55563-79-6

Basic information

• Product Name: (S)-(+)-4-PENTEN-2-OL
• Synonyms: (S)-(+)-4-PENTEN-2-OL;(S)-(+)-2-HYDROXYPENT-4-ENE;(S)-(+)-4-PENTEN-2-OL, 95% (98% EE/GLC);(2S)-4-Pentene-2-ol;(S)-4-Pentene-2-ol;[S,(+)]-4-Pentene-2-ol;(S)-(+)-4-Penten-2-ol 95%;(2S)-pent-4-en-2-ol
• CAS NO: 55563-79-6
• Molecular Formula: C₅H₁₀O
• Molecular Weight: 86.13
• Product Categories: API intermediates;Alcohols;Chiral Building Blocks;Organic Building Blocks
• Mol File: 55563-79-6.mol
• Article Data: 38

Chemical Properties

• Boiling Point: 115-116 °C(lit.)
• Flash Point: 78 °F
• Appearance: /
• Density: 0.837 g/mL at 25 °C(lit.)
• Vapor Pressure: 9.56mmHg at 25°C
• Refractive Index: n20/D 1.4240(lit.)
• PKA: 15.10±0.20(Predicted)
• CAS DataBase Reference: (S)-(+)-4-PENTEN-2-OL(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-4-PENTEN-2-OL(55563-79-6)
• EPA Substance Registry System: (S)-(+)-4-PENTEN-2-OL(55563-79-6)

Safety Data

• Hazard Codes: H226
• Statements: 10
• RIDADR: UN 1987 3/PG 3
• WGK Germany: 3
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 55563-79-6(Hazardous Substances Data)

Usage

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.

InChI:InChI=1/C5H10O/c1-3-4-5(2)6/h3,5-6H,1,4H2,2H3/t5-/m0/s1

Upstream product

• 75-07-0 acetaldehyde 
• 111957-98-3 Pent-4-en-2-ol 
• 3536-96-7 vinylmagnesium chloride 
• 16088-62-3 (S)-Propylene oxide 
• 1384108-43-3 C₅H₉O₄S^(1-)*Na⁽¹⁺⁾ 
• 1384108-64-8 C₅H₉O₄S^(1-)*Na⁽¹⁺⁾ 
• 124821-92-7 d-B-allylbis(2-isocaranyl)borane 
• 64584-91-4 phthalic acid mono-(1-methyl-but-3-enyl) ester 
• 874660-40-9 (R)-2-(4-Methoxy-benzyloxy)-pent-4-enal 
• 142561-89-5 (R)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol 
• 847049-72-3 1-methoxy-4-{[(2S)-pent-4-en-2-yloxy]methyl}benzene 
• 760181-72-4 (R)-2-(4-methoxybenzyloxy)pent-4-en-1-ol 
• 108-05-4 vinyl acetate 
• 1826-67-1 vinyl magnesium bromide 

Downstream Products

• 626-95-9 (2S)-2-methylbutane-1,4-diol 
• 871565-63-8 benzyl 3,5-dimethyl-4-[(S)-(1-methyl-but-3-enyloxycarbonyl)methyl]-1H-pyrrole-2-carboxylate 
• 853645-34-8 2,4-dihydroxy-6-methylbenzoic acid 1-methylbut-3-enyl ester 
• 1147106-37-3 (2Z,4E)-((S)-pent-4-en-2-yl) 3-ethyl-4-(4-methylbenzoyl)hexa-2,4-dienoate 
• 1147106-49-7 (2Z,4E)-((S)-pent-4-en-2-yl) 4-(4-bromobenzoyl)-3-methylnona-2,4,8-trienoate 
• 1147106-54-4 (S,2Z,4E)-((S)-pent-4-en-2-yl) 4-(4-bromobenzoyl)-3-ethyl-7,11-dimethyldodeca-2,4,10-trienoate 
• 1333331-64-8 tert-butyl (((2S,8R,9R)-11-((S)-1-((4-methoxybenzyl)oxy)propan-2-yl)-2,9-dimethyl-14-nitro-12-oxo-2,3,6,8,9,10,11,12-octahydrobenzo[b][1,9,5]dioxaazacyclotetradecin-8-yl)methyl)(methyl)carbamate 
• 1333331-66-0 tert-butyl (((2S,8R,9R)-14-amino-11-((S)-1-((4-methoxybenzyloxy)prop-2-yl)-2,9-dimethyl-12-oxo-2,3,4,5,6,8,9,10,11,12-ecahydrobenzo[b][1,9,5]dioxaazacyclotetradec-8-yl)methyl)-methyl)carbamate 
• 1400236-70-5 (1R,2R,3R,5R,7S,8aR)-1,2-bis(benzyloxy)-3-[(benzyloxy)-methyl]-5-methyloctahydroindolizin-7-ol 
• 1446397-77-8 C₃₀H₃₆O₈ 

Relevant articles and documents

Total synthesis of (–)-cephalosporolide D

In this communication, a concise and efficient synthetic route for the synthesis of (–)-Cephalosporolide D in enantioselective way has been described. In this synthesis, Mitsunobu esterification and Ring Closing Metathesis (RCM) for macrocyclic ring formation have been applied as key steps.

A Short Synthesis of (+)-Brefeldin C through Enantioselective Radical Hydroalkynylation

A very concise total synthesis of (+)-brefeldin C starting from 2-furanylcyclopentene is described. This approach is based on an unprecedented enantioselective radical hydroalkynylation process to introduce the two cyclopentane stereocenters in a single step. The use of a furan substituent allows a high trans diastereoselectivity to be achieved during the radical process and it contains the four carbon atoms C1–C4 of the natural product in an oxidation state closely related to the one of the target molecule. The eight-step synthesis requires six product purifications and it provides (+)-brefeldin C in 18 % overall yield.

Synthesis and Stereochemical Assignment of Arenolide

The convergent synthesis of candidate stereoisomers of the natural product arenolide was accomplished using recently developed catalytic boron-based reactions. Comparison of the spectral data for candidate structures with that reported for the authentic natural product revealed the likely stereostructure of the natural compound.