4-(5-dibenzylamino-1H-indol-3-yl)-butan-2-one | 890408-47-6

• 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: 4-(5-dibenzylamino-1H-indol-3-yl)-butan-2-one
• 英文别名: 4-[5-(dibenzylamino)-1H-indol-3-yl]butan-2-one
• CAS: 890408-47-6
• 化学式: C₂₆H₂₆N₂O
• 分子量: 382.505
• InChiKey: AGNVSWZJRRDUAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  36.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(5-dibenzylamino-1H-indol-3-yl)-butan-2-one 、 烯丙醇 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 9-borabicyclo[3.3.1]nonane dimer 、 1-己烯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 (3S)-4-(3-allyl-5-dibenzylamino-3H-indol-3-yl)butan-2-one 、 (3R)-4-(3-allyl-5-dibenzylamino-3H-indol-3-yl)butan-2-one
  参考文献：
  名称：

  Palladium-Catalyzed Enantioselective C-3 Allylation of 3-Substituted-1H-Indoles Using Trialkylboranes

  摘要：

  We have developed a new enantioselective C-3 allylation of 3-substituted indoles using allyl alcohol and trialkylboranes. Asymmetric syntheses of 3,3-disubstituted indolines and indolenines in enantiomeric excesses up to 90% have been achieved using the bulky borane 9-BBN-C6H13 as the promoter of the reaction. The dependence of the selectivity on the nature of the borane suggests that the boron reagent has a role beyond promoting ionization of the allyl alcohol. A protocol for oxidation of indolenines to oxindoles has also been developed and led to a formal synthesis of (-)-phenserine.

  DOI：

  10.1021/ja0608139
• 作为产物：
  描述：

  5-硝基吲哚 在 indium(III) chloride 、 palladium on activated charcoal 氢气 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 16.0h， 生成 4-(5-dibenzylamino-1H-indol-3-yl)-butan-2-one
  参考文献：
  名称：

  Palladium-Catalyzed Enantioselective C-3 Allylation of 3-Substituted-1H-Indoles Using Trialkylboranes

  摘要：

  We have developed a new enantioselective C-3 allylation of 3-substituted indoles using allyl alcohol and trialkylboranes. Asymmetric syntheses of 3,3-disubstituted indolines and indolenines in enantiomeric excesses up to 90% have been achieved using the bulky borane 9-BBN-C6H13 as the promoter of the reaction. The dependence of the selectivity on the nature of the borane suggests that the boron reagent has a role beyond promoting ionization of the allyl alcohol. A protocol for oxidation of indolenines to oxindoles has also been developed and led to a formal synthesis of (-)-phenserine.

  DOI：

  10.1021/ja0608139

文献信息

• Silica-Supported Sodium Sulfonate with Ionic Liquid:  A Neutral Catalyst System for Michael Reactions of Indoles in Water
  作者：Yanlong Gu、Chikako Ogawa、Shū Kobayashi

  DOI：10.1021/ol062446b

  日期：2007.1.1

  A neutral catalytic system for Michael reactions of indoles has been developed by combining silica-supported benzenesulfonic acid sodium salt with hydrophobic ionic liquid in water. An efficient hydrophobic environment could be created on the surface of the silica-sodium material under the conditions. Various indole derivatives and alpha,beta-unsaturated carbonyl compounds including some acid-labile

  通过将二氧化硅负载的苯磺酸钠盐与疏水性离子液体在水中混合，开发了一种中性的吲哚迈克尔反应催化体系。在这种条件下，可以在硅酸钠材料的表面上创建有效的疏水环境。各种吲哚衍生物和α，β-不饱和羰基化合物（包括一些对酸不稳定的底物）已成功地应用于该系统，用水为唯一溶剂，以高收率提供了所需的迈克尔加合物。[结构：见文字]。