5-[3-(二甲基氨基)丙基]-5,10-二氢-11H-二苯并[b,e][1,4]二氮杂卓-11-酮 | 13450-72-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 中文名称: 5-[3-(二甲基氨基)丙基]-5,10-二氢-11H-二苯并[b,e][1,4]二氮杂卓-11-酮
• 英文名称: 5-(3-(dimethylamino)propyl)-5H-dibenzo[b,e][1,4]diazepin-11(10H)-one
• 英文别名: 5-(3-dimethylamino-propyl)-5,10-dihydro-dibenzo[b,e][1,4]diazepin-11-one；5-<3-Dimethylamino-propyl>-10.11-dihydro-5H-dibenzo<1.4>diazepinon-(11)；5-<3-Dimethylamino-propyl>-11-oxo-10.11-dihydro-5H-dibenzo<1.4>diazepin；5-(3-Dimethylaminopropyl)-5,10-dihydro-11H-dibenzo-<1,4>-diazepin-on-(11)；5-<3-Dimethylamino-propyl>-11-oxo-10.11-dihydro-5H-dibenzo-1.4-diazepin；5-(3-Dimethylaminopropyl)-5,10-dihydro-11H-dibenzo-<1,4>-diazepin-11-on；5-(3-(Dimethylamino)propyl)-5,10-dihydro-11H-dibenzo(b,e)(1,4)diazepin-11-one；11-[3-(dimethylamino)propyl]-5H-benzo[b][1,4]benzodiazepin-6-one
• CAS: 13450-72-1
• 化学式: C₁₈H₂₁N₃O
• 分子量: 295.384
• InChiKey: SUKRRJYMPHOCIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  35.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为产物：
  描述：

  N,N-二甲基-1,3-二氨基丙烷 、 2-bromo-N-(2-bromophenyl)benzamide 在 potassium phosphate 、 1,10-菲罗啉 、 copper(l) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以80%的产率得到5-[3-(二甲基氨基)丙基]-5,10-二氢-11H-二苯并[b,e][1,4]二氮杂卓-11-酮
  参考文献：
  名称：

  The N-Aryl Aminocarbonyl ortho-Substituent Effect in Cu-Catalyzed Aryl Amination and Its Application in the Synthesis of 5-Substituted 11-Oxo-dibenzodiazepines

  摘要：

  Double amination of ortho-substituted aryl bromides proceeded under mild conditions to afford 5-substituted 11-oxo-dibenzodiazepines, which revealed that there is a strong ortho-substituent effect caused by N-aryl aminocarbonyl groups during copper-catalyzed aryl amination.

  DOI：

  10.1021/ol202721h

文献信息

• Tricyclic compounds as selective antimuscarinics. 1. Structural requirements for selectivity towards the muscarinic acetylcholine receptor in a series of pirenzepine and imipramine analogs
  作者：Wolfgang G. Eberlein、Guenter Trummlitz、Wolfhard W. Engel、Guenther Schmidt、Helmut Pelzer、Norbert Mayer

  DOI：10.1021/jm00391a019

  日期：1987.8

  The M1-selective antiulcer drug pirenzepine (1) is a tricyclic compound with close resemblance to tricyclic psychotropic agents such as imipramine (2). Despite this fact, pirenzepine is devoid of any psychotropic effects, exhibiting measurable antagonistic effects in biochemical assays and receptor binding studies only toward the muscarinic receptor system. To understand how different groups in these tricyclic molecules affect binding affinities, a set of nine compounds structurally related to pirenzepine (1) and imipramine (2) has been selected for analysis, comprising three different tricycles and three different side chains. The compounds were tested for their affinity to the imipramine and muscarinic receptors in homogenized rat cortex tissue. The result of these studies suggests that it is the nature and placement of accessory groups that determine the differences in receptor recognition and the binding process. In the case of pirenzepine (1), preferential binding toward the muscarinic receptor is brought about by the endocyclic amide group, by the positioning of the protonated N atom of the side chain, and to a minor extent by the exocyclic amide group. From these findings a putative model for the explanation of selective binding of pirenzepine (1) to the muscarinic receptor has been derived.
• EBERLEIN, W. G.;TRUMMLITZ, G.;ENGEL, W. W.;SCHMIDT, G.;PELZER, H.;MAYER, +, J. MED. CHEM., 30,(1987) N 8, 1378-1382
  作者：EBERLEIN, W. G.、TRUMMLITZ, G.、ENGEL, W. W.、SCHMIDT, G.、PELZER, H.、MAYER, +

  DOI：——

  日期：——
• The <i>N</i>-Aryl Aminocarbonyl <i>ortho</i>-Substituent Effect in Cu-Catalyzed Aryl Amination and Its Application in the Synthesis of 5-Substituted 11-Oxo-dibenzodiazepines
  作者：Xiaoqiong Diao、Lanting Xu、Wei Zhu、Yongwen Jiang、Haoyang Wang、Yinlong Guo、Dawei Ma

  DOI：10.1021/ol202721h

  日期：2011.12.16

  Double amination of ortho-substituted aryl bromides proceeded under mild conditions to afford 5-substituted 11-oxo-dibenzodiazepines, which revealed that there is a strong ortho-substituent effect caused by N-aryl aminocarbonyl groups during copper-catalyzed aryl amination.