8-Azabicyclo[3.2.1]octan-3-ol, benzoate (ester), endo- | 18470-33-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 8-Azabicyclo[3.2.1]octan-3-ol, benzoate (ester), endo-
• 英文别名: 3-benzoyloxy-nortropane；3-(8-azabicyclo[3.2.1]octan-3-yl)benzoic acid；Nortropacocaine；3α-benzoyloxy-8-azabicyclo[3.2.1]octane；3β-benzoyloxynortropane；N-nortropacocaine；Nor-tropacocaine；8-azabicyclo[3.2.1]octan-3α-yl benzoate
• CAS: 18470-33-2；20811-95-4；123202-90-4
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: AZHSHGVBEAPALY-CLLJXQQHSA-N

物化性质

• 沸点：
  347.5±35.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.13
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.33
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  8-Azabicyclo[3.2.1]octan-3-ol, benzoate (ester), endo- 在 聚合甲醛 、 甲酸 作用下， 生成 8-Methyl-8-azabicyclo[3.2.1]oct-3-yl benzoate
  参考文献：
  名称：

  合成托烷生物碱的新途径。伪品托品和托卡卡因

  摘要：

  伪品托品和托卡卡因已通过一种简便的方法合成，该方法涉及[4 + 2]亚硝基环加成，然后内部进行S N 2置换。

  DOI：

  10.1016/s0040-4039(01)91127-x
• 作为产物：
  描述：

  pseudotropine 在 TEA 、 potassium carbonate 、 溶剂黄146 、 锌 作用下， 以 甲苯 为溶剂， 反应 7.33h， 生成 8-Azabicyclo[3.2.1]octan-3-ol, benzoate (ester), endo-
  参考文献：
  名称：

  Synthesis of Tropeines and Allosteric Modulation of Ionotropic Glycine Receptors

  摘要：

  Twenty esters of 3alpha- and 3beta-hydroxy(nor)tropanes and two amides of 3alpha-aminotropane were prepared with substituted benzoic acids. These (nor)tropeines inhibited [H-3] strychnine binding to glycine receptors in synaptosomal membranes of rat spinal cord. A ternary allosteric model was applied to determine the dissociation constants (K-A) of the tropeines having strong negative cooperativities with [H-3]strychnine binding (alpha > 10). K-A values about 10 nM are well below those of known allosteric agents. Low concentrations (0.1K(A)) of the (nor)tropeines potentiated the displacing effects of glycine. Positive cooperativity with glycine (beta < 1) decreased with the increase in concentration and binding affinity of tropeines. Displacing potencies were also measured for [H-3]granisetron binding to 5-HT3 type serotonin receptors of rat cerebral cortex. Selectivities to glycine receptors versus 5-HT3 receptors varied within 4 orders of magnitude. Nortropeines might serve as a lead to high-affinity selective allosteric modulators of glycine receptors.

  DOI：

  10.1021/jm040814g

文献信息

• Chemical Studies on Drug Metabolism: Oxidation with Ruthenium Tetroxide of Some Medicinal AlicyclicN-Methylamines
  作者：Roberto Perrone、Giuseppe Carbonara、Vincenzo Tortorella

  DOI：10.1002/ardp.19843170106

  日期：——

  Oxidation with ruthenium tetroxide of alicyclic N‐methylamines, such as nicotine (1), trans‐phendi‐metrazine (2), tropacocaine (3) and pempidine (4), leads to the N‐demethylated, N‐formyl and, where possible, lactam derivatives. Only from pempidine the N‐oxide was obtained. All products obtained by this procedure are metabolites of compounds 1, 2, 3 and 4.

  用四氧化钌氧化脂环族 N - 甲胺，如尼古丁 (1)、反式苯二甲胺 (2)、托可卡因 (3) 和哌啶 (4)，导致 N - 去甲基化、N - 甲酰基，并在可能的情况下，内酰胺衍生物。仅从哌啶获得 N-氧化物。通过该程序获得的所有产品都是化合物 1、2、3 和 4 的代谢物。
• [EN] NOVEL PHENOXAZIN-3-ONE DERIVATIVES AND THEIR USE AS MONOAMINE NEUROTRANSMITTER RE-UPTAKE INHIBITORS<br/>[FR] NOUVEAUX DÉRIVÉS DE PHÉNOXAZIN-3-ONE ET LEUR UTILISATION COMME INHIBITEURS DE LA RECAPTURE DES NEUROTRANSMETTEURS MONOAMINES
  申请人：NEUROSEARCH AS

  公开号：WO2009034043A1

  公开（公告）日：2009-03-19

  This invention relates to novel phenoxazin-3-one derivatives useful as monoamine neurotransmitter re-uptake inhibitors. In other aspects the invention relates to the use of these compounds in a method for therapy and to pharmaceutical compositions comprising the compounds of the invention.

