methyl 2-[(4-chlorophenyl)-(toluene-4-sulfonylamino)methyl]acrylate

• 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: methyl 2-[(4-chlorophenyl)-(toluene-4-sulfonylamino)methyl]acrylate
• 英文别名: methyl 2-((4-chlorophenyl)((4-methylphenyl)sulfonamido)methyl)acrylate；methyl 2-[(4-chlorophenyl)-[(4-methylphenyl)sulfonylamino]methyl]prop-2-enoate
• 化学式: C₁₈H₁₈ClNO₄S
• 分子量: 379.864
• InChiKey: BJRORJMMWMISRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  72.47
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 2-[(4-chlorophenyl)-(toluene-4-sulfonylamino)methyl]acrylate 在 四丁基溴化铵 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以76%的产率得到methyl (2E)-3-(4-chlorophenyl)-2-[(toluene-4-sulfonylamino)methyl]acrylate
  参考文献：
  名称：

  Highly Efficient aza-Baylis−Hillman Reaction of N-Tosylated Imines with MVK, Acrolein, and Phenyl Acrylate or α-Naphthyl Acrylate:  Lewis Base Effects and A Convenient Method to Synthesize α,β-Unsaturated β-Amino Carbonyl Compounds

  摘要：

  This paper describes several highly efficient aza-Baylis-Hillman reactions of N-tosylated imines with MVK, acrolein, and phenyl acrylate or alpha-naphthyl acrylate in the presence of a Lewis base. In most cases, the reaction can be completed within 1 h using the appropriate Lewis base catalyst. An efficient method to synthesize beta-amino ketones, aldehydes and esters in high yields and short reaction time has been developed.

  DOI：

  10.1021/jo035103p
• 作为产物：
  描述：

  丙烯酸甲酯（MA） 、 N-(4-chlorobenzylidene)-4-methylbenzenesulfonamide 在 hydroxyl ionic liquid-supported quinuclidine 作用下， 反应 4.0h， 以91%的产率得到methyl 2-[(4-chlorophenyl)-(toluene-4-sulfonylamino)methyl]acrylate
  参考文献：
  名称：

  Hydroxyl ionic liquid (HIL)-immobilized quinuclidine for Baylis–Hillman catalysis: synergistic effect of ionic liquids as organocatalyst supports

  摘要：

  Hydroxyl ionic liquid (HIL) has been explored as a novel support for Baylis-Hillman catalyst. The HIL-supported catalyst showed a better catalytic activity compared to other IL-immobilized catalyst that has no hydroxyl group attached to the IL scaffold. The hydroxyl group linked on IL played an important role in facilitating efficient catalysis under solvent-free conditions. The corresponding Baylis-Hillman and aza-Baylis-Hillman adducts were obtained in good to excellent yields in all cases examined. The HIL-supported quinuclidine can be readily recovered and reused for six times without significant loss of catalytic activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.12.045

文献信息

• Application of the ring-closing metathesis to the formation of 2-aryl-1H-pyrrole-3-carboxylates as building blocks for biologically active compounds
  作者：Katarzyna Grychowska、Bartłomiej Kubica、Marcin Drop、Evelina Colacino、Xavier Bantreil、Maciej Pawłowski、Jean Martinez、Gilles Subra、Paweł Zajdel、Frédéric Lamaty

  DOI：10.1016/j.tet.2016.09.059

  日期：2016.11

  kinetics on the RCM. After an aromatization step, this methodology allowed for an efficient generation of variously substituted and unprecedented 2-aryl-1H-pyrrole-3-carboxylates in good yields and cost-effectiveness. The resulting molecules might serve as key building blocks for the generation of CNS-oriented compound libraries.

  闭环复分解（RCM）是制备环状有机化合物的有力工具。然而，该方法的主要限制之一是难以制备大量靶分子。在本文中，我们描述了基于相应β-氨基酯的闭环复分解过程作为关键步骤的关于2芳基1 H-吡咯-3-羧酸的克级合成的综合研究。这项研究包括在RCM上评估溶剂和催化剂以及反应动力学。进行芳构化步骤后，此方法可有效生成各种取代的和前所未有的2-芳基-1 H-吡咯-3-羧酸酯具有良好的产率和成本效益。所得的分子可以作为生成面向CNS的化合物库的关键构件。
• On the tandem Morita-Baylis-Hillman/transesterification processes. Mechanistic insights for the role of protic solvents
  作者：Arthur G. Carpanez、Fernando Coelho、Giovanni W. Amarante

