2-methyl-1-(3-methyl-1H-indol-2-yl)propan-1-one | 1419101-58-8

• 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-methyl-1-(3-methyl-1H-indol-2-yl)propan-1-one
• CAS: 1419101-58-8
• 化学式: C₁₃H₁₅NO
• 分子量: 201.268
• InChiKey: QWRJTQCVAJAERB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-diazo-3-methylbutan-2-one 、 邻氨基苯乙酮 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.5h， 以85%的产率得到2-methyl-1-(3-methyl-1H-indol-2-yl)propan-1-one
  参考文献：
  名称：

  Cu(OTf)₂-Catalyzed Synthesis of 2,3-Disubstituted Indoles and 2,4,5-Trisubstituted Pyrroles from α-Diazoketones

  摘要：

  A novel method has been devised for the synthesis of 2,4,5-trisubstituted pyrrole derivatives through the coupling of alpha-diazoketones with beta-enaminoketones and esters using 10 mol % of Cu(OTf)(2). A wide range of 2,3-disubstituted indole derivatives were also prepared from alpha-diazoketones and 2-aminoaryl or alkyl ketones. The synthetic versatility of this approach has been exemplified In the formal synthesis of homofascaplysin C.

  DOI：

  10.1021/ol303206w

文献信息

• Microwave Energized Synthesis of 2-Aroylindole Derivatives: Piperidine/DMF as an Effective Medium
  作者：Jayaprakash Soora Haranath、Satheesh Krishna Balam、Syama Sundar Chereddy、Siva Prasad Sthanikam、Santhisudha Sarva、Mohan Gundluru、Suresh Reddy Cirandur

  DOI：10.1002/jhet.2334

  日期：2016.3

  been developed for the synthesis of 2‐aroylindoles (3a, 3b, 3c, 3d, 3e, 3f, 3g, 3h, 3i, 3j) in good yields by the reaction of 2‐aminoketones (1a, 1b, 1c) with phenacyl bromides (2a, 2b, 2c, 2d). The reaction success varied with different bases and solvents in both conventional and microwave methods. But finally, it was established that piperidine in DMF was an effective medium to carry out the reaction

  通过2-氨基酮（1a，1b）的反应以高收率合成了2-芳基吲哚（3a，3b，3c，3d，3e，3f，3g，3h，3i，3j）的便捷高效方法，1c）与苯甲酰溴（2a，2b，2c，2d）。在常规方法和微波方法中，反应成功因碱和溶剂的不同而不同。但是最后，确定了在DMF中的哌啶是在微波辐射条件下进行反应的有效介质。
• Cu(OTf)₂-Catalyzed Synthesis of 2,3-Disubstituted Indoles and 2,4,5-Trisubstituted Pyrroles from α-Diazoketones
  作者：B. V. Subba Reddy、M. Ramana Reddy、Y. Gopal Rao、J. S. Yadav、B. Sridhar

  DOI：10.1021/ol303206w

  日期：2013.2.1

  A novel method has been devised for the synthesis of 2,4,5-trisubstituted pyrrole derivatives through the coupling of alpha-diazoketones with beta-enaminoketones and esters using 10 mol % of Cu(OTf)(2). A wide range of 2,3-disubstituted indole derivatives were also prepared from alpha-diazoketones and 2-aminoaryl or alkyl ketones. The synthetic versatility of this approach has been exemplified In the formal synthesis of homofascaplysin C.