2-(2,4,6-trifluorophenyl)acetyl chloride | 714963-55-0

• 物质功能分类: 有机原料 - 烃类化合物及其衍生物 - 芳香烃
• 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-(2,4,6-trifluorophenyl)acetyl chloride
• 英文别名: 2,4,6-trifluorophenylacetyl chloride
• CAS: 714963-55-0
• 化学式: C₈H₄ClF₃O
• 分子量: 208.567
• InChiKey: GAMFEVYAONWFME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2,4,6-trifluorophenyl)acetyl chloride 在 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 4-(4-methylpiperazin-1-yl)-N-[5-[2-(2,4,6-trifluorophenyl)acetyl]-4,6-dihydro-1H-pyrrolo[3,4-c]pyrazol-3-yl]benzamide
  参考文献：
  名称：

  The human Aurora kinase inhibitor danusertib is a lead compound for anti-trypanosomal drug discovery via target repurposing

  摘要：

  New drugs for neglected tropical diseases such as human African trypanosomiasis (HAT) are needed, yet drug discovery efforts are not often focused on this area due to cost. Target repurposing, achieved by the matching of essential parasite enzymes to those human enzymes that have been successfully inhibited by small molecule drugs, provides an attractive means by which new drug optimization programs can be pragmatically initiated. In this report we describe our results in repurposing an established class of human Aurora kinase inhibitors, typified by danusertib (1), which we have observed to be an inhibitor of trypanosomal Aurora kinase 1 (TbAUK1) and effective in parasite killing in vitro. Informed by homology modeling and docking, a series of analogs of I were prepared that explored the scope of the chemotype and provided a nearly 25-fold improvement in cellular selectivity for parasite cells over human cells. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.07.038
• 作为产物：
  描述：

  2,4,6-三氟苯乙酸 在 氯化亚砜 作用下， 以 甲苯 为溶剂， 生成 2-(2,4,6-trifluorophenyl)acetyl chloride
  参考文献：
  名称：

  氟苯基丙氨酸作为人和猪氨基肽酶N的抑制剂的膦酸类似物：芳香环取代重要性的验证。

  摘要：

  合成了在芳环上被氟，氯和三氟甲基取代的苯丙氨酸的膦酸类似物文库，并评估了其对人（hAPN）和猪（pAPN）氨基肽酶的抑制活性。荧光筛查表明，这些类似物是微摩尔或亚微摩尔抑制剂，两种酶对hAPN的活性更高。为了更好地了解最具活性的化合物的作用方式，使用了分子模型。已经证实，在所有研究的化合物中，酶的氨基膦酸部分几乎相同地结合，而活性的差异是由抑制剂的芳族侧链的位置引起的。有趣的是，单个化合物的两种对映异构体通常非常相似地结合。

  DOI：

  10.3390/biom10040579

文献信息

• [EN] FUNGICIDES<br/>[FR] FONGICIDES
  申请人：SYNGENTA LTD

  公开号：WO2004056826A1

  公开（公告）日：2004-07-08

  Fungicidal compositions having the general formula (1): formula (1) wherein W and Y are both N and X and Z are both CR8 or X and Z are both N and W and Y are both CR8, R8 is H, halo, C1-4 alkyl, C1-4 alkoxy or halo(C1-4)alkyl; R and R2 are independently H, halo, C1-8 alkyl, C1-8 alkoxy, C1-8 alkylthio, C2-8 alkenyl, C2-8 alkynyl, cyano or NR3R4, provided that at least one of R and R2 is NR3R4; R1 is halo, C 1-8 alkyl, C2-8 alkenyl, C2-8 alkynyl, C3-8 cycloalkyl, C3-8 cycloalkyl(C1-6)-alkyl, C1-8 alkoxy, C1-8 alkylthio, aryl, aryloxy, arylthio, heteroaryl, heteroaryloxy, heteroarylthio, aryl(C1-4)alkyl, aryl(C1-4)alkoxy, heteroaryl(C1-4)alkyl, heteroaryl(C1-4)alkoxy, aryl(C1-4)alkylthio, heteroaryl(C1-4)alkylthio, morpholino, piperidino or pyrrolidino.

