3-(dimethylhydrazono)-4,4,4-trifluorobutanoic acid ethyl ester | 59916-69-7

• 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: 3-(dimethylhydrazono)-4,4,4-trifluorobutanoic acid ethyl ester
• 英文别名: dimethylhydrazone of ethyl trifluoroacetate；ethyl (3E)-3-(dimethylhydrazinylidene)-4,4,4-trifluorobutanoate
• CAS: 59916-69-7
• 化学式: C₈H₁₃F₃N₂O₂
• 分子量: 226.199
• InChiKey: SZKXYATUDUASBJ-WUXMJOGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  41.9
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-(dimethylhydrazono)-4,4,4-trifluorobutanoic acid ethyl ester 、 溴甲苯 生成 ethyl (3E)-2-benzyl-3-(dimethylhydrazinylidene)-4,4,4-trifluorobutanoate
  参考文献：
  名称：

  CHARPENTIER-MORIZE, MICHELINE;AUBERT, CORINNE;LANGLOIS, BERNARD;BEGUE, JE+

  摘要：

  DOI：
• 作为产物：
  描述：

  4,4,4-三氟-2-丁炔乙酯 、 偏二甲肼 以 二氯甲烷 为溶剂， 以76%的产率得到3-(dimethylhydrazono)-4,4,4-trifluorobutanoic acid ethyl ester
  参考文献：
  名称：

  Cyclocondensation of alkylhydrazines and .beta.-substituted acetylenic esters: synthesis of 3-hydroxypyrazoles

  摘要：

  Addition of monosubstituted alkylhydrazines to acetylenic esters with either electron-withdrawing or sterically bulky beta-substituents afforded 1-alkyl-3-hydroxy-5-substituted-pyrazoles 1 as the major regioisomeric product. By comparison, the classical cyclocondensation of alkylhydrazines with beta-keto esters gives the regioisomeric pyrazol-5-ones 2. The reaction solvent employed in these cyclocondensations can have a profound effect on regioisomeric product ratios. Addition of methylhydrazine to 5g in methylene chloride gave regiospecific formation of pyrazolinone 2o, whereas addition in water-methanol mixtures afforded hydroxypyrazole 1o as the major product. Structural assignment of regioisomers 1 and 2 are based on C-13 NMR chemical shifts, long-range heteronuclear coupling constants, and comparisons with regiochemically known hydroxypyrazoles and/or pyrazolinones. Additions of acetylene 5b to 1,1-dimethylhydrazine afforded either acyclic enehydrazone 12 or pyrazolium betaine 13 depending on the reaction conditions.

  DOI：

  10.1021/jo00047a021

文献信息

• Yakimovich,S.I.; Khrustalev,V.A., Journal of Organic Chemistry USSR (English Translation), 1976, vol. 12, p. 957 - 963
  作者：Yakimovich,S.I.、Khrustalev,V.A.

  DOI：——

  日期：——
• Yakimovich, S. I.; Zerova, I. V., Journal of Organic Chemistry USSR (English Translation), 1983, p. 1048 - 1053
  作者：Yakimovich, S. I.、Zerova, I. V.

  DOI：——

  日期：——
• CHARPENTIER-MORIZE, MICHELINE;AUBERT, CORINNE;LANGLOIS, BERNARD;BEGUE, JE+
  作者：CHARPENTIER-MORIZE, MICHELINE、AUBERT, CORINNE、LANGLOIS, BERNARD、BEGUE, JE+

  DOI：——

  日期：——
• AUBERT, CORINNE;BEGUE, JEAN-PIERRE;CHARPENTIER-MORIZE, MICHELINE;NEE, GER+, J. FLUOR. CHEM., 44,(1989) N, C. 377-394
  作者：AUBERT, CORINNE、BEGUE, JEAN-PIERRE、CHARPENTIER-MORIZE, MICHELINE、NEE, GER+

  DOI：——

  日期：——
• YAKIMOVICH, S. I.;ZEROVA, I. V., ZH. ORGAN. XIMII, 1983, 19, N 6, 1175-1181
  作者：YAKIMOVICH, S. I.、ZEROVA, I. V.

  DOI：——

  日期：——