1-(2,2-difluoro-2-(phenylsulfonyl)ethyl)naphthalene | 1258013-08-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(2,2-difluoro-2-(phenylsulfonyl)ethyl)naphthalene
• 英文别名: 1-[2-(Benzenesulfonyl)-2,2-difluoroethyl]naphthalene；1-[2-(benzenesulfonyl)-2,2-difluoroethyl]naphthalene
• CAS: 1258013-08-9
• 化学式: C₁₈H₁₄F₂O₂S
• 分子量: 332.371
• InChiKey: DMZVUDFNZHCALD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2,2-difluoro-2-(phenylsulfonyl)ethyl)naphthalene 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 以76%的产率得到1,1-二氟-2-(1-萘基)乙烯
  参考文献：
  名称：

  Nucleophilic (phenylsulfonyl)difluoromethylation of alkyl halides using PhSO2CF2SiMe3: preparation of gem-difluoroalkenes and trifluoromethyl compounds

  摘要：

  Nucleophilic (phenylsulfonyl)difluoromethylation of both alkyl iodides and bromides was successfully accomplished by using CsF/15-crown-5 as an initiating system in DME, and the amount of 15-crown-5 was found to be critical to the yield of the product. The prepared (phenylsulfonyl)difluoromethylated alkanes were converted into gem-difluoroalkenes by a base-mediated 1,2-elimination reaction, and the latter species could be further transformed into trifluoromethyl compounds in the presence of KF/18-crown-6 or TBAF. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.09.068
• 作为产物：
  描述：

  1-溴甲基萘 、 [二氟(苯基磺酰基)甲基](三甲基)硅烷 在 15-冠醚-5 、 cesium fluoride 作用下， 以 乙二醇二甲醚 为溶剂， 以77%的产率得到1-(2,2-difluoro-2-(phenylsulfonyl)ethyl)naphthalene
  参考文献：
  名称：

  Nucleophilic (phenylsulfonyl)difluoromethylation of alkyl halides using PhSO2CF2SiMe3: preparation of gem-difluoroalkenes and trifluoromethyl compounds

  摘要：

  Nucleophilic (phenylsulfonyl)difluoromethylation of both alkyl iodides and bromides was successfully accomplished by using CsF/15-crown-5 as an initiating system in DME, and the amount of 15-crown-5 was found to be critical to the yield of the product. The prepared (phenylsulfonyl)difluoromethylated alkanes were converted into gem-difluoroalkenes by a base-mediated 1,2-elimination reaction, and the latter species could be further transformed into trifluoromethyl compounds in the presence of KF/18-crown-6 or TBAF. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.09.068

文献信息

• Nucleophilic (phenylsulfonyl)difluoromethylation of alkyl halides using PhSO2CF2SiMe3: preparation of gem-difluoroalkenes and trifluoromethyl compounds
  作者：Lingui Zhu、Ya Li、Yanchuan Zhao、Jinbo Hu

  DOI：10.1016/j.tetlet.2010.09.068

  日期：2010.11

  Nucleophilic (phenylsulfonyl)difluoromethylation of both alkyl iodides and bromides was successfully accomplished by using CsF/15-crown-5 as an initiating system in DME, and the amount of 15-crown-5 was found to be critical to the yield of the product. The prepared (phenylsulfonyl)difluoromethylated alkanes were converted into gem-difluoroalkenes by a base-mediated 1,2-elimination reaction, and the latter species could be further transformed into trifluoromethyl compounds in the presence of KF/18-crown-6 or TBAF. (C) 2010 Elsevier Ltd. All rights reserved.