methyl (2E,4R,5S,6E)-5-(2-oxoethyl)-4-phenylocta-2,6-dienoate

• 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: methyl (2E,4R,5S,6E)-5-(2-oxoethyl)-4-phenylocta-2,6-dienoate
• 化学式: C₁₇H₂₀O₃
• 分子量: 272.344
• InChiKey: DMYPTIYLQRBJNI-QXPCPDHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-methyl 2-diazo-4-phenylbut-3-enoate 、 (2E,4E)-2,4-hexadien-1-ol trimethylsilyl ether 在 dirhodium tetrakis(S-(N-dodecylbenzenesulfonyl)prolinate) 作用下， 以 various solvent(s) 为溶剂， 反应 2.33h， 生成 methyl (2E,4R,5S,6E)-5-(2-oxoethyl)-4-phenylocta-2,6-dienoate 、 methyl (2E,4S,5R,6E)-5-(2-oxoethyl)-4-phenylocta-2,6-dienoate 、 methyl (2R,3S,4E,6E)-2-((E)-styryl)-3-(trimethylsiloxy)octa-4,6-dienoate 、 methyl (2S,3R,4E,6E)-2-((E)-styryl)-3-(trimethylsiloxy)octa-4,6-dienoate
  参考文献：
  名称：

  Catalytic Asymmetric Reactions for Organic Synthesis:  The Combined C−H Activation/Siloxy-Cope Rearrangement

  摘要：

  Tetrakis(N-[4-dodecylbenzenesulfonyl]-(L)-prolinate) dirhodium [Rh-2(S-DOSP)(4)]-catalyzed decomposition of vinyldiazoacetates in the presence of allyl silyl ethers results in the formation of the direct C-H insertion product and the product derived from a combined C-H activation/siloxy-Cope rearrangement. Both products are formed with very high diastereoselectivity (>94% de) and high enantioselectvity (78-93% ee). Under thermal or microwave conditions, the direct C-H insertion product undergoes a siloxy-Cope rearrangement in a stereoselective manner.

  DOI：

  10.1021/jo048429m

文献信息

• Catalytic Asymmetric Reactions for Organic Synthesis:  The Combined C−H Activation/Siloxy-Cope Rearrangement
  作者：Huw M. L. Davies、Rohan E. J. Beckwith

  DOI：10.1021/jo048429m

  日期：2004.12.1

  Tetrakis(N-[4-dodecylbenzenesulfonyl]-(L)-prolinate) dirhodium [Rh-2(S-DOSP)(4)]-catalyzed decomposition of vinyldiazoacetates in the presence of allyl silyl ethers results in the formation of the direct C-H insertion product and the product derived from a combined C-H activation/siloxy-Cope rearrangement. Both products are formed with very high diastereoselectivity (>94% de) and high enantioselectvity (78-93% ee). Under thermal or microwave conditions, the direct C-H insertion product undergoes a siloxy-Cope rearrangement in a stereoselective manner.