(R)-(1-(2-(allylamino)-2-oxoethyl)-5-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl)methyl (4-chloro-2-(trifluoromethyl)phenyl)carbamate | 1310683-99-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-(1-(2-(allylamino)-2-oxoethyl)-5-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl)methyl (4-chloro-2-(trifluoromethyl)phenyl)carbamate
• 英文别名: [(3R)-5-methyl-2-oxo-1-[2-oxo-2-(prop-2-enylamino)ethyl]-3H-1,4-benzodiazepin-3-yl]methyl N-[4-chloro-2-(trifluoromethyl)phenyl]carbamate
• CAS: 1310683-99-8
• 化学式: C₂₄H₂₂ClF₃N₄O₄
• 分子量: 522.911
• InChiKey: FKUKRXHKPMAZIE-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  100
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (R)-(1-(2-(allylamino)-2-oxoethyl)-5-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl)methyl (4-chloro-2-(trifluoromethyl)phenyl)carbamate 、 丁烯酮 在 Hoveyda-Grubbs catalyst second generation 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以80%的产率得到(4-chloro-2-trifluoromethyl-phenyl)-carbamic acid 5-methyl-2-oxo-1-[(4-oxo-pent-2-enylcarbamoyl)-methyl]-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-ylmethyl ester
  参考文献：
  名称：

  Peptidomimetics containing a vinyl ketone warhead as falcipain-2 inhibitors

  摘要：

  The design, chemical synthesis, and enzymatic activity evaluation of a set of falcipain-2 inhibitors are reported. These compounds contain a proven peptidomimetic recognition motif based on a benzo[1,4] diazepin-2-one (1,4-BDZ) framework built on a dipeptide sequence, and a Michael acceptor terminal moiety capable of deactivating the cysteine protease active site. Our goal is to modify the P-3 site of this motif in order to identify the structural requirements for the interaction with the target. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.02.058
• 作为产物：
  描述：

  (R)-[3-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-5-methyl-2,3-dihydrobenzo[e][1,4] diazepin-1-yl]-acetic acid 在 四丁基氟化铵 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 (R)-(1-(2-(allylamino)-2-oxoethyl)-5-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl)methyl (4-chloro-2-(trifluoromethyl)phenyl)carbamate
  参考文献：
  名称：

  Peptidomimetics containing a vinyl ketone warhead as falcipain-2 inhibitors

  摘要：

  The design, chemical synthesis, and enzymatic activity evaluation of a set of falcipain-2 inhibitors are reported. These compounds contain a proven peptidomimetic recognition motif based on a benzo[1,4] diazepin-2-one (1,4-BDZ) framework built on a dipeptide sequence, and a Michael acceptor terminal moiety capable of deactivating the cysteine protease active site. Our goal is to modify the P-3 site of this motif in order to identify the structural requirements for the interaction with the target. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.02.058