6'-氯-2’-氟-3’-甲基苯乙酮 | 261762-78-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 6'-氯-2’-氟-3’-甲基苯乙酮
• 中文别名: 6′-氯2′-氟3′-甲基苯乙酮；6-氯-2-氟-3-甲基苯乙酮
• 英文名称: 6'-Chloro-2'-fluoro-3'-methylacetophenone
• 英文别名: 1-(6-chloro-2-fluoro-3-methylphenyl)ethanone
• CAS: 261762-78-1
• 化学式: C₉H₈ClFO
• mdl: MFCD01631378
• 分子量: 186.613
• InChiKey: TYZFPTDLOTXWNZ-UHFFFAOYSA-N

物化性质

• 稳定性/保质期：

  避氧化物

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• 海关编码：
  2914700090

反应信息

• 作为反应物：
  描述：

  2-噻吩甲酰胺 、 6'-氯-2’-氟-3’-甲基苯乙酮 在 sodium 2,2,2-trifluoroacetate 、 [(PAd₂-DalPhos)Ni(4-CNPh)Cl] 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以75%的产率得到N-(2-acetyl-3-fluoro-4-methylphenyl)thiophene-2-carboxamide
  参考文献：
  名称：

  Mapping Dual‐Base‐Enabled Nickel‐Catalyzed Aryl Amidations: Application in the Synthesis of 4‐Quinolones

  摘要：

  AbstractThe C−N cross‐coupling of (hetero)aryl (pseudo)halides with NH substrates employing nickel catalysts and organic amine bases represents an emergent strategy for the sustainable synthesis of (hetero)anilines. However, unlike protocols that rely on photoredox/electrochemical/reductant methods within NiI/III cycles, the reaction steps that comprise a putative Ni0/II C−N cross‐coupling cycle for a thermally promoted catalyst system using organic amine base have not been elucidated. Here we disclose an efficient new nickel‐catalyzed protocol for the C−N cross‐coupling of amides and 2′‐(pseudo)halide‐substituted acetophenones, for the first time where the (pseudo)halide is chloride or sulfonate, which makes use of the commercial bisphosphine ligand PAd2‐DalPhos (L4) in combination with an organic amine base/halide scavenger, leading to 4‐quinolones. Room‐temperature stoichiometric experiments involving isolated Ni0, I, and II species support a Ni0/II pathway, where the combined action of DBU/NaTFA allows for room‐temperature amide cross‐couplings.

  DOI：

  10.1002/anie.202200352

文献信息

• Pyrazole Derivatives For The Inhibition Of Cdk's And Gsk's
  申请人：Wyatt Paul Graham

  公开号：US20080194562A1

  公开（公告）日：2008-08-14

  The invention provides compounds of the formula (I) or a salt, tautomer, solvate or N-oxides thereof; wherein: R 1 is selected from (a) 2,6-dichlorophenyl; (b) 2,6-difluorophenyl; (c) a 2,3,6-trisubstituted phenyl group wherein the substituents are fluorine, chlorine, methyl or methoxy; and (d) a group R 0 wherein R 0 is a 3-12 membered carbocyclic or heterocyclic group; or optionally substituted C 1-8 hydrocarbyl; R 2a and R 2b are each hydrogen or methyl; and R 3 is as defined in the claims. The compounds have activity as inhibitors of Cyclin Dependent Kinases (CDK) and Glycogen Synthase Kinases (GSK) kinases and are useful in the treatment or prophylaxis of disease states or conditions mediated by the kinases.

