3-chloro-3-methyl-1-trifluoromethylcyclobutane carboxylic acid | 16200-78-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-chloro-3-methyl-1-trifluoromethylcyclobutane carboxylic acid
• 英文别名: 1-(Trifluoromethyl)-3-chloro-3-methylcyclobutane-1-carboxylic acid；3-chloro-3-methyl-1-(trifluoromethyl)cyclobutane-1-carboxylic acid
• CAS: 16200-78-5
• 化学式: C₇H₈ClF₃O₂
• 分子量: 216.588
• InChiKey: HPTGDBRNVIRWOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-chloro-3-methyl-1-trifluoromethylcyclobutane carboxylic acid 在 氯化亚砜 作用下， 反应 1.0h， 生成 3-Chloro-3-methyl-1-(trifluoromethyl)cyclobutane-1-carbonyl chloride
  参考文献：
  名称：

  Cyclobutane carboxamide inhibitors of fungal melanin: biosynthesis and their evaluation as fungicides

  摘要：

  A new fungicide lead has been identified by enzyme screening of a focused combinatorial library. The lead compound 4, a potent inhibitor of scytalone dehydratase (SD), exhibits fungicidal activity upon foliar application but does not show systemic activity. The X-ray crystal structure of the enzyme-inhibitor complex and an appreciation for the relationship between physical properties and systemic activity enabled us to rapidly improve upon this initial lead. The geminal halogen-methyl group combination was found to be optimal for interaction with the bounding serine and asparagine side-chain residues. Replacement of CF3 with methyl was a key discovery, giving inhibitors with slightly diminished enzyme inhibition potency while significantly increasing systemic activity. Amides prepared from amines with 2,4-dichloro substitution on the phenyl ring gave the most potent enzyme inhibitors. Two compounds from this series showed systemic activity comparable to the commercial standard and were selected for outdoor testing in flooded plots which simulate rice paddies. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00034-1

文献信息

• Fungicidal amides
  申请人：The Board of Trustees of the University of Arkansas

  公开号：US06504058B1

  公开（公告）日：2003-01-07

  Compounds of Formula I are disclosed which are useful as fungicides wherein R1 is hydrogen; halogen; C1-C2 alkoxy; C1-C2 haloalkoxy; cyano; or C1-C2 alkyl optionally substituted with halogen, C1-C2 alkoxy or cyano; R2 is hydrogen; halogen; or C1-C4 alkyl optionally substituted with halogen, C1-C2 alkoxy or cyano; R3 is hydrogen; halogen; C1-C4 alkoxy; C1-C4 haloalkoxy; or C1-C4 alkyl optionally substituted with halogen, C1-C2 alkoxy or cyano; or R2 and R3 can be taken together as —CH2CH2—; R4 is C1-C2 alkyl; R5 is R6, CH(R8)OR6, CH(R8)CH(R7)R6 or C(R8)═C(R7)R6; and R6, R7 and R8 are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula I and a method for controlling plant diseases caused by fungal plant pathogens which involves applying an effective amount of a compound of Formula I.

  公开了化学式I的化合物，其可用作杀菌剂，其中R1为氢; 卤素; C1-C2烷氧基; C1-C2卤代烷氧基; 腈; 或C1-C2烷基，可选择地取代卤素，C1-C2烷氧基或腈; R2为氢; 卤素; 或C1-C4烷基，可选择地取代卤素，C1-C2烷氧基或腈; R3为氢; 卤素; C1-C4烷氧基; C1-C4卤代烷氧基; 或C1-C4烷基，可选择地取代卤素，C1-C2烷氧基或腈; 或R2和R3可一起取为—CH2CH2—; R4为C1-C2烷基; R5为R6，CH（R8）OR6，CH（R8）CH（R7）R6或C（R8）═C（R7）R6; 而R6，R7和R8如定义所述。还公开了含有化学式I的化合物的组合物以及一种控制由真菌植物病原体引起的植物病害的方法，其中涉及施用化学式I的化合物的有效量。
• Fungicidally active carboxylic acid amides
  申请人：——

  公开号：US06683212B1

  公开（公告）日：2004-01-27

  Compounds of Formula (I) are disclosed which are useful as fungicides wherein R1 is hydrogen; halogen; C1-C2 alkoxy; C1-C2 haloalkoxy, cyano; or C1-C2 alkyl optionally substituted with halogen, C1-C2 alkoxy or cyano; R2 is hydrogen; halogen; or C1-C4 alkyl optionally substituted with halogen, C1-C2 alkoxy or cyano; R3 is hydrogen; halogen; C1-C4 alkoxy; C1-C4 haloalkoxy; or C1-C4 alkyl optionally substituted with halogen, C1-C2 alkoxy or cyano; or R2 and R3 can be taken together as —CH2CH2—; R4 is C1-C2 alkyl; R5 is R6, CH(R8)OR6, CH(R8)CH(R7)R6 or C(R8)═C(R7)R6; and R6, R7 and R8 are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula (I) and a method for controlling plant diseases caused by fungal plant pathogens which involves applying an effective amount of a compound of Formula (I).

  公开了化学式（I）的化合物，其可用作杀菌剂，其中R1是氢; 卤素; C1-C2烷氧基; C1-C2卤代烷氧基，氰基; 或C1-C2烷基，可选地取代卤素，C1-C2烷氧基或氰基; R2是氢; 卤素; 或C1-C4烷基，可选地取代卤素，C1-C2烷氧基或氰基; R3是氢; 卤素; C1-C4烷氧基; C1-C4卤代烷氧基; 或C1-C4烷基，可选地取代卤素，C1-C2烷氧基或氰基; 或R2和R3可一起取为—CH2CH2—; R4是C1-C2烷基; R5是R6，CH（R8）OR6，CH（R8）CH（R7）R6或C（R8）═C（R7）R6; 而R6、R7和R8如所述。还公开了含有化学式（I）的化合物的组合物和一种用于控制由真菌植物病原体引起的植物病害的方法，其中涉及施用化学式（I）的有效量的化合物。
• A new potent inhibitor of fungal melanin biosynthesis identified through combinatorial chemistry
  作者：Lee D. Jennings、Zdzislaw Wawrzak、Denise Amorose、Rand S. Schwartz、Douglas B. Jordan

  DOI：10.1016/s0960-894x(99)00424-2

  日期：1999.9

  A new fungicide lead has been identified by in vitro screening of a focused combinatorial library. Amides (768) were synthesized in pools of four and assayed as inhibitors of scytalone dehydratase. Deconvolution of one of the most active pools led to the discovery of a potent inhibitor of the enzyme 3b (K-i = 26 pM), which has fungicidal properties. (C) 1999 Elsevier Science Ltd. All rights reserved.
• US6504058B1
  申请人：——

  公开号：US6504058B1

  公开（公告）日：2003-01-07
• US6683212B1
  申请人：——

  公开号：US6683212B1

  公开（公告）日：2004-01-27