2-bromo-3-(difluoromethoxy)cyclopent-2-enone | 1422736-28-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯酯类
• 英文名称: 2-bromo-3-(difluoromethoxy)cyclopent-2-enone
• CAS: 1422736-28-4
• 化学式: C₆H₅BrF₂O₂
• 分子量: 227.005
• InChiKey: LDQWOSJYFHZHNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  2-溴-1,3-环戊二酮 、 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85%的产率得到2-bromo-3-(difluoromethoxy)cyclopent-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

• O-Difluoromethylation of 1,3-diones with S-difluoromethyl sulfonium salt
  作者：Chun-Bo Yue、Jin-Hong Lin、Ji Cai、Cheng-Pan Zhang、Gang Zhao、Ji-Chang Xiao、HengFeng Li

  DOI：10.1039/c6ra06338a

  日期：——

  The O-difluoromethylation of 1,3-diones with S-difluoromethyl sulfonium salt is described. The sulfonium salt was previously believed to be a direct difluoromethylation reagent, but our mechanistic investigation reveals that the O-difluoromethylation reaction proceeds not only via the direct transfer of the CF2H group, but also via a difluorocarbene process. This work represents the first protocol

  所述Ô的1,3-二酮与-difluoromethylation小号二氟甲基锍盐进行说明。previously盐以前被认为是直接的二氟甲基化试剂，但是我们的机理研究表明，O-二氟甲基化反应不仅通过CF 2 H基团的直接转移进行，而且还通过二氟卡宾方法进行。这项工作代表了无环1,3-二酮的轻度O-二氟甲基化的第一个方案。
• 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).