methyl (E)-4-[(1R)-3-[(2S)-2-(methoxymethyl)pyrrolidine-1-carbonyl]-1-methyl-4-oxocyclohex-2-en-1-yl]but-2-enoate | 1228108-49-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: methyl (E)-4-[(1R)-3-[(2S)-2-(methoxymethyl)pyrrolidine-1-carbonyl]-1-methyl-4-oxocyclohex-2-en-1-yl]but-2-enoate
• CAS: 1228108-49-3
• 化学式: C₁₉H₂₇NO₅
• 分子量: 349.427
• InChiKey: CRULMUSNRWOYPN-NGRLIPSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (E)-4-[(1R)-3-[(2S)-2-(methoxymethyl)pyrrolidine-1-carbonyl]-1-methyl-4-oxocyclohex-2-en-1-yl]but-2-enoate 在 三甲基膦 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 反应 24.0h， 生成 methyl (3aR,7R,7aR)-7-[(2S)-2-(methoxymethyl)pyrrolidine-1-carbonyl]-3a-methyl-6-oxo-4,5,7,7a-tetrahydro-3H-indene-1-carboxylate 、
  参考文献：
  名称：

  Enantioselective synthesis of bicarbocyclic structures with an all-carbon quaternary stereocenter through sequential cross metathesis and intramolecular Rauhut–Currier reaction

  摘要：

  A new extension of the Birch-Cope sequence is described which allows the efficient enantioselective construction of highly functionalized, fused bicarbocyclic structures with an all-carbon quaternary stereo-center in two steps. The two-step sequence includes a cross metathesis between a terminal alkene and a polarized alkene followed by an intramolecular Rauhut-Currier reaction with a trialkylphosphine catalyst. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.03.026
• 作为产物：
  描述：

  (R)-4-allyl-2-((S)-2-(methoxymethyl)pyrrolidin-1-carbonyl)-4-methylhex-2-en-1-one 、 丙烯酸甲酯（MA） 在 Hoveyda-Grubbs catalyst second generation 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 以82%的产率得到methyl (E)-4-[(1R)-3-[(2S)-2-(methoxymethyl)pyrrolidine-1-carbonyl]-1-methyl-4-oxocyclohex-2-en-1-yl]but-2-enoate
  参考文献：
  名称：

  Enantioselective synthesis of bicarbocyclic structures with an all-carbon quaternary stereocenter through sequential cross metathesis and intramolecular Rauhut–Currier reaction

  摘要：

  A new extension of the Birch-Cope sequence is described which allows the efficient enantioselective construction of highly functionalized, fused bicarbocyclic structures with an all-carbon quaternary stereo-center in two steps. The two-step sequence includes a cross metathesis between a terminal alkene and a polarized alkene followed by an intramolecular Rauhut-Currier reaction with a trialkylphosphine catalyst. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.03.026