1-(2-methyl-1H-indol-3-yl)pentan-3-one | 1314439-25-2

• 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: 1-(2-methyl-1H-indol-3-yl)pentan-3-one
• CAS: 1314439-25-2
• 化学式: C₁₄H₁₇NO
• 分子量: 215.295
• InChiKey: COJZRWTWCFYQDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(2-methyl-1H-indol-3-yl)pentan-3-one 在 i-PrNHBn*TFA 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以62.6 mg的产率得到(E)-1-(2-methyl-1H-indol-3-yl)pent-1-en-3-one
  参考文献：
  名称：

  Csp2–Csp2 bond formation via Lewis acid/ammonium salt cocatalyzed tandem addition and oxidative dehydrogenation strategy: alkenylation of indoles with α,β-unsaturated ketones

  摘要：

  The alkenylation of indoles with alpha,beta-unsaturated ketones through a tandem addition and oxidative dehydrogenation strategy has been developed. This method provides an alternative approach for C3 alkenylation of indoles with alpha,beta-unsaturated ketones. Using inexpensive and readily available BF3 center dot Et2O and an ammonium salt as the efficient cocatalyst constitutes the attractive advantage of this reaction. (C) 2012 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2012.05.053
• 作为产物：
  描述：

  2-甲基吲哚 、 1-戊烯-3-酮 在 tin(II) chloride dihdyrate 作用下， 以 异丙醇 为溶剂， 反应 48.0h， 以97%的产率得到1-(2-methyl-1H-indol-3-yl)pentan-3-one
  参考文献：
  名称：

  金属卤化物水合物作为路易斯酸催化剂，用于吲哚和活性烯烃的共轭弗里德工艺反应

  摘要：

  研究了金属卤化物水合物如SnCl2·2H2O，MnCl2·4H2O，SrCl2·6H2O，CrCl2·6H2O，CoCl2·6H2O和CeCl3·7H2O作为温和的路易斯酸催化剂，用于吲哚和活性烯烃之间的共轭Friedel-Crafts反应。反应在室温下用脂族不饱和酮在几天内进行，而查耳酮仅在回流条件下反应。与硝基苯乙烯的反应在溶剂中或在无溶剂条件下进行。在所有情况下，均获得了合理至良好的产量。

  DOI：

  10.1590/s0103-50532011000400003

文献信息

• Triethylbenzylammonium Chloride as a Useful and Efficient Catalyst for the Alkylation of Indole/substituted Indoles in Water: A Comparative Study between Conventional and Microwave Irradiation
  作者：Shokip Tumtina、Chingrishon Kathing、Ivulho Tovishe Phucho、Ridaphun Nongrum、Bekington Myrboh、Rishanlang Nongkhlaw

  DOI：10.1002/jccs.201400221

  日期：2015.4

  green and facile method for the alkylation of indole/substituted indole in water using a phase Transfer catalyst (Triethylbenzylammonium Chloride, TEBA) to synthesise bis‐indolyl methanes (BIMs) and Michael addition of indole to α,β‐unsaturated carbonyl compounds is reported. The substitution of indoles occurred exclusively at the 3‐position and products of N‐alkylation has not been observed. However

  报道了一种绿色简便的方法，该方法使用相转移催化剂（三乙基苄基氯化铵，TEBA）将水中的吲哚/取代的吲哚烷基化以合成双吲哚甲烷（BIM），并将吲哚迈克尔加成到α，β-不饱和羰基化合物上。吲哚的取代仅发生在3位，未观察到N-烷基化的产物。但是，对于3位取代的吲哚，发现在2位发生反应。还报道了常规加热和微波辐射之间的比较研究。
• Metal halide hydrates as lewis acid catalysts for the conjugated friedel-crafts reactions of indoles and activated olefins
  作者：Cristiane S. Schwalm、Marco Antonio Ceschi、Dennis Russowsky

  DOI：10.1590/s0103-50532011000400003

  日期：——

  CrCl2·6H2O, CoCl2·6H2O e CeCl3·7H2O were investigated as mild Lewis acids catalysts for the conjugate Friedel-Crafts reaction between indoles and activated olefins. The reactions were carried out with aliphatic unsaturated ketones over a period of days at room temperature, while chalcones reacted only under reflux conditions. The reactions with nitrostyrenes were either performed in solvent or under

  研究了金属卤化物水合物如SnCl2·2H2O，MnCl2·4H2O，SrCl2·6H2O，CrCl2·6H2O，CoCl2·6H2O和CeCl3·7H2O作为温和的路易斯酸催化剂，用于吲哚和活性烯烃之间的共轭Friedel-Crafts反应。反应在室温下用脂族不饱和酮在几天内进行，而查耳酮仅在回流条件下反应。与硝基苯乙烯的反应在溶剂中或在无溶剂条件下进行。在所有情况下，均获得了合理至良好的产量。
• Csp2–Csp2 bond formation via Lewis acid/ammonium salt cocatalyzed tandem addition and oxidative dehydrogenation strategy: alkenylation of indoles with α,β-unsaturated ketones
  作者：Shi-Kai Xiang、Guolin Wu、Bo Zhang、Yuxin Cui、Ning Jiao

  DOI：10.1016/j.tetlet.2012.05.053

  日期：2012.7

  The alkenylation of indoles with alpha,beta-unsaturated ketones through a tandem addition and oxidative dehydrogenation strategy has been developed. This method provides an alternative approach for C3 alkenylation of indoles with alpha,beta-unsaturated ketones. Using inexpensive and readily available BF3 center dot Et2O and an ammonium salt as the efficient cocatalyst constitutes the attractive advantage of this reaction. (C) 2012 Published by Elsevier Ltd.