methyl α-methylene-β-[(p-toluenesulfonyl)amino]-3-(4-methoxyphenyl)propionate | 364364-52-3

• 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: methyl α-methylene-β-[(p-toluenesulfonyl)amino]-3-(4-methoxyphenyl)propionate
• 英文别名: methyl 2-[(4-methoxyphenyl)-(toluene-4-sulfonylamino)methyl]acrylate；Methyl 2-[(4-methoxyphenyl)-[(4-methylphenyl)sulfonylamino]methyl]prop-2-enoate
• CAS: 364364-52-3
• 化学式: C₁₉H₂₁NO₅S
• 分子量: 375.445
• InChiKey: MRSYDQMRCBQTDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  90.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl α-methylene-β-[(p-toluenesulfonyl)amino]-3-(4-methoxyphenyl)propionate 在 (H₂IMes)Cl₂Ru(CH-o-OiPrC₆H₄) 、 potassium tert-butylate 、 potassium carbonate 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.5h， 生成 methyl 2-(4-methoxyphenyl)-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  闭环复分解在形成2-芳基-1 H-吡咯-3-羧酸盐作为生物活性化合物的基础上的应用

  摘要：

  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。

  DOI：

  10.1016/j.tet.2016.09.059
• 作为产物：
  描述：

  (E)-N-(4-methoxybenzylidene)-4-methylbenzenesulfonamide 、 丙烯酸甲酯（MA） 在 hydroxyl ionic liquid-supported quinuclidine 作用下， 反应 8.0h， 以96%的产率得到methyl α-methylene-β-[(p-toluenesulfonyl)amino]-3-(4-methoxyphenyl)propionate
  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

• Titanium Isopropoxide as Efficient Catalyst for the Aza-Baylis−Hillman Reaction. Selective Formation of α-Methylene-β-amino Acid Derivatives
  作者：Daniela Balan、Hans Adolfsson

  DOI：10.1021/jo0163952

  日期：2002.4.1

  formation of alpha-methylene-beta-amino acid derivatives is achieved using the aza version of the Baylis-Hillman protocol. The products are readily formed in a three-component one-pot reaction between arylaldehydes, sulfonamides, and alpha,beta-unsaturated carbonyl compounds. The reaction is efficiently catalyzed by titanium isopropoxide and 2-hydroxyquinuclidine in the presence of molecular sieves. The

  使用Baylis-Hillman协议的氮杂版本可直接形成α-亚甲基-β-氨基酸衍生物。在芳醛，磺酰胺和α，β-不饱和羰基化合物之间的三组分一锅反应中容易形成产物。在分子筛的存在下，该反应被异丙醇钛和2-羟基喹核啶有效地催化。该协议允许基质的结构变化，耐受贫电子和富电子芳基醛以及各种迈克尔受体。
• Efficient microwave-assisted formation of functionalized 2,5-dihydropyrroles using ruthenium-catalyzed ring-closing metathesis
  作者：Daniela Balan、Hans Adolfsson

  DOI：10.1016/j.tetlet.2004.02.100

  日期：2004.4

  A rapid method for the formation of functionalized 2,5-dihydropyrroles using ruthenium-catalyzed ring-closing metathesis under microwave irradiation is presented. The diene substrates were efficiently prepared from aza-Baylis-Hillman adducts. (C) 2004 Elsevier Ltd. All rights reserved.
• Selective Formation of α-Methylene-β-amino acid Derivatives through the Aza Version of the Baylis−Hillman Reaction
  作者：Daniela Balan、Hans Adolfsson

  DOI：10.1021/jo0158635

  日期：2001.9.1
• 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。
• 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.