(2E,4E)-2-(trimethylsilyl)ethyl 6-(diethoxyphosphoryl)hexa-2,4-dienoate | 1187629-46-4

• 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-(diethoxyphosphoryl)hexa-2,4-dienoate
• 英文别名: 2-trimethylsilylethyl (2E,4E)-6-diethoxyphosphorylhexa-2,4-dienoate
• CAS: 1187629-46-4
• 化学式: C₁₅H₂₉O₅PSi
• 分子量: 348.452
• InChiKey: WBBCOZCJHCXLCW-GFULKKFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.25
• 重原子数：
  22
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2E,4E)-2-(trimethylsilyl)ethyl 6-(diethoxyphosphoryl)hexa-2,4-dienoate 、 (2R)-3-(tert-butyldimethylsilyloxy)-2-methylpropanal 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.75h， 以86%的产率得到
  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 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

文献信息

• Synthetic Studies on Hemicalide: Development of a Convergent Approach toward the C1–C25 Fragment
  作者：Geoffroy Sorin、Etienne Fleury、Christine Tran、Elise Prost、Nicolas Molinier、François Sautel、Georges Massiot、Simon Specklin、Christophe Meyer、Janine Cossy、Marie-Isabelle Lannou、Janick Ardisson

  DOI：10.1021/ol402077e

  日期：2013.9.20

  Synthetic studies on hemicalide, a recently isolated marine natural product displaying highly potent antiproliferative activity and a unique mode of action, have highlighted a reliable Horner–Wadsworth–Emmons olefination to create the C6–C7 alkene and a remarkable efficient Suzuki–Miyaura coupling to form the C15–C16 bond, resulting in the development of a convergent approach toward the C1–C25 fragment

  hemicalide的合成研究是一种最近分离的海洋天然产物，显示出强大的抗增殖活性和独特的作用方式，强调了可靠的Horner-Wadsworth-Emmons烯烃聚合反应可生成C6-C7烯烃，并形成了有效的Suzuki-Miyaura偶联反应C15–C16键，导致针对C1–C25片段的收敛方法的发展。