(E)-5-(4-nitrophenyl)-1-phenylpent-2-en-4-yn-1-one | 1514900-17-4

• 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: (E)-5-(4-nitrophenyl)-1-phenylpent-2-en-4-yn-1-one
• CAS: 1514900-17-4
• 化学式: C₁₇H₁₁NO₃
• 分子量: 277.279
• InChiKey: JPXWLYKVXXQMMU-WEVVVXLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.39
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  60.21
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (E)-5-(4-nitrophenyl)-1-phenylpent-2-en-4-yn-1-one 、 5,5-二甲基-1,3-环己二酮 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 以86%的产率得到6,6-dimethyl-2-(4-nitrobenzyl)-3-(2-oxo-2-phenylethyl)-6,7-dihydrobenzofuran-4(5H)-one
  参考文献：
  名称：

  A Metal-Free Tandem C–C/C–O Bond Formation Approach to Diversely Functionalized Tetrasubstituted Furans

  摘要：

  A novel and efficient method for the synthesis of diversely functionalized furans is developed via DBU-mediated tandem Michael addition/5-exo-dig-cycloisomerization of enynes and keto-methylenes. This [3 + 2]-annulation is operationally simple under metal-free reaction conditions with 100% atom economy and broad substrate scope.

  DOI：

  10.1021/jo4023342
• 作为产物：
  描述：

  (4-硝基苯基)炔丙醛 、 alkaline earth salt of/the/ methylsulfuric acid 以 四氢呋喃 为溶剂， 反应 12.0h， 以85%的产率得到(E)-5-(4-nitrophenyl)-1-phenylpent-2-en-4-yn-1-one
  参考文献：
  名称：

  A Metal-Free Tandem C–C/C–O Bond Formation Approach to Diversely Functionalized Tetrasubstituted Furans

  摘要：

  A novel and efficient method for the synthesis of diversely functionalized furans is developed via DBU-mediated tandem Michael addition/5-exo-dig-cycloisomerization of enynes and keto-methylenes. This [3 + 2]-annulation is operationally simple under metal-free reaction conditions with 100% atom economy and broad substrate scope.

  DOI：

  10.1021/jo4023342

文献信息

• Applications of Thermal Activation, Ball-milling and Aqueous Medium in Stereoselective Michael Addition of Nitromethane to Enynones Catalyzed by Chiral Squaramides
  作者：Żaneta A. Ignatiuk、Mikołaj J. Janicki、Robert W. Góra、Krzysztof Konieczny、Rafał Kowalczyk

  DOI：10.1002/adsc.201801498

  日期：2019.3.5

  to conjugated en‐ynones was performed through the application of chiral squaramides. Three non‐classical approaches to promote the addition reaction were tested, including activation of the nucleophile by inorganic base in a biphasic aqueous system, thermal activation, and ball‐milling. Hydrogen‐bonding catalysis was effective in all these methods, providing 1,4‐addition products in high yields and

  硝基甲烷的立体选择性加成是通过应用手性方酰胺来实现的。测试了三种促进加成反应的非经典方法，包括双相水性体系中无机碱对亲核试剂的活化，热活化和球磨。氢键催化在所有这些方法中均有效，以高收率和高达98％的立体选择性提供1,4加成产物，需要1-5 mol％的金鸡纳生物碱方酸酰胺。