(2-hydroxy)-ethyloxanilate | 27383-59-1

• 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: (2-hydroxy)-ethyloxanilate
• 英文别名: ethyl (2-hydroxyphenylcarbamoyl)formate；ethyl N-(2-hydroxyphenyl)oxalamate；ethyl N-(2-hydroxyphenyl)oxamate；ethyl 2-(2-hydroxyanilino)-2-oxoacetate
• CAS: 27383-59-1
• 化学式: C₁₀H₁₁NO₄
• 分子量: 209.202
• InChiKey: NABLMJNFLDDYLV-UHFFFAOYSA-N

物化性质

• 熔点：
  80 °C
• 密度：
  1.328±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 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：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2-hydroxy)-ethyloxanilate 以92%的产率得到3-羟基-2H-1,4-苯并噁嗪-2-酮
  参考文献：
  名称：

  Syntheses of Cyclic Hydroxamic Acids and Lactams with 2,3-dioxo-1,4-benzoxazine skeleton

  摘要：

  Ethyl 2-nitrophenyl oxalate (1 a) and its 5-methoxy derivative (1 b) were subjected to catalytic hydrogenations over 3 % Pt (S) on carbon in different solvents. Thus, hydrogenation in acetic acid yielded 4-hydroxy-2,3-dioxo-1,4-benzoxazine (2a) and its 7-methoxy derivative (2 b) by reductive cyclization, the dehydro forms of the naturally occurring cyclic hydroxamic acids DIBOA and DIMBOA from Gramineae. In contrast, hydrogenation of esters 1 in methanol results in the formation of amides 3 by acyl group migration. On heating, amides 3 undergo lactonization to form lactone-lactames 4, which in turn undergo ring opening to give amides 3 when refluxed in ethanol.

  DOI：

  10.1002/prac.19933350409
• 作为产物：
  描述：

  Ethyl o-Nitrophenyl Oxalate 在 Pt(S)/C 甲醇 、 氢气 作用下， 以86%的产率得到(2-hydroxy)-ethyloxanilate
  参考文献：
  名称：

  Syntheses of Cyclic Hydroxamic Acids and Lactams with 2,3-dioxo-1,4-benzoxazine skeleton

  摘要：

  Ethyl 2-nitrophenyl oxalate (1 a) and its 5-methoxy derivative (1 b) were subjected to catalytic hydrogenations over 3 % Pt (S) on carbon in different solvents. Thus, hydrogenation in acetic acid yielded 4-hydroxy-2,3-dioxo-1,4-benzoxazine (2a) and its 7-methoxy derivative (2 b) by reductive cyclization, the dehydro forms of the naturally occurring cyclic hydroxamic acids DIBOA and DIMBOA from Gramineae. In contrast, hydrogenation of esters 1 in methanol results in the formation of amides 3 by acyl group migration. On heating, amides 3 undergo lactonization to form lactone-lactames 4, which in turn undergo ring opening to give amides 3 when refluxed in ethanol.

  DOI：

  10.1002/prac.19933350409

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。
• A new method for the preparation of unsymmetrical 1,4-substituted piperazine derivatives
  作者：Aurelio Ortiz、Norberto Farfán、Herbert Höpfl、Rosa Santillan、Marı́a E. Ochoa、Atilano Gutiérrez

  DOI：10.1016/s0957-4166(99)00049-x

  日期：1999.2

  Symmetrical and unsymmetrical N,N′-piperazine derivatives of (−)-norephedrine and o-aminophenol were synthesized stereoselectively in yields >70% by reduction of the corresponding N,N′-ethylenebisoxazolidine heterocycles. The stereochemistry at the ring fusion carbons was established by NMR spectroscopy and X-ray crystallography.

  （-）-去氧麻黄碱和邻氨基苯酚的对称和不对称的N，N'-哌嗪衍生物是通过选择性还原相应的N，N'-亚乙基双恶唑烷杂环以> 70％的收率立体合成的。通过NMR光谱和X射线晶体学建立了在环稠合碳上的立体化学。
• Three-center intramolecular hydrogen bonding in oxamide derivatives. NMR and X-ray diffraction study
  作者：F. J. Martínez-Martínez、I. I. Padilla-Martínez、M. A. Brito、E. D. Geniz、R. C. Rojas、J. B. R. Saavedra、H. Höpfl、M. Tlahuextl、R. Contreras

  DOI：10.1039/a704640e

  日期：——

  describes the synthesis and structural investigation of the symmetric and non-symmetric oxamides N,N′-bis(2-hydroxyphenyl)oxamide 1, N,N′-bis(5-tert-butyl-2-hydroxyphenyl)oxamide 2, N,N′-bis(3,5-dimethyl-2-hydroxyphenyl)oxamide 3, N,N′-bis(2-hydroxybenzyl)oxamide 4, N,N′-diphenethyloxamide 5, N-(2-hydroxyphenyl)-N′-(2-methoxyphenyl)oxamide 6, N-(2-hydroxyphenyl)-N′-phenethyloxamide 7, (1S,2R)-(–)-N-(2-h

