(+)-1-methyl-3-benzyl-1,4-benzodiazepin-2,5-dione | 104874-02-4

• 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-methyl-3-benzyl-1,4-benzodiazepin-2,5-dione
• 英文别名: (S)-3-benzyl-1-methyl-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione；(3S)-3-benzyl-1-methyl-3,4-dihydro-1,4-benzodiazepine-2,5-dione
• CAS: 104874-02-4
• 化学式: C₁₇H₁₆N₂O₂
• 分子量: 280.326
• InChiKey: TZRNZYMBFMGUKU-AWEZNQCLSA-N

物化性质

• 沸点：
  599.9±39.0 °C(Predicted)
• 密度：
  1.206±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+)-1-methyl-3-benzyl-1,4-benzodiazepin-2,5-dione 在 4-二甲氨基吡啶 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 13.0h， 生成 (R)-tert-butyl (3-benzyl-1-methyl-2,4-dioxo-1,2,3,4-tetrahydroquinolin-3-yl)carbamate
  参考文献：
  名称：

  Enantioselective Deprotonative Ring Contraction of N1-Methyl-N4-Boc-benzo[e][1,4]diazepine-2,5-diones

  摘要：

  N1-Methyl-N4-Boc-benzo[e][1,4] diazepine 2,5-diones were prepared in good yield an high stereo chemical purity from five amino acids Upon deprotonation these compounds undergo ring contraction to the corresponding quinolone 2,4-diones withhigh enantioselectivity, providing efficient entry to a potentially useful drug scaffold Mechanistic commentary and comparisons to related reactions are provided.

  DOI：

  10.1021/ol502586n
• 作为产物：
  描述：

  BOC-L-苯丙氨酸 在 盐酸 、 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 三氯化磷 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 (+)-1-methyl-3-benzyl-1,4-benzodiazepin-2,5-dione
  参考文献：
  名称：

  New routes to 1,4- benzodiazepin-2,5-diones

  摘要：

  1,4-benzodiazepin-2,5-diones have been synthesized in good overall yields by two routes, the first one by cyclisation of dipeptides prepared from Boc anthranilic acid and alpha-amino acid methyl esters, the second one by reaction of N-carboxy alpha-amino acid anhydrides with Boc anthranilic acid.

  DOI：

  10.1016/s0040-4020(01)85371-0

文献信息

• Design, synthesis and biological evaluation of 1,4-benzodiazepine-2,5-dione-based HDAC inhibitors
  作者：Lynda Loudni、Joëlle Roche、Vincent Potiron、Jonathan Clarhaut、Christian Bachmann、Jean-Pierre Gesson、Isabelle Tranoy-Opalinski

  DOI：10.1016/j.bmcl.2007.06.067

  日期：2007.9

  New histone deacetylase inhibitors have been synthesized and evaluated for their activity against non-small lung cancer cell line H661. These compounds have been designed with diversely substituted 1,4-benzodiazepine-2,5-dione moieties as cyclic peptide mimic cap structures, and a hydroxamate side chain. Biological evaluations demonstrated that benzodiazepine-based HDACi bearing an aromatic substituent at the N1 position exhibited promising anti proliferative and HDAC-inhibitory activities. (c) 2007 Elsevier Ltd. All rights reserved.
• New routes to 1,4- benzodiazepin-2,5-diones
  作者：M. Akssira、M. Boumzebra、H. Kasmi、A. Dahdouh、M.-L. Roumestant、Ph. Viallefont

  DOI：10.1016/s0040-4020(01)85371-0

  日期：1994.1

  1,4-benzodiazepin-2,5-diones have been synthesized in good overall yields by two routes, the first one by cyclisation of dipeptides prepared from Boc anthranilic acid and alpha-amino acid methyl esters, the second one by reaction of N-carboxy alpha-amino acid anhydrides with Boc anthranilic acid.
• Enantioselective Deprotonative Ring Contraction of <i>N</i>1-Methyl-<i>N</i>4-Boc-benzo[<i>e</i>][1,4]diazepine-2,5-diones
  作者：Stephanie A. Antolak、Zhong-Ke Yao、Gary M. Richoux、Carla Slebodnick、Paul R. Carlier

  DOI：10.1021/ol502586n

  日期：2014.10.3

  N1-Methyl-N4-Boc-benzo[e][1,4] diazepine 2,5-diones were prepared in good yield an high stereo chemical purity from five amino acids Upon deprotonation these compounds undergo ring contraction to the corresponding quinolone 2,4-diones withhigh enantioselectivity, providing efficient entry to a potentially useful drug scaffold Mechanistic commentary and comparisons to related reactions are provided.