66113-31-3

Basic information

• Product Name: (2E)-3,7-dimethyloct-2-ene-1,8-diol
• CAS NO: 66113-31-3
• Molecular Formula: C₁₀H₂₀O₂
• Molecular Weight: 172.2646
• Mol File: 66113-31-3.mol

Chemical Properties

• Boiling Point: 275.6°C at 760 mmHg
• Flash Point: 124.2°C
• Density: 0.944g/cm³
• Vapor Pressure: 0.000634mmHg at 25°C
• Refractive Index: 1.474
• CAS DataBase Reference: (2E)-3,7-dimethyloct-2-ene-1,8-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-3,7-dimethyloct-2-ene-1,8-diol(66113-31-3)
• EPA Substance Registry System: (2E)-3,7-dimethyloct-2-ene-1,8-diol(66113-31-3)

Safety Data

• Hazardous Substances Data: 66113-31-3(Hazardous Substances Data)

Upstream product

• 37905-02-5 (2E,6E)-3,7-dimethyl-8-oxoocta-2,6-dien-1-yl acetate 
• 83718-67-6 (E)-methyl 2,6-dimethyl-8-oxo-6-octenoate 
• 93107-77-8 (E)-Ethyl 7-carbethoxy-3-methyl-2-octenoate 
• 58698-19-4 ethyl (E)-2-methyl-6-oxo-2-hexenoate 
• 58698-18-3 (Z)-2-Methyl-6-oxo-hex-2-enoic acid ethyl ester 
• 5453-88-3 ethyl 1-methyl-2-oxocyclopentane-1-carboxylate 
• 16151-41-0 Ethyl 2-methyl-6-oxoheptanoate 
• 58698-20-7 2-methyl-6-oxo-hexanoic acid ethyl ester 
• 1036762-39-6 2-Methyl-5-(2-methyl-[1,3]dioxolan-2-yl)-pentanoic acid 
• 83718-65-4 methyl 2,6-dimethyl-6-hydroxy-7-octynoate 
• 2570-90-3 6-oxo-2-methyl-heptanoic acid methyl ester 
• 2570-68-5 6-oxo-2-methyl-heptanoic acid 
• 104411-05-4 (E)-3-Methyl-5,5-bis-(toluene-4-sulfonyl)-pent-2-en-1-ol 
• 104411-06-5 tert-Butyl-[(E)-3,7-dimethyl-5,5-bis-(toluene-4-sulfonyl)-octa-2,7-dienyloxy]-dimethyl-silane 

Relevant articles and documents

(S)-3,7-Dimethyl-5-octene-1,7-diol and Related Oxygenated Monoterpenoids from Petals of Rosa damascena Mill

The methanolic extract obtained from rose flowers was subjected to XAD-2 adsorption chromatography. Prefractionation of the methanolic eluate using multilayer coil countercurrent chromatography (MLCCC) yielded five subfractions. From the least polar subfraction V, a major amount of the key odorants of rose oil, that is, isomeric rose oxides 1a/b, was liberated upon heat treatment at pH 2.5. Further Chromatographic workup of fraction V led, for the first time, to the identification of the genuine rose oxide precursor (S)-3,7-dimethyl-5-octene-1,7-diol (2). In addition to diol 2, the following monoterpene diols have been identified: 3,7-dimethyl-7-octene-1,6-diol (3), 2,6-dimethyl-1,7-octadiene-3,6-diol (4), (2E,5E)-3,7-dimethyl-2,5-octadiene-1,7-diol (5), (2E)-3,7-dimethyl-2,7-octadiene-1,6-diol (6), (2Z,5E)-3,7-dimethyl-2,5-octadiene-1,7-diol (7), (2Z)-3,7-dimethyl-2,7-octadiene-1,6-diol (8), (Z)-2,6-dimethyl-2-octene-1,8-diol (9), (E)-2,6-dimethyl-2-octene-1,8-diol (10), (Z)-2,6-dimethyl-2,7-octadiene-1,6-diol (11), (E)-2,6-dimethyl-2,7-octadiene-1,6-diol (12), (2E,6E)-2,6-dimethyl-2,6-octadiene-1,8-diol (13), (2E,6Z)-2,6-dimethyl-2,6-octadiene-1,8-diol (14), 2,6-dimethyloctane-1,8-diol (15), 2,6-dimethyl-7-octene-1,6-diol (16), (E)-3,7-dimethyl-2-octene-1,8-diol (17), (Z)-3,7-dimethyl-2-octene-1,8-diol (18), 3,7-dimethyloctane-1,7-diol (19), 2,6-dimethyl-7-octene-2,6-diol (20), 3,7-dimethyl-6-octene-1,3-diol (21) and (2E)-3,7-dimethyl-2,6-octadiene-1,4-diol (22).