  这项发明涉及一种新型的苯氧嗪-3-酮衍生物，可用作单胺神经递质再摄取抑制剂。在其他方面，该发明涉及将这些化合物用于治疗方法以及包含该发明化合物的药物组合物。
• [EN] NOVEL BENZOOXAZOL- AND BENZOOXATHIOL-2-ONE DERIVATIVES AND THEIR USE AS MONOAMINE NEUROTRANSMITTER RE-UPTAKE INHIBITORS<br/>[FR] NOUVEAUX DÉRIVÉS DE BENZOOXAZOL-2-ONE ET DE BENZOOXATHIOL-2-ONE AINSI QUE LEUR UTILISATION COMME INHIBITEURS DE LA RECAPTURE DES NEUROTRANSMETTEURS MONOAMINES
  申请人：NEUROSEARCH AS

  公开号：WO2009034042A1

  公开（公告）日：2009-03-19

  This invention relates to novel benzooxazol- and benzooxathiol-2-one derivatives useful as monoamine neurotransmitter re-uptake inhibitors. In other aspects the invention relates to the use of these compounds in a method for therapy and to pharmaceutical compositions comprising the compounds of the invention.

  这项发明涉及一种新型苯并噁唑和苯并噁硫-2-酮衍生物，可用作单胺神经递质再摄取抑制剂。在其他方面，该发明涉及将这些化合物用于治疗方法以及包含该发明化合物的药物组合物。
• Electrochemical <i>N</i>-demethylation of tropane alkaloids
  作者：Ali Alipour Najmi、Zhangping Xiao、Rainer Bischoff、Frank J. Dekker、Hjalmar P. Permentier

  DOI：10.1039/d0gc00851f

  日期：——

  synthesize noratropine in high yield and purity using a convenient liquid–liquid extraction method without any need for chromatographic purification. Mechanistic studies showed that the electrochemical N-demethylation proceeds by the formation of an iminium intermediate which is converted by water as the nucleophile. The optimized method was further applied to scopolamine, cocaine, benzatropine, homatropine

  描述了一种实用，有效和选择性的将烷烃生物碱转化为正烷烃衍生物的N-脱甲基方法。降冰片烷，例如去甲肾上腺素和降冰片碱是分别半合成异丙托溴铵或溴托昔铵的重要中间体。合成是使用多孔玻璃碳电极在简单的自制电化学批量电池中进行的。反应在室温下在乙醇或甲醇和水的混合物中一步进行。该方法避免了有害的氧化剂如H 2 ö 2或米氯过苯甲酸（米-CPBA），有毒溶剂（例如氯仿）以及金属基催化剂。在电化学批量或流通池中研究了各种关键参数，并以克级规模在批量和流通池中使用了最佳条件，以方便的液-液萃取方法无需色谱纯化即可以高收率和高纯度合成去甲托品。机理研究表明，电化学的N-去甲基化通过形成亚胺中间体而进行，该亚胺中间体被水转化为亲核试剂。优化后的方法进一步应用于东pol碱，可卡因，苯扎特罗平，荷马特平和托卡卡因，表明这是一种N的通用方法烷对托烷生物碱进行脱甲基，以合成用于医药产品的有价值的前体。
• Alkaloids of some south american erythroxylum species
  作者：Y.M.A. El-Imam、W.C. Evans、T. Plowman

  DOI：10.1016/s0031-9422(00)83028-9

  日期：——

  Abstract Fourteen South American species of Erythroxylum representing four sections of the genus were examined for tropane and related alkaloids. The alkaloid content of the dried material ranged from 0.002 to 0.20 %. Commonly, the alkaloids involved were esters of various tropanols with benzoic and phenylacetic acids. A new alkaloid, nortropacocaine, was isolated from E. mamacoca. Mass spectrometry

  摘要 对代表该属 4 个部分的 14 个南美 Erythroxylum 物种进行了托烷和相关生物碱的检测。干燥材料的生物碱含量为 0.002 至 0.20%。通常，所涉及的生物碱是各种托醇与苯甲酸和苯乙酸的酯。从 E. mamacoca 中分离出一种新的生物碱，nortropacocaine。质谱分析表明存在其他新的碱，即海藻碱，在某些物种中还存在二氢海藻碱。讨论了化学分类学的影响。