(E)-4-(4-methoxystyryl)-2-oxo-2H-chromene-3-carbonitrile

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: (E)-4-(4-methoxystyryl)-2-oxo-2H-chromene-3-carbonitrile
• 英文别名: 4-[(E)-2-(4-methoxyphenyl)ethenyl]-2-oxochromene-3-carbonitrile
• 化学式: C₁₉H₁₃NO₃
• 分子量: 303.317
• InChiKey: PGTZQZYCCUIUOR-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.84
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  63.23
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  当归内酯 、 (E)-4-(4-methoxystyryl)-2-oxo-2H-chromene-3-carbonitrile 在 C₃₁H₃₂N₄O₄ 作用下， 以 二氯甲烷 为溶剂， 反应 168.0h， 以87%的产率得到4-((R)-2-(4-methoxyphenyl)-2-((R)-2-methyl-5-oxo-2,5-dihydrofuran-2-yl)ethyl)-2-oxo-2H-chromene-3-carbonitrile
  参考文献：
  名称：

  Remote Functionalization of 4‐(Alk‐1‐en‐1‐yl)‐3‐Cyanocoumarins via the Asymmetric Organocatalytic 1,6‐Addition

  摘要：

  AbstractAn organocatalytic 1,6‐addition using 4‐(alk‐1‐en‐1‐yl)‐3‐cyanocoumarins as acceptors has been developed. Dienolates derived from 5‐substituted‐furan‐2(3H)‐ones have been employed as pronucleophiles, therefore, enabling the synthesis of hybrid molecules bearing two biologically relevant units. Appropriate design of substrates and the application of quinine‐derived catalyst resulted in very good site‐selectivity as well as chemical and stereochemical efficiency of the process.magnified image

  DOI：

  10.1002/adsc.202100660
• 作为产物：
  描述：

  3-氰基-4-甲基香豆素 、 4-甲氧基苯甲醛 在 哌啶 、 苯甲酸 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以64%的产率得到(E)-4-(4-methoxystyryl)-2-oxo-2H-chromene-3-carbonitrile
  参考文献：
  名称：

  Remote Functionalization of 4‐(Alk‐1‐en‐1‐yl)‐3‐Cyanocoumarins via the Asymmetric Organocatalytic 1,6‐Addition

  摘要：

  AbstractAn organocatalytic 1,6‐addition using 4‐(alk‐1‐en‐1‐yl)‐3‐cyanocoumarins as acceptors has been developed. Dienolates derived from 5‐substituted‐furan‐2(3H)‐ones have been employed as pronucleophiles, therefore, enabling the synthesis of hybrid molecules bearing two biologically relevant units. Appropriate design of substrates and the application of quinine‐derived catalyst resulted in very good site‐selectivity as well as chemical and stereochemical efficiency of the process.magnified image

  DOI：

  10.1002/adsc.202100660

文献信息

• Organocatalytic Asymmetric Approach to γ,δ-Functionalization of 3-Cyano-4-styrylcoumarins via Bifunctional Catalysis
  作者：Marta Romaniszyn、Anna Skrzyńska、Joanna Dybowska、Łukasz Albrecht

  DOI：10.1021/acs.orglett.2c02836

  日期：2022.10.28

  A novel organocatalytic reaction cascade between 3-cyano-4-styrylcoumarins and 2-mercaptoacetophenones is described. It is based on stereocontrolled functionalization of cyanocoumarins proceeding in a sequence of thia-Michael/aldol/annulation reactions. This highly diastereo- and enantioselective reaction is realized by employing enantioselective bifunctional catalysis and exhibits a broad substrate

  描述了 3-cyano-4-styrylcoumarins 和 2-mercaptoacetophenones 之间的新型有机催化反应级联。它基于氰基香豆素的立体控制功能化，该官能化在硫杂-迈克尔/羟醛/环化反应的序列中进行。这种高度非对映和对映选择性反应是通过采用对映选择性双功能催化实现的，具有广泛的底物范围和优异的官能团耐受性。合成应用涉及酰亚胺酯基团的转化，从而打开获取生物学相关香豆素和 δ-内酯融合产物的途径。
• ANGHELOVA, Y.;DIMINOVA, E., ORG. PREP. AND PROCED. INT., 21,(1989) N, C. 341-343
  作者：ANGHELOVA, Y.、DIMINOVA, E.

  DOI：——

  日期：——
• ALY, FAWZY M.;BEDAIR, AHMED H.;SELIM, MOHAMED R., AFINIDAD, 44,(1987) N 412, 489-491
  作者：ALY, FAWZY M.、BEDAIR, AHMED H.、SELIM, MOHAMED R.

  DOI：——

  日期：——
• HAFEZ, EBTISAM ABDEL AZIZ;ELNAGDI, MOHAMED HILMY;ELAGAMEY, ABDEL GHANI AL+, HETEROCYCLES, 26,(1987) N 4, 903-907
  作者：HAFEZ, EBTISAM ABDEL AZIZ、ELNAGDI, MOHAMED HILMY、ELAGAMEY, ABDEL GHANI AL+

  DOI：——

  日期：——
• Remote Functionalization of 4‐(Alk‐1‐en‐1‐yl)‐3‐Cyanocoumarins via the Asymmetric Organocatalytic 1,6‐Addition
  作者：Marta Romaniszyn、Katarzyna Gronowska、Łukasz Albrecht

  DOI：10.1002/adsc.202100660

  日期：2021.11.23

  AbstractAn organocatalytic 1,6‐addition using 4‐(alk‐1‐en‐1‐yl)‐3‐cyanocoumarins as acceptors has been developed. Dienolates derived from 5‐substituted‐furan‐2(3H)‐ones have been employed as pronucleophiles, therefore, enabling the synthesis of hybrid molecules bearing two biologically relevant units. Appropriate design of substrates and the application of quinine‐derived catalyst resulted in very good site‐selectivity as well as chemical and stereochemical efficiency of the process.magnified image