5-methyl-trans-5-undecene | 57024-92-7

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 5-methyl-trans-5-undecene
• 英文别名: 5-methyl-5(E)-undecene；5-Undecene, 5-methyl-；(E)-5-methylundec-5-ene
• CAS: 57024-92-7
• 化学式: C₁₂H₂₄
• 分子量: 168.323
• InChiKey: KCCDVPWBXMNJFG-VAWYXSNFSA-N

物化性质

• 沸点：
  211.4±7.0 °C(Predicted)
• 密度：
  0.764±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  1-iodo-2-(trimethylsilyl)hexane 在 copper(I) bromide dimethylsulfide complex 、 叔丁基锂 、 三氟乙酸 作用下， 反应 10.58h， 生成 5-methyl-trans-5-undecene
  参考文献：
  名称：

  Triply convergent, stereospecific alkene formation via Peterson olefination

  摘要：

  alpha-Iodo silanes 8 were prepared from alpha-hydroxy silanes and after halogen/metal exchange and treatment with copper(I) bromide-dimethyl sulfide were coupled with acid chlorides to yield alpha-silyl ketones 2. Cram controlled addition with a variety of nucleophiles followed by treatment with acid or base led to either the (E)- or (Z)-alkene in good overall yields from the iodide (47-67%) and with excellent stereoselectivities ( > 95/ < 5 for disubstituted cases and 67/33 to 95/5 for trisubstituted). The procedure was used iteratively in the total synthesis of 4(E),8(Z)-tetradecadien-1-yl acetate (15) in > 95/ < 5 isomeric purity.

  DOI：

  10.1021/jo00002a028

文献信息

• Dimerization and codimerization of higher ?-olefins, catalyzed by zirconium complexes
  作者：O. S. Vostrikova、A. G. Ibragimov、G. A. Tolstikov、L. M. Zelenova、U. M. Dzhemilev

  DOI：10.1007/bf00951226

  日期：1980.10
• Stereoselective alkene synthesis via (.alpha.-chloroalkyl)(dimethyl)phenylsilanes and .alpha.-(dimethyl)phenylsilyl ketones
  作者：Anthony G. M. Barrett、Jason M. Hill、Eli M. Wallace

  DOI：10.1021/jo00027a069

  日期：1992.1
• Triply convergent, stereospecific alkene formation via Peterson olefination
  作者：Anthony G. M. Barrett、John A. Flygare

  DOI：10.1021/jo00002a028

  日期：1991.1

  alpha-Iodo silanes 8 were prepared from alpha-hydroxy silanes and after halogen/metal exchange and treatment with copper(I) bromide-dimethyl sulfide were coupled with acid chlorides to yield alpha-silyl ketones 2. Cram controlled addition with a variety of nucleophiles followed by treatment with acid or base led to either the (E)- or (Z)-alkene in good overall yields from the iodide (47-67%) and with excellent stereoselectivities ( > 95/ < 5 for disubstituted cases and 67/33 to 95/5 for trisubstituted). The procedure was used iteratively in the total synthesis of 4(E),8(Z)-tetradecadien-1-yl acetate (15) in > 95/ < 5 isomeric purity.