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

Description

2,6-Dimethylhepta-1,5-diene is an organic compound characterized by its distinct chemical structure, featuring a seven-carbon chain with two methyl groups at the 2nd and 6th positions and two carbon-carbon double bonds at the 1st and 5th positions. It is known for its volatile nature and is commonly found in certain types of tea and other natural sources.

Uses

Used in the Tea Industry:
2,6-Dimethylhepta-1,5-diene is used as a flavor compound in the tea industry for its aromatic properties. It contributes to the unique scent and taste of Pingwu Fuzhuan brick tea (Camellia sinensis var. sinensis) and honeybush tea (Cyclopia spp.), enhancing the overall sensory experience for consumers.
Used in the Fragrance Industry:
Due to its volatile nature and pleasant aroma, 2,6-dimethylhepta-1,5-diene can also be used as a component in the fragrance industry. It can be incorporated into various perfumes, colognes, and other scented products to provide a distinct and appealing fragrance profile.
Used in the Flavor and Food Industry:
2,6-dimethylhepta-1,5-diene's unique flavor characteristics make it a potential candidate for use in the flavor and food industry. It could be utilized to add depth and complexity to a variety of food products, particularly those that benefit from a rich, aromatic profile.
Used in the Chemical Industry:
2,6-Dimethylhepta-1,5-diene may also find applications in the chemical industry as a starting material or intermediate for the synthesis of more complex organic compounds. Its reactive double bonds and unique structural features make it a valuable building block for various chemical reactions and product development.

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

Upstream product

• 5392-40-5 (E/Z)-3,7-dimethyl-2,6-octadienal 
• 54166-30-2 2,6-dibromo-2,6-dimethyl-heptane 
• 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 
• 115-95-7 linalool acetate 
• 110-93-0 6-Methyl-hept-5-en-2-on 
• 13170-43-9 (trimethylsilyl)methylmagnesium chloride 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 123936-92-5 4-Methylpent-4-enyl(triphenyl)phosphonium iodide 

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 
• 124646-87-3 ((E)-1-Methoxy-3,7-dimethyl-octa-3,6-dienyl)-benzene 
• 10458-14-7 Menthone 
• 503-47-9 1,3,3-trimethyl-1-cyclohexene 
• 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 

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.