4-(4-氯苯基)-2-羟基-4-氧代丁酸 | 81008-08-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-(4-氯苯基)-2-羟基-4-氧代丁酸
• 英文名称: 4-(4-chlorophenyl)-2-hydroxy-4-oxobutyric acid
• 英文别名: 4-(4-Chlorophenyl)-4-oxo-2-hydroxybutanoic acid；4-(4-chlorophenyl)-2-hydroxy-4-oxobutanoic acid
• CAS: 81008-08-4
• 化学式: C₁₀H₉ClO₄
• 分子量: 228.632
• InChiKey: BUNUMHDTNKWXKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4-氯苯基)-2-羟基-4-氧代丁酸 生成 反-3-(4-氯苯甲酰)丙烯酸
  参考文献：
  名称：

  CHRISTIDIS, Y.;FOURNEX, R.;TOURNEMINE, C.

  摘要：

  DOI：
• 作为产物：
  描述：

  对氯苯乙酮 、 乙醛酸 95.0 ℃ 、6.67 kPa 条件下， 反应 3.0h， 以60%的产率得到4-(4-氯苯基)-2-羟基-4-氧代丁酸
  参考文献：
  名称：

  Gastric anti-secretory, anti-ulcer and cytoprotective properties of substituted (E)-4-phenyl- and heteroaryl-4-oxo-2-butenoic acids

  摘要：

  DOI：

  10.1016/0223-5234(88)90166-3

文献信息

• Novel alpha-oxygenated or alpha-thiolated carboxylic acid penethylamide derivatives
  申请人：Zeller Martin

  公开号：US20050020450A1

  公开（公告）日：2005-01-27

  The invention relates to α-oxygenated or α-thiolated carboxylic acid phenethylamide derivatives of the general formula I including the optical isomers thereof and mixtures of such isomers, wherein A stands for optionally substituted aryl or optionally substituted heteroaryl; X is oxygen or sulfur; Y is oxygen or sulfur; R 1 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl or halocycloalkyl; R 2 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxy-alkyl, alkoxy-alkenyl, alkoxy-alkynyl, whereof all alkyl- alkenyl-, alkynyl-, or cycloalkyl-groups me be optionally substituted by halogen; or optionally substituted arylalkyl, optionally substituted-aryl-alkenyl, optionally substituted aryl-alkynyl or optionally substituted aryloxy-alkyl; R 3 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkyl-alkyl, alkoxy-alkyl, alkoxy-alkenyl, alkoxy-alkynyl, whereof all alkyl- alkenyl-, alkynyl-, or cycloalkyl-groups me be optionally substituted by halogen; or is optionally substituted aryl-alkyl, optionally substituted aryl-alkenyl, optionally substituted aryl-alkynyl, optionally substituted aryloxy-alkyl, optionally substituted heteroaryl-alkyl, optionally substituted heteroaryl-alkenyl or optionally substituted heteroaryl-alkynyl; R 4 is alkyl, alkenyl, alkynyl, alkoxy-alkyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkanoyl, alkylamino, dialkylamino, alkoxycarbonyl, whereof all alkyl- alkenyl or alkynyl-groups me be optionally substituted by halogen; or is halogen, cyano, nitro, amino, formyl or carboxyl; R 5 is hydrogen, alkyl, alkenyl or alkynyl; n is an integer 0, 1, 2, 3, or 4; B 1 represents a bridge member —(CR 10 R 11 ) q — or —(CHR 10 R 11 ) r —Z—(CR 12 R 13 ) 8 , wherein q is an integer 2, 3 or 4; r is an integer 0, 1; 2, 3; s is an integer 1, 2 or 3, provided that (r+s) is either 1, 2 or 3; Z is —O—, —S—, —SO— —SO2—, NR 6 —, —CO—, —OOC—, —COO, —NR 6 —CO—or —CO—NR 6 —; R 6 is hydrogen or alkyl; R 10 , R 11 , R 12 and R 13 independently of each other are hydrogen or alkyl; and B 2 is an alkylene bridge. These compounds possess useful plant protecting properties and may advantageously be employed in agricultural practice for controlling or preventing the infestation of plants by phytopathogenic microorganisms, especially fungi.