  具有一般公式（1）的杀真菌组合物：公式（1）其中W和Y都是N，X和Z都是CR8或X和Z都是N且W和Y都是CR8，R8为H，卤素，C1-4烷基，C1-4烷氧基或卤素(C1-4)烷基；R和R2独立地为H，卤素，C1-8烷基，C1-8烷氧基，C1-8烷基硫基，C2-8烯基，C2-8炔基，氰基或NR3R4，但其中至少一个为NR3R4；R1为卤素，C1-8烷基，C2-8烯基，C2-8炔基，C3-8环烷基，C3-8环烷基(C1-6)-烷基，C1-8烷氧基，C1-8烷基硫基，芳基，芳氧基，芳硫基，杂环芳基，杂环芳氧基，杂环芳硫基，芳基(C1-4)烷基，芳基(C1-4)烷氧基，杂环芳基(C1-4)烷基，杂环芳基(C1-4)烷氧基，芳基(C1-4)烷基硫基，杂环芳基(C1-4)烷基硫基，吗啡啉基，哌啶基或吡咯啉基。
• Niementowski-type synthesis of pyrido[3,2-e][1,2,4]triazines: potent aza-analogs of pyrido[2,3-b]pyrazine fungicides
  作者：Patrick J. Crowley、Clemens Lamberth、Urs Müller、Sebastian Wendeborn、Olivia-A. Sageot、John Williams、Alexander Bartovič

  DOI：10.1016/j.tetlet.2010.03.032

  日期：2010.5

  Novel trisubstituted pyrido[3,2-e][1,2,4]triazines have been found to possess similar biological activity to the corresponding pyridopyrazine fungicides against important phytopathogens such as Mycosphaerella graminicola (wheat leaf blotch), Magnaporthe grisea (rice blast), and Rhizoctonia solani (rice sheath blight). They have been prepared for the first time from a monocyclic triazine by Niementowski-type

  已发现新型三取代的吡啶并[3,2- e ] [1,2,4]三嗪具有与相应的吡并吡嗪杀真菌剂相似的针对重要植物病原体的生物学活性，例如重要的致病性小麦霉菌（Mycosphaerella graminicola）（小麦叶片斑点病），稻瘟病菌（Magnaporthe grisea）（稻瘟病）。以及茄枯萎病（Rhizoctonia solani）。它们是由Niementowski型环缩合首次由单环三嗪制备的。
• [EN] FUNGICIDES BASED ON NITROGEN-CONTAINING HETEROCYCLES<br/>[FR] FONGICIDES A BASE D'HETEROCYCLES CONTENANT DE L'AZOTE
  申请人：SYNGENTA LTD

