(R)-(3-hydroxymethyl-2-oxo-5-phenyl-2,3-dihydro-benzo[e][1,4]diazepin-1-yl)-acetic acid ethyl ester | 1310683-83-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-(3-hydroxymethyl-2-oxo-5-phenyl-2,3-dihydro-benzo[e][1,4]diazepin-1-yl)-acetic acid ethyl ester
• 英文别名: ethyl 2-[(3R)-3-(hydroxymethyl)-2-oxo-5-phenyl-3H-1,4-benzodiazepin-1-yl]acetate
• CAS: 1310683-83-0
• 化学式: C₂₀H₂₀N₂O₄
• 分子量: 352.39
• InChiKey: SCXDMINGKQQJGF-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  79.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-(3-hydroxymethyl-2-oxo-5-phenyl-2,3-dihydro-benzo[e][1,4]diazepin-1-yl)-acetic acid ethyl ester 在 Hoveyda-Grubbs catalyst second generation 、 三苯基膦 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 lithium hydroxide 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 (R)-2-(3-(morpholinomethyl)-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-1-yl)-N-(4-oxopent-2-en-1-yl)acetamide
  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-phenyl-2,3-dihydro-benzo[e][1,4]diazepin-1-yl]-acetic acid ethyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以95%的产率得到(R)-(3-hydroxymethyl-2-oxo-5-phenyl-2,3-dihydro-benzo[e][1,4]diazepin-1-yl)-acetic acid ethyl 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