SYNTHESIS OF THE PHEROMONES, (E)-3,7-DIMETHYL-2,7-OCTADIENYL PROPIONATE, (E)-3,7-DIMETHYL-2-OCTENE-1,8-DIOL AND FRONTALIN FROM A COMMON INTERMEDIATE

Ketal ester 9 has been prepared in five steps from methyl levulinate 4 (scheme 1).The propionate 1, diol 2 and (+/-) frontalin 3 were prepared from ester 9 employing the routes shown in scheme 2,3 and 4 respectively.The branched chain alkenes 13 and 20 were prepared conveniently from the primary alcohols 11 and 10 following the procedure of S.Wolff.Triethyl phosphonopropionate 7 has been prepared by methylating triethylphosphonoacetate with methyl iodide in the presence of sodium hydride.

BIS(ARYLSULFONYL)METHANE : A VERSATILE SYNTHON IN PHEROMONE SYNTHESIS

(E)-9-oxo-2-decenoic acid (queen substance) (1); (E)-3,7-dimethyl-2,7-octadienyl propionate (2) and (E)-3,7-dimethyl-2-octene-1,8-diol (3) are easily synthesized via sequential alkylation of bis-(arylsulfonyl)methane 4 with 1,4-allylic substrates 7 and a second electrophile such as 4,4-(ethylenedioxy)pentyl iodide and ethyl 2-methylallyl carbonate.

STEREOSPECIFIC SYNTHESIS OF (E)-3,7-DIMETHYL-2-OCTENE-1,8-DIOL FROM THE TELOMER OF ISOPRENE WITH DIETHYLAMINE

The stereospecific synthesis of (E)-3,7-dimethyl-2-octene-1,8-diol, i.e., the sex pheromone of Danaus Chrisippus, was realized from N,N-diethyl-(E)-3,7-dimethyl-2,7-octadienylamine, obtained by the telomerization of isoprene with diethylamine over Pd catalysts.

A New Synthesis of (E)-3,7-Dimethyloct-2-en-1,8-diol, a Component of the Hairpencil Secretion of African Monarch Butterfly

A facile synthesis of the title compound (1) has been achieved.The key intermediate, viz, the keto acid (6) is prepared via a novel route starting from the alkenol (2).Bromination of (2), and subsequent elaboration through the alkylation of diethyl malonate or propionic acid, affords the alkenoic acid (5) which upon oxidation with Jones' reagent in presence of Hg(OAc)2, provides 6.Following a well-established sequence of reactions, 6 is then transformed into 1.

SYNTHESE A L'AIDE DE SULFONES-XXVI. SYNTHESE D'ALCOOLS ALLYLIQUES ET DE POLYPRENOLS PAR ATTACHEMENT D'UN SYNTHON PRENOL EN POSITION 4 E

The E-hydroxyalkylsulphone PhSO2CH2C(CH3)=CHCH2OH is regioselectively and stereoselectively substituted by Grignard reagents in the presence of copper(II) acetylacetonate, giving E allylic alcohols in high yield.A recurrent synthesis of polyprenols and an efficient preparation of the African Monarch pheromone are described.

A NOVEL SYNTHESIS OF (E)-3,7-DIMETHYL-2-OCTENE-1,8-DIOL SECRETED BY THE AFRICAN MONARCH USING THE RING-OPENING REACTION OF α-METHYL-β-PROPIOLACTONE

The regioselective ring-opening reaction of α-methyl-β-propiolactone with 3,3-ethylenedioxybutylmagnesium bromide in the presence of copper(I) catalyst afforded 2-methyl-6-oxoheptanoic acid, which was easily converted into (E)-3,7-dimethyl-2-octene-1,8-diol in good yield.