N-benzoyl-9-azabicyclo<3.3.1>nonan-3-one | 36146-90-4

• 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: N-benzoyl-9-azabicyclo<3.3.1>nonan-3-one
• 英文别名: 9-Benzoyl-9-azabicyclo<3.3.1>nonan-3-on；9-Benzoyl-norgranatanon-(3)；9-benzoyl-9-aza-bicyclo[3.3.1]nonan-3-one；9-Benzoyl-9-azabicyclo[3.3.1]nonan-3-one
• CAS: 36146-90-4
• 化学式: C₁₅H₁₇NO₂
• 分子量: 243.305
• InChiKey: NWIXXABSFAUOGW-UHFFFAOYSA-N

物化性质

• 沸点：
  420.3±38.0 °C(predicted)
• 密度：
  1.185±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-benzoyl-9-azabicyclo<3.3.1>nonan-3-one 在 diethylzinc 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  对映体对pinpinidine的高效合成：刚性桥接系统上的有机化学雕刻插图，作为立体化学策略

  摘要：

  （-）-吡啶和其对映异构体的不对称合成是通过从炔诺酮开始，通过不对称烯醇化，立体选择性环丙烷化和所得环丙醇系统的氧化环裂解（以高价碘）为关键步骤来完成的。

  DOI：

  10.1016/0040-4039(96)00990-2
• 作为产物：
  描述：

  苯甲酰腈 、 9-氮杂双环[3.3.1]壬烷-3-酮 以 二氯甲烷 为溶剂， 反应 7.0h， 以31%的产率得到N-benzoyl-9-azabicyclo<3.3.1>nonan-3-one
  参考文献：
  名称：

  Hypervalent λn-iodane-mediated fragmentation of tertiary cyclopropanol systems II: Application to asymmetric syntheses of piperidine and indolizidine alkaloids

  摘要：

  The asymmetric synthesis of (-)-pinidine and its enantiomer was accomplished by starting from norgranatanone via the asymmetric enolization, stereoselective cyclopropanation, and oxidative ring cleavage of the resulting cyclopropanol system with a hypervalent lambda(n)-iodane as key steps. Formal asymmetric synthesis of (+)-indolizidine 223AB was also performed via the asymmetric enolization and oxidative ring cleavage of the resulting cyclopropanol system as key steps. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00073-3

文献信息

• Hypervalent λn-iodane-mediated fragmentation of tertiary cyclopropanol systems II: Application to asymmetric syntheses of piperidine and indolizidine alkaloids
  作者：Masayuki Kirihara、Takashi Nishio、Satoshi Yokoyama、Hiroko Kakuda、Takefumi Momose

  DOI：10.1016/s0040-4020(99)00073-3

  日期：1999.3

  The asymmetric synthesis of (-)-pinidine and its enantiomer was accomplished by starting from norgranatanone via the asymmetric enolization, stereoselective cyclopropanation, and oxidative ring cleavage of the resulting cyclopropanol system with a hypervalent lambda(n)-iodane as key steps. Formal asymmetric synthesis of (+)-indolizidine 223AB was also performed via the asymmetric enolization and oxidative ring cleavage of the resulting cyclopropanol system as key steps. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Efficient synthesis of an enantiomeric pair pinpinidine: An illustration of organochemical carving on the rigid bridged system as the stereochemical tactics
  作者：Takefumi Momose、Takashi Nishio、Masayuki Kirihara

  DOI：10.1016/0040-4039(96)00990-2

  日期：1996.7

  Asymmetric synthesis of (−)-pinidine and its enantiomer was accomplished by starting from norgranatar one via the asymmetric enolization, stereoselective cyclopropanation, and oxidative ring cleavage of the resulting cyclopropanol system with a hypervalent iodoid as key steps.

  （-）-吡啶和其对映异构体的不对称合成是通过从炔诺酮开始，通过不对称烯醇化，立体选择性环丙烷化和所得环丙醇系统的氧化环裂解（以高价碘）为关键步骤来完成的。