70473-30-2

Basic information

• Product Name: (E)-1-(methoxymethoxy)-3,7-dimethylocta-2,6-diene
• Synonyms: (E)-1-(methoxymethoxy)-3,7-dimethylocta-2,6-diene;(2E)-1-(Methoxymethoxy)-3,7-dimethyl-2,6-octadiene
• CAS NO: 70473-30-2
• Molecular Formula: C₁₂H₂₂O₂
• Molecular Weight: 198.30188
• EINECS: 274-617-0
• Mol File: 70473-30-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 254.7°Cat760mmHg
• Flash Point: 88.1°C
• Appearance: /
• Density: 0.876g/cm³
• Vapor Pressure: 0.0272mmHg at 25°C
• Refractive Index: 1.451
• CAS DataBase Reference: (E)-1-(methoxymethoxy)-3,7-dimethylocta-2,6-diene(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-1-(methoxymethoxy)-3,7-dimethylocta-2,6-diene(70473-30-2)
• EPA Substance Registry System: (E)-1-(methoxymethoxy)-3,7-dimethylocta-2,6-diene(70473-30-2)

Safety Data

• Hazardous Substances Data: 70473-30-2(Hazardous Substances Data)

Usage

General Description

(E)-1-(Methoxymethoxy)-3,7-dimethylocta-2,6-diene is a chemical compound that is a derivative of the organic compound octa-2,6-diene. It contains a methoxymethoxy group attached to the first carbon of the double bond, and two methyl groups attached to the third and seventh carbons of the chain. (E)-1-(Methoxymethoxy)-3,7-dimethylocta-2,6-diene is commonly used in the synthesis of various organic compounds and is also studied for its potential biological and pharmaceutical properties. Its structure and properties make it a versatile building block for the production of fine chemicals and pharmaceuticals.

InChI:InChI=1/C12H22O2/c1-11(2)6-5-7-12(3)8-9-14-10-13-4/h6,8H,5,7,9-10H2,1-4H3/b12-8+

Upstream product

• 106-24-1 Geraniol 
• 107-30-2 chloromethyl methyl ether 

Downstream Products

• 1327239-29-1 (E)-(3-((3,7-dimethylocta-2,6-dien-1-yl)oxy)prop-1-yn-1-yl)benzene 
• 72530-79-1 C₂₄H₃₀O₄S₂ 
• 94853-04-0 ((E)-8-Methoxymethoxy-2,6-dimethyl-octa-1,6-diene-3-sulfinyl)-benzene 
• 105-87-3 3,7-dimethyl-2E,6-octadien-1-yl acetate 
• 72530-62-2 C₂₄H₃₀O₂S₂ 
• 94836-05-2 ((E)-1-Isopropylidene-6-methoxymethoxy-4-methyl-hex-4-enylsulfanyl)-benzene 
• 70473-52-8 ((E)-1-isopropenyl-6-methoxymethoxy-4-methyl-hex-4-enylsulfanyl)-benzene 

Relevant articles and documents

The asymmetric total synthesis of cinbotolide: A revision of the original structure

The structure 3,4-dihydroxy-2,4,6,8-tetramethyldec-8-enolide (1) was assigned to a metabolite of Botrytis cinerea, but the spectra of several synthetic analogues had significant differences from that of 1. Examination of the constituents of a B. cinerea mutant that overproduces polyketides gave sufficient quantities of 1, now named cinbotolide, for chemical transformations. These led to a revised γ-butyrolactone structure for the metabolite. This structure has been confirmed by an asymmetric total synthesis, which also established its absolute configuration.

Expanded substrate scope and improved reactivity of ether-forming cross-coupling reactions of organotrifluoroborates and acetals

Mixed acetals and organotrifluoroborates undergo BF3· OEt2-promoted cross-couplings to give dialkyl ethers under simple, mild conditions. A survey of reaction partners identified a hydroxamate leaving group that improves the regioselectivity and product yield in the BF 3·OEt2-promoted coupling reaction of mixed acetals and potassium alkynyl-, alkenyl-, aryl- and heteroaryltrifluoroborates to access substituted dialkyl ethers. This leaving group enables the reaction to proceed rapidly under mild conditions (0 °C, 5-60 min) and permits reactions with electron-deficient potassium aryltrifluoroborates that are less reactive with other acetal substrates. A study of the reaction mechanism and characterization of key intermediates by NMR spectroscopy and X-ray crystallography identified a role for the hydroxamate moiety as a reversible leaving group that serves to stabilize the key oxocarbenium intermediate and the need for a slight excess of organodifluoroborane to serve as a catalyst. A secondary role for the boron nucleophile as an activating ligand was also considered. These studies provide the basis for a general class of reagents that lead to dialkyl ethers by a simple, predictable cross-coupling reaction.

FACILE FUNCTIONALIZATION OF THE ISOPROPYLIDENE TERMINUS OF ACYCLIC MONOTERPENES BY WAY OF BENZENESULFENYL CHLORIDE ADDITION

Highly site- and regioselective terminal functionalizations of acyclic monoterpenes 1 via benzenesulfenyl chloride addition followed by hydrolysis assisted by silica gel, dehydrochlorination under neutral or weakly basic condition, or dehydrochlorination by strongly basic treatment respectively providing β-hydroxy sulfides 3, terminal methallylic sulfides 4, or vinylsulfides 5 are developed.Conversion of 4 to terminal trans-allylic alcohols 10 via sulfoxides 9 by the Evans procedure is also described.