{p-[(α,α,α-trifluoro-p-tolyl)oxy]phenyl}acetic acid | 148401-41-6

• 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: {p-[(α,α,α-trifluoro-p-tolyl)oxy]phenyl}acetic acid
• 英文别名: {4-[4-(Trifluoromethyl)phenoxy]phenyl}acetic acid；2-[4-[4-(trifluoromethyl)phenoxy]phenyl]acetic acid
• CAS: 148401-41-6
• 化学式: C₁₅H₁₁F₃O₃
• 分子量: 296.246
• InChiKey: JRTULMQCKMTDED-UHFFFAOYSA-N

物化性质

• 沸点：
  385.6±42.0 °C(Predicted)
• 密度：
  1.340±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  {p-[(α,α,α-trifluoro-p-tolyl)oxy]phenyl}acetic acid 在 劳森试剂 、 氯化亚砜 作用下， 以 二氯甲烷 、 xylene 、 苯 为溶剂， 反应 124.0h， 生成 N-(4-chloro-3-methyl-5-isothiazolyl)thio-2-{p-[(α,α,α-trifluoro-p-tolyl)oxy]phenyl}acetamide
  参考文献：
  名称：

  N-Alkyl-N-(5-isothiazolyl)- and N-(Alkylisothiazolin-5-ylidene)- phenylacetamides. Synthesis and Biological Activity

  摘要：

  Treatment of 5-amino-4-chloro-3-methylisothiazole (3) with the acid chloride of [p-[(alpha,alpha,alpha-trifluoro-p-tolyl)oxy]phenyl]acetic acid (6) afforded the amide N-(4-chloro-3-methyl-5-isothiazolyl)-2-[p-[(alpha,alpha, alpha-trifluoro-p-tolyl)oxy]phenyl]acetamide (1), which was substituted with various alkyl groups in an effort to alleviate toxicity toward non-target organisms through a proinsecticide approach. Alkylations of 1 under a variety of reaction conditions afforded two major products which were derived from amide-nitrogen substitution, N-alkyl-N-(4-chloro-3- methyl-5-isothiazolyl)-2-[p-[(alpha,alpha,alpha-trifluoro-p-tolyl)oxy]phenyl]acetamides (a), and ring-nitrogen substitution, N-(2-alkyl-4-chloro-3-methyl-3-isothiazolin-5-ylidene)-2-[p- [(alpha,alpha,alpha-trifluoro-p-tolyl)oxy]phenyl] acetamides(8). Derivatives 7 and 8 were found to exhibit lessened toxicity to trout as well as insects, but, in general, efficacy toward insects was retained to a greater degree. In particular methoxymethyl, ethoxymethyl, ethyl, and ethyl-d(5) substituents demonstrated the best combination of insect efficacy and safening toward trout. Significantly different in vivo efficacies of the N-methyl and N-CD3 analogs suggest that 7 and 8 are proinsecticides requiring activation by dealkylation.

  DOI：

  10.1021/jf960679j
• 作为产物：
  描述：

  对羟基苯乙酸 、 对氯三氟甲苯 在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 反应 16.0h， 以79%的产率得到{p-[(α,α,α-trifluoro-p-tolyl)oxy]phenyl}acetic acid
  参考文献：
  名称：

  N-Alkyl-N-(5-isothiazolyl)- and N-(Alkylisothiazolin-5-ylidene)- phenylacetamides. Synthesis and Biological Activity

