4-(2,6-difluoro-phenyl)-3-buten-2-one | 374925-25-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 4-(2,6-difluoro-phenyl)-3-buten-2-one
• 英文别名: 4-(2,6-Difluorophenyl)-3-buten-2-one；4-(2,6-difluorophenyl)but-3-en-2-one
• CAS: 374925-25-4
• 化学式: C₁₀H₈F₂O
• 分子量: 182.17
• InChiKey: BLVPHVLDBNYNNO-UHFFFAOYSA-N

物化性质

• 沸点：
  251.9±25.0 °C(Predicted)
• 密度：
  1.194±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2,6-difluoro-phenyl)-3-buten-2-one 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 [双(2-甲氧基乙基)胺]三氟化硫 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.91h， 生成 5-(2,6-difluorophenyl)-4-[(2,4-difluorophenyl)fluoromethyl]-1,3-dimethyl-1H-pyrazole
  参考文献：
  名称：

  [EN] FUNGICIDAL PYRAZOLES
  [FR] PYRAZOLES FONGICIDES

  摘要：

  揭示了公式（1）和公式（1A）的化合物，包括所有立体异构体、N-氧化物和盐，其中Q1、Q2、R1、R2、R4、R5和X的定义如本公开中所述。还揭示了含有公式（1）或公式（1A）化合物的组合物以及用于控制由真菌病原体引起的植物疾病的方法，包括施用本发明的化合物或组合物的有效量。

  公开号：

  WO2012030922A1
• 作为产物：
  描述：

  2,6-二氟苯甲醛 、 丙酮 在 sodium hydroxide 作用下， 反应 1.5h， 生成 4-(2,6-difluoro-phenyl)-3-buten-2-one
  参考文献：
  名称：

  [EN] FUNGICIDAL PYRAZOLES
  [FR] PYRAZOLES FONGICIDES

  摘要：

  揭示了公式（1）和公式（1A）的化合物，包括所有立体异构体、N-氧化物和盐，其中Q1、Q2、R1、R2、R4、R5和X的定义如本公开中所述。还揭示了含有公式（1）或公式（1A）化合物的组合物以及用于控制由真菌病原体引起的植物疾病的方法，包括施用本发明的化合物或组合物的有效量。

  公开号：

  WO2012030922A1

文献信息

• Aryl and heteroarylcyclopropyl oxime ethers and their use as fungicides
  申请人：Dow AgroSciences LLC

  公开号：US06348627B1

  公开（公告）日：2002-02-19

  Compounds with fungicidal and insecticidal properties having formula wherein X is N or CH; Z is O, S or NR8; A is hydrogen, halo, cyano, (C1-C12)alkyl, or (C1-C12)alkoxy; R1 and R8 are independently hydrogen or (C1-C4)alkyl; R2 is hydrogen, (C1-C12)alkyl, halo(C1-C12)alkyl, (C3-C7)cycloalkyl, halo(C3-C7)cycloalkyl, (C2-C8)alkenyl, halo(C2-C8)alkenyl, (C2-C8)alkynyl, halo(C2-C8)alkynyl, aryl, aralkyl, heterocyclic, heterocyclic(C1-C4)alkyl or C(R10)═N—OR9; R3 is hydrogen, (C1-C12)alkyl, halo(C1-C12)alkyl, (C3-C7)cycloalkyl, halo(C3-C7)cycloalkyl, (C2-C8)alkenyl, halo(C2-C8)alkenyl, (C2-C8)alkynyl, halo(C2-C8)alkynyl, aryl, aralkyl, aryl(C3-C7)cycloalkyl, heterocyclic or heterocyclic(C1-C4)alkyl; R4 and R5 are independently hydrogen, (C1-C12)alkyl, halo(C1-C12)alkyl, (C3-C7)cycloalkyl, halo(C3-C7)cycloalkyl, (C2-C8)alkenyl, halo(C2-C8)alkenyl, (C2-C8)alkynyl, halo(C2-C8)alkynyl, halo, cyano, (C1-C4)alkoxycarbonyl, aryl, aralkyl, aryl(C3-C7)cycloalkyl, heterocyclic or heterocyclic(C1-C4)alkyl; R6 is hydrogen, (C1-C12)alkyl, halo(C1-C12)alkyl, (C3-C7)cycloalkyl, halo(C3-C7)cycloalkyl, (C2-C8)alkenyl, halo(C2-C8)alkenyl, (C2-C8)alkynyl, halo(C2-C8)alkynyl, halo, cyano, (C1-C4)alkoxycarbonyl, aryl, aralkyl, aryl(C3-C7)cycloalkyl, heterocyclic or heterocyclic(C1-C4)alkyl; R7 is aryl, aralkyl, heterocyclic or heterocyclic(C1-C4)alkyl; R9 is hydrogen, (C1-C12)alkyl, halo(C1-C12)alkyl, (C2-C8)alkenyl, halo(C2-C8)alkenyl, (C2-C8)alkynyl, halo(C2-C8)alkynyl, (C1-C4)alkylcarbonyl, (C1-C4)alkoxycarbonyl, aryl, or aralkyl; and R10 is hydrogen, (C1-C12)alkyl, halo(C1-C12)alkyl, (C3-C7)cycloalkyl, halo(C3-C7)cycloalkyl, (C2-C8)alkenyl, halo(C2-C8)alkenyl, (C2-C8)alkynyl, halo(C2-C8)alkynyl, aryl, aralkyl, heterocyclic, or heterocyclic(C1-C4)alkyl.

