N-[2-(3-methoxy-4-(prop-2-ynyloxy)phenyl)ethyl]formamide | 374728-19-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-[2-(3-methoxy-4-(prop-2-ynyloxy)phenyl)ethyl]formamide
• 英文别名: N-[2-(3-methoxy-4-prop-2-ynyloxyphenyl)ethyl]formamide；N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-formamide；Formamide, N-[2-[3-methoxy-4-(2-propynyloxy)phenyl]ethyl]-；N-[2-(3-methoxy-4-prop-2-ynoxyphenyl)ethyl]formamide
• CAS: 374728-19-5
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: RGJPLNVAOFLJGL-UHFFFAOYSA-N

物化性质

• 沸点：
  440.0±45.0 °C(Predicted)
• 密度：
  1.112±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[2-(3-methoxy-4-(prop-2-ynyloxy)phenyl)ethyl]formamide 在 盐酸 、 三乙胺 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 生成 2-(ethylsulfonylamino)-N-[2-(3-methoxy-4-prop-2-ynoxyphenyl)ethyl]-2-(4-methylphenyl)acetamide
  参考文献：
  名称：

  N-Sulfonyl Amino Acid Amides, a Novel Class of Compounds with Fungicidal Activity [1]

  摘要：

  已经设计和制备了新型的疫霉菌杀菌剂。这些N-磺酰氨基酸酰胺的合成方法已经概述。生物测定表明它们对重要植物病害如晚疫病菌（番茄和马铃薯晚疫病）和葡萄霜霉病（葡萄霜霉病）具有很高的效力。结构活性关系研究也已讨论。

  DOI：

  10.2533/000942903777678542
• 作为产物：
  描述：

  4-(2-氨基乙基)-2-甲氧基苯酚 在 sodium methylate 、 乙酸酐 作用下， 生成 N-[2-(3-methoxy-4-(prop-2-ynyloxy)phenyl)ethyl]formamide
  参考文献：
  名称：

  N-Sulfonyl Amino Acid Amides, a Novel Class of Compounds with Fungicidal Activity [1]

  摘要：

  已经设计和制备了新型的疫霉菌杀菌剂。这些N-磺酰氨基酸酰胺的合成方法已经概述。生物测定表明它们对重要植物病害如晚疫病菌（番茄和马铃薯晚疫病）和葡萄霜霉病（葡萄霜霉病）具有很高的效力。结构活性关系研究也已讨论。

  DOI：

  10.2533/000942903777678542

文献信息

• Phenyl-propargylether derivatives
  申请人：Syngenta Crop Protection, Inc.

  公开号：US06683211B1

  公开（公告）日：2004-01-27

  The invention relates to phenyl-propargylether derivatives of the general formula I including the optical isomers thereof and mixtures of such isomers, wherein R1 is hydrogen, alkyl, cycloalkyl or optionally substituted aryl, R2 and R3 are each independently hydrogen or alkyl, R4 is alkyl, alkenyl or alkynyl, R5, R6, R7, and R8 are each independently hydrogen or alkyl, R9 is hydrogen, optionally substituted alkyl, optionally substituted alkenyl or optionally substituted alkynyl, R10 is optionally substituted aryl or optionally substituted heteroaryl, and Z is halogen, optionally substituted aryloxy, optionally substituted alkoxy, optionally substituted alkenyloxy, optionally substituted alkynyloxy, optionally substituted arylthio, optionally substituted alkylthio, optionally substituted alkenylthio; optionally substituted alkynylthio, optionally substituted alkylsulfinyl, optionally substituted alkenylsulfinyl, optionally substituted alkynylsulfinyl, optionally substituted alkylsulfonyl, optionally substituted alkenylsulfonyl or optionally substituted alkynylsulfonyl. 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.

