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

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

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 
• 5949-05-3 (S)-Citronellal 

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.

Oxidative Dehydroxymethylation of Alcohols to Produce Olefins

Catalyst compositions for the conversion of aldehyde compounds and primary alcohol compounds to olefins are disclosed herein. Reactions include oxidative dehydroxymethylation processes and oxidative dehydroformylation methods, which are beneficially conducted in the presence of a sacrificial acceptor of H2 gas, such as N,N-dimethylacrylamide.

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.

Total Synthesis of Xanthoangelol B and Its Various Fragments: Toward Inhibition of Virulence Factor Production of Staphylococcus aureus

As an alternative strategy to fight antibiotic resistance, two-component systems (TCSs) have emerged as novel targets. Among TCSs, master virulence regulators that control the expression of multiple virulence factors are considered as excellent antivirulence targets. In Staphylococcus aureus, virulence factor expression is tightly regulated by a few master regulators, including the SaeRS TCS. In this study, we used a SaeRS GFP-reporter system to screen natural compound inhibitors of SaeRS, and identified xanthoangelol B 1, a prenylated chalcone from Angelica keiskei as a hit. We have synthesized 1 and its derivative PM-56 and shown that 1 and PM-56 both had excellent inhibitory potency against the SaeRS TCS, as demonstrated by various in vitro and in vivo experiments. As a mode of action, 1 and PM-56 were shown to bind directly to SaeS and inhibit its histidine kinase activity, which suggests a possibility of a broad spectrum inhibitor of histidine kinases.

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.

Selective Synthesis of Silacycles by Borane-Catalyzed Domino Hydrosilylation of Proximal Unsaturated Bonds: Tunable Approach to 1,n-Diols

The tris(pentafluorophenyl)boron-catalyzed domino hydrosilylation of substrates carrying unsaturated functionalities in a proximal arrangement is presented to produce silacycles. Excellent levels of efficiency and selectivity were achieved in the cyclization by the deliberate choice of the hydrosilane reagents. The key to successful cyclic hydrosilylation is the reactivity enhancement of the second intramolecular hydrosilylation by a proximity effect. Not only dienes but also enones, enynes, ynones and enimines readily afford medium-sized silacycles under convenient and mild conditions. The cyclization proceeds with acceptable diastereoselectivity mainly controlled by the conformational bias towards inducing additional stereogenic centers. The silacycles obtained from this reaction were converted to 1,n-diols or 1,n-amino alcohols upon oxidation, thus rendering the present cyclization a powerful tool for accessing synthetically valuable building blocks. (Figure presented.).

Rh-catalyzed C-C bond cleavage by transfer hydroformylation

The dehydroformylation of aldehydes to generate olefins occurs during the biosynthesis of various sterols, including cholesterol in humans. Here, we implement a synthetic version that features the transfer of a formyl group and hydride from an aldehyde substrate to a strained olefin acceptor. A Rhodium(Xantphos)(benzoate) catalyst activates aldehyde carbon-hydrogen (C-H) bonds with high chemoselectivity to trigger carbon-carbon (C-C) bond cleavage and generate olefins at low loadings (0.3 to 2 mole percent) and temperatures (22° to 80°C). This mild protocol can be applied to various natural products and was used to achieve a three-step synthesis of (+)-yohimbenone. A study of the mechanism reveals that the benzoate counterion acts as a proton shuttle to enable transfer hydroformylation.

A general and efficient aldehyde decarbonylation reaction by using a palladium catalyst

A facile decarbonylation reaction of aldehydes has been developed by employing Pd(OAc)2. A wide variety of substrates are decarbonylated, without using any exogenous ligand for palladium as well as CO-scavenger.

On the ethenolysis of natural rubber and squalene

We report here the ethenolysis of squalene and natural rubber utilizing (NHC)(NHCewg)RuCl2(= CRR') and Grubbs-Hoveyda complexes. 0.01 mol% [Ru] per double bond are sufficient for extensive squalene cleavage, resulting in the formation of numerous terminal olefins, which were identified by GC/MS. The depolymerization of natural rubber requires 0.1 mol% [Ru] and leads to the formation of various oligomeric isoprenes, several of which (n = 2-6) were isolated and characterized.

The iridium-catalyzed decarbonylation of aldehydes under mild conditions

The catalytic decarbonylation of aldehydes has been developed using commercially available [IrCl(cod)]2 and PPh3 under mild conditions, and the method could be widely applicable to various substrates with different functionalities. The Royal Society of Chemistry.