  摘要：

  Treatment of 5-amino-4-chloro-3-methylisothiazole (3) with the acid chloride of [p-[(alpha,alpha,alpha-trifluoro-p-tolyl)oxy]phenyl]acetic acid (6) afforded the amide N-(4-chloro-3-methyl-5-isothiazolyl)-2-[p-[(alpha,alpha, alpha-trifluoro-p-tolyl)oxy]phenyl]acetamide (1), which was substituted with various alkyl groups in an effort to alleviate toxicity toward non-target organisms through a proinsecticide approach. Alkylations of 1 under a variety of reaction conditions afforded two major products which were derived from amide-nitrogen substitution, N-alkyl-N-(4-chloro-3- methyl-5-isothiazolyl)-2-[p-[(alpha,alpha,alpha-trifluoro-p-tolyl)oxy]phenyl]acetamides (a), and ring-nitrogen substitution, N-(2-alkyl-4-chloro-3-methyl-3-isothiazolin-5-ylidene)-2-[p- [(alpha,alpha,alpha-trifluoro-p-tolyl)oxy]phenyl] acetamides(8). Derivatives 7 and 8 were found to exhibit lessened toxicity to trout as well as insects, but, in general, efficacy toward insects was retained to a greater degree. In particular methoxymethyl, ethoxymethyl, ethyl, and ethyl-d(5) substituents demonstrated the best combination of insect efficacy and safening toward trout. Significantly different in vivo efficacies of the N-methyl and N-CD3 analogs suggest that 7 and 8 are proinsecticides requiring activation by dealkylation.

  DOI：

  10.1021/jf960679j

文献信息

• Chemoselective Decarboxylative Oxygenation of Carboxylic Acids To Access Ketones, Aldehydes, and Peroxides
  作者：Renpeng Guan、Guanhong Chen、Elliot L. Bennett、Zhiliang Huang、Jianliang Xiao

  DOI：10.1021/acs.orglett.3c00649

  日期：2023.4.14

  Reported here is a photocatalytic strategy for the chemoselective decarboxylative oxygenation of carboxylic acids using Ce(III) catalysts and O2 as the oxidant. By simply changing the base employed, we demonstrate that the selectivity of the reaction can be channeled to favor hydroperoxides or carbonyls, with each class of products obtained in good to excellent yields and high selectivity. Notably

  此处报道的是一种使用 Ce(III) 催化剂和 O 2作为氧化剂的羧酸化学选择性脱羧氧化的光催化策略。通过简单地改变所用的碱，我们证明反应的选择性可以引导到有利于氢过氧化物或羰基化合物，每一类产品都以良好到极好的收率和高选择性获得。值得注意的是，有价值的酮、醛和过氧化物是直接从容易获得的羧酸中生产出来的，无需额外的步骤。
• [EN] 4-(ARALKOXY OR ARALKYLAMINO)PYRIDINE PESTICIDES_________________
  申请人：DOWELANCO

  公开号：WO1993005050A1

  公开（公告）日：1993-03-18

  (EN) 4-(Aralkoxy or aralkylamino)pyridines, for example 4-[2-[4-(2,2,2-trifluoroethoxy)phenyl]ethoxy]pyridine, are active against nematodes, insects, mites, and plant pathogens.(FR) Les composés 4-(aralcoxy ou aralkylamino)pyridines, par exemple 4-[2-[4-(2,2,2, tri-fluoroéthoxy)phényl]éthoxy]pyridine sont actifs contre les nématodes, les insectes, les mites et les agents pathogènes végétaux.

  4-(取代基或取代氨基的)吡咯，例如4-[2-[4-(2,2,2-三氟乙氧基)苯基]乙氧基]吡咯，能够对抗蜱虫、lesion无害、昆虫、和植物病原体。 4-(有基团或有取代氨基的)吡咯，例如4-[2-[4-(2,2,2-三氟乙氧基)苯基]乙氧基]吡咯，是抗蜱虫、防治昆虫、虫卵以及植物病原体的有效物质。
• 4-(ARALKOXY OR ARALKYLAMINO)PYRIDINE PESTICIDES-----------------
  申请人：DOWELANCO

  公开号：EP0555469A1

  公开（公告）日：1993-08-18
• EP0555469A4
  申请人：——

  公开号：EP0555469A4

  公开（公告）日：1995-06-21
• EP0556381A4
  申请人：——

  公开号：EP0556381A4

  公开（公告）日：1995-06-21