  该发明涉及一般式I的苯基-丙炔醚衍生物，包括其光学异构体和这些异构体的混合物，其中 R1为氢、烷基、环烷基或可选择取代的芳基， R2和R3分别独立为氢或烷基， R4为烷基、烯基或炔基， R5、R6、R7和R8分别独立为氢或烷基， R9为氢、可选择取代的烷基、可选择取代的烯基或可选择取代的炔基， R10为可选择取代的芳基或可选择取代的杂环芳基，以及 Z为卤素、可选择取代的芳氧基、可选择取代的烷氧基、可选择取代的烯氧基、可选择取代的炔氧基、可选择取代的芳硫基、可选择取代的烷硫基、可选择取代的烯硫基、可选择取代的炔硫基、可选择取代的烷亚砜基、可选择取代的烯亚砜基、可选择取代的炔亚砜基、可选择取代的烷砜基、可选择取代的烯砜基或可选择取代的炔砜基。这些化合物具有有用的植物保护性能，并可有利地用于农业实践中，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。
• Synthesis and fungicidal activity ofN-2-(3-methoxy-4-propargyloxy) phenethyl amides. Part 3: stretched and heterocyclic mandelamide oomyceticides
  作者：Clemens Lamberth、Hans-Joachim Kempf、Miroslav Križ

  DOI：10.1002/ps.1308

  日期：2007.1

  Novel analogues of mandipropamid have been designed and prepared. The synthetic approach to these stretched and heterocyclic mandelamides is outlined. Biological data demonstrate their high efficacy against important plant diseases like tomato and potato late blight (Phytophthora infestans De Bary) and grape downy mildew (Plasmopara viticola Berliner & de Toni). Structure-activity relationship studies

  已经设计和制备了新的曼地拉米类似物。概述了这些拉伸的和杂环的扁桃酰胺的合成方法。生物数据表明，它们对重要的植物病害（如番茄和马铃薯晚疫病（Phytophthora infestans De Bary）和葡萄霜霉病（Plasmopara viticola Berliner＆de Toni））具有很高的功效。讨论了构效关系研究。
• Novel n-p-propargyloxyphenethyl-thioacetic acid amides
  申请人：——

  公开号：US20040127739A1

  公开（公告）日：2004-07-01

  The invention relates to N-propargyloxy-phenethyl thioacetic acid amide derivatives of the general formula (I) including the optical isomers thereof and mixtures of such isomers, wherein R 1 is hydrogen, alkyl, cycloalkyl or optionally substituted aryl, R 2 and R 3 are each independently hydrogen or alkyl, R 4 is alkyl, alkenyl or alkynyl, R 5 , R 6 , R 7 and R 8 are each independently hydrogen or alkyl, R 9 is hydrogen, optionally substituted alkyl, optionally substituted alkenyl or optionally substituted alkynyl, R 10 is optionally substituted aryl or optionally substituted heteroaryl, and Z is hydroxy, optionally substituted aryloxy, optionally substituted alkoxy, optionally substituted alkynyloxy, optionally substituted arylthio, optionally substituted alkylthio, optionally substituted alkynylthio, optionally substituted alkylsulfinyl, optionally substituted alkenysulfinyl, optionally substituted alkynylsulfinyl, optionally substituted alkylsulfonyl, optionally substituted alkenylsulfonyl, optionally substituted alkynylsulfonyl or a group —O—CO—R 11 , —O—CO—O—R 11 or —O—CO—CO—O—R 11 wherein R 11 is hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl or optionally substituted heteroaryl. 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. 1

  本发明涉及一般式（I）的N-丙炔氧基-苯乙硫酸酰胺衍生物，包括其光学异构体和混合物，其中R1是氢、烷基、环烷基或可选取代芳基，R2和R3各自独立地是氢或烷基，R4是烷基、烯基或炔基，R5、R6、R7和R8各自独立地是氢或烷基，R9是氢、可选取代烷基、可选取代烯基或可选取代炔基，R10是可选取代芳基或可选取代杂环芳基，Z是羟基、可选取代芳氧基、可选取代烷氧基、可选取代炔基氧基、可选取代芳硫基、可选取代烷硫基、可选取代炔基硫基、可选取代烷基亚砜基、可选取代烯基亚砜基、可选取代炔基亚砜基、可选取代烷基磺酰基、可选取代烯基磺酰基、可选取代炔基磺酰基或基团—O—CO—R11，—O—CO—O—R11或—O—CO—CO—O—R11，其中R11是氢、可选取代烷基、可选取代环烷基、可选取代芳基或可选取代杂环芳基。这些化合物具有有用的植物保护特性，并可优势地用于农业实践中控制或预防植物受植物病原微生物（尤其是真菌）侵害。
• 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 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。