(R)-2-[((2S,3aR,8aS)-3a-{3-[(S)-2-Amino-2-((R)-1-methoxycarbonyl-2-phenyl-ethylcarbamoyl)-ethyl]-1H-indol-7-yl}-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carbonyl)-amino]-3-phenyl-propionic acid methyl ester | 950887-03-3

• 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: (R)-2-[((2S,3aR,8aS)-3a-{3-[(S)-2-Amino-2-((R)-1-methoxycarbonyl-2-phenyl-ethylcarbamoyl)-ethyl]-1H-indol-7-yl}-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carbonyl)-amino]-3-phenyl-propionic acid methyl ester
• CAS: 950887-03-3
• 化学式: C₄₂H₄₄N₆O₆
• 分子量: 728.848
• InChiKey: ABXIQCQQUOSBHN-QOCACHIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.24
• 重原子数：
  54.0
• 可旋转键数：
  13.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  176.67
• 氢给体数：
  6.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (R)-2-[((2S,3aR,8aS)-3a-{3-[(S)-2-Amino-2-((R)-1-methoxycarbonyl-2-phenyl-ethylcarbamoyl)-ethyl]-1H-indol-7-yl}-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carbonyl)-amino]-3-phenyl-propionic acid methyl ester 在 溶剂黄146 作用下， 以 正丁醇 为溶剂， 生成 (+)-asperazine
  参考文献：
  名称：

  Total Synthesis of Asperazine

  摘要：

  The first total synthesis of the structurally novel cyclotryptophan alkaloid asperazine is reported. The central step in the synthetic sequence is a diastereoselective intramolecular Heck reaction in which the substituent controlling stereoselection is external to the ring being formed. This synthesis confirmed the structure of (+)-asperazine (1) proposed by Crews and co-workers and provided material for additional biological studies. The in vitro cytotoxicity originally reported for the marine isolate was not confirmed with synthetic (+)-asperazine.

  DOI：

  10.1021/ja016616l
• 作为产物：
  描述：

  ditert-butyl (2S,3aS,8bS)-8b-[3-[(2S)-3-[[(2R)-1-methoxy-1-oxo-3-phenylpropan-2-yl]amino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopropyl]-1H-indol-7-yl]-2-[[(2R)-1-methoxy-1-oxo-3-phenylpropan-2-yl]carbamoyl]-2,3a-dihydro-1H-pyrrolo[2,3-b]indole-3,4-dicarboxylate 在 甲酸 作用下， 生成 (R)-2-[((2S,3aR,8aS)-3a-{3-[(S)-2-Amino-2-((R)-1-methoxycarbonyl-2-phenyl-ethylcarbamoyl)-ethyl]-1H-indol-7-yl}-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carbonyl)-amino]-3-phenyl-propionic acid methyl ester
  参考文献：
  名称：

  Total Synthesis of Asperazine

  摘要：

  The first total synthesis of the structurally novel cyclotryptophan alkaloid asperazine is reported. The central step in the synthetic sequence is a diastereoselective intramolecular Heck reaction in which the substituent controlling stereoselection is external to the ring being formed. This synthesis confirmed the structure of (+)-asperazine (1) proposed by Crews and co-workers and provided material for additional biological studies. The in vitro cytotoxicity originally reported for the marine isolate was not confirmed with synthetic (+)-asperazine.

  DOI：

  10.1021/ja016616l

文献信息

• Total synthesis of (+)-asperazine
  作者：Steven P. Govek、Larry E. Overman

  DOI：10.1016/j.tet.2007.05.127

  日期：2007.8

  The first total synthesis of the structurally novel cyclotryptophan alkaloid asperazine is reported. The central step in the synthetic sequence is a diastereoselective intramolecular Heck reaction in which the substituent controlling stereoselection is external to the ring being formed. This synthesis confirmed the structure of (+)- asperazine (1) proposed by Crews and co- workers and provided material for additional biological studies. The in vitro cytotoxicity originally reported for the marine isolate was not confirmed with synthetic (+)- asperazine. (c) 2007 Elsevier Ltd. All rights reserved.