4-(4-bromo-phenyl)-1,3-dihydro-benzo[b][1,4]diazepin-2-one | 66752-04-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: 4-(4-bromo-phenyl)-1,3-dihydro-benzo[b][1,4]diazepin-2-one
• 英文别名: 4-(4-Bromophenyl)-1,3-dihydro-1,5-benzodiazepin-2-one
• CAS: 66752-04-3
• 化学式: C₁₅H₁₁BrN₂O
• 分子量: 315.169
• InChiKey: KGABHJWOOLJQKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(4-bromo-phenyl)-1,3-dihydro-benzo[b][1,4]diazepin-2-one 在 (3R,5S)-5-(hydroxydiphenylmethyl)-1-picolinoylpyrrolidin-3-yl pivalate 、 三氯硅烷 、 caesium carbonate 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (S)-1-benzyl-4-(4-bromophenyl)-4,5-dihydro-1H-benzo[b][1,4]diazepin-2(3H)-one
  参考文献：
  名称：

  Enantioselective Synthesis of 4-Substituted 4,5-Dihydro-1H-[1,5]benzodiazepin-2(3H)-ones by the Lewis Base-Catalyzed Hydrosilylation

  摘要：

  Enantioselective synthesis of 4-substituted 4,5-dihydro-1H-[1,5]benzodiazepin-2(3H)-ones has been accomplished through chiral Lewis base-catalyzed hydrosilylation. The corresponding products were obtained in excellent yields (up to 99%) and enantioselectivities (up to 98%). The absolute configuration of product 3n has been determined as S by X-ray crystallographic analysis.

  DOI：

  10.1021/jo201334n
• 作为产物：
  描述：

  5-(4-溴苯基)呋喃-2,3-二酮 以 苯 为溶剂， 反应 2.5h， 生成 4-(4-bromo-phenyl)-1,3-dihydro-benzo[b][1,4]diazepin-2-one
  参考文献：
  名称：

  Andreichikov, Yu. S.; Gein, V. L.; Kozlov, A. P., Journal of Organic Chemistry USSR (English Translation), 1988, vol. 24, p. 189 - 194

  摘要：

  DOI：

文献信息

• Asymmetric Hydrogenation of Cyclic Imines of Benzoazepines and Benzodiazepines with Chiral, Cationic Ruthenium-Diamine Catalysts
  作者：Zhusheng Yang、Ziyuan Ding、Fei Chen、Yan-Mei He、Nianfa Yang、Qing-Hua Fan

  DOI：10.1002/ejoc.201700236

  日期：2017.4.10

  The title hydrogenation reaction is achieved in the presence of phosphine‐free, chiral, cationic ruthenium–diamine complexes and provides facile access to various chiral seven‐membered N‐containing heterocycles. A reversal of enantioselectivity is observed simply by changing the achiral counteranion of the catalyst.

  标题氢化反应是在无膦，手性，阳离子钌-二胺配合物存在下完成的，可轻松接近各种手性七元含氮杂环。简单地通过改变催化剂的非手性抗衡阴离子就可以观察到对映选择性的逆转。
• ANDREJCHIKOV, YU. S.;GEJN, V. L.;KOZLOV, A. P.;VINOKUROVA, O. V., ZH. ORGAN. XIMII, 24,(1988) N 1, 210-217
  作者：ANDREJCHIKOV, YU. S.、GEJN, V. L.、KOZLOV, A. P.、VINOKUROVA, O. V.

  DOI：——

  日期：——
• Andreichikov, Yu. S.; Gein, V. L.; Kozlov, A. P., Journal of Organic Chemistry USSR (English Translation), 1988, vol. 24, p. 189 - 194
  作者：Andreichikov, Yu. S.、Gein, V. L.、Kozlov, A. P.、Vinokurova, O. V.

  DOI：——

  日期：——
• Enantioselective Synthesis of 4-Substituted 4,5-Dihydro-1<i>H</i>-[1,5]benzodiazepin-2(3<i>H</i>)-ones by the Lewis Base-Catalyzed Hydrosilylation
  作者：Xing Chen、Yongsheng Zheng、Chang Shu、Weicheng Yuan、Bo Liu、Xiaomei Zhang

  DOI：10.1021/jo201334n

  日期：2011.11.4

  Enantioselective synthesis of 4-substituted 4,5-dihydro-1H-[1,5]benzodiazepin-2(3H)-ones has been accomplished through chiral Lewis base-catalyzed hydrosilylation. The corresponding products were obtained in excellent yields (up to 99%) and enantioselectivities (up to 98%). The absolute configuration of product 3n has been determined as S by X-ray crystallographic analysis.