6-keto-PGF1α via three-component coupling". . . Retrieved 2019/09/17.