4-(羧甲基氨基)-苯甲酸甲酯 | 89101-04-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-(羧甲基氨基)-苯甲酸甲酯
• 英文名称: 4-(carboxymethylamino)-benzoic acid methyl ester
• 英文别名: N-(4-(methoxycarbonyl)phenyl)glycine；N-[4-(methoxycarbonyl)phenyl]glycine；2-(4-methoxycarbonylanilino)acetic acid
• CAS: 89101-04-2
• 化学式: C₁₀H₁₁NO₄
• 分子量: 209.202
• InChiKey: ZRMRHQSYCNOLOR-UHFFFAOYSA-N

物化性质

• 沸点：
  430.4±30.0 °C(Predicted)
• 密度：
  1.324±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  5
• 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：
  5

反应信息

• 作为反应物：
  描述：

  4-(羧甲基氨基)-苯甲酸甲酯 在 盐酸 、 硫酸 、 溴 、 乙酸酐 、 一水合肼 、 potassium hydroxide 作用下， 以 乙醇 、 水 、 二甲基亚砜 为溶剂， 反应 10.17h， 生成 2-[4-(5-mercapto[1,3,4]oxadiazol-2-yl)phenyl]-5-methyl-4-[(1H-pyrrol-2-ylmethylene)-amino]-2,4-dihydro[1,2,4]triazol-3-one
  参考文献：
  名称：

  Synthesis of some novel 1,2,4-triazole and 1,3,4-oxadiazole derivatives of biological interest

  摘要：

  In this study, a series of novel [1,2,4]-triazolo-[1,3,4]oxadiazole (8), [1,2,4]-triazolo-[1,3,4]oxadiazole thioethers (9a-b), [1,2,4]-triazolo-[1,3,4]oxadiazole arylidines (10a-g), and bis[1,2,4]-triazole (11) derivatives were prepared with the objective of developing better antimicrobial activity. The structures of the compounds were elucidated by spectral analysis. The newly synthesized compounds (8), (9a-b), (10a-g), and (11) were screened for their antimicrobial activity. Among all the tested compounds (10b) shows significant antibacterial activity.

  DOI：

  10.1007/s00044-012-0332-3
• 作为产物：
  描述：

  4-氨基苯甲酸甲酯 在 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 4-(羧甲基氨基)-苯甲酸甲酯
  参考文献：
  名称：

  Synthesis of some novel 1,2,4-triazole and 1,3,4-oxadiazole derivatives of biological interest

  摘要：

  In this study, a series of novel [1,2,4]-triazolo-[1,3,4]oxadiazole (8), [1,2,4]-triazolo-[1,3,4]oxadiazole thioethers (9a-b), [1,2,4]-triazolo-[1,3,4]oxadiazole arylidines (10a-g), and bis[1,2,4]-triazole (11) derivatives were prepared with the objective of developing better antimicrobial activity. The structures of the compounds were elucidated by spectral analysis. The newly synthesized compounds (8), (9a-b), (10a-g), and (11) were screened for their antimicrobial activity. Among all the tested compounds (10b) shows significant antibacterial activity.

  DOI：

  10.1007/s00044-012-0332-3

文献信息

• Visible-Light Photoredox-Catalyzed Giese Reaction: Decarboxylative Addition of Amino Acid Derived α-Amino Radicals to Electron-Deficient Olefins
  作者：Anthony Millet、Quentin Lefebvre、Magnus Rueping

  DOI：10.1002/chem.201602257

  日期：2016.9.12

  A tin‐ and halide‐free, visible‐light photoredox‐catalyzed Giese reaction was developed. Primary and secondary α‐amino radicals were generated readily from amino acids in the presence of catalytic amounts of an iridium photocatalyst. The reactivity of the α‐amino radicals has been evaluated for the functionalization of a variety of activated olefins.

