tert-butyl (4E)-4-[[(3S)-3-[3-[[(4S)-2,2-dimethyl-3-[(2-methylpropan-2-yl)oxycarbonyl]-1,3-oxazolidin-4-yl]methyl]-1H-indol-7-yl]-2-oxo-1H-indol-3-yl]methylidene]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate | 950886-80-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: tert-butyl (4E)-4-[[(3S)-3-[3-[[(4S)-2,2-dimethyl-3-[(2-methylpropan-2-yl)oxycarbonyl]-1,3-oxazolidin-4-yl]methyl]-1H-indol-7-yl]-2-oxo-1H-indol-3-yl]methylidene]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 950886-80-3
• 化学式: C₃₈H₄₈N₄O₇
• 分子量: 672.822
• InChiKey: ZWBHFTDERLEOAW-NVSZHCFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  49
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  122
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl (4E)-4-[[(3S)-3-[3-[[(4S)-2,2-dimethyl-3-[(2-methylpropan-2-yl)oxycarbonyl]-1,3-oxazolidin-4-yl]methyl]-1H-indol-7-yl]-2-oxo-1H-indol-3-yl]methylidene]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 在 palladium on activated charcoal 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 camphor-10-sulfonic acid 、 氢气 作用下， 以 四氢呋喃 、 乙醇 、 乙二醇 、 N,N-二甲基甲酰胺 为溶剂， 23.0 ℃ 、5.52 MPa 条件下， 生成
  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. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.127
• 作为产物：
  描述：

  (R)-2,2-二甲基-3-(n-boc)-4-乙炔噁唑啉 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 四(三苯基膦)钯 1,2,2,6,6-五甲基哌啶 、 正丁基锂 、 三(2-呋喃基)膦 、 四丁基氟化铵 、 三甲基铝 、 三正丁基氢锡 、 sodium hydride 、 potassium carbonate 、 二甲基亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基乙酰胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 tert-butyl (4E)-4-[[(3S)-3-[3-[[(4S)-2,2-dimethyl-3-[(2-methylpropan-2-yl)oxycarbonyl]-1,3-oxazolidin-4-yl]methyl]-1H-indol-7-yl]-2-oxo-1H-indol-3-yl]methylidene]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
  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. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.127

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.