4,5-dihydro-2H-benzazepine-1,3-dione | 36004-53-2

• 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: 4,5-dihydro-2H-benzazepine-1,3-dione
• 英文别名: 4,5-dihydro-2H-benzo[c]azepine-1,3-dione；4,5-Dihydro-2-benzazepin-1,3-dion；4,5-Dihydro-2H-2-benzazepin-1,3-dion；4,5-dihydro-benzo[c]azepine-1,3-dione；1,3,4,5-tetrahydro-2-benzazepine-1,3-dione；4,5-dihydro-2-benzazepine-1,3-dione
• CAS: 36004-53-2
• 化学式: C₁₀H₉NO₂
• 分子量: 175.187
• InChiKey: BAJFIIDLKRVKOP-UHFFFAOYSA-N

物化性质

• 熔点：
  103-105 °C
• 沸点：
  383.5±35.0 °C(Predicted)
• 密度：
  1.224±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,5-dihydro-2H-benzazepine-1,3-dione 在 sodium hydride 、 potassium carbonate 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 4-[4-[4-(2-pyrimidinyl)piperazin-1-yl]butyl]-4,5-dihydro-2H-benzazepine-1,3-dione
  参考文献：
  名称：

  Synthesis, SAR studies, and evaluation of 1,4-benzoxazepine derivatives as selective 5-HT1A receptor agonists with neuroprotective effect: Discovery of Piclozotan

  摘要：

  A new series of 1,4-benzoxazepine derivatives was designed, synthesized, and evaluated for binding to 5-HT1A receptor and cerebral anti-ischemic effect. A lot of compounds exhibited nanomolar affinity for 5-HT1A receptor with good selectivity over both dopamine D, and alpha(1)-adrenergic receptors. Among these compounds, 3-chloro-4-[4-[4-(2-pyridinyl)-1,2,3,6-tetrahydropyridin-1-y]butyl]-1, 4-benzoxazepin-5(4H)-one (50: SUN N4057 (Piclozotan) as 2HCl salt) showed remarkable neuroprotective activity in a transient middle cerebral artery occlusion (t-MCAO) model. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.10.046
• 作为产物：
  描述：

  3-(2-羧基苯基)丙酸 在 硫酸 、 氨 、 sodium hydride 、 氯化铵 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 504000.67h， 生成 4,5-dihydro-2H-benzazepine-1,3-dione
  参考文献：
  名称：

  Synthesis, SAR studies, and evaluation of 1,4-benzoxazepine derivatives as selective 5-HT1A receptor agonists with neuroprotective effect: Discovery of Piclozotan

  摘要：

  A new series of 1,4-benzoxazepine derivatives was designed, synthesized, and evaluated for binding to 5-HT1A receptor and cerebral anti-ischemic effect. A lot of compounds exhibited nanomolar affinity for 5-HT1A receptor with good selectivity over both dopamine D, and alpha(1)-adrenergic receptors. Among these compounds, 3-chloro-4-[4-[4-(2-pyridinyl)-1,2,3,6-tetrahydropyridin-1-y]butyl]-1, 4-benzoxazepin-5(4H)-one (50: SUN N4057 (Piclozotan) as 2HCl salt) showed remarkable neuroprotective activity in a transient middle cerebral artery occlusion (t-MCAO) model. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.10.046

文献信息

• Synthesis and Reactivity of Ortho-Palladated 3-Phenylpropanamides. Insertion of CO, XyNC, and Alkynes into the Pd–C Bond. Synthesis of Seven- and Nine-Membered Palladacycles and Benzazepine- and Benzazonine-Based Heterocycles
  作者：Roberto Frutos-Pedreño、Pablo González-Herrero、José Vicente、Peter G. Jones

  DOI：10.1021/om4000192

  日期：2013.3.25

  Aryl palladium complexes [PdC6H4(CH2)2C(O)NRR′)-2}I(tmeda)] [NRR′ = NH2 (1a), NHMe (1b), NMe2 (1c); tmeda = N,N,N′,N′-tetramethylethylenediamine] are prepared by oxidative addition of the corresponding 3-(2-iodophenyl)propanamides to “Pd(dba)2” ([Pd2(dba)3]·dba; dba = dibenzylideneacetone) in the presence of tmeda. The cationic seven-membered palladacycles [Pdκ2C,O-C6H4(CH2)2C(O)NRR′)-2}(tmeda)]TfO

  芳基钯络合物[Pd C 6 H 4（CH 2）2 C（O）NRR'）-2} I（tmeda）] [NRR'= NH 2（1a），NHMe（1b），NMe 2（1c） ; 通过将相应的3-（2-碘苯基）丙酰胺氧化加成到“ Pd（dba）2 ”（[Pd 2（dba）3 ]·dba中，制备tmeda ＝N，N，N ′，N′-四甲基乙二胺）。在tmeda存在下dba =二亚苄基丙酮）。阳离子7元钯环[钯κ 2 Ç，Ò-C 6 H 4（CH 2）2 C（O）NRR'）-2}（tmeda）] TfO（2a – c）是通过1a – c与AgTfO反应获得的。类型[钯κ的中性配合物酰胺化物2 Ç，Ñ -C 6 ħ 4（CH 2）2 C（O）NR）-2}（TMEDA）] [R = H（图3a）中，Me（图3b）]通过用KO t Bu使1a或1b中的酰胺官能团去质子化而获得。1a的反应在室温下用CO生成稳定的酰基衍生物[Pd
• Condensed heterocyclic compounds and psychopharmaceutical composition
  申请人：Suntory Limited

