(3aS)-2,3,3a,4-tetrahydro-1H,1H-pyrrolo<2,1-c>benzoxazepin-10-one | 94225-47-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aS)-2,3,3a,4-tetrahydro-1H,1H-pyrrolo<2,1-c>benzoxazepin-10-one
• 英文别名: (2aS)-2H-<2,1-c>pyrrolidino-1,4-benzoxazepin-5-one；(2aS)-2H-[2,1-c]pyrrolidino-1,4-benzoxazepin-5-one；(6aS)-6a,7,8,9-tetrahydro-6H-pyrrolo[2,1-c][1,4]benzoxazepin-11-one
• CAS: 94225-47-5
• 化学式: C₁₂H₁₃NO₂
• 分子量: 203.241
• InChiKey: UWRIUQGPFHZNOG-VIFPVBQESA-N

物化性质

• 沸点：
  377.1±22.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3aS)-2,3,3a,4-tetrahydro-1H,1H-pyrrolo<2,1-c>benzoxazepin-10-one 在 氨 、 sodium 、 叔丁醇 作用下， 生成 (3aS)-2,3,3a,4,6,7-hexahydro-1H,10H-pyrrolo<2,1-c><1,4>benzoxazepin-10-one
  参考文献：
  名称：

  对映体在手性苯甲酸衍生物的桦木还原烷基化中

  摘要：

  描述了苯并a氮杂酮3的制备和非对映选择性的Birch还原烷基化。3转化为对映体纯的11证实了烷基化步骤中〜98：2非对映异构。

  DOI：

  10.1016/s0040-4039(01)91207-9
• 作为产物：
  描述：

  L-脯氨醇 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 (3aS)-2,3,3a,4-tetrahydro-1H,1H-pyrrolo<2,1-c>benzoxazepin-10-one
  参考文献：
  名称：

  -取代的苯甲酸对映体选择性转化为手性环己烷衍生物

  摘要：

  1a-1c还原甲基化生成2a-2c和11生成12的非对映选择性分别为260：1和> 99：1。

  DOI：

  10.1016/s0040-4039(00)98755-0

文献信息

• Studies on the asymmetric Birch reductive alkylation to access spiroimines
  作者：Thierry Jousseaume、Pascal Retailleau、Laurent Chabaud、Catherine Guillou

  DOI：10.1016/j.tetlet.2012.01.008

  日期：2012.3

  The asymmetric Birch reductive alkylation has been investigated to synthesize spiroimine analogs of the neurophycotoxin (−)-gymnodimine A 1. Two types of chiral aromatic substrates, an acyclic benzamide 2 and a benzoxazepinone 3 were studied. We found that the chiral auxiliary of benzoxazepinone could be easily removed in a three step procedure to afford β-ketoester 14 that was converted into spiroimines

  已经研究了不对称的桦木还原性烷基化反应以合成神经藻毒素（-）-gymnodimine A 1的螺胺类似物。研究了两种类型的手性芳族底物，无环苯甲酰胺2和苯并a庚酮3。我们发现，benzoxazep​​inone的手性助剂可以三步过程，得到β酮酯中被容易地移除14，将其转变成spiroimines 23 - 24个具有上烟碱乙酰胆碱受体（nAChRs）拮抗剂作用。
• Benzoxazepines derivatives and their use as ampa receptor stimulators
  申请人：——

  公开号：US20040171605A1

  公开（公告）日：2004-09-02

  The present invention relates to benzoxazepine derivative having the general formula I, wherein X represents CO or SO 2 ; R 1 , R 2 , R 3 and R 4 are independently selected from H, (C 1-4 )alkyl, (C 1-4 )alkyloxy, (C 1-4 )alkyloxy(C 1-4 )alkyl, halogen, nitro, cyano, NR 8 R 9 , NR 8 COR 10 , and CONR 8 R 9 , R 5 , R 6 and R 7 are independently H or (C 1-4 )alkyl; R 8 and R 9 are independently H or (C 1-4 )alkyl; or R 8 and R 9 form together with the nitrogen atom to which they are bound a 5- or 6-membered saturated heterocyclic ring, optionally containing a further heteroatom selected from O, S or NR 11 ; R 10 is (C 1-4 )alkyl; R 11 is (C 1-4 )alkyl; A represents the residue of a 4-7 membered saturated heterocyclic ring, optionally containing an oxygen atom, the ring being optionally substituted with 1-3 substituents selected from (C 1-4 )alkyl, (C 1-4 )alkyloxy, hydroxy, halogen and oxo; or a pharmaceutically acceptable salt thereof. The invention also relates to pharmaceutical compositions comprising said derivatives, and to the use of these benzoxazepine derivatives in the treatment of neurological diseases and psychiatric disorders which are responsive to enhancement of synaptic responses mediated by AMPA receptors in the central nervous system. 1

