2-benzyl-3-(difluoromethoxy)-5-methylcyclohex-2-enone | 1422736-38-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-benzyl-3-(difluoromethoxy)-5-methylcyclohex-2-enone
• CAS: 1422736-38-6
• 化学式: C₁₅H₁₆F₂O₂
• 分子量: 266.288
• InChiKey: UYJXIHPYDSIZDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  S-bromodifluoromethyl-S-phenyl-2,3,4,5-tetramethylphenylsulfonium triflate 、 2-benzyl-5-methylcyclohexane-1,3-dione 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以75%的产率得到2-benzyl-3-(difluoromethoxy)-5-methylcyclohex-2-enone
  参考文献：
  名称：

  Selective O-Difluoromethylation of 1,3-Diones by Bromodifluoromethylating Reagents

  摘要：

  The regioselective Odifluoromethylation of 1,3-diones was achieved via in situ generation of difluorocarbene from bromodifluoromethylating reagents in the presence of an organic base. A wide variety of difluormethyl enol ethers were obtained in good to excellent yields. The reaction mechanism is discussed based on ab initio calculations (kcal/mol).

  DOI：

  10.1021/ol4000313

文献信息

• Selective O-difluoromethylation of 1,3-diones using S-(difluoromethyl) sulfonium salt
  作者：Guo-Kai Liu、Xin Li、Wen-Bing Qin、Wei-Feng Lin、Li-Ting Lin、Jia-Yi Chen、Jian-Jian Liu

  DOI：10.1016/j.cclet.2019.03.036

  日期：2019.8

  A facile and highly efficient approach for selective O-difluoromethylation of 1,3-diones by recently developed bench-stable S-(difluoromethyl)sulfonium salt was described. And a broad range of difluoromthyl enol ethers were readily accessed in good to excellent yields under mild reaction conditions. Mechanistic studies revealed that the O-difluoromethylation reaction proceeds mainly via a difluorocarbene pathway. (C) 2019 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.