73670-87-8

Usage

Uses

Used in Perfumery and Flavor Industry:
3,5-Hexadien-1-ol, (3E)is used as a fragrance ingredient for its sweet, floral scent, contributing to the creation of various perfumes and flavorings in the perfumery and flavor industry.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3,5-Hexadien-1-ol, (3E)is utilized as an intermediate in the synthesis of various pharmaceutical compounds, playing a crucial role in the development of new medications.
Used in Organic Synthesis:
3,5-Hexadien-1-ol, (3E)serves as a versatile intermediate in organic synthesis, enabling the production of a wide range of organic compounds for various applications.
Used in Antimicrobial and Insecticidal Applications:
3,5-Hexadien-1-ol, (3E)has been studied for its potential antimicrobial and insecticidal properties, indicating its possible use in applications requiring the control of microorganisms and insects.
However, it is essential to handle 3,5-Hexadien-1-ol, (3E)with care, as it may pose health risks if swallowed, inhaled, or absorbed through the skin, and can cause irritation to the eyes and respiratory system.

Upstream product

• 50-00-0 formaldehyd 
• 591-93-5 1,4-Pentadiene 
• 74054-58-3 ethyl (E)-3,5-hexadienoate 
• 110-44-1 sorbic Acid 
• 2396-84-1 ethyl hexa-2,4-dienoate 
• 689-89-4 (2E,4E)-methylhexa-2,4-dienoate 
• 2396-84-1 (2E,4E)-ethyl hexa-2,4-dienoate 
• 73670-84-5 (E)-3,5-hexadienoyl chloride 
• 1121-66-0 2-Cyclohepten-1-one 
• 220701-86-0 (3E)-3,5-hexadien-1-ol trimethylsilyl ether 
• 102067-72-1 cis-3-chloro-2-vinyltetrahydrofuran 
• 32775-95-4 (E)-3,5-hexadienoic acid 
• 32775-94-3 methyl (E)-3,5-hexadienoate 

Downstream Products

• 86611-27-0 2-(2'-hydroxyethyl)-5,6-dihydro-2H-pyran 
• 86611-31-6 2-((2R,6R)-6-Methyl-5,6-dihydro-2H-pyran-2-yl)-ethanol 
• 86611-30-5 cis-5,6-dihydro-6-methyl-2H-pyrane-2-ethanol 
• 907999-88-6 3E,5-hexadien-1-yl methyl 2E-butenedioate 
• 109183-38-2 3-<(E)-3,5-hexadienyloxy>-2-cyclohexen-1-one 
• 133147-91-8 3,5-hexadienyl-1-oxyacetic acid 
• 87463-34-1 3E,5-hexadien-1-yl prop-2-enoate 
• 126199-93-7 Propynoic acid (E)-hexa-3,5-dienyl ester 
• 87568-03-4 (E)-6-Ethoxymethoxy-hexa-1,3-diene 
• 151535-32-9 (E)-3,5-hexadien-1-yl vinylsulfonate 
• 85083-91-6 trans-1-iodo-3,5-hexadiene 
• 57261-22-0 (E)-hexa-3,5-dienyl bromide 

Relevant academic research and scientific papers

A new entry to the synthesis of (±)-β-lysine

A 3-step synthesis of (±)-β-lysine from ethyl sorbate featuring the aza-Diels-Alder reaction is described.

Rh(i)-Catalyzed enantioselective and scalable [4 + 2] cycloaddition of 1,3-dienes with dialkyl acetylenedicarboxylates

An asymmetric intermolecular [4 + 2] cycloaddition of 1,3-dienes with dialkyl acetylenedicarboxylates, which was catalyzed by a rhodium(i)-chiral phosphoramidite complex, was developed. This protocol provided a highly enantioselective access to prepare carbonyl substituted cyclohexa-1,4-dienes with up to 96% yield and >99% ee. Notably, a cycloaddition on the 10 g scale gave the product in 92% yield and with 99% ee, which showed great potential for the scale-up synthesis of carbonyl substituted cyclohexa-1,4-dienes. In addition, oxidative aromatizations and hydrolysis of the products were also investigated.

