2-hydroxy-4-hydroxymethyl-3-(1-methoxylindol-3-yl)-cyclopent-2-enone | 303014-31-5

• 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: 2-hydroxy-4-hydroxymethyl-3-(1-methoxylindol-3-yl)-cyclopent-2-enone
• 英文别名: 3-(1'-methoxy-3'-indolyl)-2-hydroxy-4-hydroxymethylcyclopent-2-enone；2-hydroxy-3-(N-methoxyindol-3-yl)-4-hydroxymethylcyclopent-2-enone；2-hydroxy-4-(hydroxymethyl)-3-(1-methoxyindol-3-yl)cyclopent-2-en-1-one
• CAS: 303014-31-5
• 化学式: C₁₅H₁₅NO₄
• 分子量: 273.288
• InChiKey: QWBXEAVURUVPNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  71.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-hydroxy-4-hydroxymethyl-3-(1-methoxylindol-3-yl)-cyclopent-2-enone 在 盐酸 、 水 作用下， 反应 1.5h， 生成 2-hydroxy-4-hydroxymethyl-5-(indol-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
• 作为产物：
  描述：

  2-C-(1-methoxyindol-3-yl)-β-L-xylo-3-hexulofuranosonic acid γ-lactone 在 维生素 C 作用下， 以 水 为溶剂， 反应 48.0h， 以27%的产率得到2-hydroxy-4-hydroxymethyl-3-(1-methoxylindol-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

• Investigation of neoascorbigen
  作者：L. N. Yudina、A. M. Korolev、M. I. Reznikova、M. N. Preobrazhenskaya

  DOI：10.1007/bf02283542

  日期：2000.2
• 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.