N-(4-methylbenzyl)-1H-indole-2-carboxamide | 1095888-19-9

• 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: N-(4-methylbenzyl)-1H-indole-2-carboxamide
• 英文别名: N-[(4-methylphenyl)methyl]-1H-indole-2-carboxamide
• CAS: 1095888-19-9
• 化学式: C₁₇H₁₆N₂O
• 分子量: 264.327
• InChiKey: MNSFAYNIKGKNAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  44.9
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(4-ethoxyphenyl)-3-(4-methylphenyl)prop-2-yn-1-ol 、 N-(4-methylbenzyl)-1H-indole-2-carboxamide 在 碘 作用下， 以 乙腈 为溶剂， 以63%的产率得到2-(4-methylbenzyl)-3-(4-methylphenyl)-4-iodo-5-(4-ethoxyphenyl)-5,10-dihydroazepino[3,4-b]indol-1(2H)-one
  参考文献：
  名称：

  Synthesis of Iodo-Indoloazepinones in an Iodine-Mediated Three-Component Domino Reaction via a Regioselective 7-endo-dig Iodo-Cyclization PathwayCDRI Communication No. 8094

  摘要：

  An efficient and rapid synthetic strategy for the naturally occurring indoloazepinone scaffold via a three-component reaction of indole-2-carboxamides, 1,3-disubstituted propargyl alcohols, and I-2 is described. The strategy involves a C-H functionalization-alkyne activation-intramolecular hydroamidation-deprotonation domino sequence. The salient feature of this sequence is regioselective electrophilic 7-endo-dig iodo-cyclization during the intramolecular hydroamidation to afford a seven-membered azepinone ring annulated to the indole.

  DOI：

  10.1021/jo201228t
• 作为产物：
  描述：

  吲哚-2-羧酸 、 4-甲基苄胺 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.5h， 以93%的产率得到N-(4-methylbenzyl)-1H-indole-2-carboxamide
  参考文献：
  名称：

  Synthesis of Iodo-Indoloazepinones in an Iodine-Mediated Three-Component Domino Reaction via a Regioselective 7-endo-dig Iodo-Cyclization PathwayCDRI Communication No. 8094

  摘要：

  An efficient and rapid synthetic strategy for the naturally occurring indoloazepinone scaffold via a three-component reaction of indole-2-carboxamides, 1,3-disubstituted propargyl alcohols, and I-2 is described. The strategy involves a C-H functionalization-alkyne activation-intramolecular hydroamidation-deprotonation domino sequence. The salient feature of this sequence is regioselective electrophilic 7-endo-dig iodo-cyclization during the intramolecular hydroamidation to afford a seven-membered azepinone ring annulated to the indole.

  DOI：

  10.1021/jo201228t

文献信息

• Synthesis of Iodo-Indoloazepinones in an Iodine-Mediated Three-Component Domino Reaction via a Regioselective 7-<i>endo</i>-<i>dig</i> Iodo-Cyclization PathwayCDRI Communication No. 8094
  作者：Sudhir K. Sharma、Anil K. Mandadapu、Brijesh Kumar、Bijoy Kundu

  DOI：10.1021/jo201228t

  日期：2011.8.19

  An efficient and rapid synthetic strategy for the naturally occurring indoloazepinone scaffold via a three-component reaction of indole-2-carboxamides, 1,3-disubstituted propargyl alcohols, and I-2 is described. The strategy involves a C-H functionalization-alkyne activation-intramolecular hydroamidation-deprotonation domino sequence. The salient feature of this sequence is regioselective electrophilic 7-endo-dig iodo-cyclization during the intramolecular hydroamidation to afford a seven-membered azepinone ring annulated to the indole.