39846-56-5

Basic information

• Product Name: heptane-1,2-diyl diacetate
• Synonyms: heptane-1,2-diyl diacetate;1,2-Heptanediol diacetate;Diacetic acid 1,2-heptanediyl ester
• CAS NO: 39846-56-5
• Molecular Formula: C₁₁H₂₀O₄
• Molecular Weight: 216.2741
• EINECS: 254-651-2
• Mol File: 39846-56-5.mol

Chemical Properties

• Boiling Point: 268.1°Cat760mmHg
• Flash Point: 122.1°C
• Appearance: /
• Density: 0.994g/cm³
• Vapor Pressure: 0.00782mmHg at 25°C
• Refractive Index: 1.433
• CAS DataBase Reference: heptane-1,2-diyl diacetate(CAS DataBase Reference)
• NIST Chemistry Reference: heptane-1,2-diyl diacetate(39846-56-5)
• EPA Substance Registry System: heptane-1,2-diyl diacetate(39846-56-5)

Safety Data

• Hazardous Substances Data: 39846-56-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H20O4/c1-4-5-6-7-11(15-10(3)13)8-14-9(2)12/h11H,4-8H2,1-3H3

Upstream product

• 108-24-7 acetic anhydride 
• 153904-69-9 Acetic acid (R)-1-hydroxymethyl-hexyl ester 
• 592-76-7 1-Heptene 
• 3710-31-4 1,2-heptanediol 
• 124190-20-1 halicholactone 
• 84711-24-0 (R)-(+)-2-acetoxyheptanal 
• 64-19-7 acetic acid 
• 137226-14-3 1-Benzyloxy-heptan-2-ol 

Downstream Products

• 78843-64-8 (2R)-heptane-1,2-diol 
• 61229-00-3 (2S)-heptane-1,2-diol 

Relevant articles and documents

HALICHOLACTONE AND NEOHALICHOLACTONE, TWO NOVEL FATTY ACID METABOLITES FROM THE MARINE SPONGE HALICHONDRIA OKADAI KADOTA

Halicholactone (1) and neohalicholactone (2), unusual fatty acid metabolites having a cyclopropane ring and a nine-membered lactone were isolated from the marine sponge Halichondria okadai Kadota.The planar structures of the new metabolites were elucidated on the basis of spectral and chemical means.

Asymmetric synthesis of (S)-Massoialactone

An asymmetric synthesis of (S)-(+)-Massoialactone is described using the Sharpless asymmetric dihydroxylation and the regiospecific nucleophilic opening of a cyclic sulfate as key steps.

Aerobic oxidation of alkenes to esters of vicinal diols with a syn-configuration catalyzed by I2 and the H5PV 2Mo10O40 polyoxometalate

A new method for the synthesis of vicinal diols from alkenes has been developed. Reaction of molecular iodine in the presence of a polyoxometalate as oxidation catalyst under aerobic conditions in acetic acid solvent leads to the oxidative iodoacetoxylation of an alkene, i.e. formation of a 1,2-iodoacetate. Further in situ substitution of the iodide by water yields the 1,2-diol monoacetate with a predominantly (ca. 4.5:1) cis-configuration. Further esterification under the reaction's acidic conditions leads also to the cis-diacetate. The method may be valuable for the synthesis of cis-vicinal diols without use of toxic osmium catalysts. Georg Thieme Verlag Stuttgart.

Kinetic resolution of 2-acylated-1,2-diols by lipase-catalyzed enantiomer selective acylation

Enantiomer selectivity of lipase catalyzed acylation of 2-acylated 1,2-diols was studied. First, acylation of 2-acetoxyheptan-1-ol rac-3b with vinyl acetate was investigated by varying the enzymes and the solvent, showing the highest enantiomer selectivity by using lipase from Pseudomonas fluorescens (PfL) in hexane-vinyl acetate (VA). We have found varying or even reversed enantiomer selectivity for different secondary acyl moieties in 2-acyloxyheptan-1-ols rac-3bA-F. Next, all six possible types of enantiomer selective biotransformations (hydrolysis of diacetate and the two kinds of monoacetetes; acylation of diol and the two kinds of monoacetates) were compared on two model diols rac-4b,d. Among the transformations investigated, acetylation of secondary monoacetates rac-3b,d showed the highest enantiomer selectivity. Finally, PfL catalyzed acetylations of several 2-acetylated 1,2-diols rac-3a-g were investigated under our optimum conditions.

Lipase-Catalyzed Enantiomer Selective Hydrolysis of 1,2-Diol Diacetates

Enantiomer selective hydrolysis of racemic 1,2-diol diacetates (rac-2a-h) was investigated by using the inexpensive commercial porcine pancreatic lipase.The hydrolysis proceeds with variable regioselectivity but with moderate to good enantioselectivity yielding a mixture of isomeric monoacetates (3a-h and 4a-h) and unchanged diacetate enantiomers (2a-h).Evidence was found that both monoacetates (3a-h and 4a-h) are formed with the same sense of enantiomer selectivity.