5-phenyl-2-(thiophen-2-yl)thiazole | 96461-08-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-phenyl-2-(thiophen-2-yl)thiazole
• 英文别名: 5-Phenyl-2-thiophen-2-yl-1,3-thiazole
• CAS: 96461-08-4
• 化学式: C₁₃H₉NS₂
• 分子量: 243.353
• InChiKey: IODHFOFATXAXON-UHFFFAOYSA-N

物化性质

• 沸点：
  421.9±37.0 °C(Predicted)
• 密度：
  1.266±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-噻吩羧酸乙酯 在 劳森试剂 、 C₁₉H₃₄O₈Rh₂ 作用下， 以 氯仿 、 对二甲苯 为溶剂， 反应 26.0h， 生成 5-phenyl-2-(thiophen-2-yl)thiazole
  参考文献：
  名称：

  从末端炔烃，磺酰基叠氮化物和亚硫酸酯轻松合成2,5-二取代的噻唑

  摘要：

  据报道从末端炔烃，磺酰基叠氮化物和硫代磺酸酯合成2，5-二取代的噻唑的顺序方法。末端炔烃与磺酰基叠氮化物的铜（I）催化的1,3-偶极环加成反应生成1-磺酰基-1,2,3-三唑，然后在铑（II）催化剂存在下与硫磺酸酯反应。随后通过消除磺酰基基团将所得的3-磺酰基-4-噻唑啉芳香化为相应的2，5-二取代的噻唑。

  DOI：

  10.1021/acs.orglett.5b00960

文献信息

• Pd-Catalyzed Decarbonylative C−H Coupling of Azoles and Aromatic Esters
  作者：Kaoru Matsushita、Ryosuke Takise、Tomoya Hisada、Shin Suzuki、Ryota Isshiki、Kenichiro Itami、Kei Muto、Junichiro Yamaguchi

  DOI：10.1002/asia.201800478

  日期：2018.9.4

  decarbonylative C−H coupling of azoles and aromatic esters by palladium catalysis is described. Our previously reported Ni‐catalyzed C−H coupling of azoles and aromatic esters has a significant drawback regarding the substrate scope. Herein, we employ palladium catalysis instead of nickel, resulting in a broader substrate scope in terms of azoles and aromatic esters.

  描述了通过钯催化的唑和芳族酯的脱羰CH键偶联。我们先前报道的唑和芳族酯的Ni催化的CH偶联在底物范围方面存在重大缺陷。在本文中，我们使用钯催化代替镍，从而在吡咯和芳族酯方面产生了更广阔的底物范围。
• Bisheterocycle Tandem Compounds Useful as Antiviral Agents, the Uses Thereof and the Compositions Comprising Such Compounds
  申请人：Nan Fajun

  公开号：US20080306121A1

  公开（公告）日：2008-12-11

  The present invention provides small molecule compounds of bisheterocycle in tandem having the structural formula of P1-P2, and the use thereof as well as a composition containing the compounds, each of P1 and P2 is an unsaturated 5-member heterocyclic ring having one or two heteroatoms. This compound may effectively inhibit the replication of influenza virus, the DNA replication of hepatitis B virus (HBV), and the formation of HBsAg and HBeAg. These compounds can be used for the preparation of a medicament for viral diseases, and may overcome the limitations of the known nucleosides drugs, including cytotoxicity, the requirement of other drugs having different structures for against the drug-resistant virus variants induced by long-term therapy. The structure of the compounds according to the invention is relatively simple and easy to be prepared.