  该贡献描述了对称和非对称的草酰胺N，N'-双（2-羟苯基）草酰胺1，N，N'-双（5-叔丁基-2-羟苯基）草酰胺2的合成和结构研究。N，N'-双（3,5-二甲基-2-羟基苯基）乙酰胺3，N，N'-双（2-羟基苄基）乙酰胺4，N，N'-二苯乙基乙酰胺5，N-（2-羟基苯基）- N '-（2-甲氧基苯基）草酰胺6，N-（2-羟基苯基）-N'-苯乙基草酰胺7，（1 S，2 R）-（-）- N-（2-羟基苯基氨基甲酰基羰基）去氧麻黄碱8，（1 R，2 S）-（-）- N-（2-羟基苯基氨基甲酰基羰基）9，乙基N-（2-羟基苯基）草酸酯10和乙基N -（2-甲氧基苯基）草酸酯11.通过1 H，13 C，15 N和可变温度NMR光谱确定结构。化合物1-4和6-11通过酰胺质子和两个氧原子之间的分子内三中心氢键而稳定。的1 1 H NMRΔ δ /Δ Ť酰胺质子相关因素的具有值15N NMR化学位移。1
• Synthesis and structure of new bicopper(II) complexes bridged by N-(2- aminopropyl)-N′-(2-oxidophenyl)oxamide: The effects of terminal ligands on structures, anticancer activities and DNA-binding properties
  作者：Xiao-Wen Li、Yong-Jun Zheng、Yan-Tuan Li、Zhi-Yong Wu、Cui-Wei Yan

  DOI：10.1016/j.ejmech.2011.05.053

  日期：2011.9

  ligand, N-(2-aminopropyl)-N′-(2-oxido- phenyl)oxamide (H3apopoxd) (L), and its three bicopper(II) complexes, [Cu2(apopoxd)(bpy)]- (ClO4)·H2O (1), [Cu2(apopoxd)(dabt)](ClO4)·2H2O (2), and [Cu2(apopoxd)(phen)2](ClO4) (3) (bpy = 2,2′-bipyridine; dabt = 2,2′-diamino-4,4′-bithiazole; phen = 1,10-phenanthroline) have been synthesized and characterized. The crystal structures of the three bicopper(II) complexes

  一种新型的不对称N，N'-双（取代）草酰胺配体N-（2-氨基丙基）-N'-（2-氧化苯基）草酰胺（H 3 apopoxd）（L）及其三个双铜（II）络合物[Cu 2（apopoxd）（bpy）]-（ClO 4）·H 2 O （1），[Cu 2（apopoxd）（dabt）]（ClO 4）·2H 2 O（2）和[Cu 2（apopoxd）（phen）2 ]（ClO 4）（3）（bpy = 2,2'-联吡啶; dabt = 2,2'-二氨基-4,4'-bithiazole; phen = 1,10-菲咯啉）已合成并表征。通过X射线单晶衍射确定了三种bicopper（II）配合物的晶体结构。在配合物1和2中，顺式-apopoxd 3-配体以正方形平面几何形状桥接两个铜离子，对应的间距分别为5.1868（3）和5.2016（4）Å。而在复合物3中，apopoxd 3-配体采用反式构象在扭曲的方锥环
• Synthesis, characterization, and biological properties of N-phenolato-N′-(3-dimethylaminopropyl)oxamide and its binuclear copper(II) complexes
  作者：Wan-Ju Zhang、Fang Wang、Yan-Tuan Li、Zhi-Yong Wu

  DOI：10.1007/s11243-012-9662-8

  日期：2013.2

  diffraction. Both structures contain binuclear Cu(II) cationic complexes with pdmapo3− ligands. The asymmetric pdmapo3− ligands bridge two Cu(II) atoms in the cis conformation and the Cu···Cu separations through the oxamide bridge are 5.2046(18) and 5.207(2) Å for complexes 1 and 2, respectively. The coordination environments of the two Cu(II) atoms in each binuclear complex are different. The copper occupying

  一种新的不对称 N,N'-双（取代基）草酰胺配体 N-phenolato-N'-(3-二甲氨基丙基)草酰胺 (H3pdmapo) 及其两种具有不同末端配体的双核 Cu(II) 配合物，即 [Cu2 (pdmapo)(phen)(H2O)](ClO4) (1) 和 [Cu2(pdmapo)(bpy)(CH3OH)]( ) (2)，其中 phen = 1,10-菲咯啉和 bpy = 2,2 '-联吡啶，已被合成和表征。两种配合物的晶体结构均已通过单晶 X 射线衍射确定。两种结构都包含带有 pdmapo3− 配体的双核 Cu(II) 阳离子配合物。不对称 pdmapo3− 配体以顺式构象桥接两个 Cu(II) 原子，通过草酰胺桥的 Cu…Cu 分离对于配合物 1 和 2 分别为 5.2046(18) 和 5.207(2) Å。每个双核络合物中两个Cu(II)原子的配位环境不同。占据 pdmapo3−