(5-氯-2-(二甲氨基)苯基)(苯基)甲酮 | 23751-99-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (5-氯-2-(二甲氨基)苯基)(苯基)甲酮
• 英文名称: (5-chloro-2-(dimethylamino)phenyl)(phenyl)methanone
• 英文别名: [5-Chloro-2-(dimethylamino)phenyl](phenyl)methanone；[5-chloro-2-(dimethylamino)phenyl]-phenylmethanone
• CAS: 23751-99-7
• 化学式: C₁₅H₁₄ClNO
• 分子量: 259.735
• InChiKey: LAQBFAVTSZKGBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• 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：

  (5-氯-2-(二甲氨基)苯基)(苯基)甲酮 在 lithium aluminium tetrahydride 、 2-异丁吲哚丁醇 作用下， 以 乙醚 为溶剂， 反应 0.5h， 以86%的产率得到(R)-(5-Chloro-2-dimethylamino-phenyl)-phenyl-methanol
  参考文献：
  名称：

  Synthesis of chiral alcohols by asymmetric reductions of various ketones including α-aminophenones

  摘要：

  LiAlH4 previously treated with 2.5 equiv. of (S)-(+) or (R)-(-)-2-(2-isoindolinyl)butan-1-ol 1 reduced the six alpha-aminophenones 4-9 into the corresponding optically active beta-aminoalcohols 10-15 whose ee's were in the range 40-97% after chromatography and recrystallization. The asymmetric reduction of the ortho-dimethylaminobenzophenone 18, using the same reducing agents afforded the enantiomerically pure benzhydrols (R)-(-)-19 and (S)-(+)-19, respectively, and in 86-100% yields. The ortho-aminobenzhydrol (S)-(+)-20 and a-fluorenyl ethanol (R)-(+)-23 and (S)-(-)-23 were similarly obtained from the corresponding ketones 17 and 25, respectively. The latter carbinols were obtained in an enantiomerically pure state after recrystallization. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00245-5
• 作为产物：
  描述：

  地西泮 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 600.0h， 生成 (5-氯-2-(二甲氨基)苯基)(苯基)甲酮
  参考文献：
  名称：

  地西epa和阿普唑仑水解和光降解的动力学和机理研究

  摘要：

  通常报道相应的邻氨基二苯甲酮是1，4-苯并二氮杂酮水解中的主要降解产物。然而，在先前在酸性水性介质中地西epa（DZ）的研究中，我们分离并表征了七个意外的降解产物。在几种反应条件下的动力学测量为发生的复杂反应的机理提供了一些启示，光化学研究为氯化和脱核过程的机理提供了提示。阿普唑仑（AL）在多种条件下似乎表现出极高的抗水解稳定性。然而，该结构对光解裂解敏感。AL的光降解在水溶液和甲醇溶液中进行了研究。通过1 H和13 C NMR和质谱对分离出的产物进行表征，结果表明发生了电子转移，氧化和重排反应。研究了pH，溶剂组成和光辐照等几个变量的影响，并提出了形成三种光产物的机理。开发了一种在光产物存在下测定AL的特定方法，该方法可以动力学测定AL的光稳定性。在某些接受AL治疗的患者中观察到的光敏性似乎归因于特征化的光产物之一。版权所有©2004 John Wiley＆Sons，Ltd.

  DOI：

  10.1002/poc.861

文献信息

• Acid hydrolysis of diazepam. Kinetic study of the reactions of 2-(N-methylamino)-5-chlorobenzophenone, with HCl in MeOH–H2O
  作者：N. Sbarbati Nudelman、R.G. de Waisbaum

  DOI：10.1002/jps.2600840817

  日期：1995.8

  In the acid hydrolysis of diazepam (1), several unusual products, apart from 2-(N-methylamino)-5-chlorobenzophenone (2) and glycine, were isolated. On the assumption that some of those products could arise from further degradation of 2, the reaction of this compound with 0.5-2 M HCl was studied, in 1:1 MeOH-H2O, at 60 and 80 degrees C. Several unexpected products were isolated from the reaction of 2