  公开号：WO2004056829A1

  公开（公告）日：2004-07-08

  Fungicidal compounds having the general formula (1): formula (1) wherein W, Z and one of X and Y are N and the other one of X and Y is CR8; R8 is H, halo, C1-4 alkyl, C1-4 alkoxy, C1-4 alkylthio or halo(C1-4)alkyl; R and R2 are independently H, halo, C1-8 alkyl, C1-8 alkoxy, C1-8 alkylthio, C2-8 alkenyl, C2-8 alkynyl, cyano or NR3R4, provided that at least one of R and R2 is NR3R4; R1 is halo, C1-8 alkyl, C2-8 alkenyl, C2-8 alkynyl, C3-8 cycloalkyl, C3-8 cycloalkyl(C1-6)­-alkyl, C1-8 alkoxy, C1-8 alkylthio, aryl, aryloxy, arylthio, heteroaryl, heteroaryloxy, heteroarylthio, aryl(C1-4)alkyl, aryl(C1-4)alkoxy, heteroaryl(C1-4)alkyl, heteroaryl­(C1-4)alkoxy, aryl(C1-4)alkylthio, heteroaryl(C1-4)alkylthio, morpholino, piperidino or pyrrolidino; R3 and R4 are independently H, C1-8 alkyl, C2-8 alkenyl, C2-8 alkynyl, aryl, aryl(C1-8)­- alkyl, C3-8 cycloalkyl, C3-8 cycloalkyl(C1-6)alkyl, heteroaryl, heteroaryl(C1-8)alkyl, NR5R6, provided that not both R3 and R4 are H or NR5R6, or R3 and R4 together form a C3-7 alkylene or C3-7 alkenylene chain optionally substituted with one or more C1-4 alkyl or C1-4 alkoxy groups, or, together with the nitrogen atom to which they are attached, R3 and R4 form a morpholine, thiomorpholine, thiomorpholine S-oxide or thiomorpholine S-dioxide ring or a piperazine or piperazine N-(C1-4)alkyl (especially N-methyl) ring; and R5 and R6 are independently H, C1-8 alkyl, C2-8 alkenyl, C2-8 alkynyl, aryl, aryl(C1-8)­alkyl, C3-8 cycloalkyl, C3-8 cycloalkyl(C1-6)alkyl, heteroaryl or heteroaryl(C1-8)alkyl; any of the foregoing alkyl, alkenyl, alkynyl or cycloalkyl groups or moieties (other than for R8) being optionally substituted with halogen, cyano, C1-6 alkoxy, C1-6 alkylcarbonyl, C1-6 alkoxycarbonyl, C1-6 haloalkoxy, C1-6 alkylthio, tri(C1-4)alkylsilyl, C1-6 alkylamino or C1-6 dialkylamino, any of the foregoing morpholine, thiomorpholine, piperidine, piperazine and pyrrolidine rings being optionally substituted with C1-4 alkyl (especially methyl), and any of the foregoing aryl or heteroaryl groups or moieties being optionally substituted with one or more substituents selected from halo, hydroxy, mercapto, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 alkoxy, C2-6 alkenyloxy, C2-6 alkynyloxy, halo(C1-6)alkyl, halo(C1-6)alkoxy, C1-6 alkylthio, halo(C1-6)alkylthio, hydroxy(C1-6)alkyl, C1-4 alkoxy(C1-6)alkyl, C3-6 cycloalkyl, C3-6 cycloalkyl(C1-4)alkyl, phenoxy, benzyloxy, benzoyloxy, cyano, isocyano, thiocyanato, isothiocyanato, nitro, -NR''R'', NHCOR'', -NHCONR''R'', -CONR''R'', -SO2R'', -OSO2R'', -COR'', -CR''=NR'' or -N=CR ''R'', in which R'' and R'' are independently hydrogen, C1-4 alkyl, halo-(C1-4)alkyl, C1-4 alkoxy, halo(C1-4)alkoxy, C1-4 alkylthio, C3-6 cycloalkyl, C3-6 cycloalkyl(C1-4)alkyl, phenyl or benzyl, the phenyl and benzyl groups being optionally substituted with halogen, C1-4 alkyl or C1-4 alkoxy.

