185999-07-9

Basic information

• Product Name: tert-butyl(hex-5-enyloxy)diphenylsilane
• Synonyms: tert-butyl(hex-5-enyloxy)diphenylsilane
• CAS NO: 185999-07-9
• Molecular Weight: 338.565
• Mol File: 185999-07-9.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: tert-butyl(hex-5-enyloxy)diphenylsilane(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl(hex-5-enyloxy)diphenylsilane(185999-07-9)
• EPA Substance Registry System: tert-butyl(hex-5-enyloxy)diphenylsilane(185999-07-9)

Safety Data

• Hazardous Substances Data: 185999-07-9(Hazardous Substances Data)

Upstream product

• 821-41-0 5-Hexen-1-ol 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 592-90-5 oxepane 

Downstream Products

• 103791-54-4 (+/-)-6-[(tert-butyldiphenylsilyl)oxy]-1,2-epoxyhexane 
• 131216-47-2 5-(tert-butyldiphenylsilyloxy)pentanal 
• 908357-57-3 (4S)-4-[4-(tert-butyldiphenylsilyloxy)-butyl]-γ-butyrolactone 
• 1010685-68-3 C₂₈H₃₅ClOSi 
• 1010685-69-4 C₂₈H₃₅ClOSi 
• 1208517-84-3 (2E)-6-((tert-butyldiphenylsilyl)oxy)hex-2-en-1-yl acetate 

Relevant articles and documents

Total Synthesis of (+)-Cornexistin

Herein, we describe the first total synthesis of (+)-cornexistin as well as its 8-epi-isomer starting from malic acid. The robust and scalable route features a Nozaki–Hiyama–Kishi reaction, an auxiliary-controlled syn-Evans-aldol reaction, and a highly efficient intramolecular alkylation to form the nine-membered carbocycle. The delicate maleic anhydride moiety of the nonadride skeleton was constructed from a β-keto nitrile. The developed route enabled the synthesis of 165 mg (+)-cornexistin.

Copper-Catalyzed Oxyboration of Unactivated Alkenes

The first regiodivergent oxyboration of unactivated terminal alkenes is reported, using copper alkoxide as a catalyst, bis(pinacolato)diboron [(Bpin)2] as a boron source, and (2,2,6,6-tetramethylpiperidin-1-yl)oxyl (TEMPO) as an oxygen source. The reaction is compatible with various functional groups. Two regioisomers are selectively produced by selecting the appropriate ligands on copper. The products may be used as a linchpin precursor for various other functionalizations, and net processes such as carbooxygenation, aminooxygenation, and dioxygenation of alkenes can be achieved after C-B bond transformations. Mechanistic studies indicate that the reaction involves the following steps: 1)Transmetalation between CuOtBu and (Bpin)2 to generate a borylcopper species; 2)regiodivergent borylcupration of alkenes; 3) oxidation of the thus-generated C-Cu bond to give an alkyl radical; 4)trapping of the resulting alkyl radical by TEMPO.

Lewis acid-promoted addition of 1,3-bis(silyl)propenes to aldehydes: A route to 1,3-dienes

The Lewis acid-promoted addition of 1,3-bis(silyl)-propenes to aldehydes to provide the corresponding (E)-1,3-dienes in excellent stereoselectivity and good to excellent yields is reported. The procedure is mild, base-free, and operationally straightforward.