ethyl 3-[(2R*,3R*)-2-cyano-3-isobutyl-2-({[(1S)-1-benzyl-2-methoxy-2-oxoethyl]carbamoyl}aziridin-1-yl)]-3-oxopropanoate | 1020065-29-5

• 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: ethyl 3-[(2R*,3R*)-2-cyano-3-isobutyl-2-({[(1S)-1-benzyl-2-methoxy-2-oxoethyl]carbamoyl}aziridin-1-yl)]-3-oxopropanoate
• 英文别名: methyl (2S)-2-[[2-cyano-1-(3-ethoxy-3-oxopropanoyl)-3-(2-methylpropyl)aziridine-2-carbonyl]amino]-3-phenylpropanoate
• CAS: 1020065-29-5
• 化学式: C₂₃H₂₉N₃O₆
• 分子量: 443.5
• InChiKey: NDISUYJQEXJZKB-FMPVJGDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  126
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 3-[(2R*,3R*)-2-cyano-3-isobutyl-2-({[(1S)-1-benzyl-2-methoxy-2-oxoethyl]carbamoyl}aziridin-1-yl)]-3-oxopropanoate 在 双氧水 、 sodium carbonate 作用下， 以 丙酮 为溶剂， 反应 18.0h， 以90%的产率得到ethyl 3-[(2R*,3R*)-2-carbamoyl-3-isobutyl-2-({[(1S)-1-benzyl-2-methoxy-2-oxoethyl]carbamoyl}aziridin-1-yl)]-3-oxopropanoate
  参考文献：
  名称：

  Solution-phase synthesis of 2-cyano and 2-amido aziridinyl peptides

  摘要：

  Starting from a library of 2-L-alpha-amino acyl (E)-acrylonitriles, different short 2-cyano and 2-amino aziridinyl peptides, potential protease inhibitors. were obtained under parallel solution-phase conditions. The transformations include careful selection of conditions for aziridine deprotection and cyano group partial hydrolysis. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.098
• 作为产物：
  描述：

  (2R*,3R*)-2-{[(1S)-1-benzyl-2-methoxy-2-oxoethyl]carbamoyl}-2-cyano-3-isobutylaziridine 、 氯甲酰乙酸乙酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以96%的产率得到ethyl 3-[(2R*,3R*)-2-cyano-3-isobutyl-2-({[(1S)-1-benzyl-2-methoxy-2-oxoethyl]carbamoyl}aziridin-1-yl)]-3-oxopropanoate
  参考文献：
  名称：

  Solution-phase synthesis of 2-cyano and 2-amido aziridinyl peptides

  摘要：

  Starting from a library of 2-L-alpha-amino acyl (E)-acrylonitriles, different short 2-cyano and 2-amino aziridinyl peptides, potential protease inhibitors. were obtained under parallel solution-phase conditions. The transformations include careful selection of conditions for aziridine deprotection and cyano group partial hydrolysis. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.098

文献信息

• Solution-phase synthesis of 2-cyano and 2-amido aziridinyl peptides
  作者：Stefania Fioravanti、Davide Massari、Alberto Morreale、Lucio Pellacani、Paolo A. Tardella

  DOI：10.1016/j.tet.2008.01.098

  日期：2008.3

  Starting from a library of 2-L-alpha-amino acyl (E)-acrylonitriles, different short 2-cyano and 2-amino aziridinyl peptides, potential protease inhibitors. were obtained under parallel solution-phase conditions. The transformations include careful selection of conditions for aziridine deprotection and cyano group partial hydrolysis. (c) 2008 Elsevier Ltd. All rights reserved.