  具有通式（1）的杀真菌化合物：式（1）其中W，Z和X和Y中的另一个是N，另一个是CR8；R8是H，卤素，C1-4烷基，C1-4烷氧基，C1-4烷基硫基或卤代（C1-4）烷基；R和R2独立地是H，卤素，C1-8烷基，C1-8烷氧基，C1-8烷基硫基，C2-8烯基，C2-8炔基，氰基或NR3R4，但至少其中之一是NR3R4；R1是卤素，C1-8烷基，C2-8烯基，C2-8炔基，C3-8环烷基，C3-8环烷基（C1-6）-烷基，C1-8烷氧基，C1-8烷基硫基，芳基，芳氧基，芳硫基，杂芳基，杂芳氧基，杂芳硫基，芳基（C1-4）烷基，芳基（C1-4）烷氧基，杂芳基（C1-4）烷基，杂芳基（C1-4）烷氧基，芳基（C1-4）烷基硫基，杂芳基（C1-4）烷基硫基，吗啉基，哌啶基或吡咯啉基；R3和R4独立地是H，C1-8烷基，C2-8烯基，C2-8炔基，芳基，芳基（C1-8）-烷基，C3-8环烷基，C3-8环烷基（C1-6）-烷基，杂芳基，杂芳基（C1-8）-烷基，NR5R6，但不是R3和R4都是H或NR5R6，或R3和R4一起形成一个C3-7烷基或C3-7烯基链，可选择地用一个或多个C1-4烷基或C1-4烷氧基取代，或与它们所连接的氮原子一起，R3和R4形成吗啉，硫吗啉，硫吗啉S-氧化物或硫吗啉S-二氧化物环或哌嗪或哌嗪N-（C1-4）烷基（特别是N-甲基）环；R5和R6独立地是H，C1-8烷基，C2-8烯基，C2-8炔基，芳基，芳基（C1-8）-烷基，C3-8环烷基，C3-8环烷基（C1-6）-烷基，杂芳基或杂芳基（C1-8）-烷基；任何上述烷基，烯基，炔基或环烷基基团（R8除外）可选择地用卤素，氰基，C1-6烷氧基，C1-6烷基羰基，C1-6烷氧羰基，C1-6卤代烷氧基，C1-6烷基硫基，三（C1-4）烷基硅烷基，C1-6烷基氨基或C1-6二烷基氨基取代，上述任何吗啉，硫吗啉，哌啶，哌嗪和吡咯啉环可选择地用C1-4烷基（特别是甲基）取代，上述任何芳基或杂芳基基团可选择地用一个或多个取代基取代，所述取代基选择自卤素，羟基，硫醇基，C1-6烷基，C2-6烯基，C2-6炔基，C1-6烷氧基，C2-6烯氧基，C2-6炔氧基，卤代（C1-6）烷基，卤代（C1-6）烷氧基，C1-6烷基硫基，卤代（C1-6）烷基硫基，羟基（C1-6）烷基，C1-4烷氧基（C1-6）烷基，C3-6环烷基，C3-6环烷基（C1-4）烷基，苯氧基，苄氧基，苯甲酰氧基，氰基，异氰酸基，硫氰酸基，异硫氰酸基，硝基，-NR''R''，NHCOR''，-NHCONR''R''，-CONR''R''，-SO2R''，-OSO2R''，-COR''，-CR''=NR''或-N=CR''R''，其中R''和R''独立地是氢，C1-4烷基，卤代（C1-4）烷基，C1-4烷氧基，卤代（C1-4）烷氧基，C1-4烷基硫基，C3-6环烷基，C3-6环烷基（C1-4）烷基，苯基或苄基，苯基和苄基可选择地用卤素，C1-4烷基或C1-4烷氧基取代。
• [EN] PYRIDODIAZINES AS PLANT FUNGICIDES<br/>[FR] UTILISATION DE PYRIDODIAZINES COMME FONGICIDES
  申请人：SYNGENTA LTD

  公开号：WO2004056825A1

  公开（公告）日：2004-07-08

  Fungicidal compounds of general formula (1) wherein R, R<1>, R<2>, W, X, Y and Z are as defined in the specification.

