2-((R)-3-Oxiranyl-propyl)-isoindole-1,3-dione | 205322-55-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-((R)-3-Oxiranyl-propyl)-isoindole-1,3-dione
• 英文别名: 2-[3-[(2R)-oxiran-2-yl]propyl]isoindole-1,3-dione
• CAS: 205322-55-0
• 化学式: C₁₃H₁₃NO₃
• 分子量: 231.251
• InChiKey: DDJPULUYCYQIBS-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  49.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-((R)-3-Oxiranyl-propyl)-isoindole-1,3-dione 在 盐酸 、 4-二甲氨基吡啶 、 sodium hydroxide 、 copper(l) iodide 、 sodium hydride 、 一水合肼 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 24.5h， 生成 N-Cbz-2-tetradecylpyrrolidine
  参考文献：
  名称：

  New Asymmetric Synthesis of Enantiomeric Pairs of the 2-Substituted Pyrrolidines Bgugaine and Irniine

  摘要：

  A new asymmetric route to 2-substituted pyrrolidines starting with the Sharpless asymmetric dihydroxylation (AD) of 4-pentenylphthalimide (5) followed by aminocyclization of the resultant amino alcohol is presented. The application to the asymmetric synthesis has been examined for two 2-substituted pyrrolidine alkaloids, bgugaine (1) and irniine (2).

  DOI：

  10.3987/com-97-s26
• 作为产物：
  描述：

  2-戊-4-烯基异吲哚-1,3-二酮 在 hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether 、 sodium sulfite 作用下， 反应 42.5h， 生成 2-((R)-3-Oxiranyl-propyl)-isoindole-1,3-dione
  参考文献：
  名称：

  New Asymmetric Synthesis of Enantiomeric Pairs of the 2-Substituted Pyrrolidines Bgugaine and Irniine

  摘要：

  A new asymmetric route to 2-substituted pyrrolidines starting with the Sharpless asymmetric dihydroxylation (AD) of 4-pentenylphthalimide (5) followed by aminocyclization of the resultant amino alcohol is presented. The application to the asymmetric synthesis has been examined for two 2-substituted pyrrolidine alkaloids, bgugaine (1) and irniine (2).

  DOI：

  10.3987/com-97-s26

文献信息

• New synthesis of all the four stereoisomers of indolizidine 209D and their affinity for nicotinic acetylcholine receptor
  作者：Hiroki Takahata、Minoru Kubota、Kozue Ihara、Naoki Okamoto、Takefumi Momose、Nehad Azer、Amira T. Eldefrawi、Mohyee E. Eldefrawi

  DOI：10.1016/s0957-4166(98)00338-3

  日期：1998.9

  Both enantiomers of a 2-(4-pentenyl)pyrrolidine derivative 4 (65-90% ee), prepared via the asymmetric dihydroxylation (AD) of terminal olefin 2, underwent a second AD to provide all of the four stereoisomers of indolizidine 209D 1 with enantiomeric enhancement (92-98% ee). The affinity of 1 for nicotinic acetylcholine receptor was evaluated. (C) 1998 Elsevier Science Ltd. All rights reserved.
• New Asymmetric Synthesis of Enantiomeric Pairs of the 2-Substituted Pyrrolidines Bgugaine and Irniine
  作者：Hiroki Takahata、Kozue Ihara、Minoru Kubota、Takefumi Momose

  DOI：10.3987/com-97-s26

  日期：——

  A new asymmetric route to 2-substituted pyrrolidines starting with the Sharpless asymmetric dihydroxylation (AD) of 4-pentenylphthalimide (5) followed by aminocyclization of the resultant amino alcohol is presented. The application to the asymmetric synthesis has been examined for two 2-substituted pyrrolidine alkaloids, bgugaine (1) and irniine (2).