  具有杀真菌和杀虫特性的化合物的化学式，其中X为N或CH；Z为O、S或NR8；A为氢、卤素、氰基、(C1-C12)烷基或(C1-C12)烷氧基；R1和R8独立地为氢或(C1-C4)烷基；R2为氢、(C1-C12)烷基、卤素(C1-C12)烷基、(C3-C7)环烷基、卤素(C3-C7)环烷基、(C2-C8)烯基、卤素(C2-C8)烯基、(C2-C8)炔基、卤素(C2-C8)炔基、芳基、芳基烷基、杂环基、杂环基(C1-C4)烷基或C(R10)═N—OR9；R3为氢、(C1-C12)烷基、卤素(C1-C12)烷基、(C3-C7)环烷基、卤素(C3-C7)环烷基、(C2-C8)烯基、卤素(C2-C8)烯基、(C2-C8)炔基、卤素(C2-C8)炔基、芳基、芳基烷基、芳基(C3-C7)环烷基、杂环基或杂环基(C1-C4)烷基；R4和R5独立地为氢、(C1-C12)烷基、卤素(C1-C12)烷基、(C3-C7)环烷基、卤素(C3-C7)环烷基、(C2-C8)烯基、卤素(C2-C8)烯基、(C2-C8)炔基、卤素(C2-C8)炔基、卤素、氰基、(C1-C4)烷氧羰基、芳基、芳基烷基、芳基(C3-C7)环烷基、杂环基或杂环基(C1-C4)烷基；R6为氢、(C1-C12)烷基、卤素(C1-C12)烷基、(C3-C7)环烷基、卤素(C3-C7)环烷基、(C2-C8)烯基、卤素(C2-C8)烯基、(C2-C8)炔基、卤素(C2-C8)炔基、卤素、氰基、(C1-C4)烷氧羰基、芳基、芳基烷基、芳基(C3-C7)环烷基、杂环基或杂环基(C1-C4)烷基；R7为芳基、芳基烷基、杂环基或杂环基(C1-C4)烷基；R9为氢、(C1-C12)烷基、卤素(C1-C12)烷基、(C2-C8)烯基、卤素(C2-C8)烯基、(C2-C8)炔基、卤素(C2-C8)炔基、(C1-C4)烷基羰基、(C1-C4)烷氧羰基、芳基或芳基烷基；R10为氢、(C1-C12)烷基、卤素(C1-C12)烷基、(C3-C7)环烷基、卤素(C3-C7)环烷基、(C2-C8)烯基、卤素(C2-C8)烯基、(C2-C8)炔基、卤素(C2-C8)炔基、芳基、芳基烷基、杂环基或杂环基(C1-C4)烷基。
• FUNGICIDAL PYRAZOLES
  申请人：Long Jeffrey Keith

  公开号：US20130143940A1

  公开（公告）日：2013-06-06

  Disclosed are compounds of Formula 1 and Formula 1A including all stereoisomers, N-oxides, and salts thereof, wherein Q 1 , Q 2 , R 1 , R 2 , R 4 , R 5 and X are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula 1 or Formula 1A and methods for controlling plant disease caused by a fungal pathogen comprising applying an effective amount of a compound or a composition of the invention.

