17123-60-3

Basic information

• Product Name: 2-METHYL-1,5-HEXADIEN-3-OL
• Synonyms: 2-METHYL-1,5-HEXADIEN-3-OL;2-Methyl-1,5-hexadiene-3-ol
• CAS NO: 17123-60-3
• Molecular Formula: C₇H₁₂O
• Molecular Weight: 112.17
• Mol File: 17123-60-3.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 159.4°Cat760mmHg
• Flash Point: 60.8°C
• Appearance: /
• Density: 0.85g/cm³
• Vapor Pressure: 0.885mmHg at 25°C
• Refractive Index: 1.447
• CAS DataBase Reference: 2-METHYL-1,5-HEXADIEN-3-OL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHYL-1,5-HEXADIEN-3-OL(17123-60-3)
• EPA Substance Registry System: 2-METHYL-1,5-HEXADIEN-3-OL(17123-60-3)

Safety Data

• Hazardous Substances Data: 17123-60-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C7H12O/c1-4-5-7(8)6(2)3/h4,7-8H,1-2,5H2,3H3

Upstream product

• 78-85-3 2-methylpropenal 
• 1730-25-2 allylmagnesium bromide 
• 106-95-6 allyl bromide 
• 42322-69-0 2-(2-methyl-2-propenyl)-3-chloromethyloxirane 
• 107-37-9 allyltrichlorosilane 
• 14289-96-4 2-methyl-3-prop-2-enoxyprop-1-ene 
• 64549-05-9 allyldibutyltin chloride 
• 556-56-9 allyl iodid 
• 2622-05-1 allylmagnesium bromide 

Downstream Products

• 1232672-41-1 C₂₉H₄₀O₅ 
• 512205-57-1 (2E)-2-methylhexa-2,5-dienyl benzoate 
• 41233-72-1 trans-2-Methyl-1,3,5-Hexatrien 
• 19264-50-7 2-methyl-1,3,5-hexatriene 
• 663599-90-4 (S)-3-{(R)-3-Benzyloxy-2-[(S)-1-((R)-1-benzyloxy-but-3-enyl)-1,4-dimethyl-pent-3-enyloxy]-propionyl}-4-isopropyl-oxazolidin-2-one 
• 663599-96-0 (2R,7R,8S)-7-Benzyloxy-2-benzyloxymethyl-8-[1,3]dithian-2-ylmethyl-8-methyl-oxocan-3-ol 

Relevant articles and documents

-

-

Cobalt-Catalyzed Allylic C(sp3)-H Carboxylation with CO2

Catalytic carboxylation of the allylic C(sp3)-H bond of terminal alkenes with CO2 was developed with the aid of a Co/Xantphos complex. A wide range of allylarenes and 1,4-dienes were successfully transformed into the linear styrylacetic acid and hexa-3,5-dienoic acid derivatives in moderate to high yields, with excellent regioselectivity. The carboxylation showed remarkable functional group tolerability, so that selective addition to CO2 occurred in the presence of other carbonyl groups such as amide, ester, and ketone. Since styrylacetic acid derivatives can be readily converted into optically active γ-butyrolactones through Sharpless asymmetric dihydroxylation, this allylic C(sp3)-H carboxylation showcases a facile synthesis of γ-butyrolactones from simple allylarenes via short steps.

Diastereoselective, three-component cascade synthesis of tetrahydrofurans and tetrahydropyrans employing the tandem Mukaiyama aldol-lactonization process

(Chemical Equation Presented) A full account of studies leading to the development of a cascade sequence that generates as many as two C-C bonds, one C-O bond, and three new stereocenters providing substituted tetrahydrofurans (THFs) from simple γ-ketoaldehydes and thiopyridyl ketene acetals is described. The process involves a tandem Mukaiyama aldol-lactonization (TMAL) and accumulated evidence suggests the intermediacy of a silylated β-lactone that is intercepted by the pendant ketone. Formation of a cyclic oxocarbenium is followed by reduction with silicon-based nucleophiles leading to a highly diastereoselective synthesis of tetrahydrofurans. This cascade process has now been extended to the synthesis of tetrahydropyrans from simple δ-ketoaldehydes. The stereochemical outcome of the cascade processes described was determined by NOE correlations, coupling constant analysis, and X-ray crystallography of the derived oxygen heterocycles and is in accord with established and recently proposed models for nucleophilic additions to cyclic 5- and 6-membered oxocarbenium ions. The utility of this process was demonstrated by the synthesis of the tetrahydrofuran fragment of colopsinol B.