58649-21-1

Basic information

• Product Name: Cyclohexane, (3-chloro-1-propenyl)-, (E)-
• CAS NO: 58649-21-1
• Molecular Formula: C9H15Cl
• Molecular Weight: 158.671
• Mol File: 58649-21-1.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: Cyclohexane, (3-chloro-1-propenyl)-, (E)-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexane, (3-chloro-1-propenyl)-, (E)-(58649-21-1)
• EPA Substance Registry System: Cyclohexane, (3-chloro-1-propenyl)-, (E)-(58649-21-1)

Safety Data

• Hazardous Substances Data: 58649-21-1(Hazardous Substances Data)

Upstream product

• 4352-44-7 1-cyclohexylprop-2-en-1-ol 
• 42134-55-4 (Z)-3-cyclohexyl-2-propene-1-ol 
• 2043-61-0 cyclohexanecarbaldehyde 
• 17343-88-3 (E)-3-cyclohexyl-acrylic acid ethyl ester 
• 42134-55-4 (E)-3-cyclohexyl-2-propen-1-ol 
• 1826-67-1 vinyl magnesium bromide 

Downstream Products

• 125847-56-5 (R)-(but-3-en-2-yl)cyclohexane 
• 1172595-23-1 (E)-(3-cyclohexylallyl)(phenyl)sulfane 
• 1334681-05-8 C₉H₁₅F 
• 1334680-88-4 (S)-(1-fluoroallyl)cyclohexane 
• 1314581-23-1 (E)-1-(3-cyclohexylallyl)-2,3,4,5,6-pentafluorobenzene 
• 1427549-15-2 (S)-2-(4-cyclohexylhexa-1,5-dien-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1237786-79-6 (S)-hexa-1,5-dien-3-ylcyclohexane 
• 1446029-60-2 (E)-(4,4,4-trifluorobut-1-enyl)cyclohexane 
• 1262617-01-5 3-(cyclohexylmethylene)-2,3-dihydro-4H-1-benzopyran-4-one 
• 691-37-2 4-Methyl-1-pentene 
• 135987-59-6 1-cyclohexylheptene 

Relevant articles and documents

Gold-Catalyzed Asymmetric Thioallylation of Propiolates via Charge-Induced Thio-Claisen Rearrangement

A gold(I)-catalyzed enantioselective thioallylation of propiolates with allyl sulfides is described. The key mechanistic element is a sulfonium-induced Claisen rearrangement which helps minimize the allyl dissociation and render higher enantioselectivity. This protocol features remarkable scope of the allyl moiety, allowing enantiocontrolled synthesis of all-carbon quaternary centers, and exhibits exceptional functional group compatibility with many Lewis bases and π-bonds. This intermolecular variant of Claisen rearrangement forges both C-S and C-C bonds concomitantly, providing efficient access to interesting optically active organosulfur compounds which can be transformed further through the vinyl sulfide as a functional handle. The rate of the reaction was zeroth order with respect to allyl sulfides, which suggested a reversible inhibition, providing a resting state for the catalyst. The Hammett plot displayed a correlation with σp values, suggesting a turnover-limiting sigmatropic rearrangement where decreased electron-density on sulfur accelerated the rearrangement.

Rhodium(ii)-catalyzed intramolecular formal [4 + 3] cycloadditions of dienyltriazoles: Rapid access to fused 2,5-dihydroazepines

Rhodium(ii)-catalyzed intramolecular [4 + 3] cycloadditions of dienyltriazoles have been developed, which enable the efficient synthesis of various fused 2,5-dihydroazepines. Mechanistically, the titled reaction proceeds via an interesting tandem cyclopropanation/aza-cope rearrangement.

Palladium-catalyzed regio- and enantioselective fluorination of acyclic allylic halides

This report describes the Pd(0)-catalyzed fluorination of linear allylic chlorides and bromides, yielding branched allylic fluorides in high selectivity. Many of the significant synthetic limitations previously associated with the preparation of these products are overcome by this catalytic method. We also demonstrate that a chiral bisphosphine-ligated palladium catalyst enables highly enantioselective access to a class of branched allylic fluorides that can be readily diversified to valuable fluorinated products.