2-hydroxy-N-[(2S)-1-hydroxy-3-(4-hydroxyphenyl)propan-2-yl]-2-(1H-indol-3-yl)acetamide | 1026700-95-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-hydroxy-N-[(2S)-1-hydroxy-3-(4-hydroxyphenyl)propan-2-yl]-2-(1H-indol-3-yl)acetamide
• CAS: 1026700-95-7
• 化学式: C₁₉H₂₀N₂O₄
• 分子量: 340.379
• InChiKey: RGOYGPHMUBSXHO-FVRDMJKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  106
• 氢给体数：
  5
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-hydroxy-N-[(2S)-1-hydroxy-3-(4-hydroxyphenyl)propan-2-yl]-2-(1H-indol-3-yl)acetamide 在 4-甲基苯磺酸吡啶 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成 (2S,5S)-oxazinine-3 、 (2R,5S)-oxazinine-3
  参考文献：
  名称：

  Synthetic studies towards oxazinins. An expedient first total synthesis and proof of the absolute stereochemistry of oxazinin-3

  摘要：

  A synthetic strategy, based on intramolecular addition of an appropriate hydroxyl substituent to a 3-methyleneindolenine, towards the naturally occurring marine toxins oxazinin-1, -2 and -3 is presented. The expedient first total synthesis of oxazinin-3, thus accomplished, demonstrated the efficiency of the approach and established the absolute stereochernistry of oxazinin-3 as 2S,5S. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.08.054
• 作为产物：
  描述：

  3-吲哚乙醛酸 在 锂硼氢 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 2-hydroxy-N-[(2S)-1-hydroxy-3-(4-hydroxyphenyl)propan-2-yl]-2-(1H-indol-3-yl)acetamide
  参考文献：
  名称：

  Synthetic studies towards oxazinins. An expedient first total synthesis and proof of the absolute stereochemistry of oxazinin-3

  摘要：

  A synthetic strategy, based on intramolecular addition of an appropriate hydroxyl substituent to a 3-methyleneindolenine, towards the naturally occurring marine toxins oxazinin-1, -2 and -3 is presented. The expedient first total synthesis of oxazinin-3, thus accomplished, demonstrated the efficiency of the approach and established the absolute stereochernistry of oxazinin-3 as 2S,5S. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.08.054

文献信息

• Synthetic studies towards oxazinins. An expedient first total synthesis and proof of the absolute stereochemistry of oxazinin-3
  作者：Elias A. Couladouros、Vassilios I. Moutsos、Emmanuel N. Pitsinos

  DOI：10.1016/j.tetlet.2004.08.054

  日期：2004.10

  A synthetic strategy, based on intramolecular addition of an appropriate hydroxyl substituent to a 3-methyleneindolenine, towards the naturally occurring marine toxins oxazinin-1, -2 and -3 is presented. The expedient first total synthesis of oxazinin-3, thus accomplished, demonstrated the efficiency of the approach and established the absolute stereochernistry of oxazinin-3 as 2S,5S. (C) 2004 Elsevier Ltd. All rights reserved.