methyl 3-(4-chlorophenyl)-5-trifluoromethyl-4-isoxazolecarboxylate | 104721-44-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 3-(4-chlorophenyl)-5-trifluoromethyl-4-isoxazolecarboxylate
• 英文别名: Methyl 3-(4-chlorophenyl)-5-(trifluoromethyl)-1,2-oxazole-4-carboxylate
• CAS: 104721-44-0
• 化学式: C₁₂H₇ClF₃NO₃
• 分子量: 305.641
• InChiKey: UASKNWWAIFMWID-UHFFFAOYSA-N

物化性质

• 熔点：
  41-42 °C
• 沸点：
  413.7±45.0 °C(Predicted)
• 密度：
  1.427±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 3-(4-chlorophenyl)-5-trifluoromethyl-4-isoxazolecarboxylate 在 盐酸 、 草酰氯 、 溶剂黄146 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 73.0h， 生成
  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
• 作为产物：
  描述：

  4-chlorobenzaldoxime 在 sodium hydroxide 、 N-氯代丁二酰亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 生成 methyl 3-(4-chlorophenyl)-5-trifluoromethyl-4-isoxazolecarboxylate
  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

• A Facile Synthesis of Fluoroalkylisoxazoles
  作者：YANCHANG Shen、JIANHUA Zheng、YAOZENG Huang

  DOI：10.1055/s-1985-31408

  日期：——

  Fluorinated isoxazoles are synthesized from aromatic nitrile oxides and methyl perfluoro-2-alkynoates.

  氟代异噁唑是由芳香族腈氧化物和全氟-2-炔酸甲酯合成的。
• A novel resin-bound CF3-containing building block: application to the solid-phase synthesis of CF3-containing acrylates and 4-isoxazolecarboxylates
  作者：Hong-Jun Wang、Wen Ling、Long Lu

  DOI：10.1016/s0022-1139(01)00461-4

  日期：2001.10

  CF3-containing building block (3) was prepared. Stereospecific Suzuki cross-coupling of compound 3 with a variety of aryl boronic acids gave the corresponding resin-bound coupling products (4), which can be cleaved with sodium methoxide to afford methyl (E)-3-aryl-4,4,4-trifluoro-2-butenoate (5). 1,3-Dipolar cycloaddition of compound 3 with aryl nitrile oxides followed by cleavage with TFA led to methyl

  制备了新型的树脂结合的含CF 3的结构单元（3）。化合物3与各种芳基硼酸的立体定向Suzuki交叉偶联反应得到相应的树脂结合偶联产物（4），可以用甲醇钠裂解该产物，得到甲基（E）-3-芳基-4,4,4 -三氟-2-丁烯酸酯（5）。化合物3与芳基腈氧化物的1，3-偶极环加成，然后用TFA裂解导致区域选择性地由3- NMR确定了3-芳基-5-三氟甲基-4-异恶唑羧酸甲酯。
• SHEN, YANCHANG;ZHENG, JIANHUA;HUANG, YAOZENG, SYNTHESIS, BRD, 1985, N 10, 970-971
  作者：SHEN, YANCHANG、ZHENG, JIANHUA、HUANG, YAOZENG

  DOI：——

  日期：——
• Synthesis and Herbicidal Activity of 3-Aryl-5-(haloalkyl)-4-isoxazolecarboxamides and Their Derivatives
  作者：Bruce C. Hamper、Kindrick L. Leschinsky、Steven S. Massey、Crystal L. Bell、Lawrence H. Brannigan、S. Douglas Prosch

  DOI：10.1021/jf00049a040

  日期：1995.1

  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.