1,2-Dihydro-1-isopropyl-2-oxo-5-phenyl-7-chlor-3H-1,4-benzodiazepin | 17615-40-6

• 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: 1,2-Dihydro-1-isopropyl-2-oxo-5-phenyl-7-chlor-3H-1,4-benzodiazepin
• 英文别名: 7-chloro-1-isopropyl-5-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one；7-Chloro-1-isopropyl-5-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one；7-chloro-5-phenyl-1-propan-2-yl-3H-1,4-benzodiazepin-2-one
• CAS: 17615-40-6
• 化学式: C₁₈H₁₇ClN₂O
• 分子量: 312.799
• InChiKey: YAUYJWXVCCYSJT-UHFFFAOYSA-N

物化性质

• 沸点：
  506.4±50.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2-Dihydro-1-isopropyl-2-oxo-5-phenyl-7-chlor-3H-1,4-benzodiazepin 在 十二羰基三钌 、 C₁₀H₁₆ClNO₂S 、 1,3-双(2,4,6-三甲基苯基)氯化咪唑 、 [双(三氟乙酰氧基)碘]苯 作用下， 反应 48.0h， 以36%的产率得到7-chloro-5-(3-chlorophenyl)-1-isopropyl-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one
  参考文献：
  名称：

  使用N -chloro-2,10-camphorsultam †的 配体促进的钌催化的芳烃的间位C–H氯化氯化物†

  摘要：

  一种实用的元C-H氯化协议建立经由一个钌（0） -催化的邻-metalation策略。使用Ñ氯2,10-樟脑磺内作为新的氯化剂是用于当前反应和N-杂环卡宾（NHC）的成功是至关重要的配体可以显著增强催化转化的反应性。机理研究表明，可能涉及一个不寻常的带有C-Ru键的邻位氯化的邻位C-H钌接替过程。

  DOI：

  10.1039/c8cc03195a
• 作为产物：
  描述：

  三氟甲磺酸异丙酯 、 去甲西泮 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.67h， 以55%的产率得到1,2-Dihydro-1-isopropyl-2-oxo-5-phenyl-7-chlor-3H-1,4-benzodiazepin
  参考文献：
  名称：

  Enantioselective Synthesis of “Quaternary” 1,4-Benzodiazepin-2-one Scaffolds via Memory of Chirality

  摘要：

  Glycine-derived 1,4-benzodiazepine-2-ones such as diazepam are chiral by virtue of the boat-shaped conformation of the diazepine ring and exist as a racemic mixture of conformational enantiomers. However, the presence of a chiral center at C-3 of the benzodiazepine perturbs this equilibrium and preferentially stabilizes one ring conformer. We report that N-i-Pr 1,4-benzodiazepine-2-ones derived from (S)-Ala and (S)-Phe can be deprotonated and alkylated in 86-99% ee, despite the fact that the original chiral center is destroyed in the deprotonation step. We attribute this highly enantioselective alkylation to the chiral memory of the benzodiazepine ring. This protocol provides easy access to the previously unexplored "quaternary" 1,4-benzodiazepine-2-ones.

  DOI：

  10.1021/ja0365781

文献信息

• Novel benzo-fused heterocycles as endothelin antagonisits
  申请人：Bolli Martin

  公开号：US20050124605A1

  公开（公告）日：2005-06-09

  The invention relates to novel benzo-fused heterocycles and their use as active ingredients in the preparation of pharmaceutical compositions. The invention also concerns related aspects including processes for the preparation of the compounds, pharmaceutical compositions containing one or more of those compounds and especially their use as endothelin receptor antagonists.

  本发明涉及新型苯并杂环化合物及其用作制备药物组成物的活性成分。本发明还涉及相关方面，包括制备化合物的过程，含有其中一种或多种化合物的药物组成物，特别是它们作为内皮素受体拮抗剂的用途。
• METHODS AND COMPOSITIONS FOR INTERFERING WITH EXTRACTION OR CONVERSION OF A DRUG SUSCEPTIBLE TO ABUSE
  申请人：Acura Pharmaceuticals, Inc.

  公开号：EP3151819B1

  公开（公告）日：2020-08-05
• US7238685B2
  申请人：——

  公开号：US7238685B2

  公开（公告）日：2007-07-03
• [EN] NOVEL BENZO-FUSED HETEROCYCLES AS ENDOTHELIN ANTAGONISITS<br/>[FR] HETEROCYCLES A FUSION BENZO UTILISES COMME ANTAGONISTES VIS-A-VIS DE L'ENDOTHELINE
  申请人：ACTELION PHARMACEUTICALS LTD

  公开号：WO2003013545A1

  公开（公告）日：2003-02-20

  The invention relates to novel benzo-fused heterocycles of structure (I) and their use as active ingredients in the preparation of pharmaceutical compositions. The invention also concerns related aspects including processes for the preparation of the compounds, pharmaceutical compositions containing one or more of those compounds and especially their use as endothelin receptor antagonists. Formula (I)
• Enantioselective Synthesis of “Quaternary” 1,4-Benzodiazepin-2-one Scaffolds via Memory of Chirality
  作者：Paul R. Carlier、Hongwu Zhao、Joe DeGuzman、Polo C.-H. Lam

  DOI：10.1021/ja0365781

  日期：2003.9.1

  Glycine-derived 1,4-benzodiazepine-2-ones such as diazepam are chiral by virtue of the boat-shaped conformation of the diazepine ring and exist as a racemic mixture of conformational enantiomers. However, the presence of a chiral center at C-3 of the benzodiazepine perturbs this equilibrium and preferentially stabilizes one ring conformer. We report that N-i-Pr 1,4-benzodiazepine-2-ones derived from (S)-Ala and (S)-Phe can be deprotonated and alkylated in 86-99% ee, despite the fact that the original chiral center is destroyed in the deprotonation step. We attribute this highly enantioselective alkylation to the chiral memory of the benzodiazepine ring. This protocol provides easy access to the previously unexplored "quaternary" 1,4-benzodiazepine-2-ones.