5-tert-Butyl-3-(3,5-dichloro-phenyl)-3H-oxazol-2-one | 177212-53-2

• 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: 5-tert-Butyl-3-(3,5-dichloro-phenyl)-3H-oxazol-2-one
• 英文别名: 5-Tert-butyl-3-(3,5-dichlorophenyl)-1,3-oxazol-2-one
• CAS: 177212-53-2
• 化学式: C₁₃H₁₃Cl₂NO₂
• 分子量: 286.158
• InChiKey: GOVQSUBDJOPUJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-tert-Butyl-3-(3,5-dichloro-phenyl)-3H-oxazol-2-one 在 4-二甲氨基吡啶 、 氯 、 邻硝基苯磺酰氯 、 N,N-二异丙基乙胺 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 5-tert-Butyl-4-chloro-3-(3,5-dichloro-phenyl)-3H-oxazol-2-one
  参考文献：
  名称：

  Synthesis and Herbicidal Activities of 4-Substituted 3-Aryl-5-tert-butyl-4-oxazolin-2-ones

  摘要：

  A series of novel 3-aryl-5-tert-butyl-4-chloro-4-oxazolin-2 (16) have been prepared and found to show significant herbicidal activity in the grams per are range against broadleaf and narrowleaf weeds. The key step in the introduction of the chlorine atom at the 4-position of the 4-chloro-4-oxazolin-2-one ring is dichlorination using chlorine gas and subsequent dehydrochlorination using diazabicyclo[5.4.0]undecene. 4-Alkylthio- and 4-methyl-4-oxazolin-2-one rings were synthesized from alpha-substituted alpha-bromopinacolone by cyclization reaction. Among the synthesized compounds, 5-tert-butyl-4-chloro-3-[4-chloro-2-fluoro-5-(2-propynyloxy)phenyl]-4-oxazolin-2-one (16h) showed the greatest activity against several weeds without damage to transplanted rice in the paddy field.

  DOI：

  10.1021/jf980281i
• 作为产物：
  描述：

  ethyl (3,5-dichlorophenyl)carbamate 、 1-溴频哪酮 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以55.6%的产率得到5-tert-Butyl-3-(3,5-dichloro-phenyl)-3H-oxazol-2-one
  参考文献：
  名称：

  A Novel Synthesis of 3-Aryl-5-tert-butyl-4-oxazolin-2-ones.

  摘要：

  一种合成3-芳基-5-丁基-4-恶唑啉-2-酮（6）的高效合成方法被描述。通过使用2.2当量的双(三甲基硅基)胺锂，将N-芳基氨基甲酸乙酯（10）与1-溴-3,3-二甲基-2-丁酮（9a）或1-溴-3-乙基-3-甲基-2-戊酮（9b）反应，可以得到较高产率的6。同时，反应机理也进行了讨论。

  DOI：

  10.1248/cpb.44.699

文献信息

• A Novel Synthesis of 3-Aryl-5-tert-butyl-4-oxazolin-2-ones.
  作者：Noriaki KUDO、Misa TANIGUCHI、Kazuo SATO

  DOI：10.1248/cpb.44.699

  日期：——

  An efficient synthetic method for 3-aryl-5-butyl-4-oxazolin-2-ones (6) is described. The reaction of ethyl N-arylcarbamates (10) with 1-bromo-3, 3-dimethyl-2-butanone (9a) or 1-bromo-3-ethyl-3-methyl-2-pentanone (9b) using 2.2 eq of lithium bis(trimethylsilyl)amide afforded 6 in good yields. The reaction mechanisms are discussed.

  一种合成3-芳基-5-丁基-4-恶唑啉-2-酮（6）的高效合成方法被描述。通过使用2.2当量的双(三甲基硅基)胺锂，将N-芳基氨基甲酸乙酯（10）与1-溴-3,3-二甲基-2-丁酮（9a）或1-溴-3-乙基-3-甲基-2-戊酮（9b）反应，可以得到较高产率的6。同时，反应机理也进行了讨论。
• Synthesis and Herbicidal Activities of 4-Substituted 3-Aryl-5-<i>tert</i>-butyl-4-oxazolin-2-ones
  作者：Noriaki Kudo、Misa Taniguchi、Satoru Furuta、Kazuo Sato、Takeshi Endo、Toyokuni Honma

  DOI：10.1021/jf980281i

  日期：1998.12.1

  A series of novel 3-aryl-5-tert-butyl-4-chloro-4-oxazolin-2 (16) have been prepared and found to show significant herbicidal activity in the grams per are range against broadleaf and narrowleaf weeds. The key step in the introduction of the chlorine atom at the 4-position of the 4-chloro-4-oxazolin-2-one ring is dichlorination using chlorine gas and subsequent dehydrochlorination using diazabicyclo[5.4.0]undecene. 4-Alkylthio- and 4-methyl-4-oxazolin-2-one rings were synthesized from alpha-substituted alpha-bromopinacolone by cyclization reaction. Among the synthesized compounds, 5-tert-butyl-4-chloro-3-[4-chloro-2-fluoro-5-(2-propynyloxy)phenyl]-4-oxazolin-2-one (16h) showed the greatest activity against several weeds without damage to transplanted rice in the paddy field.