2-chloro-3-p-tolyl-propionic acid methyl ester | 51698-36-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-chloro-3-p-tolyl-propionic acid methyl ester
• 英文别名: 2-Chlor-3-p-tolyl-propionsaeure-methylester；2-Chloro-3-p-tolyl-propionic acid methyl ester；methyl 2-chloro-3-(4-methylphenyl)propanoate
• CAS: 51698-36-3
• 化学式: C₁₁H₁₃ClO₂
• 分子量: 212.676
• InChiKey: YVRTYSFWBGXWAL-UHFFFAOYSA-N

物化性质

• 沸点：
  288.1±25.0 °C(Predicted)
• 密度：
  1.138±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-chloro-3-p-tolyl-propionic acid methyl ester 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 4-methylcinnamic acid
  参考文献：
  名称：

  由不饱和化合物的阴离子芳基化产物合成杂环。7.苯并[b]噻吩衍生物的合成中丙烯酸的卤代芳基化反应及其酯

  摘要：

  DOI：

  10.1023/a:1026190103546
• 作为产物：
  描述：

  乙烷,三氯氟- 在 盐酸 、 水 、 sodium acetate 、 copper dichloride 、 sodium nitrite 作用下， 生成 2-chloro-3-p-tolyl-propionic acid methyl ester
  参考文献：
  名称：

  A Synthesis of Cinnamic Acids from Methyl Acrylate or Acrylonitrile and Diazonium Salts

  摘要：

  DOI：

  10.1021/ja01241a019

文献信息

• Arenediazonium tetrachlorocuprates(II). Modification of the Meerwein and Sandmeyer reactions
  作者：Mykola D. Obushak、Mykhaylo B. Lyakhovych、Mykola I. Ganushchak

  DOI：10.1016/s0040-4039(98)02165-0

  日期：1998.12

  In the copper-catalysed reactions of arenediazonium chlorides with unsaturated compounds arenediazonium tetrachlorocuprates(II) are formed as intermediates. A general method of preparation of these complexed diazonium salts is described. In polar solvents these salts undergo chlorinative dediazoniation to give chloroarenes in high yield. The reaction of an arenediazonium tetrachlorocuprate(II) with

  在铜催化的壬二鎓氯化物与不饱和化合物的铜催化反应中，形成了四氯铜鎓（II）间二氮杂鎓。描述了这些络合的重氮盐的一般制备方法。在极性溶剂中，这些盐会进行氯化脱重氮反应，从而以高收率得到氯代芳烃。芳烯二鎓四氯铜酸酯（II）与活化的烯烃的反应产生与Meerwein反应相同的产物。提出了用于该反应的自由基阳离子机理。
• Asymmetric catalysis, part 108 copper catalysts with optically active ligands in the enantioselective Meerwein arylation of activated olefins
  作者：Henri Brunner、Christian Blüchel、Michael P. Doyle

  DOI：10.1016/s0022-328x(97)00018-1

  日期：1997.8

  arylation. Replacement of the p-tolyldiazonium salt by the mesityldiazonium salt caused the optical induction in the formation of the corresponding mesityl product rise to 19.5% ee. Thus, though considered to be a radical reaction, the Meerwein arylation of activated olefins can be rendered enantioselective by using copper catalysts with optically active ligands.

  活化烯烃与卤代芳氮zon的铜催化Meerwein反应导致芳基卤化物正式加成到烯烃双键上。使用丙烯酸甲酯，对甲苯基重氮四氟硼酸盐和四丁基氯化铵在无水乙腈中的模型系统，产物为α-氯-β-甲苯基丙酸甲酯。应用新建立的方法，将分离的四氟硼酸重氮盐和等量的四丁基氯化铵加到烯烃和铜催化剂中，该催化剂含有光学活性的配体，例如2-和2,6-吡啶基恶唑啉和双恶唑啉。在室温反应中获得的低光感应可以提高到8.7 ee在−40°C的低温变量中。催化剂的双恶唑啉配体中手性中心附近的两个苯基取代基和底物的酯基（甲基，乙基，薄荷基）中增加的空间体积增加了Meerwein芳基化的立体选择性。用间苯二甲重氮盐代替对甲苯基重氮盐在形成相应的间苯二酚产物时引起光感应升至19.5％ee。因此，尽管被认为是自由基反应，但通过使用具有光学活性配体的铜催化剂，可使活化烯烃的Meerwein芳基化成为对映选择性。
• Chloride based ionic liquids as promoting agents for Meerwein reaction in solventless conditions
  作者：Piero Mastrorilli、Cosimo F. Nobile、Nicola Taccardi

  DOI：10.1016/j.tetlet.2006.04.072

  日期：2006.7

  Chloride based ionic liquids were used as chloride source in Meerwein reaction either in [bmim]X (bmim = 1-butyl-3-methylimidazolium, X = BF4, PF6) as solvents or in solventless conditions. Satisfactory yields (49–71%) with diversely substituted diazonium salts were achieved by using 1,3-dibutylimidazolium chloride in the presence of a bimetallic Zn/Cu catalyst.

  氯化物基离子液体在Memwein反应中作为溶剂或在无溶剂条件下以[bmim] X（bmim = 1-丁基-3-甲基咪唑鎓，X = BF 4，PF 6）用作Meerwein反应中的氯化物源。在双金属Zn / Cu催化剂存在下，通过使用1,3-二丁基咪唑鎓氯化物，获得了不同取代的重氮盐的令人满意的收率（49-71％）。
• 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。
• α-Oxygenated or α-thiolated carboxylic acid phenethylamide derivatives
  申请人：Syngenta Crop Protection, Inc.

  公开号：US07700522B2

  公开（公告）日：2010-04-20

  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 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 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.

  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、炔基或环烷基基团均可选取代卤素；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、可选取代的杂芳基烷基、可选取代的杂芳基烯基或可选取代的杂芳基炔基；R4为烷基、烯基、炔基、烷氧基烷基、烷氧基、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取代卤素；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；B代表桥接成员-CR10R11-，其中R10和R11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，并可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，特别是真菌的侵染。