3-(4-chlorophenyl)-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynoxyphenyl)ethyl]propanamide | 528578-00-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(4-chlorophenyl)-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynoxyphenyl)ethyl]propanamide
• CAS: 528578-00-9
• 化学式: C₂₁H₂₂ClNO₄
• 分子量: 387.863
• InChiKey: GBTHSCCAGKFMBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-chlorophenyl)-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynoxyphenyl)ethyl]propanamide 、 3-溴丙炔 在 sodium hydroxide 、 四丁基溴化铵 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 生成 3-(4-chlorophenyl)-N-[2-(3-methoxy-4-prop-2-ynoxyphenyl)ethyl]-2-prop-2-ynoxypropanamide
  参考文献：
  名称：

  Multicomponent reactions in fungicide research: The discovery of mandipropamid

  摘要：

  Isocyanide-based multicomponent reactions of the Ugi- and Passerini-type have been valuable tools for the rapid exploration of the novel fungicidal compound classes of phenylglycinamides and mandelamides. Mandipropamid (6), which was discovered during this derivatisation, displays excellent activity against the economically important phytopathogens Phytophthora infestans (potato and tomato late blight) and Plasmopara viticola (grape downy mildew). (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.10.019
• 作为产物：
  描述：

  (4-氯苯基)乙醛 、 N-[2-(3-methoxy-4-(prop-2-ynyloxy)phenyl)ethyl]formamide 在 三光气 、 三乙胺 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 生成 3-(4-chlorophenyl)-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynoxyphenyl)ethyl]propanamide
  参考文献：
  名称：

  Multicomponent reactions in fungicide research: The discovery of mandipropamid

  摘要：

  Isocyanide-based multicomponent reactions of the Ugi- and Passerini-type have been valuable tools for the rapid exploration of the novel fungicidal compound classes of phenylglycinamides and mandelamides. Mandipropamid (6), which was discovered during this derivatisation, displays excellent activity against the economically important phytopathogens Phytophthora infestans (potato and tomato late blight) and Plasmopara viticola (grape downy mildew). (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.10.019

文献信息

• Novel $g(a)-oxygenated or $g(a)-thiolated carboxylic acid phenethylamide derivatives
  申请人：Zeller Martin

  公开号：US20050038082A1

  公开（公告）日：2005-02-17

  The invention relates to α-oxygenated or α-thiolated carboxylic acid phenethylamide derivatives of 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 may be optionally substituted by halogen; or optionally substituted aryl-alkyl, 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 may 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, alkenyloxy, 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; R 5 is hydrogen, alkyl, alkenyl or alkynyl; n is an integer 0, 1, 2, 3, or 4; B, represents a bridge member —CR 10 R 11 —, wherein R 10 and R 11 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-硫醇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、炔基或环烷基基团均可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、炔基或环烷基基团均可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、烯氧基、烯氧基、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、烯基或炔基基团均可选择性地被卤素取代；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；B表示桥接成员-CR10R11-，其中R10和R11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，并可以在农业实践中优势地用于控制或预防植物被植物病原微生物，特别是真菌的侵害。
• NOVEL ALPHA-OXYGENATED OR ALPHA-THIOLATED CARBOXYLIC ACID PHENETHYLAMIDE DERIVATIVES
  申请人：Syngenta Participations AG

  公开号：EP1448514A1

  公开（公告）日：2004-08-25
• NOVEL ALPHA-OXYGENATED CARBOXYLIC ACID PHENETHYLAMIDE DERIVATIVES
  申请人：Syngenta Participations AG

  公开号：EP1448514B1

  公开（公告）日：2010-05-19
• US7700522B2
  申请人：——

  公开号：US7700522B2

  公开（公告）日：2010-04-20
• [EN] NOVEL DOLLAR G(a)-OXYGENATED OR DOLLAR G(a)-THIOLATED CARBOXYLIC ACID PHENETHYLAMIDE DERIVATIVES<br/>[FR] NOUVEAUX DERIVES PHENETHYLAMIDES D'ACIDE CARBOXYLIQUE DOLLAR G(A)-OXYGENES OU DOLLAR G(A)-THIOLES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2003042168A1

  公开（公告）日：2003-05-22

  The invention relates to α-oxygenated or α-thiolated carboxylic acid phenethylamide derivatives of 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 may 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 may 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, alkenyloxy, 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; B, represents a bridge member -CR10R11-, wherein R10 and R11 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.