N-benzyl-N-(tetrahydrofuran-2-yl)methanesulfonamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-benzyl-N-(tetrahydrofuran-2-yl)methanesulfonamide
• 英文别名: N-benzyl-N-(oxolan-2-yl)methanesulfonamide
• 化学式: C₁₂H₁₇NO₃S
• 分子量: 255.338
• InChiKey: XMHFMPHMYVSJRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苄胺 在 吡啶 、 sodium hydride 作用下， 以 二氯甲烷 、 mineral oil 为溶剂， 反应 19.0h， 生成 N-benzyl-N-(tetrahydrofuran-2-yl)methanesulfonamide
  参考文献：
  名称：

  室温下无​​过渡金属的醚类分子间α-CH胺化

  摘要：

  AbstractWe describe a new method for the intermolecular amination of the α‐CH bonds of ethers. A hypervalent iodine reagent was used as oxidant to enable the amination of cyclic and acyclic alkyl ethers with a wide range of amides, imides, and amines. The amination occurred at room temperature and without a transition metal catalyst. The method could be used to synthesize the anti‐cancer prodrug Tegafur and its analogues.magnified image

  DOI：

  10.1002/adsc.201400646

文献信息

• Halogen-Bond-Promoted α-C−H Amination of Ethers for the Synthesis of Hemiaminal Ethers
  作者：Zhangjin Pan、Zhenwei Fan、Beili Lu、Jiajia Cheng

  DOI：10.1002/adsc.201800006

  日期：2018.5.2

  A simple halogen‐bond‐promoted α‐C−H amination of ether/thioether with a variety of N−H compounds has been accomplished. In the presence of low‐cost and readily available perfluorobutyl iodide, a diverse range of hemiaminal ether derivatives, including the valuable hydrazone hemiaminal ethers, were quickly assembled under thermal or visible‐light irradiation conditions. Mechanistic studies suggest

  已经完成了醚/硫醚与各种NH化合物的卤素键促进的简单α-CH胺化反应。在存在低成本且易于获得的全氟丁基碘的情况下，在热或可见光辐照条件下，迅速组装了各种各样的半胱氨酸醚衍生物，包括有价值的半胱氨酸醚。机理研究表明，形成了卤素键加合物，自由基链途径可能起作用。通过制备抗病毒和抗肿瘤药物替加福证明了该方法的综合应用。
• Transition Metal-Free Intermolecular α-CH Amination of Ethers at Room Temperature
  作者：Ivan Buslov、Xile Hu

  DOI：10.1002/adsc.201400646

  日期：2014.11.3

  AbstractWe describe a new method for the intermolecular amination of the α‐CH bonds of ethers. A hypervalent iodine reagent was used as oxidant to enable the amination of cyclic and acyclic alkyl ethers with a wide range of amides, imides, and amines. The amination occurred at room temperature and without a transition metal catalyst. The method could be used to synthesize the anti‐cancer prodrug Tegafur and its analogues.magnified image