4-[Bromo-(8-furan-3-ylmethyl-8-aza-bicyclo[3.2.1]oct-3-ylidene)-methyl]-N-ethyl-benzamide | 809275-58-9

• 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: 4-[Bromo-(8-furan-3-ylmethyl-8-aza-bicyclo[3.2.1]oct-3-ylidene)-methyl]-N-ethyl-benzamide
• 英文别名: 4-[bromo-[8-(furan-3-ylmethyl)-8-azabicyclo[3.2.1]octan-3-ylidene]methyl]-N-ethylbenzamide
• CAS: 809275-58-9；810671-78-4；810671-79-5
• 化学式: C₂₂H₂₅BrN₂O₂
• 分子量: 429.357
• InChiKey: ZBZQAORTBQOLGF-UHFFFAOYSA-N

物化性质

• 沸点：
  579.5±50.0 °C(Predicted)
• 密度：
  1.357±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-氨基苯硼酸 、 4-[Bromo-(8-furan-3-ylmethyl-8-aza-bicyclo[3.2.1]oct-3-ylidene)-methyl]-N-ethyl-benzamide 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 0.17h， 生成 4-[(3-Amino-phenyl)-(8-furan-3-ylmethyl-8-aza-bicyclo[3.2.1]oct-3-ylidene)-methyl]-N-ethyl-benzamide
  参考文献：
  名称：

  Parallel methods for the preparation and SAR exploration of N-ethyl-4-[(8-alkyl-8-aza-bicyclo[3.2.1]oct-3-ylidene)-aryl-methyl]-benzamides, powerful mu and delta opioid agonists

  摘要：

  Two parallel synthetic methods were developed to explore the structure-activity relationships (SAR) of a series of potent opioid agonists. This series of tropanylidene benzamides proved extremely tolerant of structural variation while maintaining excellent opioid activity. Evaluation of several representative compounds from this series in the mouse hot plate test revealed potent antinociceptive effects upon oral administration. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.09.004
• 作为产物：
  描述：

  3-糠醛 、 4-[(8-aza-bicyclo[3.2.1]oct-3-ylidene)-bromo-methyl]-N-ethyl-benzamide 在 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.1h， 生成 4-[Bromo-(8-furan-3-ylmethyl-8-aza-bicyclo[3.2.1]oct-3-ylidene)-methyl]-N-ethyl-benzamide
  参考文献：
  名称：

  Parallel methods for the preparation and SAR exploration of N-ethyl-4-[(8-alkyl-8-aza-bicyclo[3.2.1]oct-3-ylidene)-aryl-methyl]-benzamides, powerful mu and delta opioid agonists

  摘要：

  Two parallel synthetic methods were developed to explore the structure-activity relationships (SAR) of a series of potent opioid agonists. This series of tropanylidene benzamides proved extremely tolerant of structural variation while maintaining excellent opioid activity. Evaluation of several representative compounds from this series in the mouse hot plate test revealed potent antinociceptive effects upon oral administration. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.09.004