5-(4-氯苯基)噻吩-2-羧酸甲酯 | 649569-56-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 5-(4-氯苯基)噻吩-2-羧酸甲酯
• 英文名称: methyl 5-(4-chlorophenyl)thiophene-2-carboxylate
• CAS: 649569-56-2
• 化学式: C₁₂H₉ClO₂S
• mdl: MFCD02180480
• 分子量: 252.721
• InChiKey: JZCUTYCKIFLPKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.083
• 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：

  5-(4-氯苯基)噻吩-2-羧酸甲酯 在 六甲基磷酰三胺 、 lithium aluminium tetrahydride 、 氯化亚砜 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 2-(Chloromethyl)-5-(4-chlorophenyl)thiophene
  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
• 作为产物：
  描述：

  4,4'-二氯苯丁酮 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 5-(4-氯苯基)噻吩-2-羧酸甲酯
  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

• Direct Carboxylation of Electron‐Rich Heteroarenes Promoted by LiO‐ <i>t</i> Bu with CsF and [18]Crown‐6
  作者：Masanori Shigeno、Kazuya Hanasaka、Keita Sasaki、Kanako Nozawa‐Kumada、Yoshinori Kondo

  DOI：10.1002/chem.201805926

  日期：——

  We herein demonstrate that the combination of LiO‐tBu, CsF, and [18]crown‐6 efficiently promotes the direct C−H carboxylation of electron‐rich heteroarenes (benzothiophene, thiophene, benzofuran, and furan derivatives). A variety of functional groups, including methyl, methoxy, halo, cyano, amide, and keto moieties, are compatible with this system. The reaction proceeds via the formation of a tert‐butyl

  本文我们证明LiO-的组合吨卜，CsF和[18]冠-6有效地促进富电子杂芳烃（苯并噻吩，噻吩，苯并呋喃，和呋喃的衍生物）的直接C-H羧基化。该系统可兼容多种官能团，包括甲基，甲氧基，卤素，氰基，酰胺和酮基。反应通过形成碳酸叔丁酯物质而进行。