ethyl 5-(p-tolyl) thiophene-2-carboxylate | 61100-11-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: ethyl 5-(p-tolyl) thiophene-2-carboxylate
• 英文别名: 5-p-tolyl-thiophene-2-carboxylic acid ethyl ester；Ethyl 5-(4-methylphenyl)thiophene-2-carboxylate
• CAS: 61100-11-6
• 化学式: C₁₄H₁₄O₂S
• mdl: MFCD01860762
• 分子量: 246.33
• InChiKey: AFGHNUXPONWSCT-UHFFFAOYSA-N

物化性质

• 熔点：
  85-88 °C(Solv: ethanol (64-17-5))
• 沸点：
  375.9±30.0 °C(Predicted)
• 密度：
  1.146±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 5-(p-tolyl) thiophene-2-carboxylate 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以92%的产率得到5-(4-methylphenyl)thiophene-2-carbohydrazide
  参考文献：
  名称：

  Synthesis, cytotoxicity and effects of some 1,2,4-triazole and 1,3,4-thiadiazole derivatives on immunocompetent cells

  摘要：

  Novel derivatives of 4,5-substituted-1,2,4-triazole-thiones and 2,5-substituted-1,3,4-thiadiazoles were synthesized and evaluated for their cytotoxicity. The biological study indicated that compounds 4-ethyl-5-(4,5,6,7-tetrahydro-1-benzothien-2-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione 13, N-ethyl-5-(4,5,6,7-tetrahydro-1-benzothien-2-yl)-1,3,4-thiadiazol-2-amine 16, 4-amino-5-(4,5,6,7-tetrahydro-1-benzothien-2-yl)-2, 4-dihydro-3H-1,2,4-triazole-3-thione 20 and 4-amino-5-(5-phenylthien-2-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione 21 possessed high cytotoxicity in vitro against thymocytes, The corresponding IC50 values were 0.46 mu M, 5.2 x 10(-6) mu M, 0.012 mu M and 1.0 x 10(-6) mu M. Most toxic against lymphocytes was compound 21, IC50 - 0.012 mu M. The tested compounds showed a general stimulation effect on B-cells' response. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.03.006
• 作为产物：
  描述：

  4-氯-4`-甲基苯丁酮 在 sodium hydroxide 、 硫酸 、 silver(l) oxide 、 三氯氧磷 作用下， 以 甲醇 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 49.0h， 生成 ethyl 5-(p-tolyl) thiophene-2-carboxylate
  参考文献：
  名称：

  Synthesis and structure–activity relationships of 5-phenylthiophenecarboxylic acid derivatives as antirheumatic agents

  摘要：

  5-(Phenylthiophene)-3-carboxylic acid (2a), a metabolite of esonarimod (1), which was developed as a new antirheumatic drug, was considered as a lead compound for new antirheumatic drugs. A new series of 2a derivatives were synthesized and their characteristic pharmacological effects, that is their antagonistic effect toward interleukin (IL)-1 in mice and the suppressive effect against adjuvant-induced arthritis (AIA) in rats, were evaluated and compared with those of 1. The structure-activity relationships indicated that [5-(4-bromophenyl)- thiophen-3-yl]acetic acid (5d), methyl [5-(4-chlorophenyl)-thiophen-3-yl]acetate acid (5d), and methyl [5-(4-bromophenyl)-thiophen-3-yl]acetate (5i) suppressed AIA more potently than 1 and all of the other synthesized compounds. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.08.009

文献信息

• Base catalyzed reaction of ethyl thioglycolate with β-aryl-β-(methylthio) acroleins: a general method for the synthesis of 2-carbethoxy-5-substituted/4,5-annulated thiophenes in high overall yields
  作者：G. Byre Gowda、C.S. Pradeepa kumara、N. Ramesh、M.P. Sadashiva、H. Junjappa

  DOI：10.1016/j.tetlet.2016.01.055

  日期：2016.2

  were shown to be stable unlike their counterpart the chloroacroleins and their efficacy as 1,3-dielectrophilic properties have now been examined successfully in this work. They are shown to react with ethyl thioglycolate in the presence of anhydrous potassium carbonate in boiling ethanol to yield the corresponding 5-substituted/4,5-annulated-2-carbethoxy thiophenes in 70–80% overall high yields.

  已证明（甲硫基）丙烯醛1a - m是稳定的，不同于其对应的氯丙烯醛，并且已成功地检测了它们作为1,3-二亲电子性质的功效。它们在无水碳酸钾存在下于沸腾的乙醇中与硫代乙醇酸乙酯反应，可产生相应的5-取代/ 4,5-环化-2-羰基乙氧基噻吩，总产率为70-80％。
• Biaryl Amino Acids and Their Use in Dna Binding Oligomers
  申请人：Howard Wilson Philip

  公开号：US20070249591A1

  公开（公告）日：2007-10-25

  Compounds of formula (1): Z′-CO-A-B—NH-Z (I) wherein: Z is H or an amino protecting group; Z′ is OH, a protected or activated hydroxyl group or Cl; A is an optionally substituted C 5-6 arylene group; and B is an optionally substituted C 5-6 arylene group.

  公式（1）的化合物：Z'-CO-A-B—NH-Z（I），其中：Z为H或氨保护基；Z'为OH，受保护或活化羟基或Cl；A为可选取代的C5-6芳基烃基；B为可选取代的C5-6芳基烃基。
• BIARYL AMINO ACIDS AND THEIR USE IN DNA BINDING OLIGOMERS
  申请人：Howard Philip Wilson

  公开号：US20110160192A1

  公开（公告）日：2011-06-30

  Compounds of formula (I): Z′-CO-A-B—NH-Z (I) wherein: Z is H or an amino protecting group; Z′ is OH, a protected or activated hydroxyl group or Cl; A is an optionally substituted C 5-6 arylene group; and B is an optionally substituted C 5-6 arylene group.

  化合物的化学式(I)：Z'-CO-A-B—NH-Z (I)，其中：Z为氢或氨基保护基；Z'为OH，受保护或活化的羟基或Cl；A为可选取代的C5-6芳基烃基；B为可选取代的C5-6芳基烃基。
• BIARYL AMINO ACIDS AND THEIR USE IN DNA BINDING OLIGOMERS
  申请人：Spirogen Limited

  公开号：EP1727808B1

  公开（公告）日：2008-11-12
• Synthesis and structure–activity relationships of 5-phenylthiophenecarboxylic acid derivatives as antirheumatic agents
  作者：Toshiya Noguchi、Masahiro Hasegawa、Kazuyuki Tomisawa、Morihiro Mitsukuchi

  DOI：10.1016/j.bmc.2003.08.009

  日期：2003.11

  5-(Phenylthiophene)-3-carboxylic acid (2a), a metabolite of esonarimod (1), which was developed as a new antirheumatic drug, was considered as a lead compound for new antirheumatic drugs. A new series of 2a derivatives were synthesized and their characteristic pharmacological effects, that is their antagonistic effect toward interleukin (IL)-1 in mice and the suppressive effect against adjuvant-induced arthritis (AIA) in rats, were evaluated and compared with those of 1. The structure-activity relationships indicated that [5-(4-bromophenyl)- thiophen-3-yl]acetic acid (5d), methyl [5-(4-chlorophenyl)-thiophen-3-yl]acetate acid (5d), and methyl [5-(4-bromophenyl)-thiophen-3-yl]acetate (5i) suppressed AIA more potently than 1 and all of the other synthesized compounds. (C) 2003 Elsevier Ltd. All rights reserved.