  DOI：10.1016/j.molstruc.2017.10.039

  日期：2018.2

  Abstract Despite the remarkable rate acceleration under protic solvents such as alcohols and water, the use of acrylates as activated alkenes places a problem due to the possibility of ester hydrolysis or transesterification. Therefore, the tandem transesterification/Morita-Baylis-Hillman (MBH) reactions were investigated by ESI(+)-MS/(MS) and 1 H NMR techniques. For the first time, the MBH back-reaction

  摘要 尽管在醇和水等质子溶剂下速率加速显着，但由于酯水解或酯交换的可能性，使用丙烯酸酯作为活化烯烃存在问题。因此，串联酯交换/Morita-Baylis-Hillman (MBH) 反应通过 ESI(+)-MS/(MS) 和 1 H NMR 技术进行了研究。首次使用标记试剂通过 ESI(+)-MS/(MS) 对 MBH 反反应进行了全面检查，揭示了涉及 DABCO 到丙烯酸酯的迈克尔型加成步骤的复杂平衡。在这个阶段观察到 C-和 O-质子化，表明酯交换过程发生在羟醛步骤之前，这是该机制的速率决定步骤。在这个阶段，可能会涉及一个短寿命的四面体中间体，应该在这些过程中加以考虑。
• Efficient synthesis of benzimidazo[1,2-<i>a</i>]pyrimidinone derivatives<i>via</i>catalyst-free reactions of Baylis-Hillman acetates, alcohols, and amines with 2-aminobenzimidazole
  作者：Yan Wang、Zahid Shafiq、Li Liu、Dong Wang、Yong-Jun Chen

  DOI：10.1002/jhet.324

  日期：——

  Benzimidazo[1,2‐a]pyrimidinone and its derivatives were easily prepared in good to excellent yields via tandem reactions of 2‐aminobenzimidazole with Baylis–Hillman acetates, alcohols, and amines without the use of catalyst and additive in one‐pot process. The method provided an efficient and facile route to the title fused heterocyclic compounds with different functional groups. J. Heterocyclic Chem

  苯并咪唑并[1,2一]嘧啶酮及其衍生物在良好很容易制备优异的产率通过2-氨基苯并咪唑的串联反应用的Baylis-希尔曼乙酸盐，醇，和没有在一锅法中使用的催化剂和添加剂的胺。该方法为具有不同官能团的标题稠合杂环化合物提供了一种有效而简便的途径。J.杂环化​​学。（2010）。
• Highly Efficient aza-Baylis−Hillman Reaction of <i>N</i>-Tosylated Imines with MVK, Acrolein, and Phenyl Acrylate or α-Naphthyl Acrylate:  Lewis Base Effects and A Convenient Method to Synthesize α,β-Unsaturated β-Amino Carbonyl Compounds
  作者：Yong-Mei Xu、Min Shi

  DOI：10.1021/jo035103p

  日期：2004.1.1

  This paper describes several highly efficient aza-Baylis-Hillman reactions of N-tosylated imines with MVK, acrolein, and phenyl acrylate or alpha-naphthyl acrylate in the presence of a Lewis base. In most cases, the reaction can be completed within 1 h using the appropriate Lewis base catalyst. An efficient method to synthesize beta-amino ketones, aldehydes and esters in high yields and short reaction time has been developed.
• Hydroxyl ionic liquid (HIL)-immobilized quinuclidine for Baylis–Hillman catalysis: synergistic effect of ionic liquids as organocatalyst supports
  作者：Xueling Mi、Sanzhong Luo、Hui Xu、Long Zhang、Jin-Pei Cheng

  DOI：10.1016/j.tet.2005.12.045

  日期：2006.3

  Hydroxyl ionic liquid (HIL) has been explored as a novel support for Baylis-Hillman catalyst. The HIL-supported catalyst showed a better catalytic activity compared to other IL-immobilized catalyst that has no hydroxyl group attached to the IL scaffold. The hydroxyl group linked on IL played an important role in facilitating efficient catalysis under solvent-free conditions. The corresponding Baylis-Hillman and aza-Baylis-Hillman adducts were obtained in good to excellent yields in all cases examined. The HIL-supported quinuclidine can be readily recovered and reused for six times without significant loss of catalytic activity. (c) 2005 Elsevier Ltd. All rights reserved.