2-Benzyl-2-azabicyclo<3.3.1>nonan-7-one | 43152-29-0

• 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: 2-Benzyl-2-azabicyclo<3.3.1>nonan-7-one
• 英文别名: 2-Benzyl-2-azabicyclo[3.3.1]nonan-7-one
• CAS: 43152-29-0
• 化学式: C₁₅H₁₉NO
• 分子量: 229.322
• InChiKey: GZTCYJHRAZVXDA-UHFFFAOYSA-N

物化性质

• 沸点：
  353.1±17.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Benzyl-2-azabicyclo<3.3.1>nonan-7-one 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 23.0h， 生成 3-Benzyl-1,2,3,4,5,6-hexahydro-2,6-methanoazocino<4,5-b>indole
  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：

  1-(1-苄基-4-哌啶基)丙-2-酮 在 mercury(II) diacetate 、 溶剂黄146 作用下， 以32.5%的产率得到2-Benzyl-2-azabicyclo<3.3.1>nonan-7-one
  参考文献：
  名称：

  功能化的2-氮杂双环[3.3.1]壬烷。IV。吲哚[3，2- f ]吗啉体系的合成。

  摘要：

  描述了到2-氮杂双环[3.3.1]壬南-7-一系统的短路径。将4-哌啶酮与2-氧代丙基膦酸二乙酯缩合，然后催化氢化，得到相应的哌啶基丙烷，将其与乙酸汞在乙酸中环化成目标目标双环酮。由Fischer吲哚合成可选择性地提供吲哚[3,2- f ]吗啡，一种新的异吗啡类型。

  DOI：

  10.1016/0040-4020(82)85014-x

文献信息

• Functionalized 2-azabicyclo[3.3.1]nonanes. IV. synthesis of the indolo[3,2-f]morphan system.
  作者：Josep Bonjoch、Nuria Casamitjana、Joan Bosch

  DOI：10.1016/0040-4020(82)85014-x

  日期：1982.1

  A short route to the 2-azabicyclo[3.3.1]nonan-7-one system is described. Condensation of 4-piperidones with diethyl 2-oxopropylphosphonate, followed by catalytic hydrogenation furnished the corresponding piperidylpropanones which were cyclized with mercuric acetate in acetic acid to the target target bicyclic ketones . The Fischer indole synthesis from afforded regioselectively the indole [3,2-f]morphan

  描述了到2-氮杂双环[3.3.1]壬南-7-一系统的短路径。将4-哌啶酮与2-氧代丙基膦酸二乙酯缩合，然后催化氢化，得到相应的哌啶基丙烷，将其与乙酸汞在乙酸中环化成目标目标双环酮。由Fischer吲哚合成可选择性地提供吲哚[3,2- f ]吗啡，一种新的异吗啡类型。
• Total Synthesis of Uleine-Type and Strychnos Alkaloids through a Common Intermediate
  作者：Jordi Gracia、Nuria Casamitjana、Josep Bonjoch、Joan Bosch

  DOI：10.1021/jo00093a028

  日期：1994.7

  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.