2-叠氮基-1,3-二氯-5-(三氟甲基)苯 | 133152-04-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-叠氮基-1,3-二氯-5-(三氟甲基)苯
• 英文名称: 2-azido-1,3-dichloro-5-(trifluoromethyl)benzene
• 英文别名: 2,6-dichloro-4-trifluoromethylphenyl azide；1-azido-2,6-dichloro-4-trifluoromethylbenzene；2,6-Dichloro-4-trifluoromethylphenylazide
• CAS: 133152-04-2
• 化学式: C₇H₂Cl₂F₃N₃
• 分子量: 256.014
• InChiKey: JYKFDWQNPJJVFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  14.4
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2929909090

反应信息

• 作为反应物：
  描述：

  2-叠氮基-1,3-二氯-5-(三氟甲基)苯 在 copper(ll) sulfate pentahydrate 、 硫酸 、 硝酸 、 potassium carbonate 、 sodium ascorbate 作用下， 以 甲醇 、 水 为溶剂， 反应 72.0h， 生成
  参考文献：
  名称：

  三氟甲基取代的N-芳基-聚1,2,3-三唑衍生物的合成†

  摘要：

  报道了–CF 3和–NO 2取代的N-芳基-聚三唑衍生物的合成，表征和物理性质。这些分子是通过在–CF 3取代的芳基叠氮化物和炔烃之间进行可靠的Cu催化的[3 + 2]环加成而制备的，随后是硝化序列，以及由1,2,3引起的卤素基团的碱基促进的亲核取代-三唑。该化合物通过分析和光谱学方法表征。X射线衍射技术证实了某些化合物的固态结构。合成材料在195–308°C的范围内分解。大部分–CF 3和–NO 2带有基团的芳基三唑显示出良好的密度和可接受的爆炸特性。一些含氟聚三唑的化合物显示出正的形成热。

  DOI：

  10.1039/c3ta15184k
• 作为产物：
  描述：

  2,6-二氯-4-三氟甲基苯胺 在 盐酸 、 sodium nitrite 、 sodium azide 、 sodium acetate 作用下， 以 水 为溶剂， 反应 2.0h， 以95%的产率得到2-叠氮基-1,3-二氯-5-(三氟甲基)苯
  参考文献：
  名称：

  1-(2,6-二氯-4-三氟甲基苯基)-4-烷基-1H-[1,2,3]-三唑的区域选择性合成。

  摘要：

  一种通过室温 1,3-偶极环加成反应合成 1-(2,6-二氯-4-三氟甲基苯基)-4-烷基-1H-[1,2,3]-三唑的高效新方法2-叠氮基-1,3-二氯-5-三氟甲基）苯与末端炔烃在Cu（I）盐作为催化剂的存在下被报道。所有反应都得到具有高区域选择性的 1,4-二取代产物，因为没有形成 1,5-二取代产物。所有标题化合物的结构均已通过元素分析、1H-和 13C-NMR 确认，此外，化合物 5a 的结构已通过 X 射线晶体学研究。

  DOI：

  10.3390/molecules13030556

文献信息

• 2-imidazol(in)e substituted aryl-1,2,3-triazole pesticides
  申请人：Schering Agrochemicals Limited

  公开号：US05109012A1

  公开（公告）日：1992-04-28

  Compounds of formula I ##STR1## and salts thereof, in which Ar, W, Z, A, R.sup.1-7, Y, m, p and n have the meanings given in the description, have pesticidal activity especially against insects, acarids and animal endoparasites.

  公式I的化合物及其盐，其中Ar、W、Z、A、R.sup.1-7、Y、m、p和n的含义如描述中所述，具有特别针对昆虫、螨虫和动物内寄生虫的杀虫活性。
• Imidazol(in)e substituted haloarylpyrazole pesticides
  申请人：Schering Agrochemicals Limited

  公开号：US05189053A1

  公开（公告）日：1993-02-23

  Compounds of formula I ##STR1## and salts thereof, in which Ar, W, Z, A, R.sup.1-7, Y, m, p and n have the meanings given in the description, have pesticidal activity especially against insects, acarids and animal endoparasites.

  式I的化合物及其盐，其中Ar，W，Z，A，R.sup.1-7，Y，m，p和n的含义如说明书中所给，具有特别的杀虫、杀螨和杀动物内寄生虫活性。
• Triazole pesticides
  申请人：SCHERING AGROCHEMICALS LIMITED

  公开号：EP0400842A1

  公开（公告）日：1990-12-05

  Compounds of formula I in which Ar is phenyl, pyridyl or pyrimidinyl, each of which is optionally substituted, and X and Z, which may be the same or different, are as defined in the description, have insecticidal and acaricidal activity. Many compounds are novel, as are certain intermediates.

