1,5-methano-2,3,4,5-tetrahydro-1H-3-benzazepine p-toluenesulfonic acid salt | 357425-93-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 1,5-methano-2,3,4,5-tetrahydro-1H-3-benzazepine p-toluenesulfonic acid salt
• 英文别名: 2,3,4,5-tetrahydro-1,5-methano-1H-3-benzazepine tosylate；1,5-methano-2,3,4,5-tetrahydro-1H-3-benzazepinium tosylate；10-Aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-triene tosylate；10-aza-tricyclo[6.3.1.0(2,7)]dodeca-2,4,6-triene para-toluenesulfonic acid salt；10-azoniatricyclo[6.3.1.02,7]dodeca-2,4,6-triene;4-methylbenzenesulfonate
• CAS: 357425-93-5
• 化学式: C₇H₈O₃S*C₁₁H₁₃N
• 分子量: 331.436
• InChiKey: UJODSSUMBIFQRE-UHFFFAOYSA-N

物化性质

• 熔点：
  207-208 °C

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  74.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,5-methano-2,3,4,5-tetrahydro-1H-3-benzazepine p-toluenesulfonic acid salt 以94的产率得到varenicline tartrate
  参考文献：
  名称：

  [EN] PROCESS FOR THE PREPARATION OF 1,3-SUBSTITUTED INDENES AND ARYL-FUSED AZAPOLYCYCLIC COMPOUNDS
  [FR] PROCEDE DE PREPARATION D'INDENES 1,3-SUBSTITUES ET COMPOSES AZAPOLYCYCLIQUES D'ARYLE FONDUS

  摘要：

  本发明涉及制备公式(Ia、Ib和Ic)中的任何1,3-取代茚芝中间体或其混合物的过程，其中R1、R2、R3、R4和R5在此定义。公式(Ia、Ib和Ic)化合物或其混合物在制备公式(II)中的化合物中有用，其中R2、R3和R6在此也被定义。

  公开号：

  WO2002085843A2
• 作为产物：
  描述：

  邻溴氰苄 在 palladium diacetate 、 palladium on activated charcoal sodium tetrahydroborate 、 硫酸 、 三氟化硼乙醚 、 氢气 、 sodium t-butanolate 、 三环己基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 17.5h， 生成 1,5-methano-2,3,4,5-tetrahydro-1H-3-benzazepine p-toluenesulfonic acid salt
  参考文献：
  名称：

  Preparation of 1,5-Methano-2,3,4,5- tetrahydro-1H-3-benzazepine via Pd-Catalyzed Cyclization

  摘要：

  A new approach to prepare 1,5-methano-2,3,4,5-tetrahydro-1H-3-benzanepine (1) is discussed. This strategy utilized a tandem Michael addition and Pd-catalyzed cyclization to afford cyanobenzofulvene acetal 13. This indene intermediate (13) was subjected to hydrogenolysis to provide an amino ester (12) and was cyclized with base to afford lactam 5. The lactam (5) was reduced with borane to afford the desired benzazepine (1).

  DOI：

  10.1021/ol049316s

文献信息

• Process for the preparation of 1,3-substituted indenes and aryl-fused azapolycyclic componunds
  申请人：——

  公开号：US20030060624A1

  公开（公告）日：2003-03-27

  The present invention relates to processes for the preparation of any of the intermediate 1,3-substituted indenes of the formulae (Ia), (Ib) and (Ic) or a mixture thereof: 1 wherein R 1 , R 2 , R 3 , R 4 , and R 5 are defined herein. Compounds of formulae (Ia), (Ib) and (IC) or mixtures thereof are useful in the preparation of compounds of formula (II): 2 wherein R 2 , R 3 and R 6 are also defined herein.

