methyl 5-(4-bromophenyl)thiophene-2-carboxylate | 649569-57-3

• 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: methyl 5-(4-bromophenyl)thiophene-2-carboxylate
• CAS: 649569-57-3
• 化学式: C₁₂H₉BrO₂S
• 分子量: 297.172
• InChiKey: GARRRQOUTNGJPB-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：
  0.08
• 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：

  methyl 5-(4-bromophenyl)thiophene-2-carboxylate 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-(4-Bromophenyl)-5-(chloromethyl)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：

  2-(4-溴苯基)噻吩 在 lithium tert-butoxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 90.0 ℃ 、200.0 kPa 条件下， 反应 17.0h， 生成 methyl 5-(4-bromophenyl)thiophene-2-carboxylate
  参考文献：
  名称：

  Ag(I)-催化的噻吩衍生物的 C-H 羧化

  摘要：

  CO 2 的利用是一个有吸引力的方面，因为它允许将 CO 2直接转化为有价值的化学品。在这方面，由于杂芳族羧酸无处不在的结构基序，将CO 2直接结合到杂芳族化合物的 C-H 键中是很重要的。在此，我们报告了 Ag 催化的噻吩衍生物的 C-H 羧化。这种涉及膦配体和叔丁醇锂的新催化系统能够在温和的反应条件下直接羧化噻吩。实验研究表明，使用叔丁基醇盐对于芳基银中间体的放能形成至关重要，密度泛函理论计算进一步支持了结果。

  DOI：

  10.1021/acs.organomet.1c00372

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。
• Ag(I)-Catalyzed C–H Carboxylation of Thiophene Derivatives
  作者：Mijung Lee、Young Kyu Hwang、Jaesung Kwak

  DOI：10.1021/acs.organomet.1c00372

  日期：2021.9.27

  thiophene derivatives. This new catalytic system involving a phosphine ligand and lithium tert-butoxide enables the direct carboxylation of thiophenes under mild reaction conditions. Experimental studies revealed that the use of tert-butyl alkoxide is critical for the exergonic formation of an arylsilver intermediate, and the results were further supported by density functional theory calculations.

  CO 2 的利用是一个有吸引力的方面，因为它允许将 CO 2直接转化为有价值的化学品。在这方面，由于杂芳族羧酸无处不在的结构基序，将CO 2直接结合到杂芳族化合物的 C-H 键中是很重要的。在此，我们报告了 Ag 催化的噻吩衍生物的 C-H 羧化。这种涉及膦配体和叔丁醇锂的新催化系统能够在温和的反应条件下直接羧化噻吩。实验研究表明，使用叔丁基醇盐对于芳基银中间体的放能形成至关重要，密度泛函理论计算进一步支持了结果。
• 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.