(S)-2-{(S)-2-[(2-Bromo-ethyl)-(2-nitro-benzenesulfonyl)-amino]-3-phenyl-propionylamino}-3-(1H-indol-3-yl)-propionic acid methyl ester | 218785-68-3

• 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: (S)-2-{(S)-2-[(2-Bromo-ethyl)-(2-nitro-benzenesulfonyl)-amino]-3-phenyl-propionylamino}-3-(1H-indol-3-yl)-propionic acid methyl ester
• 英文别名: oNos-N(EtBr)Phe-Trp-OMe；methyl (2S)-2-[[(2S)-2-[2-bromoethyl-(2-nitrophenyl)sulfonylamino]-3-phenylpropanoyl]amino]-3-(1H-indol-3-yl)propanoate
• CAS: 218785-68-3
• 化学式: C₂₉H₂₉BrN₄O₇S
• 分子量: 657.542
• InChiKey: KJQFZMKAZVAUMT-AHWVRZQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  42
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  163
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (S)-2-{(S)-2-[(2-Bromo-ethyl)-(2-nitro-benzenesulfonyl)-amino]-3-phenyl-propionylamino}-3-(1H-indol-3-yl)-propionic acid methyl ester 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 生成 (S)-2-[(S)-3-Benzyl-4-(2-nitro-benzenesulfonyl)-2-oxo-piperazin-1-yl]-3-(1H-indol-3-yl)-propionic acid methyl ester
  参考文献：
  名称：

  Efficient synthesis of substituted oxopiperazines from amino acids

  摘要：

  The synthesis of substituted oxopiperazines, which may act as conformationally constrained peptide mimics, is reported. The synthesis is based on the cyclization of sulfonamide dipeptides with dibromoethane as the 1, 2-dielectrophile. Alternatively, these mimetics were prepared via a Mitsunobu reaction. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01878-4
• 作为产物：
  描述：

  Boc-Phe-Trp-OMe 在 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 12.5h， 生成 (S)-2-{(S)-2-[(2-Bromo-ethyl)-(2-nitro-benzenesulfonyl)-amino]-3-phenyl-propionylamino}-3-(1H-indol-3-yl)-propionic acid methyl ester
  参考文献：
  名称：

  Efficient synthesis of substituted oxopiperazines from amino acids

  摘要：

  The synthesis of substituted oxopiperazines, which may act as conformationally constrained peptide mimics, is reported. The synthesis is based on the cyclization of sulfonamide dipeptides with dibromoethane as the 1, 2-dielectrophile. Alternatively, these mimetics were prepared via a Mitsunobu reaction. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01878-4

文献信息

• Efficient synthesis of substituted oxopiperazines from amino acids
  作者：Nazim Mohamed、Ulhas Bhatt、George Just

  DOI：10.1016/s0040-4039(98)01878-4

  日期：1998.11

  The synthesis of substituted oxopiperazines, which may act as conformationally constrained peptide mimics, is reported. The synthesis is based on the cyclization of sulfonamide dipeptides with dibromoethane as the 1, 2-dielectrophile. Alternatively, these mimetics were prepared via a Mitsunobu reaction. (C) 1998 Elsevier Science Ltd. All rights reserved.