  通式（1）中的真菌杀菌化合物，其中R、R1、R2、W、X、Y和Z如规范中所定义。
• Fungicides based on nitrogen-containing heterocycles
  申请人：Crowley Jelf Patrick

  公开号：US20060100203A1

  公开（公告）日：2006-05-11

  Fungicidal compounds having the general formula (1): formula (1) wherein W, Z and one of X and Y are N and the other one of X and Y is CR 8 ; R 8 is H, halo, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 alkylthio or halo(C 1-4 )alkyl; R and R 2 are independently H, halo, C 1-8 alkyl, C 1-8 alkoxy, C 1-8 alkylthio, C 2-8 alkenyl, C 2-8 alkynyl, cyano or NR 3 R 4 , provided that at least one of R and R 2 is NR 3 R 4 ; R 1 is halo, C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, C 3-8 cycloalkyl, C 3-8 cycloalkyl(C 1-6 )-alkyl, C 1-8 alkoxy, C 1-8 alkylthio, aryl, aryloxy, arylthio, heteroaryl, heteroaryloxy, heteroarylthio, aryl(C 1-4 )alkyl, aryl(C 1-4 )alkoxy, heteroaryl(C 1-4 )alkyl, heteroaryl(C 1-4 )alkoxy, aryl(C 1-4 )alkylthio, heteroaryl(C 1-4 )alkylthio, morpholino, piperidino or pyrrolidino; R 3 and R 4 are independently H, C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, aryl, aryl(C 1-8 )-alkyl, C 3-8 cycloalkyl, C 3-8 cycloalkyl(C 1-6 )alkyl, heteroaryl, heteroaryl(C 1-8 )alkyl, NR 5 R 6 , provided that not both R 3 and R 4 are H or NR 5 R 6 , or R 3 and R 4 together form a C 3-7 alkylene or C 3-7 alkenylene chain optionally substituted with one or more C 1-4 alkyl or C 1-4 alkoxy groups, or, together with the nitrogen atom to which they are attached, R 3 and R 4 form a morpholine, thiomorpholine, thiomorpholine S-oxide or thiomorpholine S-dioxide ring or a piperazine or piperazine N-(C 1-4 )alkyl (especially N-methyl) ring; and R 5 and R 6 are independently H, C 1-8 alkyl, C 2-8 alkenyl, C 2-8 -alkynyl, aryl, aryl(C 1-8 )alkyl, C 3-8 cycloalkyl, C 3-8 cycloalkyl(C 1-6 )alkyl, heteroaryl or heteroaryl(C 1-8 )alkyl; any of the foregoing alkyl, alkenyl, alkynyl or cycloalkyl groups or moieties (other than for R 8 ) being optionally substituted with halogen, cyano, C 1-6 alkoxy, C 1-6 alkylcarbonyl, C 1-6 alkoxycarbonyl, C 1-6 haloalkoxy, C 1-6 alkylthio, tri(C 1-4 )alkylsilyl, C 1-6 alkylamino or C 1-6 dialkylamino, any of the foregoing morpholine, thiomopholine, piperidine, piperazine and pyrrolidine rings being optionally substituted with C 1-4 alkyl (especially methyl), and any of the foregoing aryl or heteroaryl groups or moieties being optionally substituted with one or more substituents selected from halo, hydroxy, mercapto, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 alkoxy, C 2-6 alkenyloxy, C 2-6 alkynyloxy, halo(C 1-6 )alkyl, halo(C 1-6 )alkoxy, C 1-6 alkylthio, halo(C 1-6 )alkylthio, hydroxy(C 1-6 )alkyl, C 1-4 alkoxy(C 1-6 )alkyl, C 3-6 cycloalkyl, C 3-6 cycloalkyl(C 1-4 )alkyl, phenoxy, benzyloxy, benzoyloxy, cyano, isocyano, thiocyanato, isothiocyanato, nitro, —NR″′R″″, NHCOR″′, —NHCONR″′R″″, —CONR″′R″″, —SO 2 R″′, —OSO 2 R″′, —COR″′, —CR″′═NR″″ or —N═CR ″′R″″, in which R″′ and R″″ are independently hydrogen, C 1-4 alkyl, halo(C 1-4 )alkyl, C 1-4 alkoxy, halo(C 1-4 )alkoxy, C 1-4 alkylthio, C 3-6 cycloalkyl, C 3-6 cycloalkyl(C 1-4 )alkyl, phenyl or benzyl, the phenyl and benzyl groups being optionally substituted with halogen, C 1-4 alkyl or C 1-4 alkoxy.

