t-4-Acetonyl-1-benzyl-c-5-ethyl-r-2-piperidinecarbonitrile | 128350-36-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: t-4-Acetonyl-1-benzyl-c-5-ethyl-r-2-piperidinecarbonitrile
• 英文别名: t-4-Acetonyl-1-benzyl-t-5-ethyl-r-2-piperidinecarbonitrile
• CAS: 128350-36-7；128350-39-0
• 化学式: C₁₈H₂₄N₂O
• 分子量: 284.401
• InChiKey: PXDIHJVEMHTYHY-KSZLIROESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.41
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  44.1
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  t-4-Acetonyl-1-benzyl-c-5-ethyl-r-2-piperidinecarbonitrile 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 40.0h， 以69%的产率得到(1RS,4RS,5SR)-2-Benzyl-4-ethyl-2-azabicyclo<3.3.1>nonan-7-one
  参考文献：
  名称：

  Total Synthesis of Uleine-Type and Strychnos Alkaloids through a Common Intermediate

  摘要：

  A stereoselective total synthesis of the alkaloids of the uleine group, dasycarpidone, dasycarpidol, and nordasycarpidone, has been accomplished from the tetracyclic intermediate 1, which has been prepared by two alternative routes, either by Fischer indolization of 2-azabicyclo[3.3.1]nonanone 9 or, more efficiently, by stereocontrolled cyclization of 2-[(2-cyano-3-ethyl-4-piperidyl)methyl]i 24a and 24b. From the same tetracyclic intermediate 1, the Strychnos alkaloid tubotaiwine was also synthesized, the key step being the construction of the quaternary spiranic center by cyclization of a thionium ion upon the indole beta-position.

  DOI：

  10.1021/jo00093a028
• 作为产物：
  描述：

  cis-4-Acetonyl-1-benzyl-3-ethylpiperidine 在 sodium acetate 、 间氯过氧苯甲酸 、 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 t-4-Acetonyl-1-benzyl-c-5-ethyl-r-2-piperidinecarbonitrile
  参考文献：
  名称：

  Total Synthesis of Uleine-Type and Strychnos Alkaloids through a Common Intermediate

  摘要：

  A stereoselective total synthesis of the alkaloids of the uleine group, dasycarpidone, dasycarpidol, and nordasycarpidone, has been accomplished from the tetracyclic intermediate 1, which has been prepared by two alternative routes, either by Fischer indolization of 2-azabicyclo[3.3.1]nonanone 9 or, more efficiently, by stereocontrolled cyclization of 2-[(2-cyano-3-ethyl-4-piperidyl)methyl]i 24a and 24b. From the same tetracyclic intermediate 1, the Strychnos alkaloid tubotaiwine was also synthesized, the key step being the construction of the quaternary spiranic center by cyclization of a thionium ion upon the indole beta-position.

  DOI：

  10.1021/jo00093a028

文献信息

• Stereocontrolled synthesis of 4- and 9-ethyl-2-azabicyclo[3.3.1]nonan-7-ones via 2-cyanopiperidines
  作者：Josep Bonjoch、Núria Casamitjana、Jordi Gràcia、Joan Bosch

  DOI：10.1016/s0040-4039(01)93824-9

  日期：1989.1