(S)-8-acetyl-1-tert-butoxycarbonyl-1,2,3,8-tetrahydro-pyrrolo[2,3-b]indole-2-carboxylic acid methyl ester | 1053208-63-1

• 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)-8-acetyl-1-tert-butoxycarbonyl-1,2,3,8-tetrahydro-pyrrolo[2,3-b]indole-2-carboxylic acid methyl ester
• 英文别名: 3-O-tert-butyl 2-O-methyl (2S)-4-acetyl-1,2-dihydropyrrolo[2,3-b]indole-2,3-dicarboxylate
• CAS: 1053208-63-1
• 化学式: C₁₉H₂₂N₂O₅
• 分子量: 358.394
• InChiKey: ZRCFILGHGITANM-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  77.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-8-acetyl-1-tert-butoxycarbonyl-1,2,3,8-tetrahydro-pyrrolo[2,3-b]indole-2-carboxylic acid methyl ester 在 platinum(IV) oxide 、 氢气 作用下， 以 甲醇 为溶剂， 以74%的产率得到(2S,3aR,8aR)-8-acetyl-1-tert-butoxycarbonyl-3,3a,8,8a-tetrahydro-pyrrolo[2,3-b]indole-2-carboxylic acid methyl ester
  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：

  N-tert-butoxycarbonyl-1-acetyl-2-iodo-L-tryptophan methyl ester 在 potassium phosphate 、 copper(l) iodide 、 N,N'-二甲基乙二胺 作用下， 以 甲苯 为溶剂， 以87%的产率得到(S)-8-acetyl-1-tert-butoxycarbonyl-1,2,3,8-tetrahydro-pyrrolo[2,3-b]indole-2-carboxylic acid methyl ester
  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