2-bromo-3-(difluoromethoxy)-5,5-dimethylcyclohex-2-enone | 1422736-34-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-bromo-3-(difluoromethoxy)-5,5-dimethylcyclohex-2-enone
• 英文别名: 2-Bromo-3-(difluoromethoxy)-5,5-dimethylcyclohex-2-en-1-one；2-bromo-3-(difluoromethoxy)-5,5-dimethylcyclohex-2-en-1-one
• CAS: 1422736-34-2
• 化学式: C₉H₁₁BrF₂O₂
• 分子量: 269.086
• InChiKey: AFBJOEYKZQIAOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-溴-5,5-二甲基-1,3-环己二酮 、 S-difluoromethyl-S-phenyl-2,4,6-trimethoxyphenylsulfonium tetrafluoroborate 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 0.33h， 以89%的产率得到2-bromo-3-(difluoromethoxy)-5,5-dimethylcyclohex-2-enone
  参考文献：
  名称：

  Selective O-difluoromethylation of 1,3-diones using S-(difluoromethyl) sulfonium salt

  摘要：

  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.

  DOI：

  10.1016/j.cclet.2019.03.036

文献信息

• Selective <i>O</i>-Difluoromethylation of 1,3-Diones by Bromodifluoromethylating Reagents
  作者：Guokai Liu、Xin Wang、Xiu-Hua Xu、Xu Lu、Etsuko Tokunaga、Seiji Tsuzuki、Norio Shibata

  DOI：10.1021/ol4000313

  日期：2013.3.1

  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).