Regioselective Epoxidations by Cytochrome P450 3A4 Using a Theobromine Chemical Auxiliary to Predictably Produce N-Protected β- or γ-Amino Epoxides

N-Protected β- and γ-amino epoxides are useful chiral synthons. We report here that the enzyme cytochrome P450 3A4 can catalyze the formation of such compounds in a regio- and stereoselective manner, even in the presence of multiple double bonds or aromatic substituents. To this end, the theobromine chemical auxiliary is used not only to control the selectivity of the enzyme, but also as a masked amine, and to facilitate product recovery. Theobromine predictably directed epoxidation at the double bond of the fourth carbon from the theobromine group. Unlike with most catalysts, the selectivity did not depend on electronic or steric factors but rather on the position of the olefin relative to the theobromine group. (Figure presented.).

Synthesis of spiroindanes by palladium-catalyzed oxidative annulation of non- or weakly activated 1,3-dienes involving C-H functionalization

The synthesis of spiroindanes by the palladium-catalyzed oxidative annulation of non- or weakly activated 1,3-dienes with 2-aryl cyclic 1,3-dicarbonyl compounds is described. Examples of the dearomatizing oxidative annulation of 1,3-dienes with 1-aryl-2-naphthols are also presented. This journal is

The first intramolecular silene Diels-Alder reactions

The synthesis of silaheterocycles through the first examples of an intramolecular silene Diels-Alder reaction is described.

Chemo-, regio-, and stereoselective silver-catalyzed aziridination of dienes: Scope, mechanistic studies, and ring-opening reactions

Silver complexes bearing trispyrazolylborate ligands (Tpx) catalyze the aziridination of 2,4-diene-1-ols in a chemo-, regio-, and stereoselective manner to give vinylaziridines in high yields by means of the metal-mediated transfer of NTs (Ts = p-toluensulfonyl) units from PhI=NTs. The preferential aziridination occurs at the double bond neighboring to the hydroxyl end in ca. 9:1 ratios that assessed a very high degree of regioselectivity. The reaction with the silver-based catalysts proceeds in a stereospecific manner, i.e., the initial configuration of the C=C bond is maintained in the aziridine product (cis or trans). The degree of regioselectivity was explained with the aid of DFT studies, where the directing effect of the OH group of 2,4-diene-1-ols plays a key role. Effective strategies for ring-opening of the new aziridines, deprotection of the Ts group, and subsequent formation of β-amino alcohols have also been developed.

Molecular complexity via C-H activation: A dehydrogenative Diels-Alder reaction

Traditionally, C-H oxidation reactions install oxidized functionality onto a preformed molecular skeleton, resulting in a local molecular change. The use of C-H activation chemistry to construct complex molecular scaffolds is a new area with tremendous potential in synthesis. We report a Pd(II)/bis-sulfoxide- catalyzed dehydrogenative Diels-Alder reaction that converts simple terminal olefins into complex cycloadducts in a single operation.

Tandem Wittig-intramolecular Diels-Alder cycloaddition of ester-tethered 1,3,9-decatrienes under microwave heating

Intramolecular Diels-Alder (IMDA) cycloaddition of the ester-tethered 1,3,9,-decatrienes possessing a carbonyl substituent at C10 has been investigated under controlled microwave heating (MeCN, 180 °C) to afford a variety of 3,4,4a,7,8,8a-hexahydroisochromen-1-ones in 53-89% yields and in 64:36-79:21 ratios for the cis and trans isomers. Under the same microwave heating conditions, a tandem Wittig-IMDA cycloaddition, starting from the α-bromoacetates of 3,5-hexadien-1-ols and glyoxalate/phenylglyoxal hydrates in the presence of PPh3 and 2,6-lutidine, has been demonstrated, furnishing 3,4,4a,7,8,8a-hexahydroisochromen-1-one adducts in 73-91% yields in favor of the cis isomers. During this tandem process, three consecutive carbon-carbon bonds in the end products were efficiently formed with the aid of microwave irradiation within short reaction times.

Rhodium-catalyzed synthesis of eight-membered rings

(Chemical Equation Presented) Experiments to develop a rhodium catalyst for the [4 + 2 + 2] cycloisomerization of dienynes with a second alkyne are described. The generality of the reaction is probed in terms of dienyne structure and alkyne structure. A catalyst system that provides cyclooctatrienes in greater than 70% yield is reported. Several experiments to determine the nature of the catalyst are described.

Radical additions of xanthates to vinyl epoxides and related derivatives: A powerful tool for the modular creation of quaternary centers

(Chemical Equation Presented) An open relationship: The triethylborane/O2-mediated addition of xanthates to vinyl epoxides and derivatives represents an efficient process to form carbon-carbon bonds. Complex structures can be rapidly assembled in a modular, convergent manner, under mild conditions, using readily available reagents (see scheme, Bn = benzyl). The formation of quaternary centers proved especially facile.