  本发明提供了具有P1-P2结构式的串联双杂环小分子化合物，以及其用途和含有这些化合物的组合物，其中P1和P2分别是具有一个或两个杂原子的不饱和5元杂环。该化合物可以有效抑制流感病毒的复制、乙型肝炎病毒（HBV）的DNA复制以及HBsAg和HBeAg的形成。这些化合物可用于制备用于病毒性疾病的药物，并且可能克服已知核苷类药物的局限性，包括细胞毒性、长期治疗引起的对抗药物耐药病毒变异所需其他结构不同的药物。根据本发明的化合物结构相对简单且易于制备。
• Straightforward microwave-assisted synthesis of 2-thiazolines using Lawesson's reagent under solvent-free conditions
  作者：Julio A. Seijas、M. Pilar Vázquez-Tato、José Crecente-Campo

  DOI：10.1016/j.tet.2008.07.027

  日期：2008.9

  2-Thiazolines are synthesized from carboxylic acids and 1,2-aminoalcohols in the presence of Lawesson's reagent under solventless conditions. The developed method is valid for either substituted or unsubstituted aminoalcohols and a wide variety of aromatic, heteroaromatic and aliphatic carboxylic acids; thus it constitutes a general synthetic method for these kinds of compounds. The role of Lawesson's

  2-噻唑啉是在Lawesson试剂存在下于无溶剂条件下由羧酸和1,2-氨基醇合成的。所开发的方法适用于取代或未取代的氨基醇以及多种芳香族，杂芳香族和脂肪族羧酸；因此，它构成了这类化合物的通用合成方法。Lawesson试剂的作用是双重的：将1，2-氨基醇转化为1，2-氨基硫醇并激活其与羧酸的反应，从而形成噻唑啉环，所有反应都在一个罐中进行。
• Palladium-Catalyzed Tandem Ester Dance/Decarbonylative Coupling Reactions
  作者：Masayuki Kubo、Naomi Inayama、Eisuke Ota、Junichiro Yamaguchi

  DOI：10.1021/acs.orglett.2c01432

  日期：2022.6.3

  “Dance reaction” on the aromatic ring is a powerful method in organic chemistry to translocate functional groups on arene scaffolds. Notably, dance reactions of halides and pseudohalides offer a unique platform for the divergent synthesis of substituted (hetero)aromatic compounds when combined with transition-metal-catalyzed coupling reactions. Herein, we report a tandem reaction of ester dance and

  芳环上的“舞蹈反应”是有机化学中转移芳烃支架上官能团的有效方法。值得注意的是，卤化物和拟卤化物的舞蹈反应在与过渡金属催化的偶联反应结合时，为取代（杂）芳族化合物的不同合成提供了独特的平台。在此，我们报告了由钯催化实现的酯舞和脱羰基偶联的串联反应。在该反应中，芳环上的酯部分发生 1,2-易位后，与亲核试剂发生脱羰偶联，从而能够在起始材料中与酯相邻的位置安装各种亲核试剂。
• 2-Thiophen-2-yl-oxazole, 2-Thiophen-2-yl-thiazole and 2-Thiophen-2-yl-1H-imidazole derivatives as antiviral agents
  申请人：Shanghai Institute of Materia Medica, Chinese Academy of Sciences

  公开号：EP2223921A1

  公开（公告）日：2010-09-01

  The present invention provides small molecule compounds of bisheterocycle in tandem having the structural formula of P1-P2, and the use thereof as well as a composition containing the compounds, each of P1 and P2 is an unsaturated 5-member heterocyclic ring having one or two heteroatoms. This compound may effectively inhibit the replication of influenza virus, the DNA replication of hepatitis B virus (HBV), and the formation of HBsAg and HBeAg. These compounds can be used for the preparation of a medicament for viral diseases, and may overcome the limitations of the known nucleosides drugs, including cytotoxicity, the requirement of other drugs having different structures for against the drug-resistant virus variants induced by long-term therapy. The structure of the compounds according to the invention is relatively simple and easy to be prepared.

  本发明提供了结构式为P1-P2的串联双杂环小分子化合物及其用途以及含有该化合物的组合物，其中P1和P2各自为具有一个或两个杂原子的不饱和五元杂环。这种化合物可有效抑制流感病毒的复制、乙型肝炎病毒（HBV）DNA 的复制以及 HBsAg 和 HBeAg 的形成。这些化合物可用于制备治疗病毒性疾病的药物，并可克服已知核苷类药物的局限性，包括细胞毒性、需要使用其他不同结构的药物来对付长期治疗诱发的耐药病毒变种。本发明化合物的结构相对简单，易于制备。