2-(tert-butylamino)-1-(4-chlorophenyl)-2-oxoethyl benzoate | 1258789-19-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(tert-butylamino)-1-(4-chlorophenyl)-2-oxoethyl benzoate
• 英文别名: [2-(Tert-butylamino)-1-(4-chlorophenyl)-2-oxoethyl] benzoate；[2-(tert-butylamino)-1-(4-chlorophenyl)-2-oxoethyl] benzoate
• CAS: 1258789-19-3
• 化学式: C₁₉H₂₀ClNO₃
• 分子量: 345.826
• InChiKey: GOONIVRRZJIQTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  异氰酸叔丁酯 、 苯甲醛 、 对氯苯甲酸 以 neat (no solvent) 为溶剂， 反应 1.5h， 以67%的产率得到2-(tert-butylamino)-1-(4-chlorophenyl)-2-oxoethyl benzoate
  参考文献：
  名称：

  机械化学活化下 Ugi 4-CR 和 Passerini 3-CR 加合物的合成

  摘要：

  开发了一种机械化学活化策略的成功应用，该策略采用高速球磨 (HSBM) 条件进行基于异氰化物的多组分反应 (IMCR)。使用这种方法合成了有价值的 Ugi（通过液体辅助研磨过程）和 Passerini（在无溶剂条件下）加合物。本文公开的协议允许根据绿色化学原理模块化合成各种化合物, 特别是环境友好的条件、高原子经济性和无毒性副产物。

  DOI：

  10.1002/ejoc.201501371

文献信息

• One-pot preparation of isocyanides from amines and their multicomponent reactions: crucial role of dehydrating agent and base
  作者：Sankar K. Guchhait、Garima Priyadarshani、Vikas Chaudhary、Darshan R. Seladiya、Tapan M. Shah、Nikita P. Bhogayta

  DOI：10.1039/c3ra40347e

  日期：——

  A novel one-pot practical approach for the preparation of isocyanide directly from amine and its reaction has been developed. It employs formylation of amine, dehydration of formamide to isocyanide, and its multicomponent reactions (Ugi, Passerini, and Groebke–Blackburn–Bienaymé reactions). This method provides a significant solution to known synthetic difficulties of isocyanides. In this approach

  已开发出一种新颖的一锅实用方法，可直接从胺制备异氰酸酯及其反应。它使用胺的甲酰化，脱水甲酰胺异氰酸酯及其多组分反应（Ugi，Passerini和Groebke–Blackburn–Bienaymé反应）。该方法为解决已知的异氰酸酯合成难题提供了重要的解决方案。在这种方法中，发现脱水剂和碱的性质和化学计量的量以及副产物的催化功能起着至关重要的作用。
• Passerini three-component cascade reactions in deep eutectic solvent: an environmentally benign and rapid system for the synthesis of α-acyloxyamides
  作者：Ahmad Shaabani、Ronak Afshari、Seyyed Emad Hooshmand

  DOI：10.1007/s11164-015-2390-x

  日期：2016.6

  A greener synthesis of α-acyloxyamides was achieved by one-pot three component cascade Passerini reactions in a deep eutectic solvent (DES). Reactions proceeded rapidly and afforded the corresponding α-acyloxyamides by a variety of aldehydes, acids and isocyanides in excellent yields. The DES has the advantages of easy workup, high yield, and an environmentally benign and, moreover, shortened time as the greatest exclusivity of this system compared with previously reported methods. Passerini three-component cascade reaction in a deep eutectic solvent: an environmentally benign and rapid system for the synthesis of α-acyloxyamides.

  通过在深共熔溶剂（DES）中进行一锅三组分级联Passerini反应，成功实现了更绿色的α-酰氧基酰胺合成。反应迅速进行，并通过多种醛、酸和异氰化物获得相应的α-酰氧基酰胺，产率极高。该DES具有易于处理、高产率以及环保的优势，而且与之前报道的方法相比，其时间更短，是该系统最大的独特之处。在深共熔溶剂中进行的Passerini三组分级联反应：一种环保、快速的α-酰氧基酰胺合成系统。
• Microwave-assisted Passerini reactions under solvent-free conditions
  作者：Angélica de Fátima S Barreto、Otilie E Vercillo、Carlos Kleber Z Andrade

  DOI：10.1590/s0103-50532011000300008

  日期：——

  Various α-acyloxy carboxyamides were easily obtained combining three building blocks in one step: a carboxylic acid, an aldehyde and an isonitrile (Passerini reaction), using microwave irradiation under solvent-free conditions. The products were obtained in good yields (61-90%) and in short reaction times (< 5 min), using two different temperatures (60 and 120 ºC). At 120 ºC, the yields were higher and the reactions faster (< 1 min). Most of the obtained products are multifunctional allowing their application in consecutive Passerini reactions

  各种 α-酰氧基羧酰胺可以通过将三种构建块在一步中结合获得：一种羧酸、一种醛和一种异氰酸酯（帕塞里尼反应），使用微波辐射在无溶剂条件下进行。产物的收率良好（61-90%），反应时间短（< 5 分钟），使用两种不同的温度（60 和 120 ºC）。在 120 ºC 时，收率更高，反应更快（< 1 分钟）。大多数获得的产物是多功能的，允许在连续的帕塞里尼反应中应用。
• Fast and efficient solvent-free Passerini reaction
  作者：Till Bousquet、Mouhamad Jida、Mohamad Soueidan、Rebecca Deprez-Poulain、Francine Agbossou-Niedercorn、Lydie Pelinski

  DOI：10.1016/j.tetlet.2011.11.028

  日期：2012.1

  A Passerini three component condensation between a carboxylic acid, an aldehyde, and an isocyanide at high temperature under solvent-free conditions was developed. This methodology allows the formation of a broad range of alpha-acyloxyamides in excellent yields in short reaction times. (C) 2011 Elsevier Ltd. All rights reserved.
• Supported <i>p</i>-Toluenesulfonic Acid as a Highly Robust and Eco-Friendly Isocyanide Scavenger
  作者：Jhonny Azuaje、Alberto Coelho、Abdelaziz El Maatougui、José Manuel Blanco、Eddy Sotelo

  DOI：10.1021/co100035z

  日期：2011.1.10

  We document here the use of polymer-supported p-toluenesulfonic acid as a highly effective, robust, economical and eco-friendly isocyanide scavenger. The herein described strategy; circumvent the intense and repulsive odor of volatile isocyanides, enabling simplified and odorless workup and purifications. The usefulness of the new scavengers has been validated in a set of diverse isocyanide-based organic transformations and this approach is also amenable to parallel synthesis techniques.