  开发了一种无锡和无卤可见光氧化还原催化的Giese反应。在催化量的铱光催化剂存在下，氨基酸很容易产生伯和仲α-氨基。已经评估了α-氨基自由基的反应性，以用于各种活化烯烃的功能化。
• Decarboxylative Aminomethylation of Aryl- and Vinylsulfonates through Combined Nickel- and Photoredox-Catalyzed Cross-Coupling
  作者：Lulu Fan、Jiaqi Jia、Hong Hou、Quentin Lefebvre、Magnus Rueping

  DOI：10.1002/chem.201604452

  日期：2016.11.7

  mild approach for the decarboxylative aminomethylation of aryl sulfonates by the combination of photoredox and nickel catalysis through C−O bond cleavage is described for the first time. A wide range of aryl triflates as well as aryl mesylates, tosylates and alkenyl triflates afford the corresponding products in good to excellent yields.

  首次描述了一种温和的方法，该方法通过光氧还原和镍催化（通过C-O键断裂）的结合，对芳基磺酸盐进行脱羧氨基甲基化。各种各样的芳基三氟甲磺酸酯以及甲磺酸甲磺酸酯，甲苯磺酸酯和烯基三氟甲磺酸酯以良好或优异的收率提供了相应的产物。
• Syntheses and Biological Activities of 3-[4-(Alkoxycarbonyl)phenyl]sydnones and their Derivatives
  作者：Panchaling P. Pattanashetti、Ravindra K. Tikare、Devaraddi B. Dambal、Bharati V. Badami、Gurubasav S. Puranik

  DOI：10.1002/ardp.19843170112

  日期：——

  Four new 3‐[4‐(alkoxycarbonyl)phenyl]sydnones have been synthesised. The hydrazide 4 is condensed with various aromatic aldehydes to obtain the corresponding Schiff bases. Antimicrobial activities of the sydnones and some Schiff bases are reported. Mass spectral fragmentation of 3[4‐(ethoxycarbonyl)phenyl]sydnone is discussed.

  合成了四种新的 3-[4-（烷氧基羰基）苯基] sydnones。酰肼4与各种芳香醛缩合得到相应的席夫碱。sydnones 和一些船舶基地的抗菌活性已被报道。讨论了 3 [4-（乙氧羰基）苯基] sydnone 的质谱碎片。
• Visible-Light Photoredox-Catalyzed Intermolecular α-Aminomethyl/Carboxylative Dearomatization of Indoles with CO₂ and α-Aminoalkyl Radical Precursors
  作者：Wanxu Gao、Qi Yang、Han Yang、Yang Yao、Junxue Bai、Jianwei Sun、Song Sun

  DOI：10.1021/acs.orglett.3c03755

  日期：2024.1.19

  α-aminomethyl/carboxylative dearomatization of indoles with CO2 and α-aminoalkyl radical precursors, affording a series of functionalized indoline-3-carboxylic acids and lactams in good yields with high regioselectivity. This multicomponent reaction provides a green and facile method for the synthesis of diverse functionalized indolines by using CO2 as the carboxylic and carbonyl source.

  本文公开了一种可见光光氧化还原催化的吲哚与CO 2和α-氨基烷基自由基前体的分子间连续α-氨基甲基/羧基化脱芳构化反应，以良好的产率和高区域选择性提供一系列官能化的二氢吲哚-3-羧酸和内酰胺。该多组分反应为使用CO 2作为羧基和羰基源合成多种功能化二氢吲哚提供了一种绿色简便的方法。
• TEMPO/O2 Synergistically Mediated BiBrO‐Photocatalyzed Decarboxylative Phosphorylation of N‐Arylglycines
  作者：Wen-Tao Ouyang、Hong-Tao Ji、Yuan-Yuan Liu、Ting Li、Yan-Fang Jiang、Yu-Han Lu、Jun Jiang、Wei-Min He

  DOI：10.1002/chem.202304234

  日期：——

  The TEMPO/air double-mediated BiBrO–photocatalyzed semi-heterogeneous decarboxylative phosphorylation of N-arylglycines with diarylphosphine oxides was developed. Various α-amino phosphinoxides can be efficiently synthesized.

  开发了 TEMPO/空气双介导 BiBrO 光催化 N-芳基甘氨酸与二芳基膦氧化物的半多相脱羧磷酸化反应。可以有效地合成各种α-氨基氧化膦。