  在地西epa（1）的酸水解中，除了2-（N-甲基氨基）-5-氯二苯甲酮（2）和甘氨酸之外，还分离了几种不寻常的产物。假设其中一些产物可能是由于2的进一步降解而产生的，在60和80摄氏度下于1：1 MeOH-H2O中研究了该化合物与0.5-2 M HCl的反应。由2与HCl的反应，即2-氨基-5-氯二苯甲酮（3），2-（N，N-二甲基氨基）-5-氯二苯甲酮（4），2-（N-甲基氨基）-3,5-二氯二苯甲酮（5），2-氨基-3,5-二氯二苯甲酮（6），2,4-二氯-10-甲基-9,10- cri啶酮（7）和2,4-二氯-9,10-ac啶酮（ 8）。在当前反应条件下，产生产物3-8的甲基转移，氯化和环化反应是出乎意料的。反应速度为2
• Richter; Kasbohm; Besch, Pharmazie, 1992, vol. 47, # 10, p. 758 - 764
  作者：Richter、Kasbohm、Besch、Hagen

  DOI：——

  日期：——
• Asymmetric Synthesis of 1,3-Diamines by Diastereoselective Reduction of Enantiopure <i>N</i>-<i>tert</i>-Butanesulfinylketimines: Unusual Directing Effects of the <i>ortho</i>-Substituent
  作者：Marina Martjuga、Dmitry Shabashov、Sergey Belyakov、Edvards Liepinsh、Edgars Suna

  DOI：10.1021/jo100173f

  日期：2010.4.2

  Chiral, nonracemic 1,3-diamines were prepared in a highly diastereoselective reduction of diaryl N-tert-butanesulfinylketimines. Correlation between Facial selectivity of the reduction and E or Z geometry of the starting ketimines suggests involvement of a cyclic transition state for the reduction. The ortho-substituent controls the geometry of N-tert-butanesulfinylketimines in the solid state and provides additional stabilization of the cyclic transition state.
• Mechanism of Alkaline Hydrolysis of Diazepam
  作者：Shen K. Yang

  DOI：10.1002/jccs.199800044

  日期：1998.4

  AbstractDiazepam (1) is a frequently prescribed hypnotic/anxiolytic drug in worldwide use. Compound 1 is hydrolyzed in alkaline medium to form 2‐methylamino‐5‐chlorobenzophenone imine (2) and 2‐methylamino‐5‐chlorobenzophenone (3); the ratio of 2:3 increases with increasing NaOH concentration (J. Pharm. Sci. 85, 745–748, 1996). The mechanism in the conversion of 1 to 2 and 3 via various intermediates is the subject of this report. Results of hydrolysis kinetics and structural identification of some intermediate products indicated an initial hydroxide attack at the C2‐carbonyl carbon of 1, resulting in the formation of a dioxide (7, 7‐chloro‐1,3‐dihydro‐1‐methyl‐5‐phenyl‐2H‐1,4‐benzodiazepin‐2,2‐dioxide). Compound 7 was characterized by proton NMR spectroscopy and via its monomethyl ether (8, 7‐chloro‐1,3‐dihydro‐2‐hydroxy‐2‐methoxy‐l‐methyl‐5‐pheny]‐2H‐1,4‐benzodiazepine). The seven‐member diazepine ring of 7 opened at the N1‐C2 bond to form a glycinate [5, 2‐methylamino‐5‐chloro‐α‐(phenylhenzylidene)glycinate]. Compound 7 (and/or 5) underwent an additional hydroxide attack at the C5‐N4 imine bond to form a tetrahedral intermediate, which decomposed to form 2 and 3.
• KINETIC STUDY OF THE REACTIONS OF2-AMINO-5-CHLOROBENZOPHENONE WITH HCl in MeOH-H2O
  作者：N. Sbarbati Nudelman、R. G. de Waisbaum

  DOI：10.1002/(sici)1099-1395(199702)10:2<97::aid-poc865>3.0.co;2-w

  日期：1997.2