bis[3-(1-methyl)indolyl]-p-chloroacetophenone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: bis[3-(1-methyl)indolyl]-p-chloroacetophenone
• 英文别名: 1-(4-chlorophenyl)-2,2-bis(1-methyl-1H-indol-3-yl)ethanone；1-(4-Chlorophenyl)-2,2-bis(1-methylindol-3-yl)ethanone；1-(4-chlorophenyl)-2,2-bis(1-methylindol-3-yl)ethanone
• 化学式: C₂₆H₂₁ClN₂O
• 分子量: 412.919
• InChiKey: IBQKDXMUUQTNFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  26.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-氯苯乙烯 、 1-甲基吲哚 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bis[3-(1-methyl)indolyl]-p-chloroacetophenone
  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

• Asymmetric Friedel–Crafts Alkylations of Indoles with Ethyl Glyoxylate Catalyzed by (S)-BINOL-Titanium(IV) Complex: Direct Access to Enantiomerically Enriched 3-Indolyl(hydroxy)acetates
  作者：Hong-Ming Dong、Hai-Hua Lu、Liang-Qiu Lu、Cai-Bao Chen、Wen-Jing Xiao

  DOI：10.1002/adsc.200600495

  日期：2007.7.2

  Enantioselective Friedel–Crafts alkylation reactions of a variety of indoles with ethyl glyoxylate, catalyzed by a chiral (S)-BINOL-Ti(IV) complex (10 mol %), are reported. The corresponding ethyl 3-indolyl(hydroxy)acetates were formed in good yields and with high enantiomeric excess (up to 96 %). When methyl pyruvate or p-chlorophenylglyoxal was used, the bisindole compound was obtained in excellent

  报道了由手性（S）-BINOL-Ti（IV）配合物（10 mol％）催化的各种吲哚与乙醛酸乙酯的对映选择性Friedel-Crafts烷基化反应。相应的3-吲哚基（羟基）乙酸乙酯以良好的产率和高的对映体过量（高达96％）形成。当使用丙酮酸甲酯或对氯苯基乙二醛时，以优异的产率获得双吲哚化合物。提出了一种可能的机制。
• Metal-Free sp³ C–H Bond Dual-(Het)arylation: I₂-Promoted Domino Process to Construct 2,2-Bisindolyl-1-arylethanones
  作者：Yan-ping Zhu、Mei-cai Liu、Feng-cheng Jia、Jing-jing Yuan、Qing-he Gao、Mi Lian、An-xin Wu

  DOI：10.1021/ol301366p

  日期：2012.7.6

  A molecular I-2-promoted sp(3) C-H bond dual-(het)arylation protocol was developed for the synthesis of 2,2-bisindolyl-1-arylethanones. Through a logical design, three mechanism-different reactions (iodination, Kornblum oxidation, and Friedel Crafts reaction) were assembled in a single reactor. A variety of 2,2-bisindolyl-1-aryl ethanones were synthesized from simple and readily available aryl methyl ketones and indoles. In the reaction, metal, base, and ligand were all avoidable.
• 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.