methyl 3-(phenylethylamino)acrylate | 194150-84-0

• 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 3-(phenylethylamino)acrylate
• 英文别名: Methyl 3-(2-phenylethylamino)prop-2-enoate
• CAS: 194150-84-0
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: OBSWGZHYMQCILX-UHFFFAOYSA-N

物化性质

• 沸点：
  334.0±35.0 °C(Predicted)
• 密度：
  1.056±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  丙炔酸甲酯 、 methyl 3-(phenylethylamino)acrylate 在 乙基溴化镁 作用下， 生成 methyl 1-phenethyl-2-pyridone-5-carboxylate
  参考文献：
  名称：

  Aminoacrylates. II. An Efficient Synthesis of .ALPHA.-Pyridones by Heterocyclic Annelation Reactions of Magnesium Amides Derived from sec-Aminoacrylates with Methyl Propiolate.

  摘要：

  由仲氨基丙烯酸酯 3 和乙基溴化镁制得的镁酰胺 4 与丙炔酸甲酯（2）反应生成了 α-吡啶酮。这提供了一种高效的杂环环化反应。

  DOI：

  10.1248/cpb.47.128
• 作为产物：
  描述：

  2-苯乙胺 、 丙炔酸甲酯 以 四氢呋喃 为溶剂， 反应 5.0h， 以100%的产率得到methyl 3-(phenylethylamino)acrylate
  参考文献：
  名称：

  Aminoenylesters. I. A New Synthesis of 1,2,3,4-Tetrahydropyrimidines by Heterocyclic Annelation Reactions of Aminoenylesters with Primary Amines and Acetaldehyde.

  摘要：

  氨基烯丙酸酯 3 通过甲基丙酸酯 (1) 与初级胺 2 反应制得，随后与初级胺 2 和乙醛反应，生成了 1, 2, 3, 4-四氢嘧啶 4。这提供了一种新的杂环封合反应。

  DOI：

  10.1248/cpb.45.1117

文献信息

• A novel, chemoselective one-pot procedure for the preparation of 3H-spiro[isobenzofuran-1,2′-pyrrole]-3,3′(1′H)-dione derivatives via oxidative cleavage of 3a,8b-dihydroxyindeno[1,2-b]pyrroles
  作者：Gholam Hossein Mahdavinia、Mohammad R. Mohammadizadeh、Noushin Ariapour、Maryam Alborz

  DOI：10.1016/j.tetlet.2013.10.156

  日期：2014.3

  A one-pot, efficient and chemoselective procedure for the synthesis of new 3H-spiro[isobenzofuran-1,2′-pyrrole]-3,3′(1′H)-dione derivatives has been developed which involves room temperature oxidative cleavage of 3a,8b-dihydroxyindeno[1,2-b]pyrroles themselves synthesized from the reaction of ninhydrin and enaminones in 30% ethanol. A reasonable mechanism is proposed for the oxidation reaction based

  的单釜，新3的合成效率和化学选择性过程ħ -螺[异苯并呋喃-1,2'-吡咯] -3,3' - （1' ħ） -二酮衍生物已被开发涉及室温下的氧化裂解茚三酮和烯胺酮在30％乙醇中的反应合成的3a，8b-二羟基茚并[1,2- b ]吡咯本身。根据本研究的结果和我们先前的相关工作，提出了一种合理的氧化反应机理。
• Synthesis of Functionalized 2-Aminohydropyridines and 2-Pyridinones via Domino Reactions of Arylamines, Methyl Propiolate, Aromatic Aldehydes, and Substituted Acetonitriles
  作者：Jing Sun、Yan Sun、Er-Yan Xia、Chao-Guo Yan

  DOI：10.1021/co200071v

  日期：2011.7.11

  An efficient and practical synthetic method for the functionalized 2-amino hydropyridines and 2-pyridinones was successfully developed via the domino reactions of arylamines, methyl propiolate, aromatic aldehydes and the substituted acetonitriles with triethylamine as base catalyst. Reactions involving malononitrile and cyanoacetamide gave exclusively the 2-aminohydropyridines. On the other hand ethyl cyanoacetate resulted in the 2-pyridinones as main products.
• Domino reaction of arylamine, methyl propiolate, aromatic aldehyde, and indole for facile synthesis of functionalized indol-3-yl acrylates
  作者：Li-Li Zhang、Jing Sun、Chao-Guo Yan

  DOI：10.1016/j.tetlet.2012.10.043

  日期：2012.12

  In the presence of FeCl3 as catalyst the one-pot domino reactions of arylamines, methyl propiolate, aromatic aldehydes, and indole in ethanol at room temperature proceeded smoothly to give methyl 2-(1H-indol-3-yl)arylmethyl-3-arylamino)acrylates in good yields. H-1 NMR spectra and single crystal structures indicated that (Z)-acrylates were stereoselectively formed in the reactions. (C) 2012 Elsevier Ltd. All rights reserved.