tropane-3exo-carboxylic acid methyl ester | 5911-34-2

• 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: tropane-3exo-carboxylic acid methyl ester
• 英文别名: tropane-3exo-carboxylic acid methyl ester；Tropan-3exo-carbonsaeure-methylester
• CAS: 5911-34-2
• 化学式: C₁₀H₁₇NO₂
• 分子量: 183.25
• InChiKey: OHPLWWIUSWGASJ-PSVAKVPMSA-N

物化性质

• 沸点：
  231.6±33.0 °C(Predicted)
• 密度：
  1.067±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.03
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  tropane-3exo-carboxylic acid methyl ester 在 氨 、 sodium methylate 作用下， 生成 tropane-3-carboxamide
  参考文献：
  名称：

  The Action of Nucleophilic Agents on 3α-Chlorotropane¹

  摘要：

  DOI：

  10.1021/ja01550a064
• 作为产物：
  描述：

  Tropine-3-mesylate 在 盐酸 、 乙醇 作用下， 生成 tropane-3exo-carboxylic acid methyl ester
  参考文献：
  名称：

  The Action of Nucleophilic Agents on 3α-Chlorotropane¹

  摘要：

  DOI：

  10.1021/ja01550a064

文献信息

• Synthesis and nicotinic acetylcholine receptor binding affinities of 2- and 3-isoxazolyl-8-azabicyclo[3.2.1]octanes
  作者：Jie Cheng、Sari Izenwasser、Chunming Zhang、Suhong Zhang、Dean Wade、Mark L. Trudell

  DOI：10.1016/j.bmcl.2004.01.025

  日期：2004.4

  1]octane derivatives was synthesized and evaluated as potential ligands for neuronal nicotinic acetylcholine receptors in [(3)H]cytisine labeled rat brain. The 2beta-isoxazolyl-8-azabicyclo[3.2.1]octane 9b (K(i)=3 nM) was the most potent compound of the series with a binding affinity twice that of nicotine. The 3beta-isoxazolyl-8-azabicyclo[3.2.1]octane 15b (K(i)=148 nM) exhibited moderate affinity while

  合成了一系列的表位联苯胺同系物，被2-和3-异恶唑取代的8-氮杂双环[3.2.1]辛烷衍生物，并作为[（3）H]胱氨酸标记的大鼠脑中神经元烟碱乙酰胆碱受体的潜在配体进行了评估。2β-异恶唑基-8-氮杂双环[3.2.1]辛烷9b（K（i）= 3 nM）是该系列中最有效的化合物，其结合亲和力是尼古丁的两倍。3β-异恶唑基-8-氮杂双环[3.2.1]辛烷15b（K（i）= 148 nM）表现出中等的亲和力，而相应的2α-和3α-异构体则表现出微摩尔的结合亲和力。
• Novel 5-HT3 antagonists. Indole oxadiazoles
  作者：C. J. Swain、R. Baker、C. Kneen、J. Moseley、J. Saunders、E. M. Seward、G. Stevenson、M. Beer、J. Stanton、K. Watling

  DOI：10.1021/jm00105a021

  日期：1991.1

  The synthesis and biochemical evaluation of a series of indole oxadiazole 5-HT3 antagonists are described. The key pharmacophoric elements have been defined as a basic nitrogen, a linking group capable of H-bonding interactions, and an aromatic moiety. The steric limitations of the aromatic binding site have been determined by substitution about the indole ring. Variation of the heterocyclic linking group has shown that while two hydrogen-bonding interactions are possible, only one is essential for high affinity. The environment of the basic nitrogen has been investigated and shown to be optimal when constrained within an azabicyclic system. These results have been incorporated into a proposed binding model for the 5-HT3 antagonist binding site, in which the optimum distance between the aromatic binding site and the basic amine is 8.4-8.9 angstrom and the steric limitations are defined by van der Waals difference mapping.
• Zirkle et al., Journal of Organic Chemistry, 1962, vol. 27, p. 1269,1277
  作者：Zirkle et al.

  DOI：——

  日期：——
• 3-Substituted Tropane Derivatives. III. 3-Substituted Tropane Carbinols, Alkenes, and Alkanes
  作者：Charles L. Zirkle、Elvin L. Anderson、Paul N. Craig、Fred R. Gerns、Zena K. Indik、Alex M. Pavloff

  DOI：10.1021/jm01237a012

  日期：1962.3.1
• 3-substituted-8-alkylnortropanes and the acid and quaternary ammonium salts thereof
  申请人：SMITH KLINE FRENCH LAB

  公开号：US02800478A1

  公开（公告）日：1957-07-23