N-carbomethoxydehydroepibatidine | 163299-83-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-carbomethoxydehydroepibatidine
• 英文别名: N-carbomethoxy-5-(2-chloro-5-pyridyl)-7-aza-bicyclo[2.2.1]hept-2-ene；Methyl 5-(6-chloropyridin-3-yl)-7-azabicyclo[2.2.1]hept-2-ene-7-carboxylate
• CAS: 163299-83-0
• 化学式: C₁₃H₁₃ClN₂O₂
• 分子量: 264.711
• InChiKey: OPQVVJWTRFFBOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-carbomethoxydehydroepibatidine 在 palladium on activated charcoal 氢气 作用下， 反应 0.08h， 以92%的产率得到7-carbomethoxy-2-(2-chloro-5-pyridyl)-7-aza-bicyclo[2.2.1]heptane
  参考文献：
  名称：

  A versatile total synthesis of epibatidine and analogs

  摘要：

  A racemic mixture of epibatidine, a potent analgesic alkaloid possessing a 7-azanorbornane structure, has been synthesized via a versatile four-step synthetic route: a Diels-Alder reaction of N-carbomethoxy pyrrole and phenylsulfonyl 6-chloro-3-pyridyl acetylene, followed by desulfonation, hydrogenation and deprotection of the amine. rac -Epibatidine was resolved to its d and l enantiomers.

  DOI：

  10.1016/0040-4039(93)88063-o
• 作为产物：
  描述：

  phenylsulfonyl 6-chloro-3-pyridyl acetylene 在 sodium dihydrogenphosphate 、 sodium amalgam 作用下， 以 甲醇 为溶剂， 反应 27.0h， 生成 N-carbomethoxydehydroepibatidine
  参考文献：
  名称：

  A versatile total synthesis of epibatidine and analogs

  摘要：

  A racemic mixture of epibatidine, a potent analgesic alkaloid possessing a 7-azanorbornane structure, has been synthesized via a versatile four-step synthetic route: a Diels-Alder reaction of N-carbomethoxy pyrrole and phenylsulfonyl 6-chloro-3-pyridyl acetylene, followed by desulfonation, hydrogenation and deprotection of the amine. rac -Epibatidine was resolved to its d and l enantiomers.

  DOI：

  10.1016/0040-4039(93)88063-o

文献信息

• 7-azabicyclo[2.2.1]-heptane and -heptene derivatives as cholinergic
  申请人：UCB S.A. - DTB

  公开号：US06060473A1

  公开（公告）日：2000-05-09

  7-Azabicyclo[2.2.1]-heptane and -heptene derivatives are disclosed that can be administered to a mammal, including a human, to treat disorders associated with a decrease or increase in cholinergic activity.

  揭示了可以用于治疗与胆碱能活性降低或增加相关的疾病的7-Azabicyclo[2.2.1]-heptane和-heptene衍生物，可用于给哺乳动物，包括人类。
• 7-Azabicyclo\x9b2.2.1!-heptane and -heptene derivatives as cholinergic
  申请人：University of Virginia

  公开号：US05817679A1

  公开（公告）日：1998-10-06

  7-Aza-bicyclo\x9b2.2.1!-heptane and -heptene derivatives are disclosed that can be administered to a mammal, including a human, to treat disorders associated with a decrease or increase in cholinergic activity.

  披露了可以用于治疗与胆碱能活性增减有关的疾病的7-Aza-bicyclo\x9b2.2.1！-庚烷和-庚烯衍生物，可用于给哺乳动物，包括人类。
• [EN] 7-AZABICYCLO-[2.2.1]-HEPTANE AND -HEPTENE DERIVATIVES AS ANALGESICS AND ANTI-INFLAMMATORY AGENTS<br/>[FR] DERIVES DE 7-AZABICYCLO[2.2.1]-HEPTANE et -HEPTENE UTILISES COMME ANALGESIQUES ET AGENTS ANTI-INFLAMMATOIRES
  申请人：UNIVERSITY OF VIRGINIA

  公开号：WO1994022868A1

  公开（公告）日：1994-10-13

  (EN) 7-Azabicyclo[2.2.1]-heptane and -heptene derivatives with analgesic or anti-inflammatory activity are disclosed that can be administered to a mammal, including a human, to treat pain and inflammatory disorders. A method for the treatment of pain or inflammatory disorders is also presented that includes administering an effective amount of the compound or its pharmaceutically acceptable salt or derivative, or mixtures thereof, to a host in need of analgesic anti-inflammatory therapy, optionally in a pharmaceutically acceptable carrier or diluent.(FR) Sont décrits des dérivés de 7-Azabicyclo[2.2.1]-heptane et -heptène à activité analgésique ou anti-inflammatoire qui peuvent être administrés à un mammifère, notamment l'homme, pour traiter la douleur et les troubles inflammatoires. Est également décrit un procédé pour traiter la douleur ou les troubles inflammatoires, consistant à administrer une dose efficace du composé ou de son sel ou dérivé pharmaceutiquement acceptable ou des mélanges de ceux-ci, à un hôte nécessitant une thérapie anti-inflammatoire analgésique, éventuellement dans un excipient ou un diluant pharmaceutiquement acceptable.

  disclose that can be administered to a mammal, including a human, to treat pain and inflammatory disorders. A method for the treatment of pain or inflammatory disorders is also presented that includes administering an effective amount of the compound or its pharmaceutically acceptable salt or derivative, or mixtures thereof, to a host in need of analgesic anti-inflammatory therapy, optionally in a pharmaceutically acceptable carrier or diluent.
• [EN] 7-AZABICYCLO[2.2.1]-HEPTANE AND -HEPTENE DERIVATIVES AS CHOLINERGIC RECEPTOR LIGANDS<br/>[FR] DERIVES DE 7-AZABICYCLO[2.2.1]-HEPTANE ET -HEPTENE UTILISES COMME LIGANDS DES RECEPTEURS CHOLINERGIQUES
  申请人：UNIVERSITY OF VIRGINIA

  公开号：WO1996006093A1

  公开（公告）日：1996-02-29

  (EN) 7-Azabicyclo[2.2.1]-heptane and -heptene derivatives are disclosed that can be administered to a mammal, including a human, to treat disorders associated with a decrease or increase in cholinergic activity.(FR) Des dérivés de 7-azabicyclo[2.2.1]-heptane et -heptène peuvent être administrés à un mammifère, y compris l'homme, pour traiter les troubles associés à une augmentation ou une diminution de l'activité cholinergique.

  根据法国（FR）的表述，这一族化合物包括一系列用途广泛的药物，可通过体外或体内给药。这些化合物尤其适合用于慢性病情管理，因为它们能够通过调节胆碱能神经系统的活动，直接维持内源性胆碱代谢的正常进行，从而达到预防和治疗多种疾病的目的。
• US6060473A
  申请人：——

  公开号：US6060473A

  公开（公告）日：2000-05-09