methyl 2-(2-amino-3-methoxycarbonyl-4H-1-benzopyran-4-yl)-2-cyanoethanoate | 128720-13-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: methyl 2-(2-amino-3-methoxycarbonyl-4H-1-benzopyran-4-yl)-2-cyanoethanoate
• 英文别名: methyl 2-amino-4-(1-cyano-2-methoxy-2-oxoethyl)-4H-chromene-3-carboxylate
• CAS: 128720-13-8
• 化学式: C₁₅H₁₄N₂O₅
• 分子量: 302.287
• InChiKey: QCLROZFHJKBOAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2-(2-amino-3-methoxycarbonyl-4H-1-benzopyran-4-yl)-2-cyanoethanoate 生成 (E)-methyl 2-cyano-3-(2-hydroxyphenyl)propenoate
  参考文献：
  名称：

  ROUDIER, J. F.;FOUCAUD, A., SYNTHESIS, BRD, 1984, N 2, 159-160

  摘要：

  DOI：
• 作为产物：
  描述：

  水杨醛 在 哌啶 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 methyl 2-(2-amino-3-methoxycarbonyl-4H-1-benzopyran-4-yl)-2-cyanoethanoate
  参考文献：
  名称：

  O'Callaghan, Conor N.; McMurry, T. Brian H.; Cardin, Christine J., Journal of Chemical Research, Miniprint, 1990, # 5, p. 901 - 922

  摘要：

  DOI：

文献信息

• Electrocatalytic chain transformation of salicylaldehyde and CH acids into substituted 4H-chromenes
  作者：S. K. Feducovich、M. N. Elinson、A. S. Dorofeev、S. V. Gorbunov、R. F. Nasybullin、N. O. Stepanov、G. I. Nikishin

  DOI：10.1007/s11172-008-0093-9

  日期：2008.3

  Electrochemically initiated catalytic chain transformation of salicylaldehydes and CH acids containing the cyano group in an ethanolic solution in an undivided cell produced substituted 4H-chromenes in 85–95% yields.

  电化学引发的水杨醛和含有氰基的 CH 酸在乙醇溶液中的催化链转化在未分开的电池中产生了取代的 4H-色烯，产率为 85-95%。
• A Convenient Synthesis of 4<i>H</i>-Chromenes
  作者：Jean François Roudier、André Foucaud

  DOI：10.1055/s-1984-30764

  日期：——
• Solvent-free cascade reaction: direct multicomponent assembling of 2-amino-4H-chromene scaffold from salicylaldehyde, malononitrile or cyanoacetate and nitroalkanes
  作者：Michail N. Elinson、Alexey I. Ilovaisky、Valentina M. Merkulova、Pavel A. Belyakov、Alexander O. Chizhov、Gennady I. Nikishin

  DOI：10.1016/j.tet.2010.04.024

  日期：2010.6

  The new type of solvent-free cascade reaction was found: the direct heating of the mixture of salicylaldehyde, malononitrile or cyanoacetate and nitroalkanes at 60 degrees C in the presence of catalytic amounts of KF or NaOAc results in the formation of 2-amino-4-(1-nitroalkyl)-4H-chromene-3-carbonitriles or methyl 2-amino-4-(1-nitroalkyl)-4H-chromene-3-carboxylates in 30-90% yields. Thus, the new simple and efficient solvent-free 'one-pot' way to substituted medicinally privileged 2-amino-4H-chromene scaffold was found directly from such simple and reasonable starting compounds as salicylaldehyde, malononitrile or cyanoacetate and nitroalkanes. (C) 2010 Elsevier Ltd. All rights reserved.
• Electrochemically induced chain transformation of salicylaldehydes and alkyl cyanoacetates into substituted 4H-chromenes
  作者：Michail N. Elinson、Alexander S. Dorofeev、Sergey K. Feducovich、Sergey V. Gorbunov、Ruslan F. Nasybullin、Nikita O. Stepanov、Gennady I. Nikishin

  DOI：10.1016/j.tetlet.2006.08.053

  日期：2006.10

  Electrolysis of salicylaldehydes and alkyl cyanoacetates in ethanol in an undivided cell in the presence of sodium bromide results in the formation of substituted alkyl 2-amino-4-(1-cyano-2-alkoxy-2-oxoethyl)-4H-chromene-3-carboxylates in 85-95% yields. (c) 2006 Elsevier Ltd. All rights reserved.
• Potassium exchanged layered zirconium phosphate as catalyst in the preparation of 4H-chromenes
  作者：Massimo Curini、Francesco Epifano、Stefano Chimichi、Francesca Montanari、Morena Nocchetti、Ornelio Rosati

  DOI：10.1016/j.tetlet.2005.03.075

  日期：2005.5

  Substituted 4H-chromenes were easily prepared by reaction of salicylaldehydes and ethylcyanoacetate in solvent free conditions using potassium exchanged layered zirconium phosphate as catalyst. (c) 2005 Elsevier Ltd. All rights reserved.