Methanone, (4-chlorophenyl)[4-[(trifluoromethyl)thio]phenyl]- | 89076-25-5

• 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: Methanone, (4-chlorophenyl)[4-[(trifluoromethyl)thio]phenyl]-
• 英文别名: (4-chlorophenyl)-[4-(trifluoromethylsulfanyl)phenyl]methanone
• CAS: 89076-25-5
• 化学式: C₁₄H₈ClF₃OS
• 分子量: 316.731
• InChiKey: XDERQVNEGPJSHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methanone, (4-chlorophenyl)[4-[(trifluoromethyl)thio]phenyl]- 在 三乙胺 、 肼 作用下， 以 乙醇 、 溶剂黄146 、 甲苯 为溶剂， 生成 Acetic acid [1-(4-chloro-phenyl)-1-(4-trifluoromethylsulfanyl-phenyl)-meth-(E)-ylidene]-hydrazide
  参考文献：
  名称：

  Synthesis and insecticidal activity of 4-perhaloalkoxy (or thioalkyl) benzophenonehydrazone derivatives

  摘要：

  DOI：

  10.1002/(sici)1096-9063(199905)55:5<584::aid-ps957>3.0.co;2-g
• 作为产物：
  描述：

  三氟甲基苯硫醚 、 4-氯苯甲酰氯 在 氢氟酸 、 三氟化硼 作用下， 反应 4.0h， 以88%的产率得到Methanone, (4-chlorophenyl)[4-[(trifluoromethyl)thio]phenyl]-
  参考文献：
  名称：

  具有杀虫活性的二苯甲酮derivatives衍生物的合成及其构效关系。

  摘要：

  制备了广泛的二苯甲酮衍生物，并针对选定的咀嚼害虫进行了测试，从而分析了结构-活性关系。仅当芳环在4-位被卤素原子和三氟甲磺酸酯或全卤代烷氧基取代时，才发现良好的活性。相反，部分上的许多取代基导致活性化合物，用酰基型取代基可获得最佳结果。在针对斜纹夜蛾的半田间试验中证实了最佳代表的出色的实验室和温室活性。

  DOI：

  10.1002/1526-4998(200102)57:2<191::aid-ps275>3.0.co;2-o

文献信息

• Benzophenone hydrazone derivatives as insecticides
  申请人：NIHON BAYER AGROCHEM K.K.

  公开号：EP0742202A2

  公开（公告）日：1996-11-13

  Summary Of The Invention Novel benzophenonehydrazone derivatives represented by the formula (I): wherein, R1 is halogen; R2 is hydrogen or C1-4 alkyl; R3 is cyano, optically substituted C1-4 alkyl, C2-4 alkenyl, C3-4 alkynyl, C1-4 alkyl-carbonyl or C1-4 alkoxy-thiocarbonyl; R4 is hydrogen, phenyl, optionally substituted C1-6 alkyl, optionally substituted C2-8 alkenyl, -CO-R8, -CO-O-R9 or R5 is hydrogen, formyl, phenyl, optionally substituted C1-8 alkyl, optionally substituted C2-8 alkenyl, optionally substituted C3-8 alkynyl, optionally substituted C1-8 alkyl-carbonyl, optionally substituted C1-6 alkyl-oxalyl, optionally substituted C1-8 alkoxy-carbonyl, optionally substituted C1-8 alkoxy-oxalyl, optionally substituted C3-8 cycloalkyl-carbonyl, optionally substituted C2-8 alkenyl-carbonyl or optionally substituted benzoyl; R6 is hydrogen or halogen; R7 is hydrogen, halogen or C1-2 alkyl, C1-4 alkyl-carbonyl or C1-4 alkoxy-thiocarbonyl; n is 0, 1 or 2, provided that n is 0 when R3 is cyano, C1-4 alkyl-carbonyl or C1-4 alkoxy-thiocarbonyl, is a single bond of Anti form or of Syn form. The benzophenonehydrazone derivatives of the formula (I) have excellent insecticidal activities.

