1H-吲哚-3-乙酸丙酯 | 2122-68-1

• 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
• 中文名称: 1H-吲哚-3-乙酸丙酯
• 英文名称: propyl 2-(1H-indol-3-yl)acetate
• 英文别名: indol-3-yl-acetic acid propyl ester；Indol-3-yl-essigsaeure-propylester
• CAS: 2122-68-1
• 化学式: C₁₃H₁₅NO₂
• mdl: MFCD22415258
• 分子量: 217.268
• InChiKey: MNSTXDVFCOCNAP-UHFFFAOYSA-N

物化性质

• 熔点：
  105 °C
• 沸点：
  365.7±17.0 °C(Predicted)
• 密度：
  1.157±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.307
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  1H-吲哚-3-乙酸丙酯 在 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、 四(三苯基膦)钯 、 palladium 10% on activated carbon 、 氢气 、 三氧化硫吡啶 、 二异丁基氢化铝 、 二甲基亚砜 、 异丙胺 、 三乙胺 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 9.0h， 生成 (Z)-tert-butyl 2-(5-(tert-butyldimethylsilyloxy)pent-1-enyl)-3-(2-oxoethyl)-1H-indole-1-carboxylate
  参考文献：
  名称：

  Studies on Difficult Intramolecular Hydroaminations in the Context of Four Syntheses of Alkaloid Natural Products

  摘要：

  Examples of intramolecular alkene hydroaminations forming six-membered ring systems are rare, especially for systems in which the double bond is disubstituted. Such cyclizations have important synthetic relevance. Herein we report a systematic study of these cyclizations using recently developed Cope-type hydroamination methodologies. Difficult intramolecular alkene hydroaminations were used as key steps in syntheses of 2-epi-pumiliotoxin C, coniine, N-norreticuline and desbromoarborescidine A. This effort required the development of optimized hydroamination conditions to improve the efficiency of the cyclizations. Collectively, our results show that Cope-type cyclizations can be achieved on a variety of challenging substrates and proceed under similar conditions for both N-H and N-substituted hydroxylamines.

  DOI：

  10.1021/jo4023149
• 作为产物：
  描述：

  丙醇 、 3-吲哚乙酸 在 盐酸 作用下， 生成 1H-吲哚-3-乙酸丙酯
  参考文献：
  名称：

  The Characterization of Indole-3-acetic Acid and its Esters¹

  摘要：

  DOI：

  10.1021/ja01150a526

文献信息

• Koegl; Kostermans, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1935, vol. 235, p. 201,213
  作者：Koegl、Kostermans

  DOI：——

  日期：——
• Stereochemistry of Dimerisation of Indole-3-acetic Acid and its Propyl Ester.
  作者：Tine M. Fatum、Uffe Anthoni、Carsten Christophersen、Per Halfdan Nielsen、Yngve Stenstrøm、Ruo-Hua Zhang、Kurt V. Mikkelsen、Alexander Senning

  DOI：10.3891/acta.chem.scand.52-0784

  日期：——

  The mechanism, stereochemistry and products of the dimerisation of indole-3-acetic acid 1a and its propyl ester 1b in TFA and H3PO4 have been investigated. The major products in both acids were 2-(indolin-2-yl)indole dimers, 3a/b, which were readily converted into the corresponding pentacyclic lactams 5a/b with the pyrido[1,2-a:3,4-b']biindole skeleton. Ccompound 5a was studied by X-ray crystallography and shown to be the 2,3-trans-isomer. The reaction proceeds via electrophilic attack of the protonated species 2 on free 1 with steric approach central to form the trans-stereoisomeric 3 and/or 5.
• The Characterization of Indole-3-acetic Acid and its Esters¹
  作者：Carl T. Redemann、Sylvan H. Wittwer、Harold M. Sell

  DOI：10.1021/ja01150a526

  日期：1951.6
• Studies on Difficult Intramolecular Hydroaminations in the Context of Four Syntheses of Alkaloid Natural Products
  作者：Isabelle Dion、Jean-François Vincent-Rocan、Lei Zhang、Pamela H. Cebrowski、Marie-Eve Lebrun、Jennifer Y. Pfeiffer、Anne-Catherine Bédard、André M. Beauchemin

  DOI：10.1021/jo4023149

  日期：2013.12.20

  Examples of intramolecular alkene hydroaminations forming six-membered ring systems are rare, especially for systems in which the double bond is disubstituted. Such cyclizations have important synthetic relevance. Herein we report a systematic study of these cyclizations using recently developed Cope-type hydroamination methodologies. Difficult intramolecular alkene hydroaminations were used as key steps in syntheses of 2-epi-pumiliotoxin C, coniine, N-norreticuline and desbromoarborescidine A. This effort required the development of optimized hydroamination conditions to improve the efficiency of the cyclizations. Collectively, our results show that Cope-type cyclizations can be achieved on a variety of challenging substrates and proceed under similar conditions for both N-H and N-substituted hydroxylamines.