2-cyano-3-(3-hydroxy-4-methoxy-5-nitrophenyl)prop-2-eneamide

• 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: 2-cyano-3-(3-hydroxy-4-methoxy-5-nitrophenyl)prop-2-eneamide
• 英文别名: 2-cyano-N,N-diethyl-3-(3-hydroxy-4-methoxy-5-nitrophenyl)prop-2-enamide
• 化学式: C₁₅H₁₇N₃O₅
• 分子量: 319.317
• InChiKey: UBVWWNMKSARMHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  119
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-cyano-3-(3-hydroxy-4-methoxy-5-nitrophenyl)prop-2-eneamide 在 乙醇 、 三乙胺 作用下， 反应 12.0h， 生成 恩他卡朋
  参考文献：
  名称：

  Novel triethylamine mediated thermal reactions of 3-aryl-2-cyanoprop-2-enoic acid derivatives—demethylation, reduction and vinylogation

  摘要：

  3-Aryl-2-propenoic acid derivatives undergo interesting reactions with hot triethylamine. Substrates like 6 having a methoxyl with a nitro in the ortho and cyanoacrylic derivatives in the para positions give O-demethylated products, for example, entacapone 7. On the other hand compounds like 16 having the NO2 in the para and cyanoacrylic in the ortho position undergo reduction and vinylogation. The latter phenomenon is observed in the absence of the NO2 group also. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.01.148
• 作为产物：
  描述：

  5-硝基香兰素 、 2-氰基-N,N-二乙基乙酰胺 在 IRA 96 resin 作用下， 以 甲苯 为溶剂， 以61%的产率得到2-cyano-3-(3-hydroxy-4-methoxy-5-nitrophenyl)prop-2-eneamide
  参考文献：
  名称：

  Novel triethylamine mediated thermal reactions of 3-aryl-2-cyanoprop-2-enoic acid derivatives—demethylation, reduction and vinylogation

  摘要：

  3-Aryl-2-propenoic acid derivatives undergo interesting reactions with hot triethylamine. Substrates like 6 having a methoxyl with a nitro in the ortho and cyanoacrylic derivatives in the para positions give O-demethylated products, for example, entacapone 7. On the other hand compounds like 16 having the NO2 in the para and cyanoacrylic in the ortho position undergo reduction and vinylogation. The latter phenomenon is observed in the absence of the NO2 group also. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.01.148

文献信息

• Novel triethylamine mediated thermal reactions of 3-aryl-2-cyanoprop-2-enoic acid derivatives—demethylation, reduction and vinylogation
  作者：Attimogae Shivamurthy Harisha、Suresh Parameshwar Nayak、Kuppuswamy Nagarajan、Tayur Narasingarow Guru Row、Amar A. Hosamani

  DOI：10.1016/j.tetlet.2015.01.148

  日期：2015.3

  3-Aryl-2-propenoic acid derivatives undergo interesting reactions with hot triethylamine. Substrates like 6 having a methoxyl with a nitro in the ortho and cyanoacrylic derivatives in the para positions give O-demethylated products, for example, entacapone 7. On the other hand compounds like 16 having the NO2 in the para and cyanoacrylic in the ortho position undergo reduction and vinylogation. The latter phenomenon is observed in the absence of the NO2 group also. (C) 2015 Elsevier Ltd. All rights reserved.