4-[2,2-bis(1-methyl-1H-indol-3-yl)acetyl]benzonitrile | 1447946-97-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-[2,2-bis(1-methyl-1H-indol-3-yl)acetyl]benzonitrile
• 英文别名: 4-[2,2-Bis(1-methylindol-3-yl)acetyl]benzonitrile；4-[2,2-bis(1-methylindol-3-yl)acetyl]benzonitrile
• CAS: 1447946-97-5
• 化学式: C₂₇H₂₁N₃O
• 分子量: 403.483
• InChiKey: JVAMEXRVCPBKOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  50.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-[2,2-bis(1-methyl-1H-indol-3-yl)acetyl]benzonitrile 在 正丁基锂 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.33h， 生成 4-(9-methyl-1-(1-methyl-1H-indol-3-yl)-4-phenyl-9H-carbazol-2-yl)benzonitrile
  参考文献：
  名称：

  Cu(OTf)₂/HFIP catalyzed regioselective cycloisomerization of indole-C3-functionalized alkynols to carbazoles

  摘要：

  We report here a simple and atom economic cycloisomerization reaction of indole-tethered alkynols for constructing diverse carbazoles via 1,2-alkly migration using Cu(OTf)₂/HFIP as the excellent promoter system.

  DOI：

  10.1039/d4ob00421c
• 作为产物：
  描述：

  1-甲基吲哚 、 4-氰基苯乙烯 在 碘 、 二甲基亚砜 、 2-碘酰基苯甲酸 作用下， 以 二甲基亚砜 为溶剂， 反应 7.0h， 以70%的产率得到4-[2,2-bis(1-methyl-1H-indol-3-yl)acetyl]benzonitrile
  参考文献：
  名称：

  I2-promoted direct one-pot synthesis of 2,2-bisindolyl-1-arylethanones from multiform substrates arylethenes, 2-hydroxy-aromatic ketones, and carbinols

  摘要：

  An I-2-promoted domino protocol was developed to construct 2,2-bisindolyl-1-arylethanones from multiform substrates arylethenes, 2-hydroxy-aromatic ketones, and carbinols via three distinct pathways. Through a logical coupled oxidation/Friedel-Crafts alkylation domino process, a variety of 2,2-bisindolyl-1-arylethanones were synthesized in one-pot. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.06.054

文献信息

• I2-promoted direct one-pot synthesis of 2,2-bisindolyl-1-arylethanones from multiform substrates arylethenes, 2-hydroxy-aromatic ketones, and carbinols
  作者：Feng-Cheng Jia、Yan-Ping Zhu、Mei-Cai Liu、Mi Lian、Qing-He Gao、Qun Cai、An-Xin Wu

  DOI：10.1016/j.tet.2013.06.054

  日期：2013.8

  An I-2-promoted domino protocol was developed to construct 2,2-bisindolyl-1-arylethanones from multiform substrates arylethenes, 2-hydroxy-aromatic ketones, and carbinols via three distinct pathways. Through a logical coupled oxidation/Friedel-Crafts alkylation domino process, a variety of 2,2-bisindolyl-1-arylethanones were synthesized in one-pot. (C) 2013 Elsevier Ltd. All rights reserved.
• Cu(OTf)₂/HFIP catalyzed regioselective cycloisomerization of indole-C3-functionalized alkynols to carbazoles
  作者：Srinivasarao Yaragorla、Tabassum Khan、Sayonika Chakroborty

  DOI：10.1039/d4ob00421c

  日期：——

  We report here a simple and atom economic cycloisomerization reaction of indole-tethered alkynols for constructing diverse carbazoles via 1,2-alkly migration using Cu(OTf)₂/HFIP as the excellent promoter system.