diethyl 2-[1H-indol-3-yl(4-nitrophenyl)methyl]malonate | 1220167-31-6

• 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: diethyl 2-[1H-indol-3-yl(4-nitrophenyl)methyl]malonate
• 英文别名: diethyl 2-[1H-indol-3-yl-(4-nitrophenyl)methyl]propanedioate
• CAS: 1220167-31-6
• 化学式: C₂₂H₂₂N₂O₆
• 分子量: 410.426
• InChiKey: BCAQWRLVZBLQQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  吲哚 、 2-(4-硝基亚苄基)丙二酸二乙酯 在 1-butylsulfonic-3-methylimidazolium p-toluenesulfonate 作用下， 反应 0.17h， 以82%的产率得到diethyl 2-[1H-indol-3-yl(4-nitrophenyl)methyl]malonate
  参考文献：
  名称：

  在无溶剂条件下任务特定的离子液体催化高效合成吲哚衍生物

  摘要：

  磺酸官能化的离子液体用作布朗斯台德酸催化剂，用于在室温下在无溶剂条件下以良好到高的收率有效合成吲哚衍生物。

  DOI：

  10.1139/v09-154

文献信息

• Deep eutectic solvent: An efficient and green catalyst for the three-component condensation of indoles, aromatic aldehydes, and activated methylene compounds
  作者：Minh-Nguyet Thi Tran、Xuan-Trang Thi Nguyen、Hai Truong Nguyen、Duy-Khiem Nguyen Chau、Phuong Hoang Tran

  DOI：10.1016/j.tetlet.2019.151481

  日期：2020.2

  The deep eutectic solvent-catalyzed multicomponent reaction of aldehydes, indoles, and activated methylene compounds under sonication has been developed. The method proceeded well for a wide scope of substrates under mild condition to afford 3-substituted indoles in moderate to good yields. Interestingly, no additives or solvents are used for the protocol. Moreover, the deep eutectic solvent (zinc

  已经开发了在超声处理下，醛，吲哚和活化的亚甲基化合物的深共晶溶剂催化的多组分反应。该方法在温和条件下对多种底物进行得很好，以中等至良好的产率提供了3-取代的吲哚。有趣的是，该方案没有使用任何添加剂或溶剂。而且，深的低共熔溶剂（氯化锌和氯化胆碱）是一种廉价且可回收的催化剂，使该协议更加有效，便捷且具有成本效益。
• 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.
• Task-specific ionic-liquid-catalyzed efficient synthesis of indole derivatives under solvent-free conditions
  作者：Sudarshan Das、Matiur Rahman、Dhiman Kundu、Adinath Majee、Alakananda Hajra

  DOI：10.1139/v09-154

  日期：2010.2

  A sulfonic-acid-functionalized ionic liquid is used as a Bronsted acid catalyst for the efficient synthesis of indole derivatives in good-to-high yields at room temperature under solvent-free condi...

  磺酸官能化的离子液体用作布朗斯台德酸催化剂，用于在室温下在无溶剂条件下以良好到高的收率有效合成吲哚衍生物。