4315-35-9

Basic information

• Product Name: cyclohexa-1,4-diene-1-carboxylic acid
• Synonyms: cyclohexa-1,4-diene-1-carboxylic acid;1,4-Cyclohexadiene-1-carboxylic acid
• CAS NO: 4315-35-9
• Molecular Formula: C₇H₈O₂
• Molecular Weight: 124.14
• Mol File: 4315-35-9.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 254.8°Cat760mmHg
• Flash Point: 114.5°C
• Appearance: /
• Density: 1.201g/cm³
• Vapor Pressure: 0.00522mmHg at 25°C
• Refractive Index: 1.551
• CAS DataBase Reference: cyclohexa-1,4-diene-1-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: cyclohexa-1,4-diene-1-carboxylic acid(4315-35-9)
• EPA Substance Registry System: cyclohexa-1,4-diene-1-carboxylic acid(4315-35-9)

Safety Data

• Hazardous Substances Data: 4315-35-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C7H8O2/c8-7(9)6-4-2-1-3-5-6/h1-2,5H,3-4H2,(H,8,9)

Upstream product

• 106-99-0 buta-1,3-diene 
• 471-25-0 Propiolic acid 
• 142-45-0 Acetylenedicarboxylic acid 
• 123-91-1 1,4-dioxane 
• 69-72-7 salicylic acid 

Downstream Products

• 102872-23-1 1-acetyl-1,4-cyclohexadiene 
• 102153-40-2 (+/-)-4r,5t-dibromo-cyclohex-1-enecarboxylic acid 
• 3412-56-4 (+/-)-(4R*,5R*)-4,5-dihydroxycyclohex-1-enecarboxylic acid 
• 32937-33-0 1-(hydroxymethyl)cyclohexa-1,4-diene 
• 117919-43-4 1-Isocyanato-cyclohexa-1,4-diene 
• 3412-55-3 (+/-)-4r,5t-Diacetoxy-cyclohex-1-en-1-carbonsaeure 
• 3409-31-2 (+/-)-4r,5t-Diacetoxy-cyclohex-1-en-1-carbonsaeure-methylester 
• 72431-21-1 ethyl 1,4-cyclohexadiene-1-carboxylate 

Relevant articles and documents

Tandem Decarboxylative Cyclization/Alkenylation Strategy for Total Syntheses of (+)-Longirabdiol, (-)-Longirabdolactone, and (-)-Effusin

Structurally complex and bioactive ent-kaurane diterpenoids have well-characterized biological functions and have drawn widespread attention from chemists for many decades. However, construction of highly oxidized forms of such diterpenoids still presents considerable challenges to synthetic chemists. Herein, we report the first total syntheses of C19 oxygenated spiro-lactone ent-kauranoids, including longirabdiol, longirabdolactone, and effusin. A concise synthesis of the common intermediate used for all three syntheses was enabled via three free-radical-based reactions: (1) a newly devised tandem decarboxylative cyclization/alkenylation sequence that forges the cis-19, 6-lactone concomitantly with vicinal alkenylation, (2) a Ni-catalyzed decarboxylative Giese reaction that constructs C10 quaternary center stereoselectively, and (3) a vinyl radical cyclization that generates a rigid bicyclo[3.2.1]octane. A series of late-stage oxidations from the common intermediate then provided each of the natural products in turn. Further biological evaluation of these synthetic natural products reveals broad anticancer activities.

Direct formation of tethered Ru(II) catalysts using arene exchange

An 'arene exchange' approach has been successfully applied for the first time to the synthesis of Ru(II)-based 'tethered' reduction catalysts directly from their ligands in one step. This provides an alternative method for the formation of known complexes, and a route to a series of novel complexes. The novel complexes are highly active in both asymmetric transfer and pressure hydrogenation of ketones.

An N.M.R. Investigation of the Mills-Nixon Effect

The 4J coupling constant, previously established as a probe of bond order, was used to examine the bond orders in a series of ortho-bridged compounds: benzocyclopropene, 1,2-dihydrobenzocyclobutene, indan and tetralin.No evidence for sterically induced bond fixation (i.e. the Mills-Nixon effect) was found, but some evidence for electronic distortion in the corresponding benzylic ketones was observed.The experimental results are in accord with SCF/MO calculations.