  公开号：US05158947A1

  公开（公告）日：1992-10-27

  A condensed heterocyclic compound having the formula (I): ##STR1## wherein A and B are both carbonyl groups of one thereof represents a methylene group and the other represents a carbonyl group; Z represents an oxygen atom, a sulfur atom, a substituted or unsubstituted nitrogen atom, or a methylene group; n is an integer of 2 to 6; and R represents a group having the following formula: ##STR2## wherein R.sup.1 represents a hydrogen atom or a hydroxyl group; R.sup.2 represents a substituted or unsubstituted phenyl or 2-pyridyl group or salts thereof. The compounds according to the present invention exhibit a strong affinity to the .sigma.-receptor and are useful as psychopharmaceuticals.

  一种具有以下式子（I）的浓缩杂环化合物：##STR1## 其中A和B都是一个羰基基团，其中一个代表一个亚甲基基团，另一个代表一个羰基基团；Z代表氧原子，硫原子，取代或未取代的氮原子或亚甲基基团；n为2到6的整数；R代表具有以下式子的基团：##STR2## 其中，R.sup.1代表氢原子或羟基；R.sup.2代表取代或未取代的苯基或2-吡啶基或其盐。本发明的化合物具有对σ-受体的强亲和力，可用作精神药物。
• Fused 7-membered cyclic compound and antipsychotic preparation
  申请人：Suntory Limited

  公开号：US05312625A1

  公开（公告）日：1994-05-17

  A therapeutically effective antipsychotic preparation comprising a fused cyclic compound for the treatment of diseases involving the serotonergic pathway having the formula (I) or salts thereof: ##STR1## wherein both of A and B are carbonyl groups, or one represents a methylene group and the other a carbonyl group, Z represents a sulfur atom, or a nitrogen atom which may be substituted, or a methylene group, R represents an aromatic or heterocylcic group, which may be substituted, X represents a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.5 lower alkyl group, a C.sub.1 -C.sub.5 lower alkoxy group, a C.sub.7 -C.sub.9 arylalkoxy group, a C.sub.1 -C.sub.5 lower acyloxy group, a C.sub.7 -C.sub.10 arylcarbonyloxy group, a hydroxy group, a nitro group or an ester group, and n is an integer of 2 to 10.

  一种治疗涉及血清素通路疾病的疗效良好的抗精神病制剂，包括具有公式（I）或其盐的融合环化合物： ##STR1## 其中A和B均为羰基基团，或者一个表示亚甲基基团，另一个表示羰基基团，Z表示硫原子，或者可被取代的氮原子或亚甲基基团，R表示芳香或杂环基团，可被取代，X表示氢原子、卤原子、C.sub.1-C.sub.5低碳基、C.sub.1-C.sub.5低烷氧基、C.sub.7-C.sub.9芳基烷氧基、C.sub.1-C.sub.5低酰氧基、C.sub.7-C.sub.10芳基羰基氧基、羟基、硝基或酯基，n为2至10的整数。
• Heterocyclic compound and psychopharmaceutical composition containing same
  申请人：SUNTORY LIMITED

  公开号：EP0463810A1

  公开（公告）日：1992-01-02

  A condensed heterocyclic compound having the formula (I): wherein A and B are both carbonyl groups or one thereof represents a methylene group and the other represents a carbonyl group; Z represents an oxygen atom, a sulfur atom, a substituted or unsubstituted nitrogen atom, or a methylene group; n is an integer of 2 to 6; and R represents a group having the following formula: wherein R¹ represents a hydrogen atom or a hydroxyl group; R² represents a substituted or unsubstituted phenyl or 2-pyridyl group or salts thereof. The compounds exhibit a strong affinity to the σ-receptor and are useful as psychopharmaceuticals.

  具有式 (I) 的缩合杂环化合物： 其中 A 和 B 都是羰基，或其中一个代表亚甲基，另一个代表羰基；Z 代表氧原子、硫原子、取代或未取代的氮原子或亚甲基；n 是 2 到 6 的整数；R 代表具有下式的基团： 其中 R¹ 代表氢原子或羟基；R² 代表取代或未取代的苯基或 2-吡啶基或其盐类。 这些化合物对 σ 受体有很强的亲和力，可用作精神药物。
• Fused 7-membered cyclic compound and antipsychotic preparation containing the same
  申请人：SUNTORY LIMITED

  公开号：EP0444924B1

  公开（公告）日：1996-01-03