  发明概述 由式(I)代表的新型二苯甲酮腙衍生物： 其中，R1 是卤素；R2 是氢或 C1-4 烷基；R3 是氰基、被光学取代的 C1-4 烷基、C2-4 烯基、C3-4 炔基、C1-4 烷基-羰基或 C1-4 烷氧基-硫代羰基；R4 是氢、苯基、任选取代的 C1-6 烷基、任选取代的 C2-8 烯基、-CO-R8、-CO-O-R9 或 R5 是氢、甲酰基、苯基、任选取代的 C1-8 烷基、任选取代的 C2-8 烯基、任选取代的 C3-8 烷炔基、任选取代的 C1-8 烷基-羰基、任选取代的 C1-6 烷基-氧羰基、任选取代的 C1-8 烷氧基-羰基、任选取代的 C1-8 烷氧基-氧羰基、任选取代的 C3-8 环烷基-羰基、任选取代的 C2-8 烯基-羰基或任选取代的苯甲酰基；R6是氢或卤素；R7是氢、卤素或C1-2烷基、C1-4烷基-羰基或C1-4烷氧基-硫代羰基；n是0、1或2，但当R3是氰基、C1-4烷基-羰基或C1-4烷氧基-硫代羰基时，n为0，是Anti形式或Syn形式的单键。 式（I）的二苯甲酮腙衍生物具有优异的杀虫活性。
• Fundamental Studies and Development of Nickel-Catalyzed Trifluoromethylthiolation of Aryl Chlorides: Active Catalytic Species and Key Roles of Ligand and Traceless MeCN Additive Revealed
  作者：Guoyin Yin、Indrek Kalvet、Ulli Englert、Franziska Schoenebeck

  DOI：10.1021/jacs.5b00538

  日期：2015.4.1

  A catalytic protocol to convert aryl and heteroaryl chlorides to the corresponding trifluoromethyl sulfides is reported herein. It relies on a relatively inexpensive Ni(cod)(2)/dppf (cod = 1,5-cyclooctadiene; dppf = 1,1'-bis(diphenylphosphino)ferrocene) catalyst system and the readily accessible coupling reagent (Me4N)SCF3. Our computational and experimental mechanistic data are consistent with a Ni-(0)/Ni-(II) cycle and inconsistent with Ni-(I) as the reactive species. The relevant intermediates were prepared, characterized by X-ray crystallography, and tested for their catalytic competence. This revealed that a monomeric tricoordinate Ni-(I) complex is favored for dppf and Cl whose role was unambiguously assigned as being an off-cycle catalyst deactivation product. Only bidentate ligands with wide bite angles (e.g., dppf) are effective. These bulky ligands render the catalyst resting state as [(P-P)Ni(cod)]. The latter is more reactive than Ni(P-P)(2), which was found to be the resting state for ligands with smaller bite angles and suffers from an initial high-energy dissociation of one ligand prior to oxidative addition, rendering the system unreactive. The key to effective catalysis is hence the presence of a labile auxiliary ligand in the catalyst resting state. For more challenging substrates, high conversions were achieved via the employment of MeCN as a traceless additive. Mechanistic data suggest that its beneficial role lies in decreasing the energetic span, therefore accelerating product formation. Finally, the methodology has been applied to synthetic targets of pharmaceutical relevance.
• US4438043A
  申请人：——

  公开号：US4438043A

  公开（公告）日：1984-03-20
• US6077866A
  申请人：——

  公开号：US6077866A

  公开（公告）日：2000-06-20
• Synthesis and structure-activity relationships of benzophenone hydrazone derivatives with insecticidal activity
  作者：Manfred B�ger、Dieter D�rr、Laurenz Gsell、Roger G Hall、Friedrich Karrer、Odd Kristiansen、Peter Maienfisch、Alfons Pascual、Alfred Rindlisbacher

  DOI：10.1002/1526-4998(200102)57:2<191::aid-ps275>3.0.co;2-o

  日期：2001.2

  A broad range of benzophenone hydrazone derivatives was prepared and tested against selected chewing insect pests, allowing the analysis of structure-activity relationships. Good activity was found only when the aromatic rings were substituted at the 4-positions with an halogen atom and a triflate or perhaloalkoxy group. In contrast, a number of substituents on the hydrazone part led to active compounds

  制备了广泛的二苯甲酮衍生物，并针对选定的咀嚼害虫进行了测试，从而分析了结构-活性关系。仅当芳环在4-位被卤素原子和三氟甲磺酸酯或全卤代烷氧基取代时，才发现良好的活性。相反，部分上的许多取代基导致活性化合物，用酰基型取代基可获得最佳结果。在针对斜纹夜蛾的半田间试验中证实了最佳代表的出色的实验室和温室活性。