tert-butyl (4S)-4-[[7-[(Z)-1-[(4S)-2,2-dimethyl-3-[(2-methylpropan-2-yl)oxycarbonyl]-1,3-oxazolidin-4-yl]-3-(2-iodoanilino)-3-oxoprop-1-en-2-yl]-1H-indol-3-yl]methyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate | 370890-21-4

• 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 (4S)-4-[[7-[(Z)-1-[(4S)-2,2-dimethyl-3-[(2-methylpropan-2-yl)oxycarbonyl]-1,3-oxazolidin-4-yl]-3-(2-iodoanilino)-3-oxoprop-1-en-2-yl]-1H-indol-3-yl]methyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 370890-21-4
• 化学式: C₃₈H₄₉IN₄O₇
• 分子量: 800.734
• InChiKey: STVIBSXQYHCRNI-STUWLFSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  50
• 可旋转键数：
  10
• 环数：
  5.0
• 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 (4S)-4-[[7-[(Z)-1-[(4S)-2,2-dimethyl-3-[(2-methylpropan-2-yl)oxycarbonyl]-1,3-oxazolidin-4-yl]-3-(2-iodoanilino)-3-oxoprop-1-en-2-yl]-1H-indol-3-yl]methyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 三(2-呋喃基)膦 、 杀鼠酮 、 2,4-滴二甲胺盐 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 tert-butyl (4E)-4-[[(3R)-3-[3-[[(4S)-2,2-dimethyl-3-[(2-methylpropan-2-yl)oxycarbonyl]-1,3-oxazolidin-4-yl]methyl]-1-(2-trimethylsilylethoxymethyl)indol-7-yl]-2-oxo-1-(2-trimethylsilylethoxymethyl)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.

  DOI：

  10.1021/ja016616l
• 作为产物：
  描述：

  L-色氨酸甲酯盐酸盐 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex N-甲基吡咯烷酮 、 三乙基硅烷 、 sodium tetrahydroborate 、 copper(l) iodide 、 三(2-呋喃基)膦 、 四甲基乙二胺 、 三甲基铝 、 仲丁基锂 、 sodium carbonate 、 potassium carbonate 、 对甲苯磺酸 、 二甲基亚砜 、 三氟乙酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 lithium chloride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 乙醇 、 二氯甲烷 、 二甲基亚砜 、 甲苯 、 苯 为溶剂， 生成 tert-butyl (4S)-4-[[7-[(Z)-1-[(4S)-2,2-dimethyl-3-[(2-methylpropan-2-yl)oxycarbonyl]-1,3-oxazolidin-4-yl]-3-(2-iodoanilino)-3-oxoprop-1-en-2-yl]-1H-indol-3-yl]methyl]-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.

  DOI：

  10.1021/ja016616l