difluoromethyl 4-methoxybenzoate | 120608-84-6

• 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: difluoromethyl 4-methoxybenzoate
• CAS: 120608-84-6
• 化学式: C₉H₈F₂O₃
• 分子量: 202.158
• InChiKey: KEPPVVKSKZACLW-UHFFFAOYSA-N

物化性质

• 沸点：
  94 °C(Press