2-hydroxy-3-(indol-3-yl)-4-hydroxymethylcyclopent-2-enone | 335590-84-6

• 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-3-(indol-3-yl)-4-hydroxymethylcyclopent-2-enone
• 英文别名: 2-hydroxy-4-hydroxymethyl-3-(indol-3-yl)cyclopent-2-enone；2-hydroxy-4-hydroxymethyl-3-(indol-3-yl)cyclopenten-2-on；2-Cyclopenten-1-one, 2-hydroxy-4-(hydroxymethyl)-3-(1H-indol-3-yl)-；2-hydroxy-4-(hydroxymethyl)-3-(1H-indol-3-yl)cyclopent-2-en-1-one
• CAS: 335590-84-6
• 化学式: C₁₄H₁₃NO₃
• 分子量: 243.262
• InChiKey: ACYUZGSIDAUCIV-UHFFFAOYSA-N

物化性质

• 沸点：
  500.4±50.0 °C(Predicted)
• 密度：
  1.459±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  73.3
• 氢给体数：
  3
• 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-3-(indol-3-yl)-4-hydroxymethylcyclopent-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-deoxy-1-(indol-3-yl)-3,5-di-O-tosyl-α-L-tagatopyranose 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以90%的产率得到2-hydroxy-3-(indol-3-yl)-4-hydroxymethylcyclopent-2-enone
  参考文献：
  名称：

  1-脱氧-1-（吲哚-3-基）-1-山梨糖，1-脱氧-1-（吲哚-3-基）-1-塔格糖及其类似物的研究

  摘要：

  抗坏血酸2-C-[（（吲哚-3-基）甲基]-α-L-二甲苯基-hex-3-ulofuranosono-1,4-内酯（1a）的碱性降解导致1-deoxy-1的混合物-（吲哚-3-基）-L-山梨糖（2a）和1-脱氧-1-（吲哚-3-基）-L-塔格糖（3a）。非对映体酮糖的混合物在4-二甲基氨基吡啶（DMAP）存在下，在乙酸酐的吡啶中，在乙酸酐的作用下进行乙酰化和吡喃糖开环，形成（E）-2,3,4,5,6-混合物五-O-乙酰基-1-脱氧-1-（吲哚-3-基）-L-木基-己基-1-烯醇（4a）和（E）-2,3,4,5,6-penta-O -乙酰基-1-脱氧-1-（吲哚-3-基）-L-lyxo-己基-1-烯醇（5a），将其色谱分离。4a或5a脱乙酰基提供环化的四醇，将其甲苯磺酸化混合可生成1-deoxy-1-（吲哚-3-yl）-3,5-di-O-甲苯磺酰基-α-L-山梨糖醛糖（12a）和1 -脱氧-

  DOI：

  10.1016/s0008-6215(02)00404-4

文献信息

• ——
  作者：L. N. Lysenkova、M. I. Reznikova、A. M. Korolev、M. N. Preobrazhenskaya

  DOI：10.1023/a:1014087630107

  日期：——

  Transformation of ascorbigen in an acidic medium, which affects the carbohydrate moiety of the molecule and results in the formation of 2-hydroxy-4-hydroxymethyl-3-(indol-3-yl)cyclopent-2-enone, 5-hydroxymethyl-2-(indol-3-yl)methylidenetetrahydrofuran-3-one, and 2-(indol-3-yl)acetylfuran, was investigated. Isolation and identification of the intermediates allowed the elucidation of the mechanism of this domino-type reaction.
• Study of 1-deoxy-1-(indol-3-yl)-l-sorbose, 1-deoxy-1-(indol-3-yl)-l-tagatose, and their analogs
  作者：Sergey N Lavrenov、Alexander M Korolev、Marina I Reznikova、Andrey V Sosnov、Maria N Preobrazhenskaya

  DOI：10.1016/s0008-6215(02)00404-4

  日期：2003.1

  Alkaline degradation of the ascorbigen 2-C-[(indol-3-yl)methyl]-alpha-L-xylo-hex-3-ulofuranosono-1,4-lactone (1a) led to a mixture of 1-deoxy-1-(indol-3-yl)-L-sorbose (2a) and 1-deoxy-1-(indol-3-yl)-L-tagatose (3a). The mixture of diastereomeric ketoses underwent acetylation and pyranose ring opening under the action of acetic anhydride in pyridine in the presence of 4-dimethylaminopyridine (DMAP)

  抗坏血酸2-C-[（（吲哚-3-基）甲基]-α-L-二甲苯基-hex-3-ulofuranosono-1,4-内酯（1a）的碱性降解导致1-deoxy-1的混合物-（吲哚-3-基）-L-山梨糖（2a）和1-脱氧-1-（吲哚-3-基）-L-塔格糖（3a）。非对映体酮糖的混合物在4-二甲基氨基吡啶（DMAP）存在下，在乙酸酐的吡啶中，在乙酸酐的作用下进行乙酰化和吡喃糖开环，形成（E）-2,3,4,5,6-混合物五-O-乙酰基-1-脱氧-1-（吲哚-3-基）-L-木基-己基-1-烯醇（4a）和（E）-2,3,4,5,6-penta-O -乙酰基-1-脱氧-1-（吲哚-3-基）-L-lyxo-己基-1-烯醇（5a），将其色谱分离。4a或5a脱乙酰基提供环化的四醇，将其甲苯磺酸化混合可生成1-deoxy-1-（吲哚-3-yl）-3,5-di-O-甲苯磺酰基-α-L-山梨糖醛糖（12a）和1 -脱氧-
• 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.