23963-70-4

Basic information

• Product Name: 1-Cyclohexene-1-carboxaldehyde, 4-(1-methylethyl)-, (S)-
• CAS NO: 23963-70-4
• Molecular Formula: C10H16O
• Molecular Weight: 152.236
• Mol File: 23963-70-4.mol

Chemical Properties

• CAS DataBase Reference: 1-Cyclohexene-1-carboxaldehyde, 4-(1-methylethyl)-, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Cyclohexene-1-carboxaldehyde, 4-(1-methylethyl)-, (S)-(23963-70-4)
• EPA Substance Registry System: 1-Cyclohexene-1-carboxaldehyde, 4-(1-methylethyl)-, (S)-(23963-70-4)

Safety Data

• Hazardous Substances Data: 23963-70-4(Hazardous Substances Data)

Upstream product

• 56246-58-3 β-pinene oxide 
• 128301-02-0 (1S,2S,5S)-(+)-6,6-dimethylbicyclo[3.1.1]heptane-2-carboxaldehyde 
• 5502-72-7 dihydroperilla alcohol 
• 18031-40-8 (S)-(-)-perillaldehyde 
• 6153-17-9 (-)-β-phellandrene 

Downstream Products

• 13674-19-6 (E)-(4-isopropylcyclohexyl)methanol 
• 13828-37-0 (Z)-(4-isopropylcyclohexyl)methanol 
• 31509-43-0 7-(3.5-dinitro-benzoyloxy)-trans-p-methane 
• 31509-40-7 7-(3.5-dinitro-benzoyloxy)-cis-p-methane 
• 93724-64-2 (4-nitro-benzoyloxy)-((S)-4-isopropyl-cyclohexen-⁽¹⁾-yl)-methane 
• 19876-47-2 (-)-O-(3.5-dinitro-benzoyl)-phellandrol 
• 135355-08-7 (4S)-phellandric acid 

Relevant articles and documents

Stereoselective synthesis of perillaldehyde-based chiral β-amino acid derivatives through conjugate addition of lithium amides

The Michael addition of dibenzylamine to (+)- tert-butyl perillate ( 3) and to (+)- tert-butyl phellandrate (6), derived from ( S)-(-)-perillaldehyde (1 ), resulted in diastereomeric β-amino esters 7A-D in a moderately stereospecific reaction in a ratio of 76:17:6:1. After separation of the diastereoisomers, the major product, cis isomer 7A, was quantitatively isomerized to the minor component, trans-amino ester 7D. All four isomers were transformed to the corresponding β-amino acids 10A-D, which are promising building blocks for the synthesis of β-peptides and 1,3-heterocycles in three steps. The steric effects of the isopropyl group at position 4 and of the α-methyl substituent of (R)-N-benzyl-N-α-methylbenzylamine on the reactivity were also studied, upon application of a chiral amine, excellent stereoselectivity of the conjugate addition was observed. Amino ester 11 was obtained as a single product and transformed to the corresponding amino acids 10A and 10D in good yields on the gram scale.

Radical reduction of epoxides using a titanocene(III)/water system: Synthesis of β-deuterated alcohols and their use as internal standards in food analysis

We describe a comprehensive study into the Cp2TiCl-mediated reductive epoxide ring opening using either water as a hydrogen source or deuterium oxide as a deuterium source. The remarkable chemical profile of this reaction allows access to alcohols with anti-Markovnikov regiochemistry from different epoxides. The use of D2O as a deuterium source leads to an efficient synthesis of β-deuterated alcohols, including a deuterated sample of tyrosol, a bioactive compound contained in the leaves of the olive, which was successfully applied as an internal standard in food analysis.

Absolute configuration of a new mosquito repellent, (+)-eucamalol and the repellent activity of its epimer.

(+)-Eucamalol (1) and (-)-1-epi-eucamalol (2) were synthesized from (S)-(-)-perillaldehyde to determine the absolute configuration of 1, the structure of natural (+)-eucamalol being determined to be (1R,6R)-(+)-3-formyl-6-isopropyl-2-cyclohexen-1-ol. (+)-