1-phenyl-5-((2,2,2-trifluoroethyl)thio)-1H-tetrazole | 1465812-75-2

• 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-((2,2,2-trifluoroethyl)thio)-1H-tetrazole
• 英文别名: 1-phenyl-5-(2,2,2-trifluoroethylthio)-1H-tetrazole；1-phenyl-1H-tetrazol-5-yl 2,2,2-trifluoroethyl sulfide；1-Phenyl-5-(2,2,2-trifluoroethylsulfanyl)tetrazole
• CAS: 1465812-75-2
• 化学式: C₉H₇F₃N₄S
• 分子量: 260.243
• InChiKey: XFOROXNFVAZFKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  68.9
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-phenyl-5-((2,2,2-trifluoroethyl)thio)-1H-tetrazole 在 chromium(VI) oxide 、 高碘酸 作用下， 以 乙腈 为溶剂， 反应 22.0h， 以2.06 g的产率得到1-phenyl-5-(2,2,2-trifluoroethylsulfonyl)-1H-tetrazole
  参考文献：
  名称：

  Julia–Kocienski approach to trifluoromethyl-substituted alkenes

  摘要：

  A Julia-Kocienski approach to trifluoromethyl-substituted alkenes was evaluated in the reactions of 1,3-benzothiazol-2-yl, 1-phenyl-1H-tetrazol-5-yl, and 1-tbutyl-1H-tetrazol-5-yl 2,2,2-trifluoroethyl sulfones with aldehydes. Among the various conditions tested, the best yields were obtained with 1-phenyl-1H-tetrazol-5-yl 2,2,2-trifluoroethyl sulfone, in CsF-mediated, room temperature olefinations in DMSO. Aromatic aldehydes gave (trifluoromethyl)vinyl derivatives in 23-86% yields, with generally moderate stereoselectivity. Straightforward synthesis of the Julia-Kocienski reagent, and conversion to trifluoromethyl-substituted alkenes under mild reaction conditions, are the advantages of this approach. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.08.069
• 作为产物：
  描述：

  2-碘-1,1,1-三氟乙烷 、 1-苯基-5-巯基四氮唑 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 44.0h， 生成 1-phenyl-5-((2,2,2-trifluoroethyl)thio)-1H-tetrazole
  参考文献：
  名称：

  Julia–Kocienski approach to trifluoromethyl-substituted alkenes

  摘要：

  A Julia-Kocienski approach to trifluoromethyl-substituted alkenes was evaluated in the reactions of 1,3-benzothiazol-2-yl, 1-phenyl-1H-tetrazol-5-yl, and 1-tbutyl-1H-tetrazol-5-yl 2,2,2-trifluoroethyl sulfones with aldehydes. Among the various conditions tested, the best yields were obtained with 1-phenyl-1H-tetrazol-5-yl 2,2,2-trifluoroethyl sulfone, in CsF-mediated, room temperature olefinations in DMSO. Aromatic aldehydes gave (trifluoromethyl)vinyl derivatives in 23-86% yields, with generally moderate stereoselectivity. Straightforward synthesis of the Julia-Kocienski reagent, and conversion to trifluoromethyl-substituted alkenes under mild reaction conditions, are the advantages of this approach. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.08.069

文献信息

• Copper-Catalyzed Insertion into Heteroatom-Hydrogen Bonds with Trifluorodiazoalkanes
  作者：Stephen Hyde、Janis Veliks、Benoît Liégault、David Grassi、Marc Taillefer、Véronique Gouverneur

  DOI：10.1002/anie.201511954

  日期：2016.3.7

  Copper‐catalyzed Si−H, B−H, P−H, S−H, and N−H insertion reactions of 2,2,2‐trifluoro‐1‐diazoethane and 1‐aryl 2,2,2‐trifluorodiazoethanes generated a large number of new fluorine‐containing chemical entities for medicinal chemists. With selected Si−H and B−H insertion reactions, we demonstrate successful extension to asymmetric catalysis.

  铜催化的2,2,2-三氟-1-重氮乙烷和1-芳基2,2,2-三氟重氮乙烷的Si-H，B-H，P-H，S-H和N-H插入反应产生了大量用于药物化学家的新的含氟化学实体。通过选择的Si-H和B-H插入反应，我们证明了不对称催化的成功延伸。