(S)-(+)-4-Penten-2-ol

Base Information

• Chemical Name: (S)-(+)-4-Penten-2-ol
• CAS No.: 55563-79-6
• Molecular Formula: C₅H₁₀O
• Molecular Weight: 86.1338
• Hs Code.: 2914290090
• European Community (EC) Number: 626-193-7
• DSSTox Substance ID: DTXSID40426381
• Nikkaji Number: J1.059.957A
• Wikidata: Q72500052
• Mol file: 55563-79-6.mol

Synonyms:55563-79-6;(S)-(+)-4-Penten-2-ol;(2S)-pent-4-en-2-ol;(S)-pent-4-en-2-ol;4-Penten-2-ol, (2S)-;(S)-4-PENTEN-2-OL;(2s)-4penten-2-ol;(S)-4-Pentene-2-ol;(2S)-4-penten-2-ol;(A+/-)-pent-4-en-2-ol;DTXSID40426381;ZHZCYWWNFQUZOR-YFKPBYRVSA-N;MFCD03427200;AKOS015840154;AKOS015913109;(S)-(+)-4-Penten-2-ol, 95%;CS-0081915;EN300-211432

Chemical Property of (S)-(+)-4-Penten-2-ol

Chemical Property:

• Vapor Pressure: 9.56mmHg at 25°C
• Refractive Index: n20/D 1.4240(lit.)
• Boiling Point: 115.5 °C at 760 mmHg
• PKA: 15.10±0.20(Predicted)
• Flash Point: 25.6 °C
• PSA: 20.23000
• Density: 0.827 g/cm³
• LogP: 0.94330
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 86.073164938
• Heavy Atom Count: 6
• Complexity: 41.2

Purity/Quality:

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

(S)-(+)-2-Hydroxypent-4-ene 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): H226
• Hazard Codes: H226
• Statements: 10

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CC=C)O
• Isomeric SMILES: C[C@@H](CC=C)O
• Uses: (S)-(+)-4-Penten-2-ol is involved in the synthesis of goniothalamin, hexadecanolide, massoia lactone, and parasorbic acid through sequential allylboration-esterification ring-closing metathesis reactions. It is also used to prepare 2-pentanone.

Technology Process of (S)-(+)-4-Penten-2-ol

There total 32 articles about (S)-(+)-4-Penten-2-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%

vinyl magnesium bromide (1826-67-1) + (S)-Propylene oxide (16088-62-3) → (S)-4-penten-2-ol (625-31-0,64584-92-5,111957-98-3,55563-79-6)

Guidance literature:

With CuCN; In tetrahydrofuran; at -78 - -40 ℃; for 4h;

DOI:10.1016/j.tetlet.2006.12.068

Reference yield: 85.0%

1-methoxy-4-{[(2S)-pent-4-en-2-yloxy]methyl}benzene (847049-72-3) → (S)-4-penten-2-ol (625-31-0,64584-92-5,111957-98-3,55563-79-6)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1080/14786419.2021.1896509

Reference yield: 70.0%

vinylmagnesium chloride (3536-96-7) + (S)-Propylene oxide (16088-62-3) → (S)-4-penten-2-ol (625-31-0,64584-92-5,111957-98-3,55563-79-6)

Guidance literature:

With copper(l) iodide; In tetrahydrofuran; at -78 - 0 ℃; for 2.5h;

DOI:10.1021/ol702195w

upstream raw materials:

phthalic acid mono-(1-methyl-but-3-enyl) ester

d-B-allylbis(2-isocaranyl)borane

acetaldehyde

(-)-(1R,2S,3S,4S)-2,3-O-Allylborylen-2-endo-methyl-3-endo-phenyl-2-exo,3-exo-bornandiol

Downstream raw materials:

(2S)-2-methylbutane-1,4-diol

benzyl 3,5-dimethyl-4-[(S)-(1-methyl-but-3-enyloxycarbonyl)methyl]-1H-pyrrole-2-carboxylate

2,4-dihydroxy-6-methylbenzoic acid 1-methylbut-3-enyl ester

2,4-bis-ethoxymethoxy-6-methyl-benzoic acid 1-methyl-but-3-enyl ester

Refernces

• 1、 Kalavakuntla, Chiranjeevi,Kummari, Vijaya Babu,Yadav, Jhillu Singh. "Total synthesis of (–)-cephalosporolide D". . . Retrieved 2021/03/22.
• 2、 Yan, Lu,Meng, Yan,Haeffner, Fredrik,Leon, Robert M.,Crockett, Michael P.,Morken, James P.. "Carbohydrate/DBU Cocatalyzed Alkene Diboration: Mechanistic Insight Provides Enhanced Catalytic Efficiency and Substrate Scope". supporting information. p. 3663 - 3673. Retrieved 2018/03/21.