2-{[4-(trifluoromethyl)phenyl]hydrazono}ethanoic acid | 155432-14-7

• 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-{[4-(trifluoromethyl)phenyl]hydrazono}ethanoic acid
• 英文别名: 4-trifluoromethylphenylhydrazonoacetic acid；(4-trifluoromethylphenylhydrazono)acetic acid；{2-[4-(Trifluoromethyl)phenyl]hydrazinylidene}acetic acid；2-[[4-(trifluoromethyl)phenyl]hydrazinylidene]acetic acid
• CAS: 155432-14-7
• 化学式: C₉H₇F₃N₂O₂
• 分子量: 232.162
• InChiKey: OJNQNQLDKLPAJH-UHFFFAOYSA-N

物化性质

• 沸点：
  320.4±52.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  61.7
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-{[4-(trifluoromethyl)phenyl]hydrazono}ethanoic acid 在 二苯基膦叠氮化物 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 2-(4-trifluoromethylphenyl)-3(2H,4H)-1,2,4-triazolone
  参考文献：
  名称：

  Optically Active Antifungal Azoles. VI. Synthesis and Antifungal Activity of N-((1R,2R)-2-(2,4-Difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl)-N'-(4-substituted phenyl)-3(2H,4H)-1,2,4-triazolones and 5(1H,4H)-tetrazolones.

  摘要：

  通过(1S)-1-[(2R)-2-(2,4-二氟苯基)-2-环氧乙烷基]乙醇的三氟甲磺酸酯衍生物与一种吖唑酮阴离子经SN2取代反应及随后与1H-1,2,4-三氮唑的开环反应制备了一系列具有光学活性的新型抗真菌唑类化合物，N-[(1R,2R)-2-(2,4-二氟苯基)-2-羟基-1-甲基-3-(1H-1,2,4-三唑-1-基)丙基]-N'-(4-取代苯基)-3(2H,4H)-1,2,4-三唑酮(1,2)和5(1H,4H)-四唑酮(3)。手性环氧乙烷乙醇13是以立体控制方式由甲基(R)-乳酸制得。所制得的吖唑酮1-3在体外及体内均展现出强大的抗真菌活性。

  DOI：

  10.1248/cpb.44.314
• 作为产物：
  描述：

  乙醛酸 、 4-(三氟甲基)苯肼 在 盐酸 作用下， 反应 1.0h， 以95%的产率得到2-{[4-(trifluoromethyl)phenyl]hydrazono}ethanoic acid
  参考文献：
  名称：

  Optically Active Antifungal Azoles. VI. Synthesis and Antifungal Activity of N-((1R,2R)-2-(2,4-Difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl)-N'-(4-substituted phenyl)-3(2H,4H)-1,2,4-triazolones and 5(1H,4H)-tetrazolones.

  摘要：

  通过(1S)-1-[(2R)-2-(2,4-二氟苯基)-2-环氧乙烷基]乙醇的三氟甲磺酸酯衍生物与一种吖唑酮阴离子经SN2取代反应及随后与1H-1,2,4-三氮唑的开环反应制备了一系列具有光学活性的新型抗真菌唑类化合物，N-[(1R,2R)-2-(2,4-二氟苯基)-2-羟基-1-甲基-3-(1H-1,2,4-三唑-1-基)丙基]-N'-(4-取代苯基)-3(2H,4H)-1,2,4-三唑酮(1,2)和5(1H,4H)-四唑酮(3)。手性环氧乙烷乙醇13是以立体控制方式由甲基(R)-乳酸制得。所制得的吖唑酮1-3在体外及体内均展现出强大的抗真菌活性。

  DOI：

  10.1248/cpb.44.314

文献信息

• Production of Di or tri-azolyl substituted 5-keto azole compounds
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US05466820A1

  公开（公告）日：1995-11-14

  An azole compound represented by the formula (I): ##STR1## wherein Ar is a substituted phenyl group; R.sup.1 and R.sup.2 independently are a hydrogen atom or a lower alkyl group, or R.sup.1 and R.sup.2 may combine together to form a lower alkylene group; R.sup.3 is a group bonded through a carbon atom; R.sup.4 is a hydrogen atom or an acyl group; X is a nitrogen atom or a methine group; and Y and Z independently are a nitrogen atom or a methine group which may optionally be substituted with a lower alkyl group, or a salt thereof, which is useful for prevention and therapy of fungal infections of mammals as antifungal agent.

  一种以式子（I）表示的唑类化合物：##STR1## 其中Ar是一个取代的苯基；R.sup.1和R.sup.2分别是氢原子或较低的烷基基团，或R.sup.1和R.sup.2可以结合形成较低的烷基烷基基团；R.sup.3是通过碳原子连接的基团；R.sup.4是氢原子或酰基基团；X是氮原子或甲基基团；Y和Z分别是氮原子或甲基基团，可以选择性地用较低的烷基基团取代，或其盐，用作哺乳动物真菌感染的预防和治疗的抗真菌剂。
• Insecticide containing hydrazone derivatives as the active ingredient and novel hydrazone derivates
  申请人：Kawata Shinji

  公开号：US20050203149A1

  公开（公告）日：2005-09-15

  A insecticide characterized by containing as active ingredient a hydrazone derivative of formula (I) wherein A and Q are an aryl or a heterocyclic group, W is oxygen atom, an aminylene, an alkylene group, an oxyalkylene group or an alkyleneoxy, X 1 and X 2 are hydrogen atom, an alkyl, an alkenyl, an alkynyl, an aryl, a heterocyclic group, formyl, an acyl, an alkoxycarbonyl, an aryloxycarbonyl, a heterocyclic oxycarbonyl, an alkylsulfinyl, an arylsulfinyl, a heterocyclic sulfinyl, an alkylsulfonyl, an arylsulfonyl or a heterocyclic sulfonyl, Y is oxygen atom or sulfur atom, Z is hydrogen atom, a halogen atom, cyano, an alkyl, an alkenyl, an alkynyl, an amino, an alkoxy or an alkylthio, the substituents may be substituted; and novel hydrazon derivatives.

