5-trifluoromethyl-3-undecyl-12,4-oxadiazole | 496862-87-4

• 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-trifluoromethyl-3-undecyl-12,4-oxadiazole
• 英文别名: 5-(Trifluoromethyl)-3-undecyl-1,2,4-oxadiazole
• CAS: 496862-87-4
• 化学式: C₁₄H₂₃F₃N₂O
• 分子量: 292.345
• InChiKey: NGGIMLDGOIEWDH-UHFFFAOYSA-N

物化性质

• 沸点：
  308.1±52.0 °C(Predicted)
• 密度：
  1.068±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  38.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-trifluoromethyl-3-undecyl-12,4-oxadiazole 在 一水合肼 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以70%的产率得到5-trifluoromethyl-3-undecyl-1,2,4-triazole
  参考文献：
  名称：

  Fluorinated Heterocyclic Compounds. An Expedient Route to 5-Perfluoroalkyl-1,2,4-triazoles via an Unusual Hydrazinolysis of 5-Perfluoroalkyl-1,2,4-oxadiazoles:  First Examples of an ANRORC-Like Reaction in 1,2,4-Oxadiazole Derivatives

  摘要：

  The hydrazinolysis reaction of 5-perfluoroalkyl1,2,4-oxadiazoles has been investigated. Nucleophilic addition of the reagent to the C(5)-N(4) double bond of the oxadiazole ring, followed by ring-opening and then ringclosure involving the beta-nitrogen atom of the hydrazino moiety and the C(3) of the oxadiazole ring, explains the formation of 5-perfluoroalkyl-1,2,4-triazoles as final products. Useful applications in synthesis of this uncommon hydrazinolysis can be claimed.

  DOI：

  10.1021/jo0262762
• 作为产物：
  描述：

  三氟乙酸酐 、 N'-羟基十二烷脒 以 甲苯 为溶剂， 反应 8.0h， 以54%的产率得到5-trifluoromethyl-3-undecyl-12,4-oxadiazole
  参考文献：
  名称：

  Fluorinated Heterocyclic Compounds. An Expedient Route to 5-Perfluoroalkyl-1,2,4-triazoles via an Unusual Hydrazinolysis of 5-Perfluoroalkyl-1,2,4-oxadiazoles:  First Examples of an ANRORC-Like Reaction in 1,2,4-Oxadiazole Derivatives

  摘要：

  The hydrazinolysis reaction of 5-perfluoroalkyl1,2,4-oxadiazoles has been investigated. Nucleophilic addition of the reagent to the C(5)-N(4) double bond of the oxadiazole ring, followed by ring-opening and then ringclosure involving the beta-nitrogen atom of the hydrazino moiety and the C(3) of the oxadiazole ring, explains the formation of 5-perfluoroalkyl-1,2,4-triazoles as final products. Useful applications in synthesis of this uncommon hydrazinolysis can be claimed.

  DOI：

  10.1021/jo0262762

文献信息

• Fluorinated Heterocyclic Compounds− The First Example of an Irreversible Ring-Degenerate Rearrangement on Five-Membered Heterocycles by Attack of an External Bidentate Nucleophile
  作者：Silvestre Buscemi、Andrea Pace、Ivana Pibiri、Nicolò Vivona、Camilla Zaira Lanza、Domenico Spinelli

  DOI：10.1002/ejoc.200300737

  日期：2004.3

  hydroxylamine in DMF give the regioisomeric 3-perfluoroalkyl-1,2,4-oxadiazoles 4 in excellent yields. This process is the first example of ring-degenerate rearrangement (RDR) occurring on five-membered heterocycles by attack of an external bidentate nucleophile, which replaces two heteroatoms of the ring. We suggest that an ANRORC-like mechanism occurs in which the addition of the nucleophilic nitrogen atom

  5-全氟烷基-1,2,4-恶二唑3 与羟胺在DMF 中的反应以优异的产率得到区域异构的3-全氟烷基-1,2,4-恶二唑4。该过程是通过外部双齿亲核试剂的攻击在五元杂环上发生环简并重排 (RDR) 的第一个例子，该亲核试剂取代了环的两个杂原子。我们建议发生类似 ANRORC 的机制，其中在 3 的 C(5) 原子上添加亲核氮原子 (NH2OH)，然后通过亲核氧原子的攻击开环和不可逆的环简并闭合（= NOH) 在原始环的 C(3) 原子上，通过 C(3)-C(5) 环形开关实现了 4 的优雅高效合成。对起始材料和最终产品以及建议的中间体进行从头算计算，支持该机制并阐明反应的特征。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)