ethyl 2-[(2,4-dimethoxyphenyl)amino]-2-oxoacetate | 24451-12-5

• 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-[(2,4-dimethoxyphenyl)amino]-2-oxoacetate
• 英文别名: N-(2',4'-dimethoxyphenyl)-2-ethoxyglyoxylamide；ethyl N-(2,4-dimethoxyphenyl)oxanilate；ethyl 2',4'-dimethoxyoxanilate；ethyl 2-(2,4-dimethoxyanilino)-2-oxoacetate
• CAS: 24451-12-5
• 化学式: C₁₂H₁₅NO₅
• mdl: MFCD01893536
• 分子量: 253.255
• InChiKey: ABFFZVWSVYADIG-UHFFFAOYSA-N

物化性质

• 熔点：
  242-244 °C
• 密度：
  1.223±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-[(2,4-dimethoxyphenyl)amino]-2-oxoacetate 在 硝酸 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 3.0h， 以75%的产率得到ethyl N-(2,4-dimethoxy-5-nitrophenyl)oxanilate
  参考文献：
  名称：

  [1,4]Benzoxazine-2,3-diones as antiallergic agents

  摘要：

  The synthesis of a series of [1,4]benzoxazine-2,3-diones and a new class of compounds, benzobisoxazinetetrones, is described. These compounds were evaluated for their effect in the rat mast cell (RMC) test passively sensitized in vitro with rat antiovalbumin serum and for their effect in inhibitory passive cutaneous anaphylaxis (PCA) in the rat. Some of these compounds are of the same potency level as disodium cromglycate in the RMC test and some are effective orally in PCA.

  DOI：

  10.1021/jm00379a006
• 作为产物：
  描述：

  草酰氯单乙酯 、 2,4-二甲氧基苯胺 以 乙醚 为溶剂， 反应 24.0h， 以95%的产率得到ethyl 2-[(2,4-dimethoxyphenyl)amino]-2-oxoacetate
  参考文献：
  名称：

  A New Approach to Methoxyisatins Leading to the Total Synthesis of Ophiuroidine and Other Hydroxytryptanthrins

  摘要：

  本文介绍了一种从相应的甲氧基苯胺制备甲氧基靛红的新方法。得到的甲氧基异砹被用于合成几种甲氧基色黄素化合物。利用微波介导的 Prey 去甲基化法，从相应的三甲氧基前体中获得了天然产物表黑啶（4,8,9-三羟基色黄素）。

  DOI：

  10.1055/s-0029-1217004

文献信息

• Synthesis of Dicarboxylic Acid Amides and Diamides on the Basis of [4-(4-Methoxyphenyl)tetrahydro-2H-pyran-4-yl]methanamine
  作者：A. A. Aghekyan、G. G. Mkryan、R. E. Muradyan、A. E. Tumajyan

  DOI：10.1134/s1070428018060106

  日期：2018.6

  ethyl N-[4-(4-methoxyphenyl)tetrahydro-2H-pyran-4-yl]methyl}oxamate prepared from [4-(4-methoxyphenyl)tetrahydro-2H-pyran-4-yl]methanamine and diethyl oxalate afforded the corresponding N,N'-disubstituted oxamides. N-Aryloxamides were synthesized by the reaction of [4-(4-methoxyphenyl)tetrahydro-2H-pyran-4-yl]methanamine with ethyl N-aryloxamates. The condensation of N-[4-(4-methoxyphenyl)tetrah

  各种非芳族胺的用乙酸乙酯缩合ñ - [4-（4-甲氧基苯基）四氢-2 ħ -吡喃-4-基]甲基}从制备草氨酸乙酯[4-（4-甲氧基苯基）四氢-2 ħ -pyran- 4-基]甲胺和草酸二乙酯得到相应的N，N′-二取代的草酰胺。Ñ -Aryloxamides由[4-（4-甲氧基苯基）四氢-2的反应合成ħ -2H-吡喃-4-基]甲胺用乙酸乙酯Ñ -aryloxamates。的缩合ñ - [4-（4-甲氧基苯基）四氢-2 ħ -吡喃-4-基]甲基}琥珀酰胺酸与伯胺，得到Ñ，Ñ'-二取代的神经酰胺。
• A New Approach to Methoxyisatins Leading to the Total Synthesis of Ophiuroidine and Other Hydroxytryptanthrins
  作者：Jan Bergman、Jeffrey Mason、Tomasz Janosik

  DOI：10.1055/s-0029-1217004

  日期：2009.11

  A new method for the preparation of methoxyisatins from the corresponding methoxyanilines is described. The resulting methoxyisatins were used in the syntheses of several methoxytryptanthrin compounds. The natural product ophiuroidine (4,8,9-trihydroxytryptanthrin) was obtained from the appropriate trimethoxy precursor using a microwave-mediated Prey demethylation.

  本文介绍了一种从相应的甲氧基苯胺制备甲氧基靛红的新方法。得到的甲氧基异砹被用于合成几种甲氧基色黄素化合物。利用微波介导的 Prey 去甲基化法，从相应的三甲氧基前体中获得了天然产物表黑啶（4,8,9-三羟基色黄素）。
• FR1516276
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis and Quantitative Structure−Activity Relationships of Oxanilates as Chemical Hybridizing Agents for Wheat (<i>Triticum aestivum </i>L.)
  作者：Kajal Chakraborty、Chakravarthi Devakumar、Shiv M. S. Tomar、Rajendra Kumar

  DOI：10.1021/jf025870+

  日期：2003.2.1

  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.
• ——
  作者：Carlos A. Escobar、Dieter Sicker、Hermann M. Niemeyer

  DOI：10.1023/a:1020832731546

  日期：——

  A total of 25 compounds including benzoxazinones, benzoxazolinones, and N-glyoxylamide derivatives were tested as antifeedants and antibiotics towards the aphid Sitobion avenae in diet bioassays. The antifeedant and mortality indexes increased with the presence of electron-donating groups in the 7 position of the benzoxazinone moiety, the replacement of the oxygen atom by sulfur in the heterocyclic ring, the presence of a hemiacetal instead of an acetal at C-2 of the benzoxazine moiety land hence the possibility of ring opening), and the presence of a hydroxyl group at C-4 of the benzoxazine moiety (hydroxamic acid) instead of a hydrogen atom (lactam). The results support earlier hypotheses on the chemical bases for the mode of action of these compounds.