  本发明提供了公式(I)的化合物或其盐、互变异构体、溶剂化物或N-氧化物；其中：R1选择自(a) 2,6-二氯苯基；(b) 2,6-二氟苯基；(c) 一种2,3,6-三取代苯基，其中取代基为氟、氯、甲基或甲氧基；和(d) 一种R0基团，其中R0是3-12成员的碳环或杂环基团；或可选取代的C1-8烃基；R2a和R2b均为氢或甲基；而R3如权利要求所定义。这些化合物具有抑制细胞周期蛋白依赖性激酶(CDK)和糖原合成酶激酶(GSK)的活性，并且可用于治疗或预防由这些激酶介导的疾病状态或病症。
• PHARMACEUTICAL COMPOUNDS
  申请人：Congreve Miles Stuart

  公开号：US20100004243A1

  公开（公告）日：2010-01-07

  The invention provides a cyclin dependent kinase (e.g. cdk-4 kinase) inhibitor of the formula (I) or a salt, tautomer, solvate or N-oxide thereof; wherein R 1 is an optionally substituted monocyclic or bicyclic aryl or heteroaryl group containing 0-2 heteroatoms selected from O, N and S wherein the optional substituents are selected from halogen, C 1-4 alkyl, C 1-4 alkoxy, C 3-4 cycloalkyl and cyano, and wherein the C 1-4 alkyl and C 1-4 alkoxy groups are each optionally further substituted by C 1-2 alkoxy or one or more halogen atoms; and E is a group E1, E2, E3 or E4: formulae E1, E2, E3, E4 wherein n, q, A5 B, T, U, V, W, Z, R 2 , R 5 , R 6 and R 7 are as defined in the claims.

  该发明提供了一种公式（I）的细胞周期依赖性激酶（例如cdk-4激酶）抑制剂或其盐，互变异构体，溶剂化合物或N-氧化物；其中R1是一个含有0-2个来自O，N和S的杂原子的可选取代的单环或双环芳基或杂芳基基团，其中可选的取代基被选自卤素，C1-4烷基，C1-4烷氧基，C3-4环烷基和氰基，其中C1-4烷基和C1-4烷氧基基团可以进一步被C1-2烷氧基或一个或多个卤素原子取代；而E是E1，E2，E3或E4的基团：公式E1，E2，E3，E4其中n，q，A5 B，T，U，V，W，Z，R2，R5，R6和R7如权利要求中所定义。
• Pyrazole Derivatives for the Inhibition of CDK'S and GSK'S
  申请人：Wyatt Paul Graham

  公开号：US20080306069A1

  公开（公告）日：2008-12-11

  The invention provides compounds of the formula (I), or salts, tautomers, N-oxides or solvates thereof wherein: R1 is selected from: (a) 2,6-dichlorophenyl; (b) 2,6-difluorophenyl; (c) a 2,3,6-trisubstituted phenyl group wherein the substituents for the phenyl group are selected from fluorine, chlorine, methyl and methoxy; (d) a group RO; (e) a group R a; (f) a group RIb; (g) a group RIc; (h) a group RId; and 0) 2,6-difluorophenylamino; wherein R) 0υ, r R>llaa, T Rj HbD, T R) HcC, r R>Iidα, r R>>2zaa, r R>22bD and RJ are as defined in the claims. The compounds have activity as inhibitors of cdk kinase (such as cdk1 or cdk2) and glycogen synthase kinase-3 activity.

  该发明提供了式(I)的化合物，或其盐、互变异构体、N-氧化物或溶剂化物，其中：R1选择自：(a)2,6-二氯苯基；(b)2,6-二氟苯基；(c)2,3,6-三取代苯基，其中苯基的取代基选择自氟、氯、甲基和甲氧基；(d)羟基取代基；(e)R a基；(f)RIb基；(g)RIc基；(h)RId基；和(i)2,6-二氟苯基氨基基；其中R) 0υ，r R>llaa，T Rj HbD，T R) HcC，r R>Iidα，r R>>2zaa，r R>22bD和RJ如权利要求所定义。该化合物具有作为cdk激酶（如cdk1或cdk2）和糖原合成酶激酶-3活性抑制剂的活性。
• [EN] PYRAZOLE DERIVATIVES FOR THE INHIBITION OF CDK' S AND GSK' S<br/>[FR] DERIVES DE PYRAZOLE DESTINES A INHIBER LES CDK ET GSK
  申请人：ASTEX THERAPEUTICS LTD

