ethyl ester of 2-acetylamino-5-ethylthiophene-3-carboxylic acid | 13130-38-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: ethyl ester of 2-acetylamino-5-ethylthiophene-3-carboxylic acid
• 英文别名: 2-Acetylamino-3-ethoxycarbonyl-5-ethylthiophen；2-acetylamino-5-ethyl-thiophene-3-carboxylic acid ethyl ester；Ethyl 2-(acetylamino)-5-ethylthiophene-3-carboxylate；ethyl 2-acetamido-5-ethylthiophene-3-carboxylate
• CAS: 13130-38-6
• 化学式: C₁₁H₁₅NO₃S
• mdl: MFCD00458470
• 分子量: 241.311
• InChiKey: JDYPHTNMKBGGLI-UHFFFAOYSA-N

物化性质

• 熔点：
  54-55 °C
• 沸点：
  419.6±45.0 °C(Predicted)
• 密度：
  1.211±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.454
• 拓扑面积：
  83.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl ester of 2-acetylamino-5-ethylthiophene-3-carboxylic acid 在 一水合肼 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and antitumor activity of α-aminophosphonate derivatives containing thieno[2,3-d]pyrimidines

  摘要：

  Two series of thieno[2,3-d]pyrimidine derivatives were designed and synthesized, in which bioactive alpha-aminophosphonate subunits were introduced at the N3 position through an N-N bond connection. The in vitro cytotoxic activity of the novel compounds was tested against human esophageal carcinoma cells (EC109), human hepatocarcinoma cells (HepG2), human gastric carcinoma cells (MGC-803), respectively, by the MIT method. The evaluation results revealed that compounds 6mb, 6mf, 6mg, 6nd and 6nh exerted the most potent inhibition against HepG2, MGC-803 and EC109 cells, respectively. In particular, compound 6mg presented excellent inhibitory effect against HepG2 (91.2%) and MGC-803 (94.4%) cells. (C) 2015 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2015.03.026
• 作为产物：
  描述：

  氰乙酸乙酯 在 sulfur 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 ethyl ester of 2-acetylamino-5-ethylthiophene-3-carboxylic acid
  参考文献：
  名称：

  Synthesis and antitumor activity of α-aminophosphonate derivatives containing thieno[2,3-d]pyrimidines

  摘要：

  Two series of thieno[2,3-d]pyrimidine derivatives were designed and synthesized, in which bioactive alpha-aminophosphonate subunits were introduced at the N3 position through an N-N bond connection. The in vitro cytotoxic activity of the novel compounds was tested against human esophageal carcinoma cells (EC109), human hepatocarcinoma cells (HepG2), human gastric carcinoma cells (MGC-803), respectively, by the MIT method. The evaluation results revealed that compounds 6mb, 6mf, 6mg, 6nd and 6nh exerted the most potent inhibition against HepG2, MGC-803 and EC109 cells, respectively. In particular, compound 6mg presented excellent inhibitory effect against HepG2 (91.2%) and MGC-803 (94.4%) cells. (C) 2015 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2015.03.026

文献信息

• Phosphoramides—V11Part IV: E.B. Pedersen, Acta Chem. Scand. B31, 261 (1977).
  作者：E.B. Pedersen、D. Carlsen

  DOI：10.1016/0040-4020(77)80318-9

  日期：——

  2-Acetamido-3-thiophenecarboxylic acid ethyl esters 1 have been heated in HMPT to reflux temperature to produce 4,6-bis(dimethylamino)thieno[2,3-b]pyridines 7. Substituents in the 4 position of the thiophene ring were found to exert steric hindrance on the reaction. Only a multistep mechanism can account for the product 7. The intermediates 2–5 were also isolated in the reaction of 1a with HMPT.

  将2-乙酰氨基-3-噻吩羧酸乙酯1在HMPT中加热至回流温度，以产生4,6-双（二甲基氨基）噻吩并[2,3-b]吡啶7。发现噻吩环的4位上的取代基对反应产生位阻。只有多步机制才能说明产品7。在1a与HMPT的反应中也分离出了中间体2–5。
• Functional derivatives of thiophen XX. Synthesis and antiviral activity of 3-aminothieno[2,3-d]pyrimidines
  作者：I. A. Kharizomenova、A. N. Grinev、N. V. Samsonova、E. K. Panisheva、N. V. Kaplina、I. S. Nikolaeva、T. V. Pushkina、G. N. Pershin

  DOI：10.1007/bf00760666

  日期：1981.9
• CLAUSEN K.; LAWESSON S.-O., NOUV. J. CHIM., 1980, 4, NO 1, 43-46
  作者：CLAUSEN K.、 LAWESSON S.-O.

  DOI：——

  日期：——
• PEDERSEN E. B.; CARLSEN D., TETRAHEDRON <TETR-AB>, 1977, 33, NO 16, 2089-2092
  作者：PEDERSEN E. B.、 CARLSEN D.

  DOI：——

  日期：——
• Synthesis and antitumor activity of α-aminophosphonate derivatives containing thieno[2,3-d]pyrimidines
  作者：Yan-Chun Guo、Jing Li、Jiao-Li Ma、Zhi-Ran Yu、Hai-Wei Wang、Wen-Juan Zhu、Xin-Cheng Liao、Yu-Fen Zhao

  DOI：10.1016/j.cclet.2015.03.026

  日期：2015.6

  Two series of thieno[2,3-d]pyrimidine derivatives were designed and synthesized, in which bioactive alpha-aminophosphonate subunits were introduced at the N3 position through an N-N bond connection. The in vitro cytotoxic activity of the novel compounds was tested against human esophageal carcinoma cells (EC109), human hepatocarcinoma cells (HepG2), human gastric carcinoma cells (MGC-803), respectively, by the MIT method. The evaluation results revealed that compounds 6mb, 6mf, 6mg, 6nd and 6nh exerted the most potent inhibition against HepG2, MGC-803 and EC109 cells, respectively. In particular, compound 6mg presented excellent inhibitory effect against HepG2 (91.2%) and MGC-803 (94.4%) cells. (C) 2015 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.