ethyl (E)-2-diazo-4-methoxycarbonyl-3-trifluoromethylbut-3-enoate | 374552-71-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (E)-2-diazo-4-methoxycarbonyl-3-trifluoromethylbut-3-enoate
• 英文别名: 5-ethyl 1-methyl 4-diazo-3-trifluoromethylpent-2-enedioate；5-O-ethyl 1-O-methyl (E)-4-diazo-3-(trifluoromethyl)pent-2-enedioate
• CAS: 374552-71-3
• 化学式: C₉H₉F₃N₂O₄
• 分子量: 266.177
• InChiKey: NZGVDVJHVPSEQY-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  54.6
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl (E)-2-diazo-4-methoxycarbonyl-3-trifluoromethylbut-3-enoate 在 三苯基膦 作用下， 以 乙醚 为溶剂， 反应 24.0h， 以58%的产率得到ethyl 6-methoxy-4-(trifluoromethyl)pyridazine-3-carboxylate
  参考文献：
  名称：

  Chemistry of diazocarbonyl compounds: XXX. Development of a synthetic approach to pyridazine structure via wittig reaction of fluoroalkyl-containing diazo keto esters

  摘要：

  3,4,6-Trisubstituted pyridazines were synthesized from fluoroalkyl-containing diazo keto esters in three steps along two different reaction sequences: (1) Wittig, Staudinger, and diaza-Wittig and (2) Staudinger, Wittig, and diaza-Wittig. According to the first of these with the initial Wittig reaction, the yield of the target 4-fluoroalkyl-substituted pyridazines is almost twice as large as in the reaction sequence involving the corresponding N-phosphanylidene derivatives as intermediates. In both sequences, the final steps (synthesis of vinylphosphazenes and the subsequent diaza-Wittig reaction) occurred as a tandem process, and intermediate vinylphosphazenes could not be isolated. Non-fluorinated diazo keto esters and the respective phosphazenes failed to react with alkoxycarbonylmethylidene(triphenyl)phosphoranes under the same conditions.

  DOI：

  10.1134/s1070428007040203
• 作为产物：
  描述：

  三氟乙酰乙酸乙酯 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 ethyl (E)-2-diazo-4-methoxycarbonyl-3-trifluoromethylbut-3-enoate
  参考文献：
  名称：

  Chemistry of diazocarbonyl compounds: XXX. Development of a synthetic approach to pyridazine structure via wittig reaction of fluoroalkyl-containing diazo keto esters

  摘要：

  3,4,6-Trisubstituted pyridazines were synthesized from fluoroalkyl-containing diazo keto esters in three steps along two different reaction sequences: (1) Wittig, Staudinger, and diaza-Wittig and (2) Staudinger, Wittig, and diaza-Wittig. According to the first of these with the initial Wittig reaction, the yield of the target 4-fluoroalkyl-substituted pyridazines is almost twice as large as in the reaction sequence involving the corresponding N-phosphanylidene derivatives as intermediates. In both sequences, the final steps (synthesis of vinylphosphazenes and the subsequent diaza-Wittig reaction) occurred as a tandem process, and intermediate vinylphosphazenes could not be isolated. Non-fluorinated diazo keto esters and the respective phosphazenes failed to react with alkoxycarbonylmethylidene(triphenyl)phosphoranes under the same conditions.

  DOI：

  10.1134/s1070428007040203

文献信息

• An efficient synthesis of 3-trifluoromethylated 8-oxabicyclo[3.2.1]octa-2,6-dienes
  作者：Yanli Wang、Shizheng Zhu、Guangyu Zhu、Qichen Huang

  DOI：10.1016/s0040-4020(01)00709-8

  日期：2001.8

  vinyldiazomethanes 3 in the presence of furans resulted in the formation of a series of 3-trifluoromethylated 8-oxabicyclo[3.2.1]octa-2,6-dienes. The 4-substituent on the vinyldiazomethanes had great effects on the product distribution and the stereo- and regiochemistry of the [3+4] annulation products. The rhodium(II) acetate catalyzed reaction of 4-carbonyl substituted vinyldiazomethanes 3a–c with furans resulted

  在呋喃存在下，乙酸铑（II）催化3-三氟甲基化的乙烯基重氮甲烷3的分解导致形成一系列3-三氟甲基化的8-氧杂双环[3.2.1] octa-2,6-二烯。乙烯基重氮甲烷上的4-取代基对产物分布以及[3 + 4]环化产物的立体和区域化学有很大影响。4-羰基取代的乙烯基重氮甲烷3a - c与呋喃的乙酸铑（II）催化反应生成环丙烯和[3 + 4]环化产物，而在氰基取代的乙烯基重氮甲烷3d的情况下，仅获得环加成产物。推测该反应遵循串联环丙烷化/ Cope重排机制。
• Chemistry of diazocarbonyl compounds: XXX. Development of a synthetic approach to pyridazine structure via wittig reaction of fluoroalkyl-containing diazo keto esters
  作者：S. V. Galiullina、V. M. Zakharova、G. P. Kantin、V. A. Nikolaev

  DOI：10.1134/s1070428007040203

  日期：2007.4

  3,4,6-Trisubstituted pyridazines were synthesized from fluoroalkyl-containing diazo keto esters in three steps along two different reaction sequences: (1) Wittig, Staudinger, and diaza-Wittig and (2) Staudinger, Wittig, and diaza-Wittig. According to the first of these with the initial Wittig reaction, the yield of the target 4-fluoroalkyl-substituted pyridazines is almost twice as large as in the reaction sequence involving the corresponding N-phosphanylidene derivatives as intermediates. In both sequences, the final steps (synthesis of vinylphosphazenes and the subsequent diaza-Wittig reaction) occurred as a tandem process, and intermediate vinylphosphazenes could not be isolated. Non-fluorinated diazo keto esters and the respective phosphazenes failed to react with alkoxycarbonylmethylidene(triphenyl)phosphoranes under the same conditions.