5-methyl-9-phenyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-2-one | 1310699-71-8

• 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: 5-methyl-9-phenyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-2-one
• 英文别名: 1-methyl-6-phenyl-3,5-dihydro-2H-1,5-benzodiazepin-4-one
• CAS: 1310699-71-8
• 化学式: C₁₆H₁₆N₂O
• 分子量: 252.316
• InChiKey: RWFQDMNUVGSJHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-methyl-9-phenyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-2-one 在 sodium hydride 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-(5-methyl-2-oxo-9-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-1-yl)-N-[(1S)-1-phenylethyl]acetamide
  参考文献：
  名称：

  Isolation and Characterization of Atropisomers of Seven-Membered-Ring Benzolactams

  摘要：

  The atropisomeric properties of seven-membered-ring benzolactams (7a-c and 8a) [1,5-benzodiazepin-2-one (a), 1,5-benzothiazepin-4-one (b), and 1-benzazepin-2-one (c)] were examined. The atropisomers were isolated as the diastereomers with an (S)-phenethylamide moiety, which were characterized by X-ray crystallography, and the barriers to their interconversion were clarified.

  DOI：

  10.1021/jo2008725
• 作为产物：
  描述：

  3-chloro-N-methyl-2-nitroaniline 在 tris-(dibenzylideneacetone)dipalladium(0) 、 磷酸 、 硫酸 、 potassium carbonate 、 锌 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 1,4-二氧六环 、 N,N-二甲基乙酰胺 、 水 为溶剂， 反应 17.0h， 生成 5-methyl-9-phenyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-2-one
  参考文献：
  名称：

  Isolation and Characterization of Atropisomers of Seven-Membered-Ring Benzolactams

  摘要：

  The atropisomeric properties of seven-membered-ring benzolactams (7a-c and 8a) [1,5-benzodiazepin-2-one (a), 1,5-benzothiazepin-4-one (b), and 1-benzazepin-2-one (c)] were examined. The atropisomers were isolated as the diastereomers with an (S)-phenethylamide moiety, which were characterized by X-ray crystallography, and the barriers to their interconversion were clarified.

  DOI：

  10.1021/jo2008725

文献信息

• Active Conformation of Seven-Membered-Ring Benzolactams as New ACAT Inhibitors: Latent Chirality at N5 in the 1,5-Benzodiazepin-2-one Nucleus
  作者：Hidetsugu Tabata、Naoya Wada、Yuko Takada、Jun Nakagomi、Tomohiro Miike、Hiroaki Shirahase、Tetsuta Oshitari、Hideyo Takahashi、Hideaki Natsugari

  DOI：10.1002/chem.201103264

  日期：2012.2.6

  Nitrogen chirality: Potent new ACAT inhibitors with seven‐membered‐ring benzolactams as the core structures were first prepared, and the axial chirality recognized by the enzyme was clarified (e.g., 1; see scheme). The chirality at the axis (aS) of 1 controls the conformation of the entire lactam ring, causing the N5‐CH3 to arrange in a pseudo‐equatorial position (i.e., the amine at N5 is a chiral center

  氮手性：首先制备了以七元环苯并内酰胺为核心结构的强力新型ACAT抑制剂，并阐明了酶识别的轴向手性（例如1；参见方案）。轴（a S）为1的手性控制整个内酰胺环的构象，从而使N 5–CH 3排列在假赤道位置（即，N 5处的胺与S的手性中心‐配置）既处于晶体状态又处于溶液状态。