2-hydroxy-4-hydroxymethyl-3-(1-benzylindol-3-yl)-cyclopent-2-enone | 335590-86-8

• 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: 2-hydroxy-4-hydroxymethyl-3-(1-benzylindol-3-yl)-cyclopent-2-enone
• 英文别名: 3-(1-Benzylindol-3-yl)-2-hydroxy-4-(hydroxymethyl)cyclopent-2-en-1-one
• CAS: 335590-86-8
• 化学式: C₂₁H₁₉NO₃
• 分子量: 333.387
• InChiKey: GFUTXQDSKVIHJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  62.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  六甲基二硅氮烷 、 2-hydroxy-4-hydroxymethyl-3-(1-benzylindol-3-yl)-cyclopent-2-enone 生成
  参考文献：
  名称：

  The formation of 2-hydroxy-4-hydroxymethyl-3-(indol-3-yl)cyclopent-2-enone derivatives from ascorbigens

  摘要：

  A facile preparation is described of 3-(indol-3-yl)-2-hydroxy-4-hydroxymethylcyclopent-2-enone and its N-derivatives in 15-40% yields by the degradation of ascorbigen or its N-derivatives in a warm solution of L-ascorbic acid through a sequential domino reaction. The same cyclopentenone derivatives were obtained in 30-40% yields by the condensation of (N-alkylindol-3-yl)glycolic acids with ascorbic acid. 2,6-Dihydroxy-1-(indol-3-yl)hexa-1,4-diene-3-one and 2-hydroxy-4-hydroxymethyl-5-(indol-3-yl)cyclopent-2-enone were identified as intermediates in this reaction. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00310-4
• 作为产物：
  描述：

  (1-benzylindol-3-yl)glyoxalic acid 在 sodium tetrahydroborate 作用下， 以 乙醇 、 水 为溶剂， 反应 21.0h， 生成 2-hydroxy-4-hydroxymethyl-3-(1-benzylindol-3-yl)-cyclopent-2-enone
  参考文献：
  名称：

  The formation of 2-hydroxy-4-hydroxymethyl-3-(indol-3-yl)cyclopent-2-enone derivatives from ascorbigens

  摘要：

  A facile preparation is described of 3-(indol-3-yl)-2-hydroxy-4-hydroxymethylcyclopent-2-enone and its N-derivatives in 15-40% yields by the degradation of ascorbigen or its N-derivatives in a warm solution of L-ascorbic acid through a sequential domino reaction. The same cyclopentenone derivatives were obtained in 30-40% yields by the condensation of (N-alkylindol-3-yl)glycolic acids with ascorbic acid. 2,6-Dihydroxy-1-(indol-3-yl)hexa-1,4-diene-3-one and 2-hydroxy-4-hydroxymethyl-5-(indol-3-yl)cyclopent-2-enone were identified as intermediates in this reaction. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00310-4

文献信息

• From ascorbigens to indolocarbazoles
  作者：Maria N. Preobrazhenskaya、Alexander M. Korolev、Ilya I. Rozhkov、Larisa N. Yudina、Eduard I. Lazhko、Enrico Aiello、Anna Maria Almerico、Francesco Mingoia

  DOI：10.1016/s0014-827x(99)00026-9

  日期：1999.5

  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.
• The formation of 2-hydroxy-4-hydroxymethyl-3-(indol-3-yl)cyclopent-2-enone derivatives from ascorbigens
  作者：Alexander M Korolev、Larisa N Yudina、Ilyia I Rozhkov、Ludmila N Lysenkova、Eduard I Lazhko、Yury N Luzikov、Maria N Preobrazhenskaya

  DOI：10.1016/s0008-6215(00)00310-4

  日期：2001.2

  A facile preparation is described of 3-(indol-3-yl)-2-hydroxy-4-hydroxymethylcyclopent-2-enone and its N-derivatives in 15-40% yields by the degradation of ascorbigen or its N-derivatives in a warm solution of L-ascorbic acid through a sequential domino reaction. The same cyclopentenone derivatives were obtained in 30-40% yields by the condensation of (N-alkylindol-3-yl)glycolic acids with ascorbic acid. 2,6-Dihydroxy-1-(indol-3-yl)hexa-1,4-diene-3-one and 2-hydroxy-4-hydroxymethyl-5-(indol-3-yl)cyclopent-2-enone were identified as intermediates in this reaction. (C) 2001 Elsevier Science Ltd. All rights reserved.