  一种杀虫剂，其特征是含有式(I)的腙衍生物作为活性成分，其中A和Q是芳基或杂环基，W是氧原子，氨基亚甲基，烷基，氧烷基或烷氧基，X1和X2是氢原子，烷基，烯基，炔基，芳基，杂环基，甲酰基，酰基，烷氧羰基，芳氧羰基，杂环氧羰基，烷基磺酰基，芳基磺酰基或杂环磺酰基，Y是氧原子或硫原子，Z是氢原子，卤素原子，氰基，烷基，烯基，炔基，氨基，烷氧基或烷硫基，这些取代基可以被取代;以及新的腙衍生物。
• Azole compounds, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US05371101A1

  公开（公告）日：1994-12-06

  An azole compound represented by the formula (I): ##STR1## wherein Ar is a substituted phenyl group; R.sup.1 and R.sup.2 independently are a hydrogen atom or a lower alkyl group, or R.sup.1 and R.sup.2 may combine together to form a lower alkylene group; R.sup.3 is a group bonded through a carbon atom; R.sup.4 is a hydrogen atom or an acyl group; X is a nitrogen atom or a methine group; and n Y and Z independently are a nitrogen atom or a methine group which may optionally be substituted with a lower alkyl group, or a salt thereof, which is useful for prevention and therapy of fungal infections of mammals as antifungal agent.

  一种氮唑化合物，其化学式表示为（I）：##STR1## 其中Ar是取代苯基；R1和R2独立地是氢原子或较低的烷基，或R1和R2可以结合形成较低的烷基链；R3是通过碳原子连接的基团；R4是氢原子或酰基基团；X是氮原子或甲基基团；n，Y和Z独立地是氮原子或甲基基团，可选择地被较低的烷基取代，或其盐，用作哺乳动物真菌感染的预防和治疗的抗真菌剂。
• Insecticide containing hydrazone derivative as the active ingredient and novel hydrazone derivative
  申请人：Nihon Nohyaku Co., Ltd.

  公开号：US07153815B2

  公开（公告）日：2006-12-26

  A insecticide characterized by containing as active ingredient a hydrazone derivative of formula (I) wherein A and Q are an aryl or a heterocyclic group, W is oxygen atom, an aminylene, an alkylene group, an oxyalkylene group or an alkyleneoxy, X1 and X2 are hydrogen atom, an alkyl, an alkenyl, an alkynyl, an aryl, a heterocyclic group, formyl, an acyl, an alkoxycarbonyl, an aryloxycarbonyl, a heterocyclic oxycarbonyl, an alkylsulfinyl, an arylsulfinyl, a heterocyclic sulfinyl, an alkylsulfonyl, an arylsulfonyl or a heterocyclic sulfonyl, Y is oxygen atom or sulfur atom, Z is hydrogen atom, a halogen atom, cyano, an alkyl, an alkenyl, an alkynyl, an amino, an alkoxy or an alkylthio, the substituents may be substituted; and novel hydrazon derivatives.

  一种杀虫剂，其特征在于其活性成分为式（I）的腙衍生物，其中A和Q为芳基或杂环基，W为氧原子，氨基亚甲基，烷基，氧烷基，或烷氧基，X1和X2为氢原子，烷基，烯基，炔基，芳基，杂环基，甲酰基，酰基，烷氧羰基，芳基氧羰基，杂环氧羰基，烷基亚磺酰基，芳基亚磺酰基，杂环亚磺酰基，烷基磺酰基，芳基磺酰基或杂环磺酰基，Y为氧原子或硫原子，Z为氢原子，卤素原子，氰基，烷基，烯基，炔基，氨基，烷氧基或烷硫基，这些取代基可能被取代；以及新的腙衍生物。
• Synthesis and Structure−activity Relationships of Antitubercular 2-Nitroimidazooxazines Bearing Heterocyclic Side Chains
  作者：Hamish S. Sutherland、Adrian Blaser、Iveta Kmentova、Scott G. Franzblau、Baojie Wan、Yuehong Wang、Zhenkun Ma、Brian D. Palmer、William A. Denny、Andrew M. Thompson

  DOI：10.1021/jm901378u

  日期：2010.1.28

  Recently described biphenyl analogues Of the antituberculosis drug PA-824 displayed improved potencies against M. tuberculosis but were poorly soluble. Heterobiaryl analogues of these, in which the first phenyl ring was replaced with various 5-membered ring heterocycles, were prepared with the aim of identifying potent new candidates with improved aqueous solubility. The compounds were constructed by coupling the chiral 2-nitroimidazooxazine alcohol with various halomethyl-substituted arylheterocycles, by cycloadditions to a propargyl ether derivative of this alcohol, or by Suzuki couplings on haloheterocyclic methyl ether derivatives. The arylheterocyclic compounds were all more hydrophilic than their corresponding biphenyl analogues, and several showed solubility improvements. 1-Methylpyrazole, 1,3-linked-pyrazole, 2,4-linked-triazole, and tetrazole analogues had 3- to 7-fold higher MIC potencies against replicating M. tb than predicted by their lipophilicities. Two pyrazole analogues were >10-fold more efficacious than the parent drug in a mouse model of acute M. tb infection, and one displayed a 2-fold higher solubility.