30801-96-8

Basic information

• Product Name: (E)-3-Methyl-2-hexen-1-ol
• Synonyms: (E)-3-Methyl-2-hexen-1-ol
• CAS NO: 30801-96-8
• Molecular Formula: C₇H₁₄O
• Molecular Weight: 114.1855
• Mol File: 30801-96-8.mol

Chemical Properties

• Boiling Point: 178°Cat760mmHg
• Flash Point: 71.2°C
• Appearance: /
• Density: 0.845g/cm³
• Vapor Pressure: 0.305mmHg at 25°C
• Refractive Index: 1.444
• PKA: 14.47±0.10(Predicted)
• CAS DataBase Reference: (E)-3-Methyl-2-hexen-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-3-Methyl-2-hexen-1-ol(30801-96-8)
• EPA Substance Registry System: (E)-3-Methyl-2-hexen-1-ol(30801-96-8)

Safety Data

• Hazardous Substances Data: 30801-96-8(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 14, p. 1277, 1973 DOI: 10.1016/S0040-4039(01)95816-2

InChI:InChI=1/C7H14O/c1-3-4-7(2)5-6-8/h5,8H,3-4,6H2,1-2H3/b7-5+

Upstream product

• 27960-21-0 trans-3-methyl-2-hexenoic acid 
• 50-00-0 formaldehyd 
• 627-19-0 1-Pentyne 
• 106-24-1 Geraniol 
• 105-87-3 3,7-dimethyl-2E,6-octadien-1-yl acetate 
• 37715-31-4 (E)-5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-enyl acetate 
• 404570-49-6 (E)-3-methylhex-2-en-1-yl acetate 
• 22210-21-5 (rac)-3-methyl-2-hexenoic acid ethyl ester 
• 74-96-4 ethyl bromide 
• 7437-61-8 2-methyl-3,4-epoxy-1-butene 
• 22146-94-7 (E)-3-methyl-hex-2-enoic acid methyl ester 
• 35334-60-2 (E)-6-acetoxy-4-methyl-4-hexenal 
• 108-22-5 Isopropenyl acetate 
• 58316-39-5 (E)-4-ethoxy-4-oxobut-2-en-2-yl benzoate 

Downstream Products

• 88192-98-7 myxopyronin A 
• 38260-14-9 ((E)-3-methyl-hex-2-enyl)-triphenyl-phosphonium; bromide 

Relevant articles and documents

Enantiocontrol over Acyclic Quaternary Stereocenters by Acylative Organocatalyzed Kinetic Resolution

In the present paper, we described the efficient enantioselective kinetic resolution (KR) of racemic diastereocontrolled secondary alcohols bearing a quaternary stereocenter using a commercially available chiral isothiourea organocatalyst. This methodology is a general KR leading to the enantiocontrol of acyclic quaternary stereocenter with high levels of stereoselectivity (s up to 185) on a large scope. The hydroxyl function can easily serve as a traceless group by oxidation or reduction process.

1H-pyrrole-2,4-dicarbonyl-derivatives and their use as flavoring agents

The present invention primarily relates to 1H-pyrrole-2,4-dicarbonyl-derivatives of Formula (I) wherein R1, R2, R3, Z. Z' and J are as defined in the description, to mixtures thereof and to the use thereof as flavoring agents. The compounds in accordance with the present invention are suitable for producing, imparting, or intensifying an umami flavor. The invention further relates to flavoring mixtures, compositions for oral consumption as well as ready-to-eat, ready-to-use and semifinished products, comprising an effective amount of the compound of Formula (I) or of a mixture of compounds of Formula (I) and to specific methods for producing, imparting, modifying and/or intensifying specific flavor impressions.

Imidazo[1,2-a]pyridine-ylmethyl-derivatives and their use as flavoring agents

The present invention primarily relates to imidazo[1,2-a]pyridine-ylmethyl-derivatives of Formula (I) wherein R1, R2, X, W e J are as defined in the description, to mixtures thereof and to the use thereof as flavoring agents. The compounds in accordance with the present invention are suitable for producing, imparting, or intensifying an umami flavor. The invention further relates to flavoring mixtures, compositions for oral consumption as well as ready-to-eat, ready-to-use and semifinished products, comprising an effective amount of the compound of Formula (I) and to specific methods for producing, imparting, modifying and/or intensifying specific flavor impressions.

