ethyl 2-diazo-4,4,5,5,6,6,6-heptafluoro-3-oxohexanoate | 15959-98-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: ethyl 2-diazo-4,4,5,5,6,6,6-heptafluoro-3-oxohexanoate
• 英文别名: (Z)-2-diazonio-1-ethoxy-4,4,5,5,6,6,6-heptafluoro-1-oxohex-2-en-3-olate
• CAS: 15959-98-5
• 化学式: C₈H₅F₇N₂O₃
• 分子量: 310.128
• InChiKey: PJAXFZHTZFOPJE-UHFFFAOYSA-N

物化性质

• 沸点：
  44-48 °C(Press: 0.6 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  45.4
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  ethyl 2-diazo-4,4,5,5,6,6,6-heptafluoro-3-oxohexanoate 在 platinum(IV) oxide 氢气 作用下， 以 溶剂黄146 为溶剂， 生成 2-Acetamino-4,4,5,5,6,6,6-heptafluor-hexansaeure-aethylester
  参考文献：
  名称：

  Steglich,W. et al., Angewandte Chemie, 1967, vol. 79, # 17/18, p. 822 - 823

  摘要：

  DOI：
• 作为产物：
  描述：

  七氟丁酰基乙酸乙酯 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 以61.4%的产率得到ethyl 2-diazo-4,4,5,5,6,6,6-heptafluoro-3-oxohexanoate
  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

• 一种合成4-多氟烷基-3,5-二羰基吡唑化合物的方法
  申请人：福州大学

  公开号：CN110272389B

  公开（公告）日：2022-11-11

  本发明公开了一种合成4‑多氟烷基‑3,5‑二羰基吡唑化合物的方法，其以芳基乙酮或芳基亚甲基丙酮作为底物，重氮基多氟乙酰乙酸乙酯作为多氟烷基源，在铜催化碱性条件下一步合成所述4‑多氟烷基‑3,5‑二羰基‑吡唑化合物。本发明合成方法具有操作简便、条件温和、原料易得、产物多样化等优点。
• Two-Stage Synthesis of 3-(Perfluoroalkyl)-Substituted Vinyldiazocarbonyl Compounds and Their Nonfluorinated Counterparts: A Comparative Study
  作者：G. Prakash、Valerij Nikolaev、Murat Supurgibekov

  DOI：10.1055/s-0032-1318309

  日期：——

  Two approaches for the synthesis of fluorinated (F) and nonfluorinated (H) 4-(alkoxycarbonyl)-substituted cis- and trans-vinyldiazocarbonyl compounds with substituents of variable stereoelectronic nature (H, Me, Ph, CF3, OTBS) at the C-3 atom of the vinyl double bond from the relevant 1,3-dicarbonyl compounds were compared: a pathway using the Wittig reaction followed by a diazo transfer reaction was most efficient for the synthesis of the H-vinyldiazocarbonyl compounds (total yields of up to 60%), while the yields of their F-analogues under similar conditions did not exceed 16-37%. An approach via diazo transfer followed by the Wittig reaction, in contrast, is more effective for the preparation of F-vinyldiazocarbonyl compounds (total yields 37-69%). The configuration of the resulting F-and H-vinyldiazocarbonyl compounds is evidently controlled by the steric bulk of the substituent at the C-3 atom of the vinyl double bond and, in addition, depends on the specific synthetic pathway.
• 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.
• Steglich,W. et al., Angewandte Chemie, 1967, vol. 79, # 17/18, p. 822 - 823
  作者：Steglich,W. et al.

  DOI：——

  日期：——