23727-16-4

Basic information

• Product Name: myrtenal,(+)-(1S)-6,6-dimethyl-bicyclo[3.1.1]hept-2-ene-2-carboxaldehyde
• Synonyms: myrtenal,(+)-(1S)-6,6-dimethyl-bicyclo[3.1.1]hept-2-ene-2-carboxaldehyde;[1S,5R,(+)]-6,6-Dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
• CAS NO: 23727-16-4
• Molecular Formula: C₁₀H₁₄O
• Molecular Weight: 150.2176
• Mol File: 23727-16-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 215.7°Cat760mmHg
• Flash Point: 78.9°C
• Appearance: /
• Density: 1.061g/cm³
• CAS DataBase Reference: myrtenal,(+)-(1S)-6,6-dimethyl-bicyclo[3.1.1]hept-2-ene-2-carboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: myrtenal,(+)-(1S)-6,6-dimethyl-bicyclo[3.1.1]hept-2-ene-2-carboxaldehyde(23727-16-4)
• EPA Substance Registry System: myrtenal,(+)-(1S)-6,6-dimethyl-bicyclo[3.1.1]hept-2-ene-2-carboxaldehyde(23727-16-4)

Safety Data

• Hazardous Substances Data: 23727-16-4(Hazardous Substances Data)

Upstream product

• 515-00-4 (+/-)-myrtenol 
• 80-56-8 rac-α-pinene 
• 1010824-89-1 (1S,5R)-2-(chloromethyl)-6,6-dimethyl-bicyclo[3.3.1]hept-2-ene 
• 65861-96-3 (+)-3-chloro-2⁽¹⁰⁾-pinene 
• 7446-08-4 selenium(IV) oxide 
• 64-17-5 ethanol 
• 7785-70-8 (+)-α-pinene 
• 80-56-8 Pinene 

Downstream Products

• 473-01-8 cis-myrtanol 
• 2111-71-9 myrtenal oxime 
• 127-91-3 (1R,5R)-(+)-β-pinene 
• 2111-75-3 perillaldehyde 
• 2111-71-9 (+/-)-myrtenal oxime 
• 515-00-4 (+/-)-myrtenol 

Relevant articles and documents

N,N,N′,N′-Tetramethylenediamine dioxide (TMEDAO2) facilitates atom economical/open atmosphere Ley-Griffith (TPAP) tandem oxidation-Wittig reactions

N,N,N′,N′-Tetramethylethylenediamine dioxide (TMEDAO2) was explored as a more atom economical co-oxidant for the Ley-Griffith oxidation of alcohols to aldehydes. TMEDAO2 was found to selectivity oxidise benzylic and allylic alcohols in comparable yields to that of the standard Ley-Griffith co-oxidant (NMO). Importantly TMEDAO2 facilitated tandem Ley-Griffith-Wittig reactions with stabilised ylides, in good to excellent yields, without the requirement of anhydrous conditions.

Hydroboration. 90. Synthesis of 2-isobutyl- and 2-Isopropylapopinenes. Rates and Stoichiometry of the Hydroboration of 2-Organylapopinenes with Borane-Methyl Sulfide and Borane-Tetrahydrofuran

Two higher analogues of α-pinene, 2-isobutyl- and 2-isopropylapopinenes, promising chiral auxiliaries for asymmetric hydroboration, were readily synthesized from α-pinene in good chemical yield.A quantitative study was made of the rates and stoichiometry of the hydroboration of a number of representative 2-organylapopinenes (2-R-apopinenes) with representative boranes, such as BH3*SMe2 (BMS) and BH3*THF, in order to develop a convenient procedure for the synthesis of mono- and bis(2-organylapoisopinocampheyl)boranes , under investigation as possible improved asymmetric hydroborating reagents.It was evident that the sterically bulkier 2-R-apopinenes such as 2-phenyl- and 2-isopropylapopinenes reacted with boranes at room temperature to form essentially RapBH2 in >/=95percent yield, while a yield of >/=90percent was realized in the case of 2-isobutylapopinene.However, α-pinene, and 2-ethyl- and 2-n-propylapopinenes smoothly reacted with boranes to form a mixture of RapBH2 and Rap2BH.Under the reaction conditions employed, 2-ethyl-, 2-n-propyl-, 2-isobutyl-, 2-phenyl-, and 2-isopropylapopinenes failed to produce clean Rap2BH.The rate of hydroboration decreased significantly with increase in bulk of the organyl group at the 2-position of the apopinene.