ethyl 2',6'-dichlorooxanilate | 56934-57-7

• 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: ethyl 2',6'-dichlorooxanilate
• 英文别名: 2',6'-dichlorooxanilic acid ethyl ester；N-(2,6-Dichlor-phenyl)-oxamidsaeure-aethylester；Ethyl 2-(2,6-dichloroanilino)-2-oxoacetate
• CAS: 56934-57-7
• 化学式: C₁₀H₉Cl₂NO₃
• mdl: MFCD02007055
• 分子量: 262.092
• InChiKey: SKVOVUFTCKFGNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2',6'-dichlorooxanilate 、 2-氨基-5-二乙基氨基戊烷 以 乙醇 为溶剂， 生成 N'-<4-Diaethylamino-1-methyl-butyl>-N-<2,6-dichlorphenyl>-oxamid
  参考文献：
  名称：

  Petyunin,P.A.; Kalugina,Z.G., Journal of general chemistry of the USSR, 1963, vol. 33, # 9, p. 2762 - 2768

  摘要：

  DOI：
• 作为产物：
  描述：

  草酸二乙酯 、 2,6-二氯苯胺 以 甲苯 为溶剂， 反应 3.0h， 以82%的产率得到ethyl 2',6'-dichlorooxanilate
  参考文献：
  名称：

  Synthesis and Quantitative Structure−Activity Relationships of Oxanilates as Chemical Hybridizing Agents for Wheat (Triticum aestivum L.)

  摘要：

  Chemical hybridizing agents (CHAs) can facilitate two-line breeding in heterosis programs of crops. Twenty-seven oxanilates having different aromatic substitutions were synthesized and screened as CHAs on two genotypes of wheat, PBW 343 and HID 2733, during two Rabi (winter) seasons, 200001 and 2001-02. The oxanilates prepared by thermal condensation of anilines with diethyl oxalate or by acylation with ethoxycarbonyl methanoyl chloride were sprayed at 1000 and 1500 ppm at the premeiotic stage of wheat, when the length of the emerging spike of the first node was 7-8 mm. Pollen sterility and spikelet sterility were measured in each treatment. Ethyl oxanilates 5, 6, and 25, containing 4-F, 4-Br, and 4-CF3 aromatic substituents, respectively, induced greater than 98% spikelet sterility, the desired level, at 1500 ppm. Quantitative structure -activity relationship analysis revealed a direct relationship between F-p and molecular mass but an inverse relationship between MR, E-S, and R in influencing the bioactivity. Several F-1 hybrids were developed using 5, and at least one showed heterosis.

  DOI：

  10.1021/jf025870+

文献信息

• Oxanilic acids, a new series of orally active antiallergic agents
  作者：John H. Sellstedt、Charles J. Guinosso、Albert J. Begany、Stanley C. Bell、Marvin Rosenthale

  DOI：10.1021/jm00243a014

  日期：1975.9

  antiallergic activity using the rat passive cutaneous anaphylaxis (PCA) test. Many of the oxanilic acid esters are active orally, with the most active species having an aryl 2'-carbamoyl group and a 3'-methoxy group. Hydrolysis of the ester from the oxanilic ester moiety causes a loss of oral activity.

  制备了大量的草酸苯甲酸酯和N-杂芳基草酰胺酸酯，并通过大鼠被动皮肤过敏反应（PCA）测试发现具有抗过敏活性。许多草酰苯甲酸酯具有口服活性，最活泼的物种具有芳基2'-氨基甲酰基和3'-甲氧基。酯从草酰胺酯部分水解会导致口服活性下降。
• [EN] OXALIC ACID MONOAMIDE LIGAND, AND USES THEREOF IN COUPLING REACTION OF COPPER-CATALYZED ARYL HALOGEN SUBSTITUTE<br/>[FR] LIGAND DE MONOAMIDE D'ACIDE OXALIQUE, ET SES USAGES DANS UNE RÉACTION DE COUPLAGE DE SUBSTITUT HALOGÉNÉ D'ARYLE CATALYSÉ AU CUIVRE<br/>[ZH] 草酸酰胺类配体及其在铜催化芳基卤代物偶联反应中的用途
  申请人：SHANGHAI INST ORGANIC CHEMISTRY CAS

  公开号：WO2017012379A1

  公开（公告）日：2017-01-26

  本发明提供了草酸酰胺类配体及其在铜催化芳基卤代物偶联反应中的用途，具体地，本发明提供了一种如下式I所示的化合物的用途；其中，各基团的定义如说明书中所述。所述的式I化合物可以用作为铜催化芳基卤代物偶联反应中的配体，用于催化形成C-N、C-O、C-S键等芳基卤代物的偶联反应。
• Synthesis of benzimidazole-2-carboxylic acid amides from o-phenylenediamine and oxamic acid esters
  作者：P. A. Petyunin、Abdul Malek Choudry

  DOI：10.1007/bf00526091

  日期：1982.5
• PETYUNIN, P. A.;ABDUL, MALEK, CHOUDRI, XIMIYA GETEROTSIKL. SOEDIN., 1982, N 5, 684-686
  作者：PETYUNIN, P. A.、ABDUL, MALEK, CHOUDRI

  DOI：——

  日期：——
• OXALIC ACID MONOAMIDE LIGAND, AND USES THEREOF IN COUPLING REACTION OF COPPER-CATALYZED ARYL HALOGEN SUBSTITUTE
  申请人：Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences

  公开号：US20180207628A1

  公开（公告）日：2018-07-26

  The present invention provides oxalic amide ligands and uses thereof in copper-catalyzed coupling reaction of aryl halides. Specifically, the present invention provides a use of a compound represented by formula I, wherein definitions of each group are described in the specification. The compound represented by formula I can be used as a ligand in copper-catalyzed coupling reaction of aryl halides for the formation of C—N, C—O and C—S bonds.