(3R)-3-<(S)-(1-phenyl)ethylamino>-quinuclidine | 120577-33-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 奎宁环
• 英文名称: (3R)-3-<(S)-(1-phenyl)ethylamino>-quinuclidine
• 英文别名: (R)-N-[(S)-α-methylbenzyl]-3-aminoquinuclidine；(3R)-3-[(S)-α-methylbenzylamino]quinuclidine；(R)-N-((S)-1-phenylethyl)quinuclidin-3-amine；(3R)-N-[(1S)-1-phenylethyl]-1-azabicyclo[2.2.2]octan-3-amine
• CAS: 120577-33-5
• 化学式: C₁₅H₂₂N₂
• 分子量: 230.353
• InChiKey: YUJLYFFNXJRLDW-WFASDCNBSA-N

物化性质

• 沸点：
  332.1±25.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3R)-3-<(S)-(1-phenyl)ethylamino>-quinuclidine 在 palladium dihydroxide 氢气 作用下， 以 甲醇 、 水 为溶剂， 生成 (3R)-1-氮杂双环[2.2.2]辛烷-3-胺盐酸盐(1:1)
  参考文献：
  名称：

  Synthesis and 5-HT-3 receptor binding activity of 5-[125I]iodo-2,3-dimethoxy-N-(1-azabicyclo[2.2.2]oct-3-yl)benzamide and its 5-halogen-2-alkoxyl homologues

  摘要：

  (S)-5-Iodo-2,3-dimethoxy-N-(1-azabicyclo[2.2.2]oct-3-yl)benzamide (MIZAC) was prepared from 5-iodo-2,3-dimethoxybenzoyl chloride and (S)-3-aminoquinuclidine. [I-125]Iodode-stannylation of its corresponding 5-tri-n-butyltin derivative gave [I-125]-MIZAC at 1800 Ci/mmol. Binding of [I-125]-MIZAC in rat entorhinal cortex revealed a K-D of 1.37 +/- 0.21 nM. A series of racemic 2-O-alkyl derivatives of MIZAC were prepared and 5-HT-3 receptor affinities were determined by inhibition of [I-125]-MIZAC binding. Optimal affinity for the receptor was obtained with small, electron-withdrawing substituents in the aromatic 5-position and with bulky substituents in the 3-position. [I-125]-MIZAC is a selective radioligand useful for in vitro identification of the 5-HT-3 receptor.

  DOI：

  10.1016/s0223-5234(97)81676-5
• 作为产物：
  描述：

  3-奎宁环酮 在 sodium tetrahydroborate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 14.0h， 生成 (3R)-3-<(S)-(1-phenyl)ethylamino>-quinuclidine
  参考文献：
  名称：

  Synthesis and 5-HT-3 receptor binding activity of 5-[125I]iodo-2,3-dimethoxy-N-(1-azabicyclo[2.2.2]oct-3-yl)benzamide and its 5-halogen-2-alkoxyl homologues

  摘要：

  (S)-5-Iodo-2,3-dimethoxy-N-(1-azabicyclo[2.2.2]oct-3-yl)benzamide (MIZAC) was prepared from 5-iodo-2,3-dimethoxybenzoyl chloride and (S)-3-aminoquinuclidine. [I-125]Iodode-stannylation of its corresponding 5-tri-n-butyltin derivative gave [I-125]-MIZAC at 1800 Ci/mmol. Binding of [I-125]-MIZAC in rat entorhinal cortex revealed a K-D of 1.37 +/- 0.21 nM. A series of racemic 2-O-alkyl derivatives of MIZAC were prepared and 5-HT-3 receptor affinities were determined by inhibition of [I-125]-MIZAC binding. Optimal affinity for the receptor was obtained with small, electron-withdrawing substituents in the aromatic 5-position and with bulky substituents in the 3-position. [I-125]-MIZAC is a selective radioligand useful for in vitro identification of the 5-HT-3 receptor.

  DOI：

  10.1016/s0223-5234(97)81676-5

文献信息

• Heterocyclic compounds
  申请人：JOHN WYETH & BROTHER LIMITED

  公开号：EP0323077A1

  公开（公告）日：1989-07-05

  Aryl or aroyl ureas and carbamic acid derivatives of formula A-X-NHCW-Y-B and pharmaceutically acceptable salts thereof wherein A is a specified aromatic radical including optionally substituted phenyl X is a direct bond or CO W is O or S Y is NH or S and B is a specified saturated azacyclic ring, eg tropan-3-yl or quinuclidin-3-yl, possess 5-HT₃-antagonistic activity and are, for example, useful in treatment of migraine, emesis, anxiety, gastro-intestinal disorders and as anti-psychotics.

  式中的芳基或芳基脲和氨基甲酸衍生物 A-X-NHCW-Y-B 及其药学上可接受的盐类 其中 A 是指定的芳香基，包括任选取代的苯基 X是直接键或CO W是O或S Y 是 NH 或 S 和 B 是特定的饱和氮杂环，例如托烷-3-基或喹吖啶-3-基、 具有 5-HT₃拮抗活性，可用于治疗偏头痛、呕吐、焦虑、胃肠道疾病和抗精神病等。
• Synthesis of (R) and (S)-3-Aminoquinuclidine from 3-Quinuclidinone and (S) and (R)-1-Phenethylamine
  作者：Langlois、Meyer、Soulier

  DOI：10.1080/00397919208021320

  日期：1992.7

  The synthesis of (R) and (S)-3-amino quinuclidine, an important building block for the synthesis of chiral 5-HT3 serotonin receptor antagonists, is described. The key reaction is the reduction by NaBH4 of the imine prepared from the 3-quinuclidinone and chiral (S) or (R)-1-phenethylamine.
• RENAUD, ALAIN;LANGIOLS, MICHEL;NAYLOR, ROBERT JOHN;NAYLOR, BRENDA
  作者：RENAUD, ALAIN、LANGIOLS, MICHEL、NAYLOR, ROBERT JOHN、NAYLOR, BRENDA

  DOI：——

  日期：——
• JPH09216888A
  申请人：——

  公开号：JPH09216888A

  公开（公告）日：1997-08-19
• US4983600A
  申请人：——

  公开号：US4983600A

  公开（公告）日：1991-01-08