123932-68-3

Basic information

• Product Name: [(2R,3S)-3-heptyloxiran-2-yl]methanol
• CAS NO: 123932-68-3
• Molecular Formula: C₁₀H₂₀O₂
• Molecular Weight: 172.2646
• Mol File: 123932-68-3.mol

Chemical Properties

• Boiling Point: 252.5°C at 760 mmHg
• Flash Point: 94.6°C
• Density: 0.941g/cm³
• Vapor Pressure: 0.003mmHg at 25°C
• Refractive Index: 1.454
• CAS DataBase Reference: [(2R,3S)-3-heptyloxiran-2-yl]methanol(CAS DataBase Reference)
• NIST Chemistry Reference: [(2R,3S)-3-heptyloxiran-2-yl]methanol(123932-68-3)
• EPA Substance Registry System: [(2R,3S)-3-heptyloxiran-2-yl]methanol(123932-68-3)

Safety Data

• Hazardous Substances Data: 123932-68-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
[(2R,3S)-3-heptyloxiran-2-yl]methanol is used as a building block in the field of organic synthesis for the creation of more complex molecules. Its unique structure allows for various chemical reactions and modifications, making it a versatile compound in this area.
Used as a Reagent in Chemical Reactions:
In the context of chemical reactions, [(2R,3S)-3-heptyloxiran-2-yl]methanol serves as a reagent, facilitating specific transformations and providing the desired products. Its properties and reactivity make it suitable for use in a range of chemical processes.

Upstream product

• 4194-71-2 (Z)-2-decen-1-ol 
• 4117-14-0 2-decyn-1-ol 
• 629-04-9 1-Bromoheptane 

Downstream Products

• 124901-75-3 (2R,3R)-1-tosyloxy-2,3-decanediol 
• 87005-03-6 (3R,9R,10R)-panaxytriol 
• 126146-63-2 (9R,10S)-3-oxo-panaxydol 
• 102369-06-2 (2S,3R)-3-heptyloxirane-2-carbaldehyde 

Relevant articles and documents

New polyacetylenes, DGAT inhibitors from the roots of Panax ginseng

The petroleum ether extract of Panax ginseng showed a significant inhibition of the diacylglycerol acyltransferase (DGAT) enzyme from rat liver microsomes. Bioactivity-guided fractionation led to the isolation of two new polyacetylenic compounds, (9R,10S)-epoxyheptadecan-4,6-diyn-3-one (1) and 1-methoxy-(9R,10S)-epoxyheptadecan-4,6-diyn-3-one (2). Their chemical structures were elucidated on the basis of spectroscopic evidence and asymmetric synthesis. IC50 values of 9 μg/mL (1) and 32 μg/ml (2) were obtained.

Total synthesis of panaxydol and its stereoisomers as potential anticancer agents

An efficient total synthesis of natural panaxydol 1a and its seven stereoisomers 1b-h was accomplished; four diastereomers of the natural form were prepared for the first time. Our strategy involves the Cadiot-Chodkiewicz cross-coupling reaction of chiral terminal alkynes with bromoalkynes, the asymmetric alkynylation of aldehydes, and the enantioselective Sharpless epoxidation of allylic alcohols. Preliminary in vitro cytotoxicity evaluation indicated that some synthetic panaxydols possess anticancer activities, and (3S,9R,10S)-panaxydol 1e showed a particularly promising cytotoxic effect.

Total synthesis and absolute stereochemistry of (9R,10S)-epoxyheptadecan-4, 6-diyn-3-one, a diacylglycerol acyltransferase inhibitor from Panax ginseng

Asymmetric synthesis of four possible stereoisomers of (9,10)- epoxyheptadecan-4,6-diyn-3-one was accomplished, and the absolute configuration of the naturally occurring (9R,10S)-epoxyheptadecan-4,6-diyn-3-one (1) was elucidated.

Studies towards the biomimetic synthesis of ginsenoyne L; efficient synthesis of 2′-epi-ginsenoyne L

The biomimetic synthesis of 2′-epi-gynsenyone L has been accomplished in 7 steps and in good yield through the novel use of bis-acetylenic enones as hetero Diels-Alder dienes for the mild and easy generation of dihydropyrans.

Catalytic Asymmetric Epoxidation and Kinetic Resolution: Modified Procedures Including in Situ Derivatization

The use of 3A or 4A molecular sieves ( zeoiltes ) substantially increases the scope of the titanium(IV)-catalyzed asymmetric epoxidation of primary allylic alcohols.Whereas without molecular sieves epoxidations employing only 5 to 10 mol percent Ti(O-i-Pr)4 generally led to low conversion or low enantioselectivity, in the presence of molecular sieves such reactions generally led to high conversion (>95percent) and high enantioselectivity (90-95percent ee).The epoxidations of 20 primary allylic alcohols are described.Especially noteworthy are the epoxidations of cinnamyl alcohol, 2-tetradecyl-2-propen-1-ol, allyl alcohol, and crotyl alcohol-compounds which heretofore had been considered difficult substrates for asymmetric epoxidation.In the case of allylic alcohol, the use of cumene hydroperoxide substantially increases both the reaction rate and the conversion, even in the absence of molecular sieves.In general, enantioselectivities are slightly depressed (by 1-5percent ee) relative to reactions employing 50-100 mol percent Ti(O-i-Pr)4.The epoxidation of low molecular weight allylic alcohols is especially facilitated and, in conjuction with in situ derivatization, provides for the synthesis of many epoxy alcohol synthons which were previously difficult to obtain.The kinetic resolution of four secondary allylic alcohols with 10 mol percent Ti(O-i-Pr)4 is also described.The role of molecular sieves in the reaction and the effects of variation in reaction stoichiometry, oxidant, and tartrate are discussed.