4-phenyl-4,5-dihydro-1H-benzo[b][1,4]diazepin-2(3H)-one | 1261084-20-1

• 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-phenyl-4,5-dihydro-1H-benzo[b][1,4]diazepin-2(3H)-one
• 英文别名: (2S)-2-phenyl-1,2,3,5-tetrahydro-1,5-benzodiazepin-4-one
• CAS: 1261084-20-1
• 化学式: C₁₅H₁₄N₂O
• 分子量: 238.289
• InChiKey: BPBSKHLEGJWMBO-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,2-二氢-4(3H)-苯基-1,5-苯并二氮杂革-2-酮 在 (11bR)-N-(2,6-Di(naphthalen-2-yl)-4-oxido-8,9,10,11,12,13,14,15-octahydrodinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-yl)-1,1,1-trifluoromethanesulfonamide 、 diallyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate 作用下， 以 甲基叔丁基醚 为溶剂， 生成 4-phenyl-4,5-dihydro-1H-benzo[b][1,4]diazepin-2(3H)-one
  参考文献：
  名称：

  催化加氢首次高对映选择性合成苯并二氮杂酮

  摘要：

  已经开发出使用有效氢化方案的苯并二氮杂酮的第一催化对映选择性合成。以高收率获得相应的产物，具有优异的对映选择性和宽泛的官能团耐受性。此外，提出了一种一锅法，涉及原位生成苯并二氮杂-2-酮，然后进行不对称还原。

  DOI：

  10.1002/adsc.201000547

文献信息

• N-Heterocyclic Carbene-Catalyzed Enantioselective β-Amination of α-Bromoenals Enabled by a Proton-Shuttling Strategy
  作者：Ming Lang、Jian Wang

  DOI：10.1002/ejoc.201800648

  日期：2018.6.22

  An enantioselective NHC‐catalyzed β‐amination of α‐bromoenals has been established. This [4+3] annulation protocol allows the rapid assembly of 1,5‐benzodiazepine pharmacophores from simple and readily available starting materials under mild conditions.

  建立了对映选择性的NHC催化的α-溴烯醛的β-胺化反应。此[4 + 3]环空方案可在温和条件下从简单易用的起始原料中快速组装1,5-苯并二氮杂卓类药物。
• 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。
• Synthesis of new chiral amidophosphite ligands and their application in hydrogenation of benzodiazepinones and enamides
  作者：M. V. Sokolovskaya、S. E. Lyubimov、V. A. Davankov

  DOI：10.1007/s11172-017-1875-8

  日期：2017.7

  New chiral amidophosphites were synthesized and tested in the Ir-catalyzed hydrogenation of 4-substituted 1,3-dihydro-2H-1,5-benzodiazepin-2-ones and Rh-catalyzed hydrogenation of dehydro amino acid derivatives. The triphenylphosphine additive can considerably increase the enantioselectivity of both processes.

  合成了新的手性亚磷酸酰胺，并在 4-取代的 1,3-二氢-2H-1,5-苯并二氮杂-2-酮的 Ir 催化氢化和脱氢氨基酸衍生物的 Rh 催化氢化中进行了测试。三苯基膦添加剂可以显着提高两种工艺的对映选择性。
• Asymmetric Ir-catalyzed hydrogenation of 1,3-dihydro-2H-1,5-benzodiazepin-2-ones using phosphoramidites
  作者：M. V. Sokolovskaya、S. E. Lyubimov、I. S. Mikhel、K. P. Birin、V. A. Davankov

  DOI：10.1007/s11172-018-2068-9

  日期：2018.2

  A series of phosphoramidite ligands was tested in the asymmetric hydrogenation of 4-arylsubstituted 1,3-dihydro-2H-benzodiazepine-2-ones and up to 52% ee was achieved. The effects of various factors (solvents, hydrogen pressure, and addition of phosphine ligands) on the hydrogenation were studied.

  在 4-芳基取代的 1,3-二氢-2H-苯并二氮杂-2-酮的不对称氢化中测试了一系列亚磷酰胺配体，获得了高达 52% 的 ee。研究了各种因素（溶剂、氢气压力和膦配体的添加）对氢化的影响。
• First Highly Enantioselective Synthesis of Benzodiazepinones by Catalytic Hydrogenation
  作者：Magnus Rueping、Estíbaliz Merino、René M. Koenigs

  DOI：10.1002/adsc.201000547

  日期：2010.10.4

  The first catalytic enantioselective synthesis of benzodiazepinones employing an efficient hydrogenation protocol has been developed. The corresponding products are obtained in good yields, with excellent enantioselectivities and broad functional group tolerance. In addition, a one-pot procedure involving in situ generation of benzodiazepin-2-ones followed by asymmetric reduction is presented.

  已经开发出使用有效氢化方案的苯并二氮杂酮的第一催化对映选择性合成。以高收率获得相应的产物，具有优异的对映选择性和宽泛的官能团耐受性。此外，提出了一种一锅法，涉及原位生成苯并二氮杂-2-酮，然后进行不对称还原。