2-(1H-indol-3-yl)-2-methyl-2,3-dihydronaphthalene-1,4-dione

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(1H-indol-3-yl)-2-methyl-2,3-dihydronaphthalene-1,4-dione
• 英文别名: 3-(1H-indol-3-yl)-3-methyl-2H-naphthalene-1,4-dione
• 化学式: C₁₉H₁₅NO₂
• 分子量: 289.334
• InChiKey: FTWZGCRMXGAHFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  49.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  吲哚 、 甲萘醌 在 bismuth(lll) trifluoromethanesulfonate 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以86%的产率得到2-(1H-indol-3-yl)-2-methyl-2,3-dihydronaphthalene-1,4-dione
  参考文献：
  名称：

  Bismuth triflate catalyzed conjugate addition of indoles to α,β-enones

  摘要：

  Reaction of indoles with electron deficient olefins under the influence of bismuth triflate has been studied at ambient temperature and affords the corresponding 3-alkylated indoles in excellent yields. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01555-7

文献信息

• Regioselective Alkylation of Heteroaromatic Compounds with 3-Methyl-2-Quinonyl Boronic Acids
  作者：Marcos Veguillas、María Ribagorda、M. Carmen Carreño

  DOI：10.1021/ol1028964

  日期：2011.2.18

  heteroaromatic compounds with 3-methyl substituted 2-quinonyl boronic acids proceeded by 1,4-addition followed by spontaneous protodeboronation, leading directly to the Friedel−Crafts alkylation products instead of the commonly observed alkenylation derivatives resulting from quinones. The boronic acid acts as a temporary regiocontroller, making the system a highly reactive quinone equivalent and opening a

  杂芳族化合物与3-甲基取代的2-喹啉基硼酸的反应是通过1,4-加成，然后是自发的原去硼硼烷，直接导致Friedel-Crafts烷基化产物，而不是通常由醌产生的烯基化衍生物。硼酸起着暂时的区域调节剂的作用，使该系统具有高反应性的醌当量，并可以直接进入5，5-二取代的环己烯-1，4-二酮。
• Bismuth triflate catalyzed conjugate addition of indoles to α,β-enones
  作者：A.Vijender Reddy、K. Ravinder、T.Venkateshwar Goud、P. Krishnaiah、T.V. Raju、Y. Venkateswarlu

  DOI：10.1016/s0040-4039(03)01555-7

  日期：2003.8

  Reaction of indoles with electron deficient olefins under the influence of bismuth triflate has been studied at ambient temperature and affords the corresponding 3-alkylated indoles in excellent yields. (C) 2003 Elsevier Ltd. All rights reserved.