145640-36-4

Basic information

• Product Name: 1-((tert-butyldiphenylsilyl)oxy)-3-(2,2-dibromoethenyl)-4-methylcyclohex-3-ene
• Synonyms: 1-((tert-butyldiphenylsilyl)oxy)-3-(2,2-dibromoethenyl)-4-methylcyclohex-3-ene
• CAS NO: 145640-36-4
• Molecular Weight: 534.406
• Mol File: 145640-36-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1-((tert-butyldiphenylsilyl)oxy)-3-(2,2-dibromoethenyl)-4-methylcyclohex-3-ene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-((tert-butyldiphenylsilyl)oxy)-3-(2,2-dibromoethenyl)-4-methylcyclohex-3-ene(145640-36-4)
• EPA Substance Registry System: 1-((tert-butyldiphenylsilyl)oxy)-3-(2,2-dibromoethenyl)-4-methylcyclohex-3-ene(145640-36-4)

Safety Data

• Hazardous Substances Data: 145640-36-4(Hazardous Substances Data)

Upstream product

• 150-76-5 4-methoxy-phenol 
• 130745-59-4 4-<(tert-Butyldiphenylsilyl)oxy>cyclohexanone 
• 69125-55-9 4-hydroxy-1-methoxy-1-cyclohexene 
• 13482-22-9 4-hydroxycyclohexanone 
• 558-13-4 carbon tetrabromide 
• 145640-32-0 5-((tert-butyldiphenylsilyl)oxy)-2-methylcyclohex-1-enecarboxaldehyde 

Downstream Products

• 29569-75-3 (S)-1-Ethynyl-5-hydroxy-2-methyl-1-cyclohexene 
• 1173-13-3 previtamin D₃ 
• 145640-38-6 1-((tert-butyldiphenylsilyl)oxy)-3-ethynyl-4-methylcyclohex-3-ene 

Relevant articles and documents

Thermal -Sigmatropic Shift of Previtamin D3 to Vitamin D3: Synthesis and Study of Pentadeuterio Derivatives

Specifically pentadeuteriated previtamin D3 11 has been synthesized to impart thermal stability to the otherwise labile material.A 12-step synthesis of the trideuteriated A-ring 14b from p-methoxyphenol was developed and employed the addition of (methyl-d3)magnesium iodide to either the keto thiomethylene intermediate 23 or the keto dioxane 27.The enantiomerically pure trideuterio A-ring (-)-14b was then coupled with the deuteriated CD fragment 13b followed by hydrogenation to afford pentadeuteriated previtamin D3 11.A primary deuterium kinetic isotope effect (KIE) study of the -sigmatropic hydrogen migration in the conversion of previtamin D3 to vitamin D3 indicated a more "normal" primary deuterium isotope effect (as compared to a previously reported literature value of ca. 45).At 80 deg C, a kH/kD for the previtamin D3 to vitamin D3 isomerization was determined to be ca. 6.2.At 25 deg C, this -sigmatropic hydrogen migration proceeds with a kH/kD of ca. 11.4.The revisible, first-order -sigmatropic hydrogen shift of previtamin D3 to D3, determined over the temperature range 60.1-85.5 deg C is characterized by the following activation parameters: log AH = 8.8 and EaH = 19.6 kcal/mol.Deuteriated pre-D3, which rearranges over this temperature range, is characterized by the activation parameters log AD = 9.5 and EaD = 21.9 kcal/mol.