6709-39-3

Basic information

• Product Name: 2,6-dimethylhepta-1,5-diene
• Synonyms: 2,6-dimethylhepta-1,5-diene;1,5-Heptadiene, 2,6-dimethyl-;Einecs 229-757-7
• CAS NO: 6709-39-3
• Molecular Formula: C₉H₁₆
• Molecular Weight: 124.22334
• EINECS: 229-757-7
• Mol File: 6709-39-3.mol
• Article Data: 17

Chemical Properties

• Melting Point: -70°C
• Boiling Point: 151.06°C (estimate)
• Flash Point: 27.7°C
• Appearance: /
• Density: 0.7648
• Vapor Pressure: 7.38mmHg at 25°C
• Refractive Index: 1.4484 (estimate)
• CAS DataBase Reference: 2,6-dimethylhepta-1,5-diene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-dimethylhepta-1,5-diene(6709-39-3)
• EPA Substance Registry System: 2,6-dimethylhepta-1,5-diene(6709-39-3)

Safety Data

• Hazardous Substances Data: 6709-39-3(Hazardous Substances Data)

Usage

Uses

2,6-Dimethylhepta-1,5-diene is a volatile substance found in Pingwu Fuzhuan brick tea (Camellia sinensis var. sinensis.) and honeybush tea (Cyclopia spp.)

InChI:InChI=1/C9H16/c1-8(2)6-5-7-9(3)4/h7H,1,5-6H2,2-4H3

Upstream product

• 6090-15-9 2,6-dimethylhept-5-en-2-ol 
• 6076-48-8 6-chloro-2,6-dimethyl-hept-2-ene 
• 855900-58-2 6-bromo-2,6-dimethyl-n-hept-2-ene 
• 459-80-3 geranic acid 
• 17663-84-2 acetic acid-(1,1,5-trimethyl-hex-4-enyl ester) 
• 4698-08-2 (E)-geranic acid 
• 105-87-3 3,7-dimethyl-2E,6-octadien-1-yl acetate 
• 110-93-0 6-Methyl-hept-5-en-2-on 
• 13170-43-9 (trimethylsilyl)methylmagnesium chloride 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 77887-46-8 2,2,6,6-tetramethyl-3,4,5,6-tetrahydro-(2H)-pyran 
• 563-47-3 3-Chloro-2-methylpropene 
• 763-89-3 4-methylpent-3-en-1-ol 
• 6257-51-8 2,6-dimethyl-2,6-heptanediol 

Downstream Products

• 503-46-8 1,5,5-trimethylcyclohexene 
• 123-76-2 levulinic acid 
• 50-00-0 formaldehyd 
• 67-64-1 acetone 
• 64-18-6 formic acid 
• 626-96-0 4-oxopentanal 
• 123-35-3 7-methyl-3-methene-1,6-octadiene 
• 13877-91-3 3,7-Dimethyl-octa-1,3,6-trien 
• 29765-76-2 2,6-dimethyl-1,6-heptadien-3-ol 
• 132998-81-3 (E)-1-(2,4-dihydroxy-3-((E)-6-hydroxy-3,7-dimethylocta-2,7-dienyl)pheny|)-3-(4-hydroxyphenyl)prop-2-en-1-one 
• 5949-05-3 (S)-Citronellal 
• 2385-77-5 (R)-Citronellal 
• 503-47-9 1,3,3-trimethyl-1-cyclohexene 
• 10458-14-7 Menthone 

Relevant articles and documents

Unified Asymmetric Total Syntheses of (?)-Alotaketals A–D and (?)-Phorbaketal A

The novel tricyclic spiroketal alotane-type sesterterpenoids showed strikingly different biological activities and potency with subtle structural alterations. Asymmetric total syntheses of the tricyclic sesterterpenoids (?)-alotaketals A–D and (?)-phorbaketal A were accomplished [29–31 steps from (?)-malic acid] in a collective way for the first time. The key features of the strategy included 1) a new cascade cyclization of vinyl epoxy δ-keto-alcohols to forge the common tricyclic spiroketal intermediate, 2) a late-stage allylic C?H oxidation, and 3) olefin cross-metathesis to install the different side chains.

Method for methyl heptanone to synthetize chiral citronellal

The invention provides a method for methyl heptanone to synthetize chiral citronellal. The method includes the following steps: (1) performing methylenenation reaction on methyl heptanone and an organic tiron so that a 2,6-dimethyl-1,5-heptadiene intermediate with high yield; and (2) performing asymmetric hydroformylation on the heptadiene intermediate under the action of a homogeneous chiral rhodium catalyst so that a chiral citronellal product can be obtained. The main advantages of the method are as follows: the method is novel in synthetic method, a synthetic route is brief, and the chiralcitronellal product can be obtained by only two steps of reaction; the tiron can be used to perform the methylenenation reaction of the methyl heptanone, so that the 2,6-dimethyl-1,5-heptadiene can be obtained with high yield, and therefore, the method is higher than other existing known methods; and the method creatively utilizes the homogeneous chiral rhodium catalyst to realize the asymmetrichydroformylation of the 2,6-dimethyl-1,5-heptadiene, so that the method is high in reaction yield and excellent in stereoselectivity.

Tandem Catalysis: Transforming Alcohols to Alkenes by Oxidative Dehydroxymethylation

We report a Rh-catalyst for accessing olefins from primary alcohols by a C-C bond cleavage that results in dehomologation. This functional group interconversion proceeds by an oxidation-dehydroformylation enabled by N,N-dimethylacrylamide as a sacrificial acceptor of hydrogen gas. Alcohols with diverse functionality and structure undergo oxidative dehydroxymethylation to access the corresponding olefins. Our catalyst protocol enables a two-step semisynthesis of (+)-yohimbenone and dehomologation of feedstock olefins.