2-(2-呋喃基)-苯并噻唑 | 1569-98-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 中文名称: 2-(2-呋喃基)-苯并噻唑
• 中文别名: 苯并噻唑,2-(2-呋喃基)-(9CI)
• 英文名称: 2-(furan-2-yl)-1,3-benzothiazole
• 英文别名: 2-(furan-2-yl)benzo[d]thiazole；2-(furan-2-yl)benzothiazole；2-(2-furyl)benzothiazole；2-(2-furanyl)benzothiazole；2-(2-furyl)-1,3-benzothiazole；2-(2-furanyl)benzo[d]thiazole
• CAS: 1569-98-8
• 化学式: C₁₁H₇NOS
• mdl: MFCD00460120
• 分子量: 201.249
• InChiKey: PYOHHBLCCRIMFM-UHFFFAOYSA-N

物化性质

• 熔点：
  105 °C
• 沸点：
  336.8±34.0 °C(Predicted)
• 密度：
  1.303±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.3
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  2-(2-呋喃基)-苯并噻唑 在 溴 作用下， 以 1,1-二氯乙烷 为溶剂， 反应 4.0h， 以86%的产率得到2-(5-bromofuran-2-yl)benzo[d]thiazole
  参考文献：
  名称：

  2-（2-呋喃基）苯并噻唑的合成及性质

  摘要：

  The electrophilic reactions (nitration, bromination, hydroxymethylation, formylation, acylation) and radical substitution reactions (nitration, arylation) of 2-(2-furyl)benzothiazole have been studied. It was found that all of the reactions occur at position 5 of the furan ring. Only nitration in PPA gave the 5',6-dinitro derivative. Quantum-chemical calculation data for the electron density distribution in the neutral and protonated 2-(2-furyl)benzothiazole molecules are given.

  DOI：

  10.1007/s10593-008-0156-8
• 作为产物：
  描述：

  呋喃-2-硫代甲酸苯胺 在 baker's yeast 作用下， 生成 2-(2-呋喃基)-苯并噻唑
  参考文献：
  名称：

  Candida antarctica lipase A in the dynamic resolution of novel furylbenzotiazol-based cyanohydrin acetates

  摘要：

  A series of novel (R)-furylbenzotiazol-based cyanohydrin acetates were prepared in over 90% isolated yields from the corresponding furancarbaldehydes. The one-pot method combines a basic resin to produce hydrogen cyanide from acetone cyanohydrin, an equilibrium between the formation and decomposition of furylbenzotiazol-based cyanohydrins and the unique enantioselectivity of Candida antarctica lipase A, allowing the acylation of (R)-cyanohydrins in the presence of vinyl acetate in anhydrous acetonitrile. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00025-9

文献信息

• Selective Construction of 2-Substituted Benzothiazoles from <i>o</i>-Iodoaniline Derivatives S₈ and <i>N</i>-Tosylhydrazones
  作者：Yubing Huang、Peiqi Zhou、Wanqing Wu、Huanfeng Jiang

  DOI：10.1021/acs.joc.7b03118

  日期：2018.2.16

  Selective construction of 2-substituted benzothiazoles from o-iodoaniline derivatives S8 and N-tosylhydrazone via a copper-promoted [3 + 1 + 1]-type cyclization reaction has been realized. In the protocol, the carbon atom on N-tosylhydrazone could be regulated to construct benzothiazole by changing the reaction system. Furthermore, the transformation has achieved the construction of multiple carbon-heteroatom

  已经实现了通过铜促进的[3 +1 + 1]型环化反应，由邻碘苯胺衍生物S 8和N-甲苯磺酰zone选择性构建2-取代的苯并噻唑。在该方案中，可以通过改变反应体系来调节N-甲苯磺酰hydr上的碳原子以构建苯并噻唑。此外，该转化实现了多个碳-杂原子键的构建。
• Antidiabetic potential and enzyme kinetics of benzothiazole derivatives and their non-bonded interactions with α-glucosidase and α-amylase
  作者：Ninad V. Puranik、Hemalata M. Puntambekar、Pratibha Srivastava

