6-methyl-5,6-dihydrodibenzo[b,e]azepin-11-one | 1143-51-7

• 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: 6-methyl-5,6-dihydrodibenzo[b,e]azepin-11-one
• 英文别名: 5-methyl-5,6-dihydro-dibenzo[b,e]azepin-11-one；5-methyl-5,6-dihydro-dibenz[b,e]azepin-11-one；5-Methyl-5,6-dihydro-dibenz[b,e]azepin-11-on；5-methyl-5,6-dihydro-5H-dibenz[b,e]azepin-11-one；5-Methyl-11-oxo-5,6-dihydro-morphanthridin；5-Methyl-5,6-dihydro-11-morphanthridon；5,6-Dihydro-5-methyl-11-oxodibenz[b,e]azepine；5-methyl-6H-benzo[c][1]benzazepin-11-one
• CAS: 1143-51-7
• 化学式: C₁₅H₁₃NO
• 分子量: 223.274
• InChiKey: DHZDMAALTXUBHX-UHFFFAOYSA-N

物化性质

• 熔点：
  143-146 °C
• 沸点：
  399.0±41.0 °C(Predicted)
• 密度：
  1.166±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-methyl-5,6-dihydrodibenzo[b,e]azepin-11-one 、 N,N-二甲基-1,3-二氨基丙烷 在 六甲基磷酰三胺 、 四氯化钛 作用下， 以 苯 为溶剂， 反应 144.0h， 以70%的产率得到N,N-Dimethyl-N'-[5-methyl-5,6-dihydro-dibenzo[b,e]azepin-(11Z)-ylidene]-propane-1,3-diamine
  参考文献：
  名称：

  Imine analogs of tricyclic antidepressants

  摘要：

  Analogues of tricyclic antidepressants were synthesized in which the alpha-carbon of the side chain was replaced by nitrogen. The antidepressant activity of these imines, as measured by the reversal of the effects of tetrabenazine in mice, showed a structure-activity relationship similar to that of the carbon analogues. The most active imine (19) was six times as potent as amitriptyline. Some of the compounds differed from amitriptyline in that they produced stimulation in mice.

  DOI：

  10.1021/jm00135a018
• 作为产物：
  描述：

  2-(methoxymethyl)benzonitrile 在 氯仿 、 氢溴酸 作用下， 生成 6-methyl-5,6-dihydrodibenzo[b,e]azepin-11-one
  参考文献：
  名称：

  Wittig et al., Justus Liebigs Annalen der Chemie, 1955, vol. 594, p. 89,111

  摘要：

  DOI：

文献信息

• Heterocyclic compounds
  申请人：Novo Nordisk A/S

  公开号：US05716949A1

  公开（公告）日：1998-02-10

  The present invention relates to novel N-substituted azaheterocyclic carboxylic acids and esters thereof in which a substituted alkyl chain forms part of the N-substituent or salts thereof, to methods for their preparation, to compositions containing them, and to their use for the clinical treatment of painful, hyperalgesic and/or inflammatory conditions in which C-fibers play a pathophysiological role by eliciting neurogenic pain or inflammation.

  本发明涉及新颖的N-取代的杂环羧酸和其酯，其中取代的烷基链构成N-取代基的一部分或其盐，以及它们的制备方法、含有它们的组合物，以及它们用于治疗临床上与C-纤维在诱发神经源性疼痛或炎症中发挥病理生理作用的疼痛、高痛敏和/或炎症条件的用途。
• Synthesis of Dibenzo[<i>b,e</i>]azepin-11-ones by Intramolecular Palladium-Catalyzed Acylation of Aryliodides with Aldehydes
  作者：Daniel Solé、Francesco Mariani

  DOI：10.1021/jo4009244

  日期：2013.8.16

  The paper describes an efficient methodology for the synthesis of diversely functionalized dihydrodibenzo[b,e]azepin-11-ones based on the Pd(0)-catalyzed intramolecular acylation of aryl iodides with aldehydes.

  本文介绍了一种有效的方法，用于基于Pd（0）催化的芳基碘化物与醛的分子内酰化反应，合成功能多样的二氢二苯并[ b，e ] azepin-11-ones。
• A Parham cyclization approach to diaryl-fused seven-membered ring heterocyclic ketones
  作者：John Farrokh、Catherine Campos、David A. Hunt

  DOI：10.1016/j.tetlet.2015.07.043

  日期：2015.9

  described. This work describes a novel synthesis route to diaryl-fused seven membered heterocyclic ketones through the generation of functionalized aryllithiums by bromine–lithium exchange, followed by intramolecular cyclization onto an electrophilic nitrile functional group. The resulting N-lithioimine can then be hydrolyzed to the desired ketone, generally in good yields. The order of addition of

  芳基稠合的七元杂环骨架出现在各种药学上相关的化合物中。但是，仅描述了很少的制备方法。这项工作描述了一种新颖的合成路线，该路线是通过溴-锂交换生成官能化的芳基锂，然后分子内环化成亲电子腈官能团，从而生成二芳基稠合的七元杂环酮的新型合成途径。然后可以通常以高收率将所得的N-硫代亚氨基亚胺水解成所需的酮。正丁基锂的添加顺序对于该方法至关重要，事实证明，反向添加可以减轻副产物的形成并提高产率。
• 11-Oxodibenz(b,e)azepines
  申请人：Teikoku Hormone Mfg. Co., Ltd.

  公开号：US04230703A1

  公开（公告）日：1980-10-28

  Compounds of the general formula ##STR1## or their salts, esters or amide derivatives; and processes for their preparation. In the formula, R.sub.O represents hydrogen or lower alkyl, R.sub.2 represents hydrogen, halogen or nitro, R.sub.3 represents hydrogen or halogen, and R.sub.4 represents hydrogen or lower alkyl; and when R.sub.O is hydrogen, R.sub.2, R.sub.3 and R.sub.4 are all hydrogens and the group ##STR2## is present at the 2-position. These compounds exhibit superior analgesic and/or anti-inflammatory actions with little gastrointestinal troubles.

  通式为##STR1##的化合物或其盐、酯或酰胺衍生物；以及它们的制备方法。在该式中，R.sub.O代表氢或低碳基，R.sub.2代表氢、卤素或硝基，R.sub.3代表氢或卤素，R.sub.4代表氢或低碳基；当R.sub.O为氢时，R.sub.2、R.sub.3和R.sub.4都为氢，且在2位存在##STR2##基团。这些化合物表现出卓越的止痛和/或抗炎作用，且几乎不会引起胃肠道问题。
• HETEROCYCLIC COMPOUNDS FOR USE IN THE TREATMENT OF NEUROGENIC INFLAMMATION
  申请人：NOVO NORDISK A/S

  公开号：EP0869954B1

  公开（公告）日：2001-09-19