Z-cyclooct-2-enyltrimethylstannane | 133816-69-0

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: Z-cyclooct-2-enyltrimethylstannane
• 英文别名: Cyclooct-2-enyltrimethylstannane
• CAS: 133816-69-0
• 化学式: C₁₁H₂₂Sn
• 分子量: 273.006
• InChiKey: YAXPESCJVBIHMI-SQDRRJMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.22
• 重原子数：
  12.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  Z-cyclooct-2-enyltrimethylstannane 在 氘代三氟乙酸 作用下， 以 氘代氯仿 为溶剂， 生成 <3-²H₁>Cyclooctene
  参考文献：
  名称：

  Penman, Kerry G.; Kitching, William; Wells, Adam P., Journal of the Chemical Society. Perkin transactions I, 1991, p. 721 - 726

  摘要：

  DOI：
• 作为产物：
  描述：

  (trimethylstannyl)lithium 、 3-氯环辛烯 以 四氢呋喃 为溶剂， 以40%的产率得到Z-cyclooct-2-enyltrimethylstannane
  参考文献：
  名称：

  Characterization of (Z)-cyclooct-2-enylstannanes

  摘要：

  (Z)-Cyclooct-2-enyltrimethylstannanes and -triphenylstannanes have been synthesized and characterized by H-1 and C-13 NMR spectra, which indicate a predominating unsymmetrical chair-boat arrangement. A mixture of the cis and trans isomers of both the (4-methylcyclooct-2-enyl)- and (8-methylcyclooct-2-enyl)trimethylstannanes (allylic stannanes) results from a sequence commencing with methylcyanocuprate opening of the monoepoxide of 1,3-cyclooctadiene, which is considered to afford regio- and stereoselectively trans-4-methylcyclooct-2-enol. Chlorination of this alcohol with both thionyl chloride and N-chlorosuccinimide/dimethyl sulfide has been conducted and the structures of the chlorides established by NMR methods and use of [1-H-2(1)]-4-methylcyclooct-2-enol. Trimethylstannylation of the chloride mixtures provides the four possible allylic stannanes, with one of the rearranged 8-methyl isomers slightly predominating. NMR spectra of various fractions from preparative gas chromatography have been obtained, and full assignment of the C-13 NMR spectra of the isomers is reported. Acidolysis of these fractions (with CF3COOD) proceeds rapidly to yield mixtures of H-2-substituted 3- and 4-methylcyclooctenes, but only one diastereomer of each system appears to be formed, on the basis of the C-13 NMR spectra. This implies that electrophile approach to the pi-face at the gamma-carbon is not influenced by the orientation of the C-Sn bond but is probably dictated by the predominant molecular conformation.

  DOI：

  10.1021/om00051a022