  本发明涉及公式1和公式1A的化合物，包括其所有立体异构体、N-氧化物和盐，其中Q1、Q2、R1、R2、R4、R5和X的定义如所述。本发明还涉及含有公式1或公式1A化合物的组合物，以及通过施用本发明化合物或组合物的有效量来控制由真菌病原体引起的植物疾病的方法。
• Fungicidal pyrazoles
  申请人：Long Jeffrey Keith

  公开号：US08754115B2

  公开（公告）日：2014-06-17

  Disclosed are compounds of Formula 1 and Formula 1A including all stereoisomers, N-oxides, and salts thereof, wherein Q1, Q2, R1, R2, R4, R5 and X are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula 1 or Formula 1A and methods for controlling plant disease caused by a fungal pathogen comprising applying an effective amount of a compound or a composition of the invention.

  本发明涉及公式1和公式1A的化合物，包括其所有立体异构体、N-氧化物和盐。其中，Q1、Q2、R1、R2、R4、R5和X如本文所定义。本发明还涉及含有公式1或公式1A的化合物的组合物，以及治疗由真菌病原体引起的植物疾病的方法，包括施用本发明的化合物或组合物的有效量。
• Cyclohexane 1,3-diones and their inhibition of mutant SOD1-dependent protein aggregation and toxicity in PC12 cells
  作者：Wei Zhang、Radhia Benmohamed、Anthony C. Arvanites、Richard I. Morimoto、Robert J. Ferrante、Donald R. Kirsch、Richard B. Silverman

  DOI：10.1016/j.bmc.2011.11.039

  日期：2012.1

  Amyotrophic lateral sclerosis (ALS) is a fatal neurodegenerative disease characterized by the progressive loss of motor neurons. Currently, there is only one FDA-approved treatment for ALS (riluzole), and that drug only extends life, on average, by 2-3 months. Mutations in Cu/Zn superoxide dismutase (SOD1) are found in familial forms of the disease and have played an important role in the study of ALS pathophysiology. On the basis of their activity in a PC12-G93A-YFP high-throughput screening assay, several bioactive compounds have been identified and classified as cyclohexane-1,3-dione (CHD) derivatives. A concise and efficient synthetic route has been developed to provide diverse CHD analogs. The structural modification of the CHD scaffold led to the discovery of a more potent analog (26) with an EC(50) of 700 nM having good pharmacokinetic properties, such as high solubility, low human and mouse metabolic potential, and relatively good plasma stability. It was also found to efficiently penetrate the blood-brain barrier. However, compound 26 did not exhibit any significant life span extension in the ALS mouse model. It was found that, although 26 was active in PC12 cells, it had poor activity in other cell types, including primary cortical neurons, indicating that it can penetrate into the brain, but is not active in neuronal cells, potentially due to poor selective cell penetration. Further structural modification of the CHD scaffold was aimed at improving global cell activity as well as maintaining potency. Two new analogs (71 and 73) were synthesized, which had significantly enhanced cortical neuronal cell permeability, as well as similar potency to that of 26 in the PC12-G93A assay. These CHD analogs are being investigated further as novel therapeutic candidates for ALS. (C) 2011 Elsevier Ltd. All rights reserved.
• [EN] FUNGICIDAL PYRAZOLES<br/>[FR] PYRAZOLES FONGICIDES
  申请人：DU PONT

  公开号：WO2012030922A1

  公开（公告）日：2012-03-08

  Disclosed are compounds of Formula (1) and Formula (1A) including all stereoisomers, N oxides, and salts thereof,wherein Q1, Q2, R1, R2, R4, R5 and X are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula (1) or Formula (1A) and methods for controlling plant disease caused by a fungal pathogen comprising applying an effective amount of a compound or a composition of the invention.

  揭示了公式（1）和公式（1A）的化合物，包括所有立体异构体、N-氧化物和盐，其中Q1、Q2、R1、R2、R4、R5和X的定义如本公开中所述。还揭示了含有公式（1）或公式（1A）化合物的组合物以及用于控制由真菌病原体引起的植物疾病的方法，包括施用本发明的化合物或组合物的有效量。