3-[Bromo-(4-carboxy-phenyl)-methylene]-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid ethyl ester | 809275-26-1

• 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: 3-[Bromo-(4-carboxy-phenyl)-methylene]-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid ethyl ester
• 英文别名: 4-[Bromo-(8-ethoxycarbonyl-8-azabicyclo[3.2.1]octan-3-ylidene)methyl]benzoic acid
• CAS: 809275-26-1
• 化学式: C₁₈H₂₀BrNO₄
• 分子量: 394.265
• InChiKey: CFFLCULRFARKQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[Bromo-(4-carboxy-phenyl)-methylene]-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid ethyl ester 在 碘代三甲硅烷 、 sodium carbonate 作用下， 生成 4-[bromo-[8-(9H-fluoren-9-ylmethoxycarbonyl)-8-azabicyclo[3.2.1]octan-3-ylidene]methyl]benzoic acid
  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：

  Ethyl 3-[(4-methoxycarbonylphenyl)methylidene]-8-azabicyclo[3.2.1]octane-8-carboxylate 在 sodium hydroxide 、 溴 作用下， 以 二氯甲烷 为溶剂， 生成 3-[Bromo-(4-carboxy-phenyl)-methylene]-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid ethyl ester
  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

文献信息

• 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
  作者：Steven J. Coats、Mark J. Schulz、John R. Carson、Ellen E. Codd、Dennis J. Hlasta、Philip M. Pitis、Dennis J. Stone、Sui-Po Zhang、Ray W. Colburn、Scott L. Dax

  DOI：10.1016/j.bmcl.2004.09.004

  日期：2004.11

  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.