methyl 5-phenylthiophene-2-carboxylate | 14597-62-7

• 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-phenylthiophene-2-carboxylate
• CAS: 14597-62-7
• 化学式: C₁₂H₁₀O₂S
• mdl: MFCD01313419
• 分子量: 218.276
• InChiKey: UTTYIXTVWNXIDC-UHFFFAOYSA-N

物化性质

• 熔点：
  96-98 °C(Solv: methanol (67-56-1))
• 沸点：
  352.1±30.0 °C(Predicted)
• 密度：
  1.198±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 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

安全信息

• 储存条件：
  室温

制备方法与用途

溶解于甲醇

反应信息

• 作为反应物：
  描述：

  methyl 5-phenylthiophene-2-carboxylate 在 一水合肼 作用下， 生成 5-phenylthiophene-2-carbohydrazide
  参考文献：
  名称：

  Synthesis and biological activity of derivatives of 5-arylthiophene-2-carboxylic acids

  摘要：

  DOI：

  10.1007/bf00772643
• 作为产物：
  描述：

  5-苯基-2-硫烷基戊-2,4-二烯酸 在 硫酸 、 双氧水 、 碘 作用下， 以 吡啶 、 乙醇 、 水 为溶剂， 反应 53.5h， 生成 methyl 5-phenylthiophene-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

• Development and Characterization of New Inhibitors of the Human and Mouse Hematopoietic Prostaglandin D₂ Synthases
  作者：Angelika N. Christ、Larisa Labzin、Gregory T. Bourne、Hirotada Fukunishi、Jane E. Weber、Matthew J. Sweet、Mark L. Smythe、Jack U. Flanagan

  DOI：10.1021/jm100194a

  日期：2010.8.12

  The hematopoietic prostaglandin D2 synthase has a proinflammatory effect in a range of diseases, including allergic asthma, where its product prostaglandin D2 (PGD2) has a role in regulating many of the hallmark disease characteristics. Here we describe the development and characterization of a novel series of hematopoietic prostaglandin D2 synthase inhibitors with potency similar to that of known

  造血前列腺素D 2合酶在包括过敏性哮喘在内的多种疾病中具有促炎作用，其中其产物前列腺素D 2（PGD 2）在调节许多标志性疾病特征中起作用。在这里，我们描述了一系列新型造血前列腺素D 2合酶抑制剂的开发和表征，其功效与已知抑制剂相似。化合物N-苯甲酰基-5-（3-羟苯基）噻吩-2-羧酰胺（化合物8）和N-（1-氨基-1-氧代-3-苯基丙-2-基）-6-（噻吩-2-基烟酰胺（化合物34）在抑制纯化的酶方面表现出较低的微摩尔效价，而在小鼠原代骨髓来源的巨噬细胞和人巨核细胞系MEG-01S中，只有34种减少的Toll样受体（TLR）诱导的PGD 2产生。重要的是，34证实了抑制PGD的更大的选择性2合成与该位于PGH的下游的其它类花生酸2（PGE 2和前列腺环素（6-酮基PGF的标志物1α）和血栓素（TXB 2））相比，已知的抑制剂HQL -79（化合物1）和2-苯基-5-（1 H-吡唑-3-基
• Highly efficient and recyclable water-soluble fullerene-supported PdCl₂ nanocatalyst in Suzuki–Miyaura cross-coupling reaction
  作者：Jingbo Li、Ping Huo、Junwei Zheng、Xiuming Zhou、Wanyun Liu

  DOI：10.1039/c8ra03754j

  日期：——

  A water-soluble fullerene-supported PdCl2 nanocatalyst [C60-TEGS/PdCl2] was prepared by coordination of water-soluble fullerene nanoparticles with palladium chloride. In pure water, the catalytic activity of nanocatalyst [C60-TEGS/PdCl2] for Suzuki–Miyaura cross-coupling reaction was investigated under different reaction conditions. The results showed that biphenyl compounds could be synthesized in

  水溶性富勒烯纳米粒子与氯化钯配位制备了水溶性富勒烯负载的PdCl 2纳米催化剂[C 60 -TEG S /PdCl 2 ]。在纯水中，研究了不同反应条件下纳米催化剂[C 60 -TEG S /PdCl 2 ]对Suzuki-Miyaura交叉偶联反应的催化活性。结果表明，以0.01 mol%的[C 60 -TEG S /PdCl 2 ]为催化剂，K 2 CO 3可以在室温下以高收率合成联苯化合物。作为碱，反应时间为 4 h。催化剂循环5次，收率明显没有下降。
• New (green) methodology for efficient hydrazine cleavage
  作者：Lenka Kubovičová、Kristýna Bürglová、Jan Hlaváč

  DOI：10.1039/c6ob00737f

  日期：——

  An efficient method for removal of the hydrazine group from (hetero)aromatic substrates has been developed. It can be realized both on a solid support and in solution by synthesis employing a low concentration solution of trimethylsilanolate in tetrahydrofuran or N,N-dimethylformamide. For water-soluble substrates, the reaction can be performed in water, highlighting the eco-friendly attributes of

  已经开发了一种从（杂）芳族底物中除去肼基的有效方法。通过使用低浓度的三甲基硅烷醇酸酯在四氢呋喃或N，N-二甲基甲酰胺中的合成可以在固体载体上和在溶液中实现。对于水溶性底物，反应可以在水中进行，突出了该方法的环保特性。
• 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。
• Design, synthesis and evaluation of aromatic heterocyclic derivatives as potent antifungal agents
  作者：Shizhen Zhao、Xiangqian Zhang、Peng Wei、Xin Su、Liyu Zhao、Mengya Wu、Chenzhou Hao、Chunchi Liu、Dongmei Zhao、Maosheng Cheng

  DOI：10.1016/j.ejmech.2017.05.043

  日期：2017.9

  To further enhance the anti-Aspergillus efficacy of our previously discovered antifungal lead compounds (1), a series of aromatic heterocyclic derivatives were designed, synthesized and evaluated for in vitro antifungal activity. Many of the target compounds showed good inhibitory activity against Candida albicans and Cryptococcus neoformans. In particular, the isoxazole nuclei were more suited for

  为了进一步增强我们先前发现的抗真菌先导化合物（1）的抗曲霉菌功效，设计，合成了一系列芳香族杂环衍生物，并对其体外抗真菌活性进行了评估。许多目标化合物对白色念珠菌和新型隐球菌均具有良好的抑制作用。特别地，异恶唑核更适合于提高针对曲霉属的活性。在这些化合物中，2-F取代的类似物23g和23h显示出对念珠菌最显着的体外活性。，C. neoformans，烟曲霉和耐氟康唑的C.alb。菌株，其活性优于或可比参比药物氟康唑和伏立康唑。值得注意的是，化合物23g和23h对人细胞色素P450的各种同工型均表现出低抑制特性，并具有出色的血浆稳定性。