methyl (2E,4R,5S,6Z)-7-(tert-butyldimethylsiloxy)-5-methyl-4-phenylhepta-2,6-dienoate | 827605-52-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl (2E,4R,5S,6Z)-7-(tert-butyldimethylsiloxy)-5-methyl-4-phenylhepta-2,6-dienoate
• 英文别名: methyl (2E,4R,5S,6Z)-7-[tert-butyl(dimethyl)silyl]oxy-5-methyl-4-phenylhepta-2,6-dienoate
• CAS: 827605-52-7
• 化学式: C₂₁H₃₂O₃Si
• 分子量: 360.569
• InChiKey: GUQTUWGRGGZHOT-MKYGHCBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.67
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (2E,4R,5S,6Z)-7-(tert-butyldimethylsiloxy)-5-methyl-4-phenylhepta-2,6-dienoate 以 甲苯 为溶剂， 生成 methyl (2S,3R,E)-3-(tert-butyldimethylsiloxy)-2-((E)-styryl)hex-4-enoate
  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
• 作为产物：
  描述：

  methyl (2S,3R,E)-3-(tert-butyldimethylsiloxy)-2-((E)-styryl)hex-4-enoate 以 甲苯 为溶剂， 生成 methyl (2E,4R,5S,6Z)-7-(tert-butyldimethylsiloxy)-5-methyl-4-phenylhepta-2,6-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.