  式I的化合物中，Ar是苯基、吡啶基或嘧啶基，每种基团都可以选择性地被取代，而X和Z可以相同也可以不同，其定义在说明书中，具有杀虫和杀螨活性。许多化合物是新颖的，某些中间体也是新颖的。
• Azole pesticides
  申请人：AgrEvo UK Limited

  公开号：EP0412849A2

  公开（公告）日：1991-02-13

  Compounds of formula I and salts thereof, in which Ar is aryl; W is N and Z is CR⁵; or W is CR¹ and Z is N or CR⁵; A is S(O)m, -CH=CH-, O or NH; R¹ is hydrogen, optionally substituted alkyl, halogen or R²⁰S(O)q; R² and R³ are hydrogen, alkyl, alkenyl or alkynyl, each of which is optionally substituted, aryl, heterocyclyl, cyano, halogen, nitro, YR²⁰, S(O)₂NR⁸R⁹, CHO and functional derivatives thereof, NR⁸R⁹ or CYNR⁸R⁹; either (i) R⁴ and R⁷ which may be the same or different, are hydrogen, optionally substituted alkyl, optionally substituted alkenyl, acyl or optionally substituted alkoxycarbonyl, and R⁶ is hydrogen, or (ii) R⁴ is as defined above and R⁶ and R⁷ form a bond or R⁷ is as defined above and R⁴ and R⁶ form a bond; R⁵ is hydrogen, alkyl, optionally substituted amino or halogen; R⁸ and R⁹ are the same or different and are hydrogen, optionally substituted alkyl, acyl or aryl, or together with the nitrogen to which they are attached, form a 5 to 7 membered ring which can contain other hetero atoms; R²⁰ is optionally substituted alkyl; Y is O or S; m is 0, 1 or 2; p is 0 or 1; n is 0, 1 or 2; and q is 0, 1 or 2, with the proviso that when W is CR¹ and Z is CR⁵ and n and p are both O, R⁴ and R⁷ are not alkyl, have pesticidal activity especially against insects, acarids and animal endoparasites.

  式 I 的化合物 及其盐类、 其中 Ar 为芳基 W 为 N，Z 为 CR⁵；或 W 为 CR¹，Z 为 N 或 CR⁵； A 是 S(O)m、-CH=CH-、O 或 NH； R¹ 是氢、任选取代的烷基、卤素或 R²⁰S(O)q； R² 和 R³ 是氢、烷基、烯基或炔基（其中每个都是任选取代的）、芳基、杂环基、氰基、卤素、硝基、YR²⁰、S(O)₂NR⁸R⁹、CHO 及其功能衍生物、NR⁸R⁹ 或 CYNR⁸R⁹； (i) R⁴ 和 R⁷ 可以相同或不同，它们是氢、任选取代的烷基、任选取代的烯基、酰基或任选取代的烷氧羰基，且 R⁶ 是氢，或 (ii) R⁴ 如上所定义，且 R⁶ 和 R⁷ 形成键，或 R⁷ 如上所定义，且 R⁴ 和 R⁶ 形成键； R⁵ 是氢、烷基、任选取代的氨基或卤素； R⁸ 和 R⁹ 既可以相同，也可以不同，它们是氢、任选取代的烷基、酰基或芳基，或者与它们所连接的氮一起形成一个 5 至 7 个成员的环，其中可以包含其他杂原子； R²⁰ 是任选取代的烷基； Y 是 O 或 S m 是 0、1 或 2 p为0或1 n 是 0、1 或 2；以及 q 为 0、1 或 2，但 W 为 CR¹，Z 为 CR⁵，n 和 p 均为 O 时，R⁴ 和 R⁷ 不是烷基、 具有杀虫活性，特别是对昆虫、害虫和动物内寄生虫。
• Synthesis and Structure−Activity Relationships of 1-Phenyl-1<i>H</i>-1,2,3-triazoles as Selective Insect GABA Receptor Antagonists
  作者：Mohammad Sayed Alam、Ryu Kajiki、Hiromi Hanatani、Xiangyu Kong、Fumiyo Ozoe、Yoshihisa Matsui、Fumio Matsumura、Yoshihisa Ozoe

  DOI：10.1021/jf052773i

  日期：2006.2.1

  To study the interaction of phenylheterocycles with gamma-aminobutyric acid (GABA) receptors, 4- or 5-alkyl(or phenyl)-1-phenyl-1 H-1,2,3-triazoles were synthesized and examined for their ability to inhibit the specific binding of [H-3]-4'-ethynyl-4-n-propylbicycloorthobenzoate (EBOB), a noncompetitive antagonist, to the housefly and rat GABA receptors, as well as to the beta 3 subunit homo-oligomer of the human GABA receptor investigated as a model receptor. 4-Substituted 1-phenyl-1 H-1,2,3-triazoles were found to be more potent competitive inhibitors than the 5-substituted regioisomers in the case of all receptors. The 4-tert-butyl or 4-n-propyl analogue of 1-(2,6-dichloro-4-trifluoromethylphenyl)1 H-1,2,3-triazole exhibited the highest level of inhibition of [H-3]EBOB binding to all receptors. Most of the synthesized analogues were more active in terms of the inhibition of EBOB binding to the housefly and human beta 3 GABA receptors than to the rat receptor. The 4-cyclohexyl analogue showed the highest (185-fold) housefly versus rat receptor selectivity. A three-dimensional quantitative structure-activity relationship (3D-QSAR) analysis demonstrated that both the 4-trifluoromethyl-2,6dichloro substitution on the phenyl ring and a small, bulky, hydrophobic substituent at the 4-position of the triazole ring played significant roles in conferring high potency in cases involving the housefly and human beta 3 receptors. The human beta 3 receptor resembled the housefly receptor in terms of their recognition of phenyltriazoles, whereas 3D-QSAR analysis revealed a slight difference between the two receptors in terms of their mechanisms of recognition of the para-substituent on the phenyl moiety. Some of the triazoles synthesized here exhibited insecticidal activity, which was correlated with their ability to inhibit [H-3]EBOB binding to the housefly receptor. Thus, 1-phenyl-1 H-1,2,3-triazoles with the appropriate substituents exert insecticidal activity by selectively acting at the site for noncompetitive antagonism of insect GABA receptors.