(Z)-3-amino-3-(3-methoxyphenyl)acrylic acid ethyl ester

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (Z)-3-amino-3-(3-methoxyphenyl)acrylic acid ethyl ester
• 英文别名: ethyl (Z)-3-amino-3-(3-methoxyphenyl)prop-2-enoate
• 化学式: C₁₂H₁₅NO₃
• 分子量: 221.256
• InChiKey: VAXGBFLZNLRUHS-FLIBITNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-碘吡啶 、 (Z)-3-amino-3-(3-methoxyphenyl)acrylic acid ethyl ester 在 copper(l) iodide 、 potassium hydrogencarbonate 、 2-二环己基磷-2'-甲基联苯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以62 %的产率得到2-(3-methoxyphenyl)-4H-pyrido[1,2-a]pyrimidin-4-one
  参考文献：
  名称：

  CuI催化串联乌尔曼型C-N交叉偶联和分子内酰胺化反应合成多取代吡啶并[1,2-a]嘧啶-4-酮

  摘要：

  通过一锅串联 CuI 催化 C-N 键形成/分子内酰胺化反应在 130 °C DMF 中合成各种多取代吡啶并[1,2- a ]嘧啶-4-酮。该方案具有操作简单、底物范围广、官能团耐受性好和克级制备的特点，从而可以从容易获得的2-卤代吡啶和( Z )-吡啶并[1,2- a ]嘧啶-4-酮进行实用和模块化合成。 3-氨基-3-芳基丙烯酸酯的产率良好至优异。

  DOI：

  10.1039/d3ra04454h
• 作为产物：
  描述：

  3-甲氧基苯腈 、 ethyl potassium malonate 在 N,N-二异丙基乙胺 、 zinc(II) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 18.0h， 以73%的产率得到(Z)-3-amino-3-(3-methoxyphenyl)acrylic acid ethyl ester
  参考文献：
  名称：

  The Decarboxylative Blaise Reaction

  摘要：

  [GRAPHICS]Reaction of aryl nitriles with potassium ethyl malonate in the presence of zinc chloride and a catalytic amount of Hunig's base provided beta-amino acrylates in moderate to good yield. Compared to the classical Blaise reaction, this reaction is safer (endothermic), devoid of lachrymatory reagent, and is possible with 0.5-1.0 equiv of zinc chloride.

  DOI：

  10.1021/jo701743m

文献信息

• CONFORMATIONALLY CONSTRAINED, FULLY SYNTHETIC MACROCYCLIC COMPOUNDS
  申请人：POLYPHOR AG

  公开号：US20150051183A1

  公开（公告）日：2015-02-19

  The conformationally restricted, spatially defined macrocyclic ring system of formula (I) is constituted by three distinct molecular parts: Template A, conformation Modulator B and Bridge C. Macrocycles described by this ring system I are readily manufactured by parallel synthesis or combinatorial chemistry in solution or on solid phase. They are designed to interact with a variety of specific biological target classes, examples being agonistic or antagonistic activity on G-protein coupled receptors (GPCRs), inhibitory activity on enzymes or antimicrobial activity. In particular, these macrocycles show inhibitory activity on endothelin converting enzyme of subtype 1 (ECE-1) and/or the cysteine protease cathepsin S (CatS), and/or act as antagonists of the oxytocin (OT) receptor, thyrotropin-releasing hormone (TRH) receptor and/or leukotriene B4 (LTB4) receptor, and/or as agonists of the bombesin 3 (BB3) receptor, and/or show antimicrobial activity against at least one bacterial strain. Thus they are showing great potential as medicaments for a variety of diseases.

  公式（I）的构象受限、空间定义的大环环系统由三个不同的分子部分组成：模板A、构象调节剂B和桥C。由这种环系统I描述的大环可通过并行合成或溶液中或固相上的组合化学轻松制造。它们被设计用于与各种特定生物靶标类相互作用，例如在G蛋白偶联受体（GPCR）上的激动或拮抗活性，酶的抑制活性或抗菌活性。特别是，这些大环显示对亚型1的内皮素转化酶（ECE-1）和/或半胱氨酸蛋白酶卡特普辛S（CatS）的抑制活性，和/或作为催产素（OT）受体、促甲状腺释放激素（TRH）受体和/或白三烯B4（LTB4）受体的拮抗剂，和/或作为瘤胃素3（BB3）受体的激动剂，和/或对至少一种细菌菌株显示抗菌活性。因此，它们显示出作为各种疾病药物的巨大潜力。
• [EN] CONFORMATIONALLY CONSTRAINED, FULLY SYNTHETIC MACROCYCLIC COMPOUNDS<br/>[FR] COMPOSÉS MACROCYCLIQUES ENTIÈREMENT SYNTHÉTIQUES ET À CONFORMATION CONTRAINTE
  申请人：POLYPHOR AG

  公开号：WO2013139697A1

  公开（公告）日：2013-09-26

  The conformationally restricted, spatially defined macrocyclic ring system of formula (I) is constituted by three distinct molecular parts: Template A, conformation Modulator B and Bridge C. Macrocycles described by this ring system I are readily manufactured by parallel synthesis or combinatorial chemistry in solution or on solid phase. They are designed to interact with a variety of specific biological target classes, examples being agonistic or antagonistic activity on G-protein coupled receptors (GPCRs), inhibitory activity on enzymes or antimicrobial activity. In particular, these macrocycles show inhibitory activity on endothelin converting enzyme of subtype 1 (ECE-1 ) and/or the cysteine protease cathepsin S (CatS), and/or act as antagonists of the oxytocin (OT) receptor, thyrotropin-releasing hormone (TRH) receptor and/or leukotriene B4 (LTB4) receptor, and/or as agonists of the bombesin 3 (BB3) receptor, and/or show antimicrobial activity against at least one bacterial strain. Thus they are showing great potential as medicaments for a variety of diseases.

