2-[(乙氧羰基)氨基]苯甲酸 | 41470-93-3

• 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: 2-[(乙氧羰基)氨基]苯甲酸
• 英文名称: 2-((ethoxycarbonyl)amino)benzoic acid
• 英文别名: N-Ethoxycarbonyl-anthranilsaeure；N-ethoxycarbonylanthranilic acid；N-Carbethoxy anthranilic acid；Ethylisothoat；N-Carbethoxy-anthranilsaeure；Carbanilsaeureaethylester-carbonsaeure-(2)；N-Aethoxycarbonyl-anthranilsaeure；2-Carbaethoxyamino-benzoesaeure；Isatosaeure-exo-aethylester；(2-Carboxy-phenyl)-urethan；N-Carbaethoxy-anthranilsaeure；N-(Ethoxycarbonyl)anthranilic acid；2-(ethoxycarbonylamino)benzoic acid
• CAS: 41470-93-3
• 化学式: C₁₀H₁₁NO₄
• mdl: MFCD01846932
• 分子量: 209.202
• InChiKey: GMFRUUXHDGHBJF-UHFFFAOYSA-N

物化性质

• 熔点：
  126-127 °C
• 沸点：
  311.7±25.0 °C(Predicted)
• 密度：
  1.324±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 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

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  2-[(乙氧羰基)氨基]苯甲酸 在 三溴化磷 作用下， 生成 靛红酸酐
  参考文献：
  名称：

  Synthesis of N-Carboxy-α-amino Acid Anhydrides from N-Carbalkoxy-α-amino Acids by the Use of Phosphorus Tribromide

  摘要：

  DOI：

  10.1021/ja01134a501
• 作为产物：
  描述：

  (2-ethoxycarbonylaminophenyl)glyoxylic acid 在 potassium dichromate 、 硫酸 作用下， 生成 2-[(乙氧羰基)氨基]苯甲酸
  参考文献：
  名称：

  Heller, Chemische Berichte, 1918, vol. 51, p. 430

  摘要：

  DOI：

文献信息

• Novel Alternative for the N<i>−</i>N Bond Formation through a PIFA-Mediated Oxidative Cyclization and Its Application to the Synthesis of Indazol-3-ones
  作者：Arkaitz Correa、Imanol Tellitu、Esther Domínguez、Raul SanMartin

  DOI：10.1021/jo060070+

  日期：2006.4.1

  The synthesis of a series of N,N‘-disubstituted indazolone derivatives starting from methyl anthranilates is presented. This general approach features a novel and easy way for access to the target N-heterocycles by formation of a new N−N single bond. The key cyclization step embraces the formation of an N-acylnitrenium intermediate, mediated by the hypervalent iodine reagent PIFA, and its succeeding

  一系列n的合成，N '选自甲基邻氨基苯甲酸开始二取代的吲唑酮衍生物被呈现。这种通用方法的特点是通过形成一个新的N - N单键来获得目标N-杂环的新颖而简便的方法。关键的环化步骤包括由高价碘试剂PIFA介导的N-酰基硝基re中间体的形成，以及在相当温和的实验条件下通过胺部分成功地分子内捕集。
• Metal-Free Synthesis of Polycyclic Quinazolinones Enabled by a (NH₄ )₂ S₂ O₈ -Promoted Intramolecular Oxidative Cyclization
  作者：Lijuan Xie、Cong Lu、Dong Jing、Xinrui Ou、Ke Zheng

  DOI：10.1002/ejoc.201900469

  日期：2019.6.16

  An efficient metal‐free, (NH4)2S2O8 mediated intramolecular oxidative cyclization for the construction of fused polycyclic quinazolinone derivatives under mild conditions was disclosed. This method provides an efficient and facile approach to the synthesis of polycyclic quinazolinone derivatives (> 40 examples), as well as the natural products tryptanthrin, rutaecarpine, and their analogues.

