(3S,4R)-3-hydroxy-4-(1H-indol-3-yl)-1-methyl-3-[(2S,3R,4S)-2,3,4-trihydroxyoxolan-2-yl]pyrrolidin-2-one | 201595-49-5

• 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: (3S,4R)-3-hydroxy-4-(1H-indol-3-yl)-1-methyl-3-[(2S,3R,4S)-2,3,4-trihydroxyoxolan-2-yl]pyrrolidin-2-one
• CAS: 201595-49-5
• 化学式: C₁₇H₂₀N₂O₆
• 分子量: 348.356
• InChiKey: WEALNSIFBHESLE-CNUSHZMNSA-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：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  126
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (3S,4R)-3-hydroxy-4-(1H-indol-3-yl)-1-methyl-3-[(2S,3R,4S)-2,3,4-trihydroxyoxolan-2-yl]pyrrolidin-2-one 在 吡啶 作用下， 生成 [(2S,3R)-2,3-diacetyloxy-4-[(3S,4R)-3-hydroxy-4-(1H-indol-3-yl)-1-methyl-2-oxopyrrolidin-3-yl]-4-oxobutyl] acetate
  参考文献：
  名称：

  Interaction of L-Ascorbic Acid with DL-N-Methyl-β-hydroxytryptamine

  摘要：

  The interaction of DL-N-methyl-beta-hydroxytryptamine 1 with L-ascorbic acid 2 proceeds through the 2-C alkylation of 2 and the intramolecular acylation of the methylamino group to yield diastereomeric 3-hydroxy-4-(indol-3-yl)-1-methyl-3-(2,3,4-trihydroxybutyryl)pyrrolid-2-one 4a and 5b. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10461-0
• 作为产物：
  描述：

  [(2S,3R)-2,3-diacetyloxy-4-[(3S,4R)-3-hydroxy-4-(1H-indol-3-yl)-1-methyl-2-oxopyrrolidin-3-yl]-4-oxobutyl] acetate 在 甲醇 、 sodium methylate 作用下， 生成 (3S,4R)-3-hydroxy-4-(1H-indol-3-yl)-1-methyl-3-[(2S,3R,4S)-2,3,4-trihydroxyoxolan-2-yl]pyrrolidin-2-one
  参考文献：
  名称：

  From ascorbigens to indolocarbazoles

  摘要：

  New methods of L-ascorbic acid derivatization with the use of polyfunctional indole-3-cabinols are described. Reaction of beta-hydroxy-N-methyltryptamine and L-ascorbic acid gave lactame derivatives; (indol-3-yl)glycolic and L-ascorbic acids produced 2-hydroxy-4-hydroxymethyl-3-(indol-3-yl) Similarly, 4-hydroxy-3-methoxyphenylglycolic and L-ascorbic acids yielded 2-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-4-hydroxymethyl-cyclopen-2-enone. Properties of N-methoxyascorbigen (neoascorbigen) were investigated. Alkylation of L-ascorbic acid with polysubstituted pyrrolecarbinols led to pyrrole analogues of ascorbigen. Acidic transformation of 3-formylindole and 1-methyl-3-formylindole led to indolocarbazoles and triindolyhmethane derivatives. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(99)00026-9