  公式（I）的构象受限、空间定义明确的大环环形系统由三个不同的分子部分构成：模板A、构象调制剂B和桥梁C。由该环系统I描述的大环可通过溶液中的并行合成或组合化学，或者在固相上制造。它们被设计用来与各种特定生物靶标类相互作用，例如在G蛋白偶联受体（GPCR）上的激动或拮抗活性，对酶的抑制活性或抗菌活性。特别是，这些大环显示对第1亚型内皮素转化酶（ECE-1）和/或半胱氨酸蛋白酶S（CatS）的抑制活性，和/或作为催产素（OT）受体、促甲状腺释放激素（TRH）受体和/或白三烯B4（LTB4）受体的拮抗剂，和/或作为瘤胃肽3（BB3）受体的激动剂，和/或对至少一种细菌菌株显示抗菌活性。因此，它们显示出作为各种疾病药物的巨大潜力。
• Conformationally constrained, fully synthetic macrocyclic compounds
  申请人：POLYPHOR AG

  公开号：US10017481B2

  公开（公告）日：2018-07-10

  The conformationally restricted, spatially defined macrocyclic ring system of formula (I) is constituted by three distinct molecular parts: Template A, conformation Modulator B and Bridge C. Macrocycles described by this ring system I are readily manufactured by parallel synthesis or combinatorial chemistry in solution or on solid phase. They are designed to interact with a variety of specific biological target classes, examples being agonistic or antagonistic activity on G-protein coupled receptors (GPCRs), inhibitory activity on enzymes or antimicrobial activity. In particular, these macrocycles show inhibitory activity on endothelin converting enzyme of subtype 1 (ECE-1) and/or the cysteine protease cathepsin S (CatS), and/or act as antagonists of the oxytocin (OT) receptor, thyrotropin-releasing hormone (TRH) receptor and/or leukotriene B4 (LTB4) receptor, and/or as agonists of the bombesin 3 (BB3) receptor, and/or show antimicrobial activity against at least one bacterial strain. Thus they are showing great potential as medicaments for a variety of diseases.

  式（I）的构象受限、空间限定的大环环系统由三个不同的分子部分构成，分别是模板 A、构象调节剂 B 和桥 C：这种环系统 I 所描述的大环很容易通过平行合成或组合化学在溶液或固相中制造出来。它们可与各种特定的生物靶标相互作用，例如对 G 蛋白偶联受体（GPCR）的激动或拮抗活性、对酶的抑制活性或抗菌活性。特别是，这些大环化合物对亚型 1 内皮素转换酶（ECE-1）和/或半胱氨酸蛋白酶 cathepsin S（CatS）具有抑制活性，和/或可作为催产素（OT）受体的拮抗剂、或白三烯 B4（LTB4）受体的拮抗剂，和/或作为弹力素 3（BB3）受体的激动剂，和/或对至少一种细菌菌株具有抗菌活性。因此，它们作为治疗各种疾病的药物显示出巨大的潜力。
• The Decarboxylative Blaise Reaction
  作者：Jae Hoon Lee、Bo Seung Choi、Jay Hyok Chang、Hee Bong Lee、Joo-Yong Yoon、Jaeick Lee、Hyunik Shin

  DOI：10.1021/jo701743m

  日期：2007.12.1

  [GRAPHICS]Reaction of aryl nitriles with potassium ethyl malonate in the presence of zinc chloride and a catalytic amount of Hunig's base provided beta-amino acrylates in moderate to good yield. Compared to the classical Blaise reaction, this reaction is safer (endothermic), devoid of lachrymatory reagent, and is possible with 0.5-1.0 equiv of zinc chloride.
• CuI-catalyzed synthesis of multisubstituted pyrido[1,2-<i>a</i>]pyrimidin-4-ones through tandem Ullmann-type C–N cross-coupling and intramolecular amidation reaction
  作者：Baichuan Mo、Chunxia Chen、Jinsong Peng

  DOI：10.1039/d3ra04454h

  日期：——

  2-a]pyrimidin-4-ones were synthesized via a one-pot tandem CuI-catalyzed C–N bond formation/intramolecular amidation reaction at 130 °C in DMF. This protocol features simple operation, broad substrate scope, good functional group tolerance and gram scale preparation, thus allowing practical and modular synthesis of pyrido[1,2-a]pyrimidin-4-ones from readily available 2-halopyridine and (Z)-3-amino-3-arylacrylate

  通过一锅串联 CuI 催化 C-N 键形成/分子内酰胺化反应在 130 °C DMF 中合成各种多取代吡啶并[1,2- a ]嘧啶-4-酮。该方案具有操作简单、底物范围广、官能团耐受性好和克级制备的特点，从而可以从容易获得的2-卤代吡啶和( Z )-吡啶并[1,2- a ]嘧啶-4-酮进行实用和模块化合成。 3-氨基-3-芳基丙烯酸酯的产率良好至优异。