2-((2-甲基-1H-吲哚-3-基)(苯基)甲基)丙二酸二乙酯 | 102559-39-7

• 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
• 中文名称: 2-((2-甲基-1H-吲哚-3-基)(苯基)甲基)丙二酸二乙酯
• 英文名称: diethyl 2-((2-methyl-1H-indol-3-yl)(phenyl)methyl)malonate
• 英文别名: diethyl 2-[(2-methyl-1H-indol-3-yl)-phenylmethyl]propanedioate
• CAS: 102559-39-7
• 化学式: C₂₃H₂₅NO₄
• 分子量: 379.456
• InChiKey: IMVGCRZRAGHDMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  68.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  sodium diethylmalonate 、 alkaline earth salt of/the/ methylsulfuric acid 生成 2-((2-甲基-1H-吲哚-3-基)(苯基)甲基)丙二酸二乙酯
  参考文献：
  名称：

  Reactions of Optically Active Indole Mannich Bases¹

  摘要：

  DOI：

  10.1021/ja01518a056

文献信息

• An Efficient Tetrabutylammonium Fluoride (TBAF)-Catalyzed Three-Component Synthesis of 3-Substituted Indole Derivatives under Solvent-Free Conditions
  作者：Neetu Singh、Bharat Kumar Allam、Dushyant Singh Raghuvanshi、Krishna Nand Singh

  DOI：10.1002/adsc.201300162

  日期：2013.6.17

  An expedient and efficient one‐pot three‐component synthesis of 3‐substituted indoles has been developed by the reaction of indoles, active methylene compounds and aldehydes using a catalytic amount of tetrabutylammonium fluoride under solvent‐free conditions.

  通过在无溶剂条件下使用催化量的氟化四丁基铵使吲哚，活性亚甲基化合物和醛反应，已开发出了一种简便，高效的三取代吲哚的单锅三组分合成方法。
• Mechanically Induced Fe(III) Catalysis at Room Temperature: Solvent-Free Cross-Dehydrogenative Coupling of 3-Benzylic Indoles with Methylenes/Indoles
  作者：Jing-Bo Yu、Yang Zhang、Zhi-Jiang Jiang、Wei-Ke Su

  DOI：10.1021/acs.joc.6b02197

  日期：2016.11.18

  An Fe(III)-catalyzed solvent-free cross-dehydrogenative coupling of 3-benzylic indoles and compounds with acidic methylene groups has been achieved under high-speed ball-milling (HSBM) conditions at room temperature. The reactions afford desired 3-arylmethylindole derivatives in moderate to high yields within 21 min of grinding. Besides, both N-substituted and N-free indoles can take part in this mechanochemical

  在室温下高速球磨（HSBM）条件下，已实现了Fe（III）催化的3-苄基吲哚和具有酸性亚甲基基团的化合物的无溶剂交叉脱氢偶联反应。该反应在研磨的21分钟内以中等至高产率提供了所需的3-芳基甲基吲哚衍生物。此外，既Ñ取代和Ñ -free吲哚可以在此机械化学反应参加作为有效的亲核试剂，得到了满意的结果双吲哚。值得注意的是，该协议显示了在HSBM条件下使用铁催化剂时诱导高活性的可能性。
• Controllable Enantioselective Friedel−Crafts Reaction¹ between Indoles and Alkylidene Malonates Catalyzed by Pseudo-<i>C</i>₃-Symmetric Trisoxazoline Copper(II) Complexes
  作者：Jian Zhou、Meng-Chun Ye、Zheng-Zheng Huang、Yong Tang

  DOI：10.1021/jo035552p

  日期：2004.2.1

  Pseudo-C-3-symmetric trisoxazoline copper(II) complexes prove to be excellent catalysts in the Friedel-Crafts alkylation of indoles with alkylidene malonates. The absolute stereochemistry of this reaction is shown to be dependent on the solvent. Reactions in isobutyl alcohol afford the Friedel-Crafts alkylation adducts in excellent yields and with up to +98% ee. In 1,1,2,2-tetrachloroethane (TTCE), however, the opposite enantiomers of the products are obtained in good yields with up to -89% ee. Water tolerance of chiral catalyst trisoxazoline 2a/Cu(OTf)(2) is examined, and it is found that the addition of up to 200 equiv of water relative to catalyst in isobutyl alcohol has almost no effect on enantioselectivity but slows down the reaction. The reaction scope is studied as well. The roles of alcohol as the solvent to accelerate the reaction are discussed. The stereochemical models of asymmetric induction for reactions both in isobutyl alcohol and in TTCE are also developed.