  本发明涉及一般式I的α-氧化或α-硫化羧酸苯乙酰胺衍生物，包括其光学异构体和混合物，其中A代表可选取代的芳基或可选取代的杂环芳基；X为氧或硫；Y为氧或硫；R1为氢，烷基，烯基，炔基，环烷基，卤代烷基，卤代烯基，卤代炔基或卤代环烷基；R2为氢，烷基，烯基，炔基，环烷基，环烷基烷基，烷氧基烷基，烷氧基烯基，烷氧基炔基，其中所有烷基，烯基，炔基或环烷基可以选择性地被卤素取代；或可选取代的芳基烷基，可选取代的芳基烯基，可选取代的芳基炔基或可选取代的芳氧基烷基；R3为氢，烷基，烯基，炔基，环烷基，环烷基烷基，烷氧基烷基，烷氧基烯基，烷氧基炔基，其中所有烷基，烯基，炔基或环烷基可以选择性地被卤素取代；或可选取代的芳基烷基，可选取代的芳基烯基，可选取代的芳基炔基，可选取代的芳氧基烷基，可选取代的杂环芳基烷基，可选取代的杂环芳基烯基或可选取代的杂环芳基炔基；R4为烷基，烯基，炔基，烷氧基烷基，烷氧基，烯基氧基，炔基氧基，烷硫基，烷酰基，烷基氨基，二烷基氨基，烷氧羰基，其中所有烷基，烯基或炔基可以选择性地被卤素取代；或为卤素，氰基，硝基，氨基，甲酰基或羧基；R5为氢，烷基，烯基或炔基；n为0、1、2、3或4的整数；B1表示桥接成员-(CR10R11)q-或-(CHR10R11)r-Z-(CR12R13)8，其中q为2、3或4的整数；r为0、1、2、3的整数；s为1、2或3的整数，前提是(r+s)为1、2或3；Z为-O-、-S-、-SO-、-SO2-、-NR6-、-CO-、-OOC-、-COO、-NR6-CO-或-CO-NR6-；R6为氢或烷基；R10、R11、R12和R13各自独立地为氢或烷基；B2为烷基桥。这些化合物具有有用的植物保护特性，可以在农业实践中优势地用于控制或预防植物受植物病原微生物，特别是真菌的侵害。
• α-oxygenated or α-thiolated carboxylic acid phenethylamide derivatives
  申请人：Syngenta Crop Protection, Inc.

  公开号：US07601674B2

  公开（公告）日：2009-10-13

  The invention relates to α-oxygenated or α-thiolated carboxylic acid phenethylamide derivatives of the general formula I including the optical isomers thereof and mixtures of such isomers, wherein A stands for optionally substituted aryl or optionally substituted heteroaryl; X is oxygen or sulfur; Y is oxygen or sulfur; R1 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl or halocycloalkyl; R2 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxy-alkyl, alkoxy-alkenyl, alkoxy-alkynyl, whereof all alkyl-alkenyl-, alkynyl-, or cycloalkyl-groups me be optionally substituted by halogen; or optionally substituted arylalkyl, optionally substituted-aryl-alkenyl, optionally substituted aryl-alkynyl or optionally substituted aryloxy-alkyl; R3 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkyl-alkyl, alkoxy-alkyl, alkoxy-alkenyl, alkoxy-alkynyl, whereof all alkyl-alkenyl-, alkynyl-, or cycloalkyl-groups me be optionally substituted by halogen; or is optionally substituted aryl-alkyl, optionally substituted aryl-alkenyl, optionally substituted aryl-alkynyl, optionally substituted aryloxy-alkyl, optionally substituted heteroaryl-alkyl, optionally substituted heteroaryl-alkenyl or optionally substituted heteroaryl-alkynyl; R4 is alkyl, alkenyl, alkynyl, alkoxy-alkyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkanoyl, alkylamino, dialkylamino, alkoxycarbonyl, whereof all alkyl-alkenyl or alkynyl-groups may be optionally substituted by halogen; or is halogen, cyano, nitro, amino, formyl or carboxyl; R5 is hydrogen, alkyl, alkenyl or alkynyl; n is an integer 0, 1, 2, 3, or 4; B1 represents a bridge member —(CR10R11)q— or —(CHR10R11)r-Z-(CR12R13)8, wherein q is an integer 2, 3 or 4; r is an integer 0, 1; 2, 3; s is an integer 1, 2 or 3, provided that (r+s) is either 1, 2 or 3; Z is —O—, —S—, —SO— —SO2-, NR6—, —CO—, —OOC—, —COO—, —NR6—CO— or —CO—NR6—; R6 is hydrogen or alkyl; R10, R11, R12 and R13 independently of each other are hydrogen or alkyl; and B2 is an alkylene bridge. These compounds possess useful plant protecting properties and may advantageously be employed in agricultural practice for controlling or preventing the infestation of plants by phytopathogenic microorganisms, especially fungi.

