18524-19-1

Basic information

• Product Name: (3R,4S)-4,5-ISOPROPYLIDENE PENT-2-EN-3-OL
• Synonyms: (3R,4S)-4,5-ISOPROPYLIDENE PENT-2-EN-3-OL
• CAS NO: 18524-19-1
• Molecular Formula: C₈H₁₄O₃
• Molecular Weight: 158.19
• Mol File: 18524-19-1.mol

Chemical Properties

• Boiling Point: 215.1°Cat760mmHg
• Flash Point: 100.2°C
• Appearance: /
• Density: 1.027g/cm³
• Vapor Pressure: 0.033mmHg at 25°C
• Refractive Index: 1.452
• PKA: 13.46±0.20(Predicted)
• CAS DataBase Reference: (3R,4S)-4,5-ISOPROPYLIDENE PENT-2-EN-3-OL(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4S)-4,5-ISOPROPYLIDENE PENT-2-EN-3-OL(18524-19-1)
• EPA Substance Registry System: (3R,4S)-4,5-ISOPROPYLIDENE PENT-2-EN-3-OL(18524-19-1)

Safety Data

• Hazardous Substances Data: 18524-19-1(Hazardous Substances Data)

Usage

Uses

Used in Chemical Industry:
(3R,4S)-4,5-ISOPROPYLIDENE PENT-2-EN-3-OL is used as an intermediate in the synthesis of various organic molecules and pharmaceuticals due to its reactivity and ability to undergo various chemical reactions.
Used in Food Industry:
(3R,4S)-4,5-ISOPROPYLIDENE PENT-2-EN-3-OL is used as a flavoring agent for its fruity odor.

InChI:InChI=1/C8H14O3/c1-4-6(9)7-5-10-8(2,3)11-7/h4,6-7,9H,1,5H2,2-3H3/t6-,7+/m0/s1

Upstream product

• 19139-74-3 2,3:4,5-di-O-isopropylidene-D-arabinitol 
• 71769-38-5 1-deoxy-2,3-o-isopropylidene-1-tosyl-D-arabinitol 
• 102418-34-8 1,2:5,6-bis-O-(1-methylethylidene)-D-mannitol 
• 223558-55-2 (2R,3S)-3-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-4-pentene-1,2,3-triol 
• 64520-58-7 ethyl (E)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate 
• 79060-23-4 (2E)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-en-1-ol 
• 80532-36-1 ((2R,3S)-3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)oxiran-2-yl)methanol 
• 127305-52-6 1,2:3,4-di-O-isopropylidene-(2R,3R,4S)-5-chloropentane-1,2,3,4-tetraol 
• 3969-59-3 mannitol triacetonide 
• 13039-93-5 2,2:4,5-di-O-isopropylidene-D-arabinose 
• 38145-93-6 1,2:3,4-di-O-isopropylidene-D-mannitol 
• 15186-48-8 2,3-isopropylidene-glyceraldehyde 
• 143706-60-9 (2R)-3-O-acetyl-1,2-O-isopropylidene-5-(trimethylsilyl)-4-pentyne-1,2,3-triol 
• 143788-59-4 (2R,3S)-1,2-O-isopropylidene-5-(trimethylsilyl)-4-pentyne-1,2,3-triol 

Downstream Products

• 954416-30-9 (4R)-4-((S)-1-(4-methoxybenzyloxy)allyl)-2,2-dimethyl-1,3-dioxolane 
• 954416-32-1 C₂₁H₂₈O₃Si 
• 954416-33-2 C₃₅H₄₀O₃Si 
• 954416-34-3 C₃₈H₄₄O₅Si 
• 954416-35-4 C₃₈H₄₆O₅Si 
• 954416-36-5 C₂₂H₂₈O₅ 
• 954416-37-6 C₂₃H₂₈O₄ 
• 954416-29-6 C₂₁H₂₄O₄ 
• 954416-27-4 C₃₄H₄₀O₆ 
• 954416-38-7 C₃₂H₃₆O₆ 
• 954416-26-3 (5S,6R,9S,10R)-5,6-di(benzyloxy)-9-hydroxy-10-methyl-3,4,5,6,9,10-hexahydro-2H-2-oxecinone 
• 954416-39-8 (2R,3S,6R,7S)-6,7-di(benzyloxy)-2-methyl-10-oxo-3,6,7,8,9,10-hexahydro-2H-3-oxecinyl (E)-but-2-enoate 
• 954416-31-0 (2R,3S)-3-(4-methoxybenzyloxy)pent-4-ene-1,2-diol 
• 954416-28-5 C₁₃H₁₈O₃ 

