(2E,4E)-2-(trimethylsilyl)ethyl 6-bromohexa-2,4-dienoate | 1187629-82-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2E,4E)-2-(trimethylsilyl)ethyl 6-bromohexa-2,4-dienoate
• 英文别名: 2-trimethylsilylethyl (2E,4E)-6-bromohexa-2,4-dienoate
• CAS: 1187629-82-8
• 化学式: C₁₁H₁₉BrO₂Si
• 分子量: 291.26
• InChiKey: QVWMPZCHJRPSAJ-YDFGWWAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.38
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2E,4E)-2-(trimethylsilyl)ethyl 6-bromohexa-2,4-dienoate 、 亚磷酸三乙酯 反应 1.0h， 生成 (2E,4E)-2-(trimethylsilyl)ethyl 6-(diethoxyphosphoryl)hexa-2,4-dienoate
  参考文献：
  名称：

  Relative Stereochemical Determination and Synthesis of the C1−C17 Fragment of a New Natural Polyketide

  摘要：

  The challenging determination of the relative stereochemistry of a complex natural polyketide portion was achieved. After careful NMR analysis, a concise synthesis of a set of possible relative diastereomers (only 6 diastereomers out of the 32 initially envisioned) has been carried out using a common strategy based on enantioselective aldol reactions. With a high predictability, final NMR comparison established the relative stereochemistry of the C1-C17 fragment of this natural product.

  DOI：

  10.1021/jo9012833
• 作为产物：
  描述：

  (2E,4E)-2-(trimethylsilyl)ethyl hexa-2,4-dienoate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 3-溴丙烯 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以62%的产率得到(2E,4E)-2-(trimethylsilyl)ethyl 6-bromohexa-2,4-dienoate
  参考文献：
  名称：

  Relative Stereochemical Determination and Synthesis of the C1−C17 Fragment of a New Natural Polyketide

  摘要：

  The challenging determination of the relative stereochemistry of a complex natural polyketide portion was achieved. After careful NMR analysis, a concise synthesis of a set of possible relative diastereomers (only 6 diastereomers out of the 32 initially envisioned) has been carried out using a common strategy based on enantioselective aldol reactions. With a high predictability, final NMR comparison established the relative stereochemistry of the C1-C17 fragment of this natural product.

  DOI：

  10.1021/jo9012833

文献信息

• Relative Stereochemical Determination and Synthesis of the C1−C17 Fragment of a New Natural Polyketide
  作者：Etienne Fleury、Marie-Isabelle Lannou、Olivia Bistri、François Sautel、Georges Massiot、Ange Pancrazi、Janick Ardisson

  DOI：10.1021/jo9012833

  日期：2009.9.18

  The challenging determination of the relative stereochemistry of a complex natural polyketide portion was achieved. After careful NMR analysis, a concise synthesis of a set of possible relative diastereomers (only 6 diastereomers out of the 32 initially envisioned) has been carried out using a common strategy based on enantioselective aldol reactions. With a high predictability, final NMR comparison established the relative stereochemistry of the C1-C17 fragment of this natural product.