  本发明涉及具有通式I的苯并噁唑衍生物，其中X代表CO或SO2；R1、R2、R3和R4分别选自H，(C1-4)烷基，(C1-4)烷氧基，(C1-4)烷氧基(C1-4)烷基，卤素，硝基，氰基，NR8R9，NR8COR10和CONR8R9，R5、R6和R7分别为H或(C1-4)烷基；R8和R9分别为H或(C1-4)烷基；或者R8和R9与它们所连接的氮原子一起形成一个5-或6-成员饱和杂环环，可选地含有进一步的杂原子，所述杂原子选自O、S或NR11；R10为(C1-4)烷基；R11为(C1-4)烷基；A代表4-7成员饱和杂环环的残基，可选地含有一个氧原子，该环可选地被1-3个取代基取代，所述取代基选自(C1-4)烷基，(C1-4)烷氧基，羟基，卤素和氧代基；或其药学上可接受的盐。本发明还涉及包含所述衍生物的制药组合物，以及在治疗中枢神经系统中响应于增强由AMPA受体介导的突触反应的神经疾病和精神障碍中使用这些苯并噁唑衍生物。
• BENZOXAPZEPINE DERIVATIVES AND THEIR USE AS AMPA RECEPTOR STIMULATORS
  申请人：Grove Simon James Anthony

  公开号：US20080139529A1

  公开（公告）日：2008-06-12

  The present invention relates to benzoxazepine derivative having the general formula I, wherein X represents CO or S0 2 ; R 1 , R 2 , R 3 and R 4 are independently selected from H, (C 1-4 )alkyl, (C 1-4 )alkyloxy, (C 1-4 )alkyloxy(C 1-4 )alkyl, halogen, nitro, cyano, NR 8 R 9 , NR 8 COR 10 , and CONR 8 R 9 , R 5 , R 6 and R 7 are independently H or (C 1-4 )alkyl; R 8 and R 9 are independently H or (C 1-4 )alkyl; or R 8 and R 9 form together with the nitrogen atom to which they are bound a 5- or 6-membered saturated heterocyclic ring, optionally containing a further heteroatom selected from O, S or NR 11 ; R 10 is (C 1-4 )alkyl; R 11 is (C 1-4 )alkyl; A represents the residue of a 4-7 membered saturated heterocyclic ring, optionally containing an oxygen atom, the ring being optionally substituted with 1-3 substituents selected from (C 1-4 )alkyl, (C 1-4 )alkyloxy, hydroxy, halogen and oxo; or a pharmaceutically acceptable salt thereof. The invention also relates to pharmaceutical compositions comprising said derivatives, and to the use of these benzoxazepine derivatives in the treatment of neurological diseases and psychiatric disorders which are responsive to enhancement of synaptic responses mediated by AMPA receptors in the central nervous system.

  本发明涉及一种具有一般式I的苯并噁唑啉衍生物，其中X代表CO或S02; R1、R2、R3和R4独立地选择自H、(C1-4)烷基、(C1-4)烷氧基、(C1-4)烷氧基(C1-4)烷基、卤素、硝基、氰基、NR8R9、NR8COR10和CONR8R9，R5、R6和R7独立地为H或(C1-4)烷基; R8和R9独立地为H或(C1-4)烷基; 或R8和R9与它们所结合的氮原子一起形成一个5-或6-成员饱和杂环环，可选含有进一步选择自O、S或NR11的杂原子; R10为(C1-4)烷基; R11为(C1-4)烷基; A代表4-7成员饱和杂环环的残基，可选含有氧原子，该环可选地用1-3个取代基选择自(C1-4)烷基、(C1-4)烷氧基、羟基、卤素和氧代基取代; 或其药学上可接受的盐。本发明还涉及包含所述衍生物的制药组合物，以及利用这些苯并噁唑啉衍生物治疗中枢神经系统中介导AMPA受体的突触反应增强的神经疾病和精神障碍的用途。
• Synthesis of chiral dibenzo-1,8-diaza-14-crown-4, dibenzo-1,9-diaza-16-crown-4, and dibenzo-1,10-diaza-18-crown-4 ethers by aromatic nucleophilic substitution. Application to the preparation of bicyclic chiral crown-lithium iodide complexes
  作者：Arthur G. Schultz、Donald J. P. Pinto、Martha Welch、Rudolph K. Kullnig

  DOI：10.1021/jo00242a006

  日期：1988.4
• An enantioselective method for reductive alkylation of aromatic carboxylic acid derivatives. Examination of the factors that provide stereoselectivity
  作者：Arthur G. Schultz、Mark. Macielag、Padmanabhan. Sundararaman、Arthur G. Taveras、Martha. Welch

  DOI：10.1021/ja00231a038

  日期：1988.11