2E-benzylidene-8-methyl-8-azabicyclo[3.2.1]-octan-3-one | 55171-45-4

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 托烷生物碱
• 英文名称: 2E-benzylidene-8-methyl-8-azabicyclo[3.2.1]-octan-3-one
• 英文别名: trans-2-Benzylidentropinon；(2E)-2-benzylidene-8-methyl-8-azabicyclo[3.2.1]octan-3-one
• CAS: 55171-45-4
• 化学式: C₁₅H₁₇NO
• 分子量: 227.306
• InChiKey: NRZRZEYFVQPWOM-UKTHLTGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  2E-benzylidene-8-methyl-8-azabicyclo[3.2.1]-octan-3-one 在 palladium on activated charcoal 盐酸 、 氢气 、 溶剂黄146 、 汞 、 锌 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 20.0 ℃ 、310.26 kPa 条件下， 生成 (1S,2R,5S)-2-Benzyl-8-methyl-8-aza-bicyclo[3.2.1]octane
  参考文献：
  名称：

  Synthesis and evaluation of a series of tropane analogues as novel vesicular monoamine transporter-2 ligands

  摘要：

  A series of tropane derivatives has been synthesized as lobelane analogues and evaluated for their binding affinity at the vesicular monoamine transporter-2 (VMAT2), and at alpha 4 beta 2* and alpha 7* nicotinic acetylcholine receptors. The trop-2-ene analogues 4a and 4b exhibited good affinity and high selectivity for VMAT2. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.032
• 作为产物：
  描述：

  托品酮 在 对甲苯磺酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正庚烷 、 乙基苯 、 甲苯 为溶剂， 反应 12.0h， 生成 2E-benzylidene-8-methyl-8-azabicyclo[3.2.1]-octan-3-one
  参考文献：
  名称：

  The Preparation of 2‐Arylmethylidene‐8‐methyl‐8‐azabicyclo[3.2.1]octan‐3‐ones

  摘要：

  An efficient and versatile two-step synthesis of 2-arylmethylidene-8-methyl-8-azabicyclo[3.2.1]octane-3-ones, via mono aldol condensation of tropinone with a variety of aryl aldehydes followed by pTsOH-catalyzed dehydration, is described.

  DOI：

  10.1081/scc-120037905

文献信息

• The Preparation of 2‐Arylmethylidene‐8‐methyl‐8‐azabicyclo[3.2.1]octan‐3‐ones
  作者：Guangrong Zheng、Linda P. Dwoskin、Peter A. Crooks

  DOI：10.1081/scc-120037905

  日期：2004.12.31

  An efficient and versatile two-step synthesis of 2-arylmethylidene-8-methyl-8-azabicyclo[3.2.1]octane-3-ones, via mono aldol condensation of tropinone with a variety of aryl aldehydes followed by pTsOH-catalyzed dehydration, is described.
• Synthesis and evaluation of a series of tropane analogues as novel vesicular monoamine transporter-2 ligands
  作者：Guangrong Zheng、Linda P. Dwoskin、Agripina G. Deaciuc、Peter A. Crooks

  DOI：10.1016/j.bmcl.2005.07.032

  日期：2005.10

  A series of tropane derivatives has been synthesized as lobelane analogues and evaluated for their binding affinity at the vesicular monoamine transporter-2 (VMAT2), and at alpha 4 beta 2* and alpha 7* nicotinic acetylcholine receptors. The trop-2-ene analogues 4a and 4b exhibited good affinity and high selectivity for VMAT2. (c) 2005 Elsevier Ltd. All rights reserved.