Z-octadecene-5 | 7206-33-9

• 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-octadecene-5
• 英文别名: Z-5-octadecene；cis-Octadec-5-en；octadec-5c-ene；Octadec-5c-en；(Z)-5-Octadecene；(Z)-octadec-5-ene
• CAS: 7206-33-9
• 化学式: C₁₈H₃₆
• 分子量: 252.484
• InChiKey: YIYQJOMDMPTKEL-LUAWRHEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  18
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  13-octadecenal N-tert-butyldimethylsilylhydrazone 在 potassium tert-butylate 、 叔丁醇 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以99%的产率得到Z-octadecene-5
  参考文献：
  名称：

  Practical Procedures for the Preparation of N-tert-Butyldimethylsilylhydrazones and Their Use in Modified Wolff−Kishner Reductions and in the Synthesis of Vinyl Halides and gem-Dihalides

  摘要：

  In this work we develop practical chemistry for the preparation of N-tert-butyldimethylsilylhydrazone (TBSH) derivatives from carbonyl-containing compounds and show that these products serve as superior alternatives to simple hydrazones in Wolff-Kishner-type reduction reactions, in the Barton vinyl iodide preparation, in the synthesis of vinyl bromides, and in the synthesis of gem-diiodides, gem-dibromides, and gem-dichlorides. In our new procedure for silyl hydrazone synthesis, aliphatic and aromatic ketones and aldehydes are shown to undergo highly efficient coupling (typically >95% yield) to form the corresponding TBSH derivatives when combined with equimolar amounts of 1,2-bis(tert-butyldimethylsilyl)hydrazine (BTBSH) and a catalytic quantity of scandium trifluoromethanesulfonate (typically, 0.01 mol %), neat, or in solvent. Optimized procedures are provided for the use of TBSH derivatives in a Wolff-Kishner-type reduction protocol that proceeds at low temperature (23-100 degreesC) and in a single reaction flask. Similarly, protocols for the use of TBSH derivatives as precursors to vinyl halides and gem-dihalides are described in detail.

  DOI：

  10.1021/ja049694s

文献信息

• Elsner; Paul, Journal of the Chemical Society, 1935, p. 3156,3160
  作者：Elsner、Paul

  DOI：——

  日期：——