Relevant articles and documents

Synthesis of Fluorinated Amides Starting from Carbohydrates Based on the Claisen Rearrangement

The search for new methods for installation of fluorine atoms into organic molecules is still a widely studied issue. In this work, an efficient synthetic protocol for the synthesis of fluorine-containing amides derived from sugar has been presented. This approach involved the Claisen rearrangement of previously obtained fluorinated vinyl ethers. The three fluorinated olefins: 1,1,3,3,3-pentafluoroprop-1-ene (2H-PFP), 1,2,3,3,3-pentafluoroprop-1-ene (1H-PFP) and hexafluoroprop-1-ene (HFP) were used as a source of fluorine. New compounds were characterized by 1H, 19F and 13C NMR spectroscopy and high resolution mass spectrometry. The X-ray crystal structures of some fluorinated derivatives were obtained confirming structure, geometry and absolute configuration. The resulting molecules, due to possibility of further transformation of their functional groups, can be valuable fluorinated scaffolds for the synthesis of subsequent chemical compounds.

Preparation of chiral sugar-derived fluorides using new nucleophilic fluorinating reagents

New fluorinating reagents, composed of (S)-2-(diphenylmethyl)pyrrolidine and 1,1,3,3,3-pentafluoropropene/hexafluoropropene, have been found to be an effective system for nucleophilic deoxyfluorination. Regio- and stereoselectivity of deoxyfluorination of sugar-derived allylic, benzylic and propargylic alcohols with new reagents have been studied.

Synthesis of polyhydroxylated decalins via two consecutive one-pot reactions: 1,4-Addition/aldol reaction followed by RCM/syn-dihydroxylation

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A simple carbohydrate-based convergent approach towards the total synthesis of herbarumin-I, a 10-membered lactone is described. The key features of the synthetic strategy include Grignard reaction and ring-closing metathesis reaction for the formation of the 10-membered ring and E-olefinic moiety. d-Mannitol has been used as a chiral pool material for the construction of the key fragment.

Stereoselective synthesis of (2S,3S)-3-hydroxy-2-phenylpiperidine from d-mannitol

A novel stereoselective synthesis of N-Boc-(2S,3S)-3-hydroxy-2-phenylpiperidine was achieved from d-mannitol involving the highly stereoselective addition of phenyl Grignard to an allyl imine (de >98%) and ring-closing metathesis (RCM) in the key steps.

PROCESS FOR PREPARING NEBIVOLOL

The present invention relates to a process for preparing nebivolol and, more particularly, to a process for preparing d-nebivolol and its enantiomer /-nebivolol or acid addition salts thereof starting from commercially available or easily obtainable 2,2-dimethyl-l,3 dioxolane-4- carbaldehyde and a vinyl Grignard reagent.

A convenient and versatile method for the preparation of α-hydroxymethyl ketone derivatives from the corresponding allyl silyl ethers or allyl carboxylates

The ozonolysis of 1-substituted allyl silyl ethers or 1-substituted allyl carboxylates followed by treatment with bases gave the corresponding α-silyloxymethyl- or α-acyloxymethyl-ketones in good yields. It is proposed to proceed via the corresponding α-silyloxy- or α-acyloxyaldehydes intermediates followed by 1,4-group migration. The results of theoretical calculations are applicable to explain the experimental results.

Total synthesis of aspinolide B: a ring-closing metathesis approach

A highly convergent stereoselective total synthesis of aspinolide B, a 10-membered lactone is described. The key step includes a ring-closing metathesis reaction to construct the 10-membered ring and the E-olefinic moiety. d-Mannitol was used as a chiral

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(3S,8R,9R,10R)-Heptadeca-1-ene-4,6-diyne tetrol and its 3-epimer were synthesized, and it was found that the relative configuration which was proposed for 1 was incorrect. Georg Thieme Verlag Stuttgart.