  公开号：WO2006077414A1

  公开（公告）日：2006-07-27

  [EN] The invention provides compounds of the formula (I), or salts, tautomers, N-oxides or solvates thereof wherein: R1 is selected from: (a) 2,6-dichlorophenyl; (b) 2,6-difluorophenyl; (c) a 2,3,6-trisubstituted phenyl group wherein the substituents for the phenyl group are selected from fluorine, chlorine, methyl and methoxy; (d) a group R0; (e) a group R a; (f) a group Rlb; (g) a group Rlc; (h) a group Rld; and 0) 2,6-difluorophenylamino ; wherein R )0?, r R> llaa, T Rj I1bD, T R) I1cC, r R> Iida, r R»2zaa, r R>22bD and RJ are as defined in the claims. The compounds have activity as inhibitors of cdk kinase (such as cdkl or cdk2) and glycogen synthase kinase-3 activity.
  [FR] La présente invention concerne des composés de formule (I), ou leurs sels, tautomères, N-oxydes ou solvates, où : R1 est choisi parmi : (a) le 2,6-dichlorophényle ; (b) le 2,6-difluorophényle; (c) un groupe phényle 2,3,6-trisubstitué dans lequel les substituants du groupe phényle sont choisis parmi le fluor, le chlore, le méthyle et le méthoxy; (d) un groupe R⁰; (e) un groupe R^1a ; (f) un groupe R^1b ; (g) un groupe R^1c ; (h) un groupe R^1d ; et (j) un 2,6-difluorophénylamino ; R⁰, R^1a, R^1b, R^1c, R^1d, R^2a, R^2b et R³ étant tels que définis dans les revendications. Ces composés présentent une activité d'inhibition de l'activité des kinases cdk (telles que cdk1 ou cdk2) et de l'activité de la glycogène synthase kinase-3.
• [EN] PYRAZOLE DERIVATIVES FOR THE INHIBITION OF CDK' S AND GSK' S<br/>[FR] DERIVES DE PYRAZOLE DESTINES A INHIBER LES KINASES DEPENDANTES DES CYCLINES (CDK) ET LES GLYCOGENE SYNTHASES KINASES (GSK)
  申请人：ASTEX THERAPEUTICS LTD

  公开号：WO2006077419A1

  公开（公告）日：2006-07-27

  [EN] The invention provides compounds of the formula (I) or a salt, tautomer, solvate or N-oxides thereof; wherein: R¹ is selected from (a) 2,6-dichlorophenyl; (b) 2,6-difluorophenyl; (c) a 2,3,6-trisubstituted phenyl group wherein the substituents are fluorine, chlorine, methyl or methoxy; and (d) a group R⁰ wherein R⁰ is a 3-12 membered carbocyclic or heterocyclic group; or optionally substituted C_1-8 hydrocarbyl; R^2a and R^2bare each hydrogen or methyl; and R³ is as defined in the claims. The compounds have activity as inhibitors of Cyclin Dependent Kinases (CDK) and Glycogen Synthase Kinases (GSK) kinases and are useful in the treatment or prophylaxis of disease states or conditions mediated by the kinases.
  [FR] La présente invention concerne des composés de formule (1), ou un sel, tautomère, solvate ou N-oxydes de ceux-ci ; R¹ est sélectionné dans le groupe composé de (a) 2,6-dichlorophényl; (b) 2,6-difluorophényl; (c) un groupe phényle trisubstitué en 2,3,6 où les substituants sont fluor, chlore, méthyle ou méthoxy ; et (d) un groupe R⁰ où R⁰ est un groupe carbocyclique ou hétérocyclique à 3-12 membres ; ou hydrocarbyle en C_1-8 facultativement substitué ; R^2a et R^2b représentent chacun hydrogène ou méthyle ; et R³ est tel que défini dans les revendications. Les composés présentent une activité en tant qu'inhibiteurs des kinases dépendantes des cyclines (CDK) et des glycogène synthases kinases, et sont utiles pour le traitement ou la prophylaxie d'états pathologiques ou de troubles induits par les kinases.