(S)-1-tert-butoxycarbonyl-2-iodo-3-(2-oxo-oxazolidin-4-ylmethyl)-indole | 1053208-92-6

• 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: (S)-1-tert-butoxycarbonyl-2-iodo-3-(2-oxo-oxazolidin-4-ylmethyl)-indole
• 英文别名: tert-butyl 2-iodo-3-[[(4S)-2-oxo-1,3-oxazolidin-4-yl]methyl]indole-1-carboxylate
• CAS: 1053208-92-6
• 化学式: C₁₇H₁₉IN₂O₄
• 分子量: 442.253
• InChiKey: GRQJCRZIHNYQJQ-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  69.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-1-tert-butoxycarbonyl-2-iodo-3-(2-oxo-oxazolidin-4-ylmethyl)-indole 在 potassium phosphate 、 copper(l) iodide 、 trans-1,2-Diaminocyclohexane 作用下， 以 甲苯 为溶剂， 以55%的产率得到tert-butyl (14S)-11-oxo-12-oxa-8,10-diazatetracyclo[7.6.0.02,7.010,14]pentadeca-1(9),2,4,6-tetraene-8-carboxylate
  参考文献：
  名称：

  Copper-Catalyzed Cyclization of Iodo-tryptophans: A Straightforward Synthesis of Pyrroloindoles

  摘要：

  Pyrroloindoles are a key structural motif found in a wide number of biologically active alkaloids. Intramolecular copper-catalyzed coupling of readily accessible 2-iodo-tryptophan derivatives occurs in excellent yield, affording a wide range of polysubstituted, enantioenriched tetrahydropyrrolo[2,3-b]indoles. Diketopiperazines are also suitable substrates for this cyclization reaction, which affords a straightforward entry to tetra- to hepta-polycyclic systems.

  DOI：

  10.1021/ol8015513
• 作为产物：
  描述：

  (S)-1-tert-butoxycarbonyl-3-(2-oxo-oxazolidin-4-ylmethyl)-indole 在 mercury(II) trifluoroacetate 、 碘 作用下， 以 二氯甲烷 为溶剂， 以49%的产率得到(S)-1-tert-butoxycarbonyl-2-iodo-3-(2-oxo-oxazolidin-4-ylmethyl)-indole
  参考文献：
  名称：

  Copper-Catalyzed Cyclization of Iodo-tryptophans: A Straightforward Synthesis of Pyrroloindoles

  摘要：

  Pyrroloindoles are a key structural motif found in a wide number of biologically active alkaloids. Intramolecular copper-catalyzed coupling of readily accessible 2-iodo-tryptophan derivatives occurs in excellent yield, affording a wide range of polysubstituted, enantioenriched tetrahydropyrrolo[2,3-b]indoles. Diketopiperazines are also suitable substrates for this cyclization reaction, which affords a straightforward entry to tetra- to hepta-polycyclic systems.

  DOI：

  10.1021/ol8015513