5-(Bromacetyl)-5H-dibenzazepin | 31552-96-2

• 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: 5-(Bromacetyl)-5H-dibenzazepin
• 英文别名: N-bromoacetyl-dibenzazepine；2-bromo-1-dibenzo[b,f]azepin-5-ylethanone；5-bromoacetyl-5H-dibenzo[b,f]azepine；5-Bromoacetyl-5h-dibenz(b,f)azepine；1-benzo[b][1]benzazepin-11-yl-2-bromoethanone
• CAS: 31552-96-2
• 化学式: C₁₆H₁₂BrNO
• 分子量: 314.181
• InChiKey: GSENZSJXBJBAIY-UHFFFAOYSA-N

物化性质

• 沸点：
  503.8±39.0 °C(Predicted)
• 密度：
  1.477±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-(Bromacetyl)-5H-dibenzazepin 在 一水合肼 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 N-(2-benzo[b][1]benzazepin-11-yl-2-oxoethyl)acetamide
  参考文献：
  名称：

  三环烷基酰胺为褪黑激素受体配体，具有拮抗或反向激动剂活性。

  摘要：

  这项工作报告了新型的烷基酰胺的设计和合成，其特征在于二苯并[a，d]环庚烯核是褪黑激素（MLT）受体配体。基于先前对MT1和MT2拮抗剂的定量结构活性研究，选择了三环支架，该研究将选择性MT2拮抗作用与MLT吲哚环平面之外的芳族取代基的存在相关。由于苯环的非共面排列，因此选择了一些二苯并七元结构，并引入了烷基酰胺链以满足MLT受体结合的要求，即在位置10处具有酰基氨基烷基侧链的二苯并环庚烯和在此侧具有二苯并氮杂源自氮原子的桥连两个苯环的链。通过2- [125I]碘弹性蛋白置换测定法测定对人克隆的MT1和MT2受体的结合亲和力，并通过GTPgammaS测试测定固有活性。大多数化合物的特征在于与MT1受体相比在MT2上具有更高的亲和力，并且固有活性值非常低，因此证实了两个芳香环的非共面排列对于选择性MT2拮抗作用的重要性。二苯并环庚烯通常显示出比二苯并氮杂finity更高的MT1和MT 2亲和力。N-（8-甲氧基-10

  DOI：

  10.1021/jm040768k
• 作为产物：
  描述：

  溴乙酰氯 、 亚氨基芪 以 1,2-二氯乙烷 为溶剂， 生成 5-(Bromacetyl)-5H-dibenzazepin
  参考文献：
  名称：

  Triplet energy transfer of the intramolecular system having benzophenone and dibenz[b,f]azepine at the chain ends: chain length dependence

  摘要：

  Intramolecular triplet-triplet energy transfer in a series of polymethylene chains having a benzophenone (BP) group as an energy donor and a dibenz[b,f]azepine (DBA) group as an energy acceptor (BP-O(CH2)nCO-DBA) has been studied by phosphorescence measurement and nanosecond laser photolysis. In a rigid solution and PMMA matrix, the quantum yield of triplet-triplet energy transfer is close to unity for the chain lengths shorter than n = 5. On the basis of the through-space mechanism of energy transfer, phosphorescence decay curves were analyzed by Dexter's equation in which the distribution of donor-acceptor distance was calculated by the conformational energy analysis. The results of the simulation were in fairly good agreement with the experimentally observed decay curves. The rate constant of triplet-triplet energy transfer is strongly dependent on the chain length, i.e., about one-tenth decrease per every methylene unit, and the rate is much smaller than that of singlet-singlet energy transfer.

  DOI：

  10.1021/j100162a009

文献信息

• Diehl, Klaus; Himbert, Gerhard, Chemische Berichte, 1986, vol. 119, # 9, p. 2874 - 2888
  作者：Diehl, Klaus、Himbert, Gerhard

  DOI：——

  日期：——
• Tricyclic Alkylamides as Melatonin Receptor Ligands with Antagonist or Inverse Agonist Activity
  作者：Valeria Lucini、Marilou Pannacci、Francesco Scaglione、Franco Fraschini、Sivia Rivara、Marco Mor、Fabrizio Bordi、Pier Vincenzo Plazzi、Gilberto Spadoni、Annalida Bedini、Giovanni Piersanti、Giuseppe Diamantini、Giorgio Tarzia

  DOI：10.1021/jm040768k

  日期：2004.8.1

  structures were thus selected because of the noncoplanar arrangement of their benzene rings, and an alkylamide chain was introduced to fit the requirements for MLT receptor binding, namely, dibenzocycloheptenes with an acylaminoalkyl side chain at position 10 and dibenzoazepines with this side chain originating from the nitrogen atom bridging the two phenyl rings. Binding affinity at human cloned MT1 and

  这项工作报告了新型的烷基酰胺的设计和合成，其特征在于二苯并[a，d]环庚烯核是褪黑激素（MLT）受体配体。基于先前对MT1和MT2拮抗剂的定量结构活性研究，选择了三环支架，该研究将选择性MT2拮抗作用与MLT吲哚环平面之外的芳族取代基的存在相关。由于苯环的非共面排列，因此选择了一些二苯并七元结构，并引入了烷基酰胺链以满足MLT受体结合的要求，即在位置10处具有酰基氨基烷基侧链的二苯并环庚烯和在此侧具有二苯并氮杂源自氮原子的桥连两个苯环的链。通过2- [125I]碘弹性蛋白置换测定法测定对人克隆的MT1和MT2受体的结合亲和力，并通过GTPgammaS测试测定固有活性。大多数化合物的特征在于与MT1受体相比在MT2上具有更高的亲和力，并且固有活性值非常低，因此证实了两个芳香环的非共面排列对于选择性MT2拮抗作用的重要性。二苯并环庚烯通常显示出比二苯并氮杂finity更高的MT1和MT 2亲和力。N-（8-甲氧基-10
• Triplet energy transfer of the intramolecular system having benzophenone and dibenz[b,f]azepine at the chain ends: chain length dependence
  作者：Hideaki Katayama、Shogo Maruyama、Shinzaburo Ito、Yoshinobu Tsujii、Akira Tsuchida、Masahide Yamamoto

  DOI：10.1021/j100162a009

  日期：1991.5

  Intramolecular triplet-triplet energy transfer in a series of polymethylene chains having a benzophenone (BP) group as an energy donor and a dibenz[b,f]azepine (DBA) group as an energy acceptor (BP-O(CH2)nCO-DBA) has been studied by phosphorescence measurement and nanosecond laser photolysis. In a rigid solution and PMMA matrix, the quantum yield of triplet-triplet energy transfer is close to unity for the chain lengths shorter than n = 5. On the basis of the through-space mechanism of energy transfer, phosphorescence decay curves were analyzed by Dexter's equation in which the distribution of donor-acceptor distance was calculated by the conformational energy analysis. The results of the simulation were in fairly good agreement with the experimentally observed decay curves. The rate constant of triplet-triplet energy transfer is strongly dependent on the chain length, i.e., about one-tenth decrease per every methylene unit, and the rate is much smaller than that of singlet-singlet energy transfer.