  本发明涉及制备公式(Ia)、(Ib)和(Ic)中任一中间体1,3-取代吲哚的过程，或其混合物： 其中R1、R2、R3、R4和R5在此处定义。公式(Ia)、(Ib)和(Ic)或其混合物的化合物在制备公式(II)的化合物中有用： 其中R2、R3和R6也在此处定义。
• Synthesis of 2,3,4,5-Tetrahydro-1,5-methano-1<i>H</i>-3-benzazepine via Oxidative Cleavage and Reductive Amination Strategies
  作者：Jotham Coe、Robert Singer、Paige Brooks、Stephane Caron、Karl Ng、Enrique Vazquez、Michael Vetelino、Harry Watson、David Whritenour、Michael Wirtz

  DOI：10.1055/s-2004-829135

  日期：——

  zepine (5) from benzonorbornadiene (1) by oxidative cleavage and reductive amination sequences were investigated. Osmium-mediated dihydroxylation of 1 followed by NaIO 4 cleavage, reductive amination and debenzylation provides 5 in 64-73% yield overall in three operations. A tandem ozonolysis-reductive amination procedure gives 5 as the tosylate salt from benzonorbornadiene with no isolation of intermediates

  研究了通过氧化裂解和还原胺化序列从苯并降冰片二烯 (1) 制备 2,3,4,5-四氢-1,5-甲氧基-1H-3-苯并氮杂 (5)。锇介导的 1 的二羟基化，然后是 NaIO 4 裂解、还原胺化和脱苄基化，在三个操作中提供 5，总产率为 64-73%。串联臭氧分解-还原胺化过程从苯并降冰片二烯中得到甲苯磺酸盐形式的 5，中间体不分离，产率为 28%。
• Process for the preparation of 1,3-substituted indenes and aryl-fused azapolycyclic compounds
  申请人：Pfizer Inc

  公开号：US07186870B2

  公开（公告）日：2007-03-06

  The present invention relates to processes for the preparation of any of the intermediate 1,3-substituted indenes of the formulae (Ia), (Ib) and (Ic) or a mixture thereof: wherein R1, R2, R3, R4, and R5 are defined herein. Compounds of formulae (Ia), (Ib) and (Ic) or mixtures thereof are useful in the preparation of compounds of formula (II): wherein R2, R3 and R6 are also defined herein.

  本发明涉及制备公式（Ia）、（Ib）和（Ic）或其混合物中的任何1,3-取代茚的中间体的方法：其中R1、R2、R3、R4和R5在此定义。公式（Ia）、（Ib）和（Ic）或其混合物的化合物在制备公式（II）的化合物中有用：其中R2、R3和R6也在此定义。
• [EN] PROCESS FOR THE PREPARATION OF 1,3-SUBSTITUTED INDENES AND ARYL-FUSED AZAPOLYCYCLIC COMPOUNDS<br/>[FR] PROCEDE DE PREPARATION D'INDENES 1,3-SUBSTITUES ET COMPOSES AZAPOLYCYCLIQUES D'ARYLE FONDUS
  申请人：PFIZER PROD INC

  公开号：WO2002085843A2

  公开（公告）日：2002-10-31

  The present invention relates to processes for the preparation of any of the intermediate 1,3-substituted indenes of formulae (Ia, Ib and Ic) or a mixture thereof, wherein R?1, R2, R3, R4, and R5¿ are defined herein. Compounds of formulae (Ia, Ib and Ic) or mixtures thereof are useful in the preparation of compounds of formula (II), wherein R?2, R3 and R6¿ are also defined herein.

  本发明涉及制备公式(Ia、Ib和Ic)中的任何1,3-取代茚芝中间体或其混合物的过程，其中R1、R2、R3、R4和R5在此定义。公式(Ia、Ib和Ic)化合物或其混合物在制备公式(II)中的化合物中有用，其中R2、R3和R6在此也被定义。
• [EN] ARYL FUSED AZAPOLYCYCLIC COMPOUNDS<br/>[FR] COMPOSES AZAPOLYCYCLIQUES A FUSION ARYLE
  申请人：PFIZER PROD INC

  公开号：WO2001062736A1

  公开（公告）日：2001-08-30

  This invention is directed to compounds of formula (I) and their pharmaceutically acceptable salts, wherein R?1, R2, and R3¿ are as defined herein; intermediates for the synthesis of such compounds, pharmaceutical compositions containing such compounds; and methods of using such compounds in the treatment of neurological and psychological disorders.

  本发明涉及公式(I)化合物及其药学上可接受的盐，其中R1、R2和R3的定义如本文所述；合成此类化合物的中间体；含有此类化合物的制药组合物；以及使用此类化合物治疗神经系统和心理障碍的方法。