4-Chloro-4,4-difluoro-but-2-ynoic acid ethyl ester | 129922-55-0

• 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: 4-Chloro-4,4-difluoro-but-2-ynoic acid ethyl ester
• 英文别名: ethyl 4-chloro-4,4-difluorobut-2-ynoate
• CAS: 129922-55-0
• 化学式: C₆H₅ClF₂O₂
• 分子量: 182.554
• InChiKey: KSOWHUDMVXNMSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-Chloro-4,4-difluoro-but-2-ynoic acid ethyl ester 、 2-fluoro-4-chloro-N-hydroxybenzenecarboximidoyl chloride 在 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以71%的产率得到5-(Chloro-difluoro-methyl)-3-(4-chloro-2-fluoro-phenyl)-isoxazole-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis and Herbicidal Activity of 3-Aryl-5-(haloalkyl)-4-isoxazolecarboxamides and Their Derivatives

  摘要：

  A series of unique 3-aryl-5-(haloalkyl)-4-isoxazolecarboxamides have been prepared which exhibit, in both greenhouse and field studies, significant preemergent and postemergent herbicidal activity in the grams per hectare range against broadleaf and narrowleaf weeds. The key step in the formation of the fully substituted isoxazole ring 2 is 1,3 dipolar cycloaddition of a haloalkyl-substituted acetylenic ester and a nitrile oxide intermediate. The 3-aryl-5-(halo alkyl)-4-isoxazolecarboxylate esters 2 are converted to isoxazole-4-carboxamide herbicides 5 and 6, secondary amides 7, and amino acid derivatives 8. Greatest activity was observed with compounds having a combination of three substituents: a substituted phenyl ring in the 3-position, a primary or secondary carboxamide in the 4-position, and a difluorochloromethyl group in the, 5-position of the isoxazole ring.

  DOI：

  10.1021/jf00049a040

文献信息

• Regioselective synthesis of 1-methyl-3-hydroxy-5-perfluoroalkylpyrazoles by the addition of methylhydrazine to perfluoroalkylacetylenic esters
  作者：Bruce C. Hamper

  DOI：10.1016/s0022-1139(00)82607-x

  日期：1990.6

  1H,3H)pyrazoles has been developed. Treatment of perfluoroalkylacetylenic esters with methylhydrazine in methanol-water at 0° or in methylene chloride at low temperature leads to 1-methyl-3-hydroxy-5-perfluoroalkyl(1H,3H)pyrazoles in a regioselective manner. Structural assignments of the regioisomers are based on 13C nmr chemical shifts, long range carbon-fluorine and carbon-proton coupling. The effect

  已开发出对1-甲基-3-羟基-5-全氟烷基（1H，3H）吡唑的区域选择性途径。在甲醇-水中于0°或在二氯甲烷中于低温下用甲基肼处理全氟烷基炔属酸酯会以区域选择性方式生成1-甲基-3-羟基-5-全氟烷基（1H，3H）吡唑。区域异构体的结构分配基于13 C nmr化学位移，远距离碳氟和碳质子偶合。讨论了乙炔结构对反应区域选择性的影响。
• HAMPER, BRUCE C., J. FLUOR. CHEM., 48,(1990) N, C. 123-131
  作者：HAMPER, BRUCE C.

  DOI：——

  日期：——