SELECTIVE HYDROGENATION OF ALDEHYDE WITH RU/BIDENTATE LIGANDS COMPLEXES

The present invention relates to processes for the reduction by hydrogenation, using molecular H2, of a C5-C20 substrate containing one or two aldehydes functional groups into the corresponding alcohol or diol, characterized in that said process is carried out in the presence of —at least one catalyst or pre-catalyst in the form of a ruthenium complex having a coordination sphere of the N2P2O2, wherein the coordinating atoms N2 are provided by a first bidentate ligand, the coordinating atoms P2 are provided by a second bidentate ligand and the coordinating atoms O2 are provided by two non-linear carboxylate ligands; and —optionally of an acidic additive.

A route to the tetrahydrofuran segment of amphidinolides X and Y, and its quaternary-carbon epimer

A short approach to the tetrahydrofuran fragment of amphidinolides X and Y has been developed through the combination of iterative Sharpless asymmetric epoxidations, Pd-catalyzed regioselective hydrogenolysis of a 4,5-epoxy-2-alkenoate and the disfavored 5-endo-tet ring closure of a β-hydroxy epoxide promoted by a double bond adjacent to the epoxide function. Georg Thieme Verlag Stuttgart.

Use of unsaturated esters as perfuming ingredients

The compound of formula 1in which the wavy line represents a bond having a configuration of the type (Z) or (E), or a mixture of the two configurations; R1 represents a hydrogen atom, a C1 to C4 linear or branched alkyl radical, a methoxy or ethoxycarbonyl radical, or an aryl radical, and R2 represents a methyl or ethyl group, possess interesting organoleptic properties and can be advantageously used for the preparation of perfuming compositions to which it gives, in particular, a very natural connotation of the pear type.

SYNTHESIS AND SOME REACTIONS OF ISOPROPENYLOXIRANE

A convenient method for the synthesis of isopropenyloxirane by dehydrohalogenation of halohydrins obtained by isomerization of 1-halo-3-methyl-2,3-epoxybutanes was developed.The reactions of isopropenyloxirane with alcohols, water, secondary amines, hydrogen halides, dichlorocarbene, acetic acid anhydrides, and Grignard reagents were studied.

Selective γ- Alkylation of Copper Enolates Derived from α,β-Unsaturated Acids: Factors Affecting Scope and Regio- and Stereoselectivity

Copper dienolates derived from α,β-unsaturated acids undergo alkylation at the γ-carbon with high regioselectivity.A systematic investigation has been made of several factors that affect the γ-alkylation process of the dienolate derived tiglic acid (1): alterations in the nature of the counterion, in the stoichiometry of cuprous ion, and in the nature of the electrophile.Compared to allylic electrophiles, nonallylic electrophiles react with copper dienolates sluggishly and with little selectivity for the γ-carbon; vinylic epoxides, however, are particularly goodalkylating agents.They undergo allylic transposition and react at the γ-carbon of the dienolate with high selectivity (70-90 percent), generating an allylic unit that forms part of a 1,5-diene skeleton oxygenated at both ends.Tiglic (1) and crotonic (3) acids react with vinylic epoxides to form a 1,5-diene with entirely E stereochemistry at the 2,3 double bond, while senecioic acid (2) forms a 1,5-diene with mostly Z stereochemistry at the 2,3 double bond.Geometry at the 6,7 double bond depends both on the α,β-unsaturated acid used and on the structure of the epoxide.With allylic electrophiles under direct (SN2) attack, stereochemical analysis showed that some isomerization occurs around the 6,7 double bond (derived from the electrophile).Addition of cuprous ion to the lithium dianion of 2-hexenoic acid (17) was found to enhance the regioselectivity of γ alkylation, but a subsequent Michael addition reaction limits the potential of γ alkylation in this system.