  本发明涉及一般式I的α-氧化或α-硫化羧酸苯乙酰胺衍生物，包括其光学异构体和混合物，其中A代表可选取代的芳基或可选取代的杂环芳基；X为氧或硫；Y为氧或硫；R1为氢、烷基、烯基、炔基、环烷基、卤代烷基、卤代烯基、卤代炔基或卤代环烷基；R2为氢、烷基、烯基、炔基、环烷基、环烷基烷基、烷氧基烷基、烷氧基烯基、烷氧基炔基，其中所有烷基、烯基、炔基或环烷基均可选取代卤素；或可选取代的芳基烷基、可选取代的芳基烯基、可选取代的芳基炔基或可选取代的芳氧基烷基；R3为氢、烷基、烯基、炔基、环烷基、环烷基烷基、烷氧基烷基、烷氧基烯基、烷氧基炔基，其中所有烷基、烯基、炔基或环烷基均可选取代卤素；或可选取代的芳基烷基、可选取代的芳基烯基、可选取代的芳基炔基、可选取代的芳氧基烷基、可选取代的杂环芳基烷基、可选取代的杂环芳基烯基或可选取代的杂环芳基炔基；R4为烷基、烯基、炔基、烷氧基烷基、烷氧基、烯氧基、炔氧基、烷硫基、酰基、烷基氨基、二烷基氨基、烷氧羰基，其中所有烷基、烯基或炔基均可选取代卤素；或卤素、氰基、硝基、氨基、甲酰基或羧基；R5为氢、烷基、烯基或炔基；n为整数0、1、2、3或4；B1表示桥接成员-(CR10R11)q-或-(CHR10R11)r-Z-(CR12R13)8，其中q为整数2、3或4；r为整数0、1、2、3；s为整数1、2或3，前提是(r+s)为1、2或3；Z为-O-、-S-、-SO-、-SO2-、-NR6-、-CO-、-OOC-、-COO-、-NR6-CO-或-CO-NR6-；R6为氢或烷基；R10、R11、R12和R13各自独立地为氢或烷基；B2为烷基桥。这些化合物具有有用的植物保护性能，并可优势地在农业实践中用于控制或预防植物受植物病原微生物（尤其是真菌）的侵害。
• Discovery of Novel Pyridazine-Tethered Sulfonamides as Carbonic Anhydrase II Inhibitors for the Management of Glaucoma
  作者：Haytham O. Tawfik、Mohamed M. Saleh、Andrea Ammara、Eman F. Khaleel、Rehab Badi、Yomna T. T. Khater、Rabab A. Rasheed、Ahmed A. Attia、Salma M. Hefny、Eslam B. Elkaeed、Alessio Nocentini、Claudiu T. Supuran、Wagdy M. Eldehna、Moataz A. Shaldam

  DOI：10.1021/acs.jmedchem.3c02279

  日期：2024.1.25

  neuropathic condition, glaucoma can cause lifelong blindness if left untreated. Novel phenylpyridazine-tethered sulfonamides were designed as selective inhibitors for carbonic anhydrase (CA) isoform II to find effective therapeutic agents for glaucoma. Subsequently, the target inhibitors were synthesized and assessed for their inhibitory action against cytosolic CA I and II. Interestingly, the synthesized

  作为一种进行性神经病变，青光眼如果不及时治疗可能会导致终身失明。新型苯基哒嗪系磺酰胺被设计为碳酸酐酶 (CA) 异构体 II 的选择性抑制剂，以寻找青光眼的有效治疗药物。随后，合成了目标抑制剂并评估了它们对胞质 CA I 和 II 的抑制作用。有趣的是，合成的分子对 CA I 的抑制效果很差，同时对 CA II 的亚纳摩尔效力较低。化合物7c具有最强的活性 (IC 50 = 0.63 nM)，对 CA II 具有高选择性（是乙酰唑酰胺选择性的 605 倍）。此外，化合物7c还在青光眼体内模型中显示出显着的体内眼压降低特性。此外，利用分子对接方法在分子水平上评估了化合物7c与 CA II 的结合。
• Novel alpha-oxygenated or alpha-thiolated carboxylic acid phenethylamide derivatives
  申请人：Syngenta Participations AG