  具有通式（1）的杀菌化合物：通式（1）其中，W，Z和X和Y中的另一个是CR8，另一个是N；R8为H，卤素，C1-4烷基，C1-4烷氧基，C1-4烷硫基或卤素（C1-4）烷基；R和R2独立地为H，卤素，C1-8烷基，C1-8烷氧基，C1-8烷硫基，C2-8烯基，C2-8炔基，氰基或NR3R4，但其中至少一个为NR3R4；R1为卤素，C1-8烷基，C2-8烯基，C2-8炔基，C3-8环烷基，C3-8环烷基（C1-6）-烷基，C1-8烷氧基，C1-8烷硫基，芳基，芳氧基，芳硫基，杂环芳基，杂环芳氧基，杂环芳硫基，芳基（C1-4）烷基，芳基（C1-4）烷氧基，杂环芳基（C1-4）烷基，杂环芳基（C1-4）烷氧基，芳基（C1-4）烷硫基，杂环芳基（C1-4）烷硫基，吗啉基，哌啶基或吡咯烷基；R3和R4独立地为H，C1-8烷基，C2-8烯基，C2-8炔基，芳基，芳基（C1-8）-烷基，C3-8环烷基，C3-8环烷基（C1-6）烷基，杂环芳基，杂环芳基（C1-8）烷基，NR5R6，但不是R3和R4都为H或NR5R6，或者R3和R4一起形成一个C3-7烷基或C3-7烯基链，可选择地取代一个或多个C1-4烷基或C1-4烷氧基，或者与它们所附着的氮原子一起，R3和R4形成吗啉，硫代吗啉，硫代吗啉S-氧化物或硫代吗啉S-二氧化物环或哌嗪或哌嗪N-（C1-4）烷基（特别是N-甲基）环；R5和R6独立地为H，C1-8烷基，C2-8烯基，C2-8炔基，芳基，芳基（C1-8）-烷基，C3-8环烷基，C3-8环烷基（C1-6）烷基，杂环芳基或杂环芳基（C1-8）烷基；除R8之外的任何上述烷基，烯基，炔基或环烷基基团（均可选择地取代卤素，氰基，C1-6烷氧基，C1-6烷基羰基，C1-6烷氧羰基，C1-6卤烷氧基，C1-6烷硫基，三（C1-4）烷基硅烷基，C1-6烷基氨基或C1-6二烷基氨基），任何上述吗啉，硫代吗啉，哌嗪，哌嗪和吡咯烷环可选择地取代C1-4烷基（特别是甲基），任何上述芳基或杂环芳基基团可选择地取代一个或多个取代基，所述取代基选自卤素，羟基，巯基，C1-6烷基，C2-6烯基，C2-6炔基，C1-6烷氧基，C2-6烯氧基，C2-6炔氧基，卤素（C1-6）烷基，卤素（C1-6）烷氧基，C1-6烷硫基，卤素（C1-6）烷硫基，羟基（C1-6）烷基，C1-4烷氧基（C1-6）烷基，C3-6环烷基，C3-6环烷基（C1-4）烷基，苯氧基，苄氧基，苯甲酰氧基，氰基，异氰基，硫氰酸基，异硫氰酸基，硝基，—NR″′R″″，NHCOR″′，—NHCONR″′R″″，—CONR″′R″″，—SO2R″′，—OSO2R″′，—COR″′，—CR″′═NR″″或—N═CR″′R″″，其中R″′和R″″独立地为氢，C1-4烷基，卤素（C1-4）烷基，C1-4烷氧基，卤素（C1-4）烷氧基，C1-4烷硫基，C3-6环烷基，C3-6环烷基（C1-4）烷基，苯基或苄基，苯基和苄基可选择地取代卤素，C1-4烷基或C1-4烷氧基。