(4R)-4-[(E)-3-(1,3-dioxolan-2-yl)prop-2-enyl]-2-[(2S)-2-(methoxymethyl)pyrrolidine-1-carbonyl]-4-methylcyclohex-2-en-1-one | 1228108-46-0

• 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: (4R)-4-[(E)-3-(1,3-dioxolan-2-yl)prop-2-enyl]-2-[(2S)-2-(methoxymethyl)pyrrolidine-1-carbonyl]-4-methylcyclohex-2-en-1-one
• CAS: 1228108-46-0
• 化学式: C₂₀H₂₉NO₅
• 分子量: 363.454
• InChiKey: GRHKVTARIJZQSM-VXYDJCMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4R)-4-[(E)-3-(1,3-dioxolan-2-yl)prop-2-enyl]-2-[(2S)-2-(methoxymethyl)pyrrolidine-1-carbonyl]-4-methylcyclohex-2-en-1-one 在 盐酸 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 C₁₈H₂₅NO₄ 、 C₁₈H₂₅NO₄
  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 、 2-乙烯基-1,3-二氧戊环 在 Hoveyda-Grubbs catalyst second generation 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 以86%的产率得到(4R)-4-[(E)-3-(1,3-dioxolan-2-yl)prop-2-enyl]-2-[(2S)-2-(methoxymethyl)pyrrolidine-1-carbonyl]-4-methylcyclohex-2-en-1-one
  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