  DOI：10.1007/s00044-016-1520-3

  日期：2016.4

  Benzothiazole derivatives were synthesized and their antidiabetic potential evaluated using α-glucosidase, α-amylase, non-enzymatic glycosylation of hemoglobin and advanced glycation end product inhibition assays. Compound 3l showed low IC50 values of 0.31, 0.98, 0.59 and 0.19 mM in α-amylase, α-glucosidase, non-enzymatic glycosylation of hemoglobin and AGE inhibition assays, respectively, and outperformed

  合成了苯并噻唑衍生物，并使用α-葡萄糖苷酶，α-淀粉酶，血红蛋白的非酶糖基化和先进的糖化终产物抑制试验评估了它们的抗糖尿病潜力。化合物31在α-淀粉酶，α-葡萄糖苷酶，血红蛋白的非酶糖基化和AGE抑制试验中分别显示出0.31、0.98、0.59和0.19mM的低IC 50值，并且优于标准的阿卡波糖。酶动力学研究表明，α-淀粉酶和α-葡萄糖苷酶的K i分别为0.39和1.5 mM。3l的非键相互作用 用α-淀粉酶（3OLD）和α-葡萄糖苷酶（2ZE0）显示其结合在活性位点口袋中，并被3OLD中的残基Asp197，Glu233，Asp300和2ZE0中的Asp199，Glu256，Asp326包围。
• 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。
• Pentafluorophenylammonium triflate: A Mild, Efficient and Reusable Catalyst for the Synthesis of 2-Arylbenzothiazole and 2-Arylbenzothiazoline Derivatives in a Green Chemical Approach
  作者：Arup Datta

  DOI：10.13005/ojc/370112

  日期：2021.2.28

  simple and environmentally benign effective synthesis of 2-substituted benzothiazole and benzothiazoline derivatives are described in presence of PFPAT (pentafluorophenylammonium triflate) catalyst in water successfully. A series of benzothiazole derivative were synthesized by the reaction between 2-aminothiophenol and various aldehydes in good yields. Recyclability of the catalyst is observed for four

  在这项工作中，在 PFPAT（五氟苯基三氟甲磺酸铵）催化剂存在下，在水中成功地一锅、简单且环境友好地有效合成 2-取代苯并噻唑和苯并噻唑啉衍生物。通过2-氨基苯硫酚与多种醛的反应合成了一系列苯并噻唑衍生物，收率良好。观察到催化剂的可回收性四次，在水介质中其活性没有损失。
• Straightforward synthesis of benzoxazoles and benzothiazoles via photocatalytic radical cyclization of 2-substituted anilines with aldehydes
  作者：Hao Anh Nguyen Le、Long Hoang Nguyen、Quynh Nhu Ba Nguyen、Hai Truong Nguyen、Khang Quoc Nguyen、Phuong Hoang Tran

  DOI：10.1016/j.catcom.2020.106120

  日期：2020.10

  Eosin Y-catalyzed one-pot coupling and cyclization of o-substituted anilines with aldehydes to form benzoxazoles and benzothiazoles under mild condition has been developed. The reaction scope was broadly tolerant of various 2-substituted anilines and aldehydes. The desired products were obtained in high yields with the use of eosin Y as a photocatalyst under a substantial refinement of reaction conditions

  曙红Y催化一锅耦合和邻位取代苯胺与醛环化在温和条件下形成苯并恶唑和苯并噻唑。反应范围广泛耐受各种2-取代的苯胺和醛。与以前的文献相比，在显着改善反应条件的条件下，使用曙红Y作为光催化剂可以高收率获得所需产物。基于观察到的实验结果，提出了一种涉及自由基过程的合理机制。