(S)-N-benzyloxycarbonyl-1-aminopropyl-10-phenyldecan-1-ol | 205322-60-7

• 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: (S)-N-benzyloxycarbonyl-1-aminopropyl-10-phenyldecan-1-ol
• 英文别名: benzyl N-[(4S)-4-hydroxy-13-phenyltridecyl]carbamate
• CAS: 205322-60-7
• 化学式: C₂₇H₃₉NO₃
• 分子量: 425.612
• InChiKey: ZSMMHJRLMAMELY-SANMLTNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  31
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-N-benzyloxycarbonyl-1-aminopropyl-10-phenyldecan-1-ol 在 4-二甲氨基吡啶 、 sodium hydride 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 生成 (R)-N-benzyloxycarbonyl-2-(9-phenylnonyl)pyrrolidine
  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 sodium hydroxide 、 copper(l) iodide 、 hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether 、 一水合肼 、 sodium sulfite 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 42.5h， 生成 (S)-N-benzyloxycarbonyl-1-aminopropyl-10-phenyldecan-1-ol
  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 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).