2-(3-trifluoromethylphenoxy)butanoic acid | 60626-14-4

• 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: 2-(3-trifluoromethylphenoxy)butanoic acid
• 英文别名: α-(3-Trifluormethylphenoxy)-buttersaeure；2-(3-Trifluormethylphenoxy)buttersaeure；2-[3-(Trifluoromethyl)phenoxy]butanoic acid
• CAS: 60626-14-4
• 化学式: C₁₁H₁₁F₃O₃
• mdl: MFCD03422235
• 分子量: 248.202
• InChiKey: HDTBFPIWBVTQGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 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：

  2-(3-trifluoromethylphenoxy)butanoic acid 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以78.3%的产率得到[2-ethyl-2-(3-trifluoromethylphenoxy)]ethanol
  参考文献：
  名称：

  Phytoene Desaturase Inhibition by O-(2-Phenoxy)ethyl-N-aralkylcarbamates

  摘要：

  O-[1-Ethyl-2-(3-trifluoromethylphenoxy)]ethyl-N-benzylcarbamate exhibits a marked inhibition of carotenoid biosynthesis. Forty-one analogues were synthesized and assayed for plant-type phytoene desaturase (PDS) and zeta-carotene desaturase (ZDS) inhibition in a cell-free system using recombinant enzymes obtained from Escherichia coli transformants. The target enzyme of all carbamates synthesized in this study is PDS and not ZDS; no inhibition of ZDS was observed using a 10(-4) M inhibitor concentration. Four compounds, O-[1-ethyl-2-(3-trifluoromethylphenoxy)]ethyl-N-(2-phenylethyl)carbamate (23), O-[1-ethyl-2-(3-trifluoromethylphenoxy)]ethyl-N-(2-chlorobenzyl)carbamate (25), O-[1-ethyl-2-(3-trifluoromethylphenoxy)]ethyl-N-(2-chlorobenzyl)carbamate (26), and a[1-methyl-2(3-trifluoromethylphenoxy)]ethyl-N-benzylcarbamate (30), were the most potent PDS inhibitors. Their p/(50) values, the negative logarithms of the molar concentration that produces a 50% inhibition, were 7.5, representing the same inhibitory activity as norflurazon. With respect to a structure-activity relationship the oxygen atom of the phenoxy group and a carbamate structure in O-(1-ethyl-2-phenoxy) ethyl-N-aralkylcarbamates studied were found to be essential for strong PDS inhibitors. Also, introduction of an ethyl group at the alpha-position of the ethylene bridge between the phenoxy group and the carbamate was important for a strong PDS inhibitor. Substituents at the 2- and/or 3-position of the phenoxybenzene ring were found to be favorable to a strong PDS inhibition of the analogues.

  DOI：

  10.1021/jf0262413
• 作为产物：
  描述：

  ethyl 2-(3-trifluoromethylphenoxy)butanoate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 2-(3-trifluoromethylphenoxy)butanoic acid
  参考文献：
  名称：

  Phytoene Desaturase Inhibition by O-(2-Phenoxy)ethyl-N-aralkylcarbamates

  摘要：

  O-[1-Ethyl-2-(3-trifluoromethylphenoxy)]ethyl-N-benzylcarbamate exhibits a marked inhibition of carotenoid biosynthesis. Forty-one analogues were synthesized and assayed for plant-type phytoene desaturase (PDS) and zeta-carotene desaturase (ZDS) inhibition in a cell-free system using recombinant enzymes obtained from Escherichia coli transformants. The target enzyme of all carbamates synthesized in this study is PDS and not ZDS; no inhibition of ZDS was observed using a 10(-4) M inhibitor concentration. Four compounds, O-[1-ethyl-2-(3-trifluoromethylphenoxy)]ethyl-N-(2-phenylethyl)carbamate (23), O-[1-ethyl-2-(3-trifluoromethylphenoxy)]ethyl-N-(2-chlorobenzyl)carbamate (25), O-[1-ethyl-2-(3-trifluoromethylphenoxy)]ethyl-N-(2-chlorobenzyl)carbamate (26), and a[1-methyl-2(3-trifluoromethylphenoxy)]ethyl-N-benzylcarbamate (30), were the most potent PDS inhibitors. Their p/(50) values, the negative logarithms of the molar concentration that produces a 50% inhibition, were 7.5, representing the same inhibitory activity as norflurazon. With respect to a structure-activity relationship the oxygen atom of the phenoxy group and a carbamate structure in O-(1-ethyl-2-phenoxy) ethyl-N-aralkylcarbamates studied were found to be essential for strong PDS inhibitors. Also, introduction of an ethyl group at the alpha-position of the ethylene bridge between the phenoxy group and the carbamate was important for a strong PDS inhibitor. Substituents at the 2- and/or 3-position of the phenoxybenzene ring were found to be favorable to a strong PDS inhibition of the analogues.

  DOI：

  10.1021/jf0262413

文献信息

• Novel prostaglandin compounds, processes for the preparation thereof and pharmaceutical compositions containing them
  申请人：AMERICAN CYANAMID COMPANY

  公开号：EP0002590A1

  公开（公告）日：1979-06-27

  The invention provides novel prostaglandin compounds and processes for the preparation thereof which are prostaglandins of the E, F, or A series having on the terminal methylene carbon of the alpha chain a substituent selected from the group consisting of wherein R is an alkyl group and R15 is C1-C4 alkyl, di-C1-C4- alkylamino and phenyl or phenyl substituted with one or more substituents selected from the group consisting of C1-C4 alkyl, OR, SR, F or C1 wherein R is as previously defined. Processes for the preparation of these compounds are described as well as pharmaceutical compositions containing them. The compounds have a potential utility in medicine as for example: hypotensive agents, anti-ulcer agents and bronchodilators.

  本发明提供了新型前列腺素化合物及其制备方法，这些化合物是 E、F 或 A 系列的前列腺素，其 α 链的末端亚甲基碳上有一个从以下组中选出的取代基：其中 R 是烷基，R15 是 C1-C4 烷基、二 C1-C4 烷基氨基和苯基或被一个或多个从以下组中选出的取代基取代的苯基，这些组包括 C1-C4 烷基、OR、SR、F 或 C1，其中 R 如前所定义。 本发明描述了这些化合物的制备方法以及含有这些化合物的药物组合物。 这些化合物在医药方面具有潜在的用途，例如：降血压剂、抗溃疡剂和支气管扩张剂。
• Anilide herbicides
  申请人：SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ B.V.

  公开号：EP0289100B1

  公开（公告）日：1992-04-01
• DISUBSTITUIERTE TRIFLUORMETHYLPYRIMIDINONE UND IHRE VERWENDUNG ALS CCR2 ANTAGONISTEN
  申请人：Bayer Pharma Aktiengesellschaft

  公开号：EP3046912A1

  公开（公告）日：2016-07-27
• US3971850A
  申请人：——

  公开号：US3971850A

  公开（公告）日：1976-07-27
• US4085272A
  申请人：——

  公开号：US4085272A

  公开（公告）日：1978-04-18