  公开了在温和条件下用于构建稠合多环喹唑啉酮衍生物的高效无金属，（NH 4）2 S 2 O 8介导的分子内氧化环化反应。该方法为合成多环喹唑啉酮衍生物（> 40个实例）以及天然产物色胺酮，芸苔芸香碱及其类似物提供了一种高效简便的方法。
• Ester vs. amide on folding: a case study with a 2-residue synthetic peptide
  作者：Kuruppanthara N. Vijayadas、Roshna V. Nair、Rupesh L. Gawade、Amol S. Kotmale、Panchami Prabhakaran、Rajesh G. Gonnade、Vedavadi G. Puranik、Pattuparambil R. Rajamohanan、Gangadhar J. Sanjayan

  DOI：10.1039/c3ob41967c

  日期：——

  Although known for their inferiority as hydrogen-bonding acceptors when compared to amides, esters are often found at the C-terminus of peptides and synthetic oligomers (foldamers), presumably due to the synthetic readiness with which they are obtained using protected peptide coupling, deploying amino acid esters at the C-terminus. When the H-bonding interactions deviate from regularity at the termini, peptide chains tend to “fray apart”. However, the individual contributions of C-terminal esters in causing peptide chain end-fraying goes often unnoticed, particularly due to diverse competing effects emanating from large peptide chains. Herein, we describe a striking case of a comparison of the individual contributions of C-terminal ester vs. amide carbonyl as a H-bonding acceptor in the folding of a peptide. A simple two-residue peptide fold has been used as a testing case to demonstrate that amide carbonyl is far superior to ester carbonyl in promoting peptide folding, alienating end-fraying. This finding would have a bearing on the fundamental understanding of the individual contributions of stabilizing/destabilizing non-covalent interactions in peptide folding.

  尽管在作为氢键受体方面与酰胺相比被认为质量较差，酯类却常常出现在肽链和合成寡聚体（折叠体）的C末端，这很可能是因为它们在使用保护性肽耦合反应、在C末端部署氨基酸酯时易于合成。当末端的氢键相互作用偏离规则时，肽链往往会“散开”。然而，C末端酯对肽链末端散开的单独贡献常常被忽视，特别是因为大型肽链存在多种竞争效应。在此，我们描述了一个引人注目的案例，比较了C末端酯与酰胺羰基在促进肽折叠中作为氢键受体的个别贡献。我们使用了一个简单的两残基肽折叠作为测试案例，证明酰胺羰基在促进肽折叠、防止末端散开方面远胜于酯羰基。这一发现将对理解稳定/不稳定非共价相互作用在肽折叠中个别贡献的基本理解产生影响。
• Solid phase synthesis of chiral 3-substituted quinazoline-2,4-diones
  作者：Laurent Gouilleux、Jean-Alain Fehrentz、F. Winternitz、Jean Martinez

  DOI：10.1016/0040-4039(96)01541-9

  日期：1996.9

  synthetic pathway was applied in solid phase, from commercially available anthranilic acid that was bound to hydroxymethyl polystyrene resin via a carbamate linker. In both cases, cyclisation occurred under basic conditions to afford non-racemized quinazolinediones in high purity.

  从N-氨基甲酸酯氨基酰胺开始，进行手性3-取代的喹唑啉-2，4-二酮的合成。该合成途径是从可商购获得的邻氨基苯甲酸固相应用的，邻氨基苯甲酸通过氨基甲酸酯连接基与羟甲基聚苯乙烯树脂结合。在这两种情况下，环化都在碱性条件下发生，以提供高纯度的非消旋喹唑啉二酮。
• Guanidinum Chloride as Dehydrocyclization Agent in the Synthesis of 2-Fuctionalized (4<i>H</i>)-3,1-Benzoxazine-4-ones
  作者：Farzad Nikpour、Asrin Bahmani、Forugh Havasi、Mahnaz Sharafi-Kolkeshvandi

  DOI：10.1002/jhet.1649

  日期：2014.1

  A facile and expedient route for the synthesis of 2‐ethoxy‐ and 2‐(ethylcarboxylate)‐(4H)‐3,1‐benzoxazine‐4‐ones is described using guanidinium chloride as a safe and convenient dehydrocyclization agent. High yields of the products obtain under mild reaction conditions without need to use of any catalyst and with easy work‐up of the reaction mixture.

  描述了一种使用氯化胍作为安全，方便的脱氢环化剂合成2-乙氧基和2-（乙基羧酸酯）-（4 H）-3,1-苯并恶嗪-4-酮的简便方法。在温和的反应条件下，无需使用任何催化剂即可轻松获得高收率的产品，而且反应混合物的后处理也很容易。