1-phenyl-5-(phenylthio)-1H-tetrazole | 917905-41-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-phenyl-5-(phenylthio)-1H-tetrazole
• 英文别名: 1-phenyl-5-phenylsulfanyltetrazole
• CAS: 917905-41-0
• 化学式: C₁₃H₁₀N₄S
• 分子量: 254.315
• InChiKey: DYGQAWJFZWGPEB-UHFFFAOYSA-N

物化性质

• 沸点：
  448.6±28.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  68.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-phenyl-5-(phenylthio)-1H-tetrazole 在 间氯过氧苯甲酸 、 sodium hydroxide 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 1-苯基-5-苯氧基-1H-四唑
  参考文献：
  名称：

  Tetrazoles: LVII. Preparation and chemical properties of 1-substituted 5-arylsulfonyltetrazoles

  摘要：

  Oxidation of 1-substituted 5-arylsulfanyltetrazoles with m-chloroperoxybenzoic acid and NaIO4 in the presence of RuCl3 leads to the formation of the 5-arylsulfonyltetrazoles. The microwave activation significantly accelerates the oxidation with sodium periodate. The phenylsulfonyl group in compounds obtained underwent the nucleophilic substitution when treated with ethanol, phenol, or benzimidazole in acetonitrile in the presence of NaOH.

  DOI：

  10.1134/s1070428013050229
• 作为产物：
  描述：

  1-苯基-5-巯基四氮唑 在 N-氯代丁二酰亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 1-phenyl-5-(phenylthio)-1H-tetrazole
  参考文献：
  名称：

  二芳基和杂芳基硫化物：通过亚磺酰氯的合成和作为选择性抗乳腺癌药物的评价

  摘要：

  描述了合成二芳基和杂芳基硫化物的温和协议。在一锅法中，硫醇被转化为亚磺酰氯并与芳基锌试剂反应。该方法可耐受芳基氟化物和氯化物、酮以及 N-杂环（包括嘧啶、咪唑、四唑和恶二唑）等官能团。通过这种方法合成的两种化合物在微摩尔范围内表现出对 MCF-7 乳腺癌细胞系的选择性活性。

  DOI：

  10.1021/jo402586v
• 作为试剂：
  描述：

  1-苯基-5-巯基四氮唑 、 N-氯代丁二酰亚胺 、 benzene,bromozinc(1+) 在 1-phenyl-5-(phenylthio)-1H-tetrazole 、 乙酸乙酯 、 hexanes 作用下， 以afforded the title compound as a colorless crystalline solid (0.102 g, 80%)的产率得到1-phenyl-5-(phenylthio)-1H-tetrazole
  参考文献：
  名称：

  AROMATIC SULFIDE COMPOUNDS AND METHODS AND USE THEREOF

  摘要：

  本文描述了芳香族硫化物组合物及其使用方法，用于治疗或预防癌症。

  公开号：

  US20150266836A1

文献信息

• Copper-catalyzed arylation of tetrazole-5-thiones upon convection heating and microwave activation conditions
  作者：U. N. Dmitrieva、S. M. Ramsh、Yu. E. Zevatskii、T. V. Artamonova、L. V. Myznikov

  DOI：10.1007/s10593-012-0996-0

  日期：2012.5

  The arylation of 1-phenyltetrazole-5-thione using a series of iodobenzene derivatives in the presence of cuprous chloride and a ligand such as ethylenediamine. It was shown that the use of microwave activation permitted shortening of the reaction time, increasing yields and simplification of the reaction products isolation.

  在氯化亚铜和配体（如乙二胺）存在下，使用一系列碘代苯衍生物将1-苯基四唑-5-硫酮芳基化。结果表明，使用微波活化可以缩短反应时间，提高产率，并简化反应产物的分离。
• Novel Mixed Complexes of Copper(II) and Ethylenediamine: Synthesis, Crystal Structure, and Catalytic Activity in the Cross-Coupling Reaction of 1-Phenyl-5H-tetrazole-5-thiol and Iodobenzene
  作者：L. V. Myznikov、A. I. Fisher、U. N. Dmitrieva、T. V. Artamonova、Yu. E. Zevatskii

  DOI：10.1134/s1070363218030155

  日期：2018.3

  Two earlier unknown complexes, [Cu(en)(2)(Hptt)]Br (Hptt = 1-phenyl-1H-terazole-5-thiol, en = ethylenediamine) and trans-[Cu(en)2(H2O)Br]Br, have been synthesized and characterized using X-ray diffraction analysis. In [Cu(en)(2)(Hptt)]Br complex, the copper cation is bonded with the N-4 atom of tetrazole ring. Catalytic activity of the obtained complexes in cross-coupling reaction of 1-phenyl-5H-tetrazole-5-thiol with iodobenzene is comparable to that of CuBr2 in the presence of 2 eq. of ethylenediamine.
• New method of 5-mercaptotetrazoles functionalization
  作者：P. A. Aleshunin、D. V. Aleshunina、V. A. Ostrovskii

  DOI：10.1134/s1070428011110273

  日期：2011.11
• Kinetic studies of the copper-catalyzed cross-coupling of 1-phenyltetrazole-5-thiol and iodobenzene
  作者：U. N. Dmitrieva、T. V. Artamonova、Yu. E. Zevatskii、N. P. Novoselov、L. V. Myznikov

  DOI：10.1134/s1070363213090132

  日期：2013.9

  Kinetics of the copper-catalyzed cross-coupling of 1-phenyltetrazole-5-thiol and iodobenzene under thermal and dielectric heating has been studied; the kinetic parameters of the reaction have been calculated. Microwave irradiation has not influenced significantly the reaction molecular mechanism; the process acceleration can be due to macrokinetic effects.
• Diaryl and Heteroaryl Sulfides: Synthesis via Sulfenyl Chlorides and Evaluation as Selective Anti-Breast-Cancer Agents
  作者：Ivelina M. Yonova、Charlotte A. Osborne、Naomi S. Morrissette、Elizabeth R. Jarvo

  DOI：10.1021/jo402586v

  日期：2014.3.7

  A mild protocol for the synthesis of diaryl and heteroaryl sulfides is described. In a one-pot procedure, thiols are converted to sulfenyl chlorides and reacted with arylzinc reagents. This method tolerates functional groups including aryl fluorides and chlorides, ketones, as well as N-heterocycles including pyrimidines, imidazoles, tetrazoles, and oxadiazoles. Two compounds synthesized by this method

  描述了合成二芳基和杂芳基硫化物的温和协议。在一锅法中，硫醇被转化为亚磺酰氯并与芳基锌试剂反应。该方法可耐受芳基氟化物和氯化物、酮以及 N-杂环（包括嘧啶、咪唑、四唑和恶二唑）等官能团。通过这种方法合成的两种化合物在微摩尔范围内表现出对 MCF-7 乳腺癌细胞系的选择性活性。