  公开号：EP2314568A2

  公开（公告）日：2011-04-27

  The invention relates to α-oxygenated or α-thiolated carboxylic acid phenethylamide derivatives of the general formula I including the optical isomers thereof and mixtures of such isomers, wherein A stands for optionally substituted aryl or optionally substituted heteroaryl; X is oxygen or sulfur; Y is oxygen or sulfur; R1 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl or halocycloalkyl; R2 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkyl-alkyl, alkoxy-alkyl, alkoxy-alkenyl, alkoxy-alkynyl, whereof all alkyl- alkenyl-, alkynyl-, or cycloalkyl-groups me be optionally substituted by halogen; or optionally substituted aryl-alkyl, optionally substituted aryl-alkenyl, optionally substituted aryl-alkynyl or optionally substituted aryloxy-alkyl; R3 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkyl-alkyl, alkoxy-alkyl, alkoxy-alkenyl, alkoxy-alkynyl, whereof all alkyl- alkenyl-, alkynyl-, or cycloalkyl-groups me be optionally substituted by halogen; or is optionally substituted aryl-alkyl, optionally substituted aryl-alkenyl, optionally substituted aryl-alkynyl, optionally substituted aryloxy-alkyl, optionally substituted heteroaryl-alkyl, optionally substituted heteroaryl-alkenyl or optionally substituted heteroaryl-alkynyl; R4 is alkyl, alkenyl, alkynyl, alkoxy-alkyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkanoyl, alkylamino, dialkylamino, alkoxycarbonyl, whereof all alkyl- alkenyl or alkynyl-groups me be optionally substituted by halogen; or is halogen, cyano, nitro, amino, formyl or carboxyl; R5 is hydrogen, alkyl, alkenyl or alkynyl; n is an integer 0,1, 2, 3, or 4; B1 represents a bridge member -(CR10R11)q- or -(CHR10R11)r-Z-(CR12R13)s , wherein q is an integer 2, 3 or 4; r is an integer 0, 1, 2, 3; s is an integer 1, 2 or 3, provided that (r + s) is either 1, 2 or 3; Z is -O-, -S-, -SO- -SO2-, NR6-, -CO-, -OOC-, -COO-, -NR6-CO- or -CO-NR6- ; R6 is hydrogen or alkyl ; R10, R11, R12 and R13 independently of each other are hydrogen or alkyl ; and B2 is an alkylene bridge. These compounds possess useful plant protecting properties and may advantageously be employed in agricultural practice for controlling or preventing the infestation of plants by phytopathogenic microorganisms, especially fungi.

  本发明涉及通式 I 的α-氧代或α-硫代羧酸苯乙酰胺衍生物 其中 A 代表任选取代的芳基或任选取代的杂芳基；X 是氧或硫；Y 是氧或硫；R1 是氢、烷基、烯基、炔基、环烷基、卤代烷基、卤代烯基、卤代炔基或卤代环烷基；R2 是氢、烷基、烯基、炔基、环烷基、环烷基-烷基、烷氧基烷基、烷氧基烯基、烷氧基炔基，其中所有烷基、烯基、炔基或环烷基可任选被卤素取代；或任选取代的芳基烷基、任选取代的芳基烯基、任选取代的芳基炔基或任选取代的芳氧基烷基；R3 是氢、烷基、烯基、炔基、环烷基、环烷基烷基、烷氧基烷基、烷氧基烯基、烷氧基炔基，其中所有烷基-烯基-、炔基-或环烷基-基团任选被卤素取代；或任选被取代的芳基烷基、任选被取代的芳基烯基、任选被取代的芳基炔基、任选被取代的芳氧基烷基、任选被取代的杂芳基烷基、任选被取代的杂芳基烯基或任选被取代的杂芳基炔基；R4 是烷基、烯基、炔基、烷氧基烷基、烷氧基、烯氧基、炔氧基、烷硫基、烷酰基、烷基氨基、二烷基氨基、烷氧基羰基，其中所有烷基-烯基或炔基均可选择被卤素取代；或卤素、氰基、硝基、氨基、甲酰基或羧基； R5 是氢、烷基、烯基或炔基； n 是整数 0、1、2、3 或 4； B1 代表桥式构件-(CR10R11)q- 或-(CHR10R11)r-Z-(CR12R13)s，其中 q 是整数 2、3 或 4； r 是整数 0、1、2 或 3；s 是整数 1、2 或 3，条件是 (r + s) 是 1、2 或 3；Z 是 -O-、-S-、-SO- -SO2-、NR6-、-CO-、-OOC-、-COO-、-NR6-CO- 或 -CO-NR6-；R6 是氢或烷基；R10、R11、R12 和 R13 相互独立地是氢或烷基；以及 B2 是亚烷基桥。 这些化合物具有有用的植物保护特性，在农业实践中可用于控制或防止植物病原微生物，特别是真菌对植物的侵染。
• CHRISTIDIS, Y.;FOURNEX, R.;TOURNEMINE, C.
  作者：CHRISTIDIS, Y.、FOURNEX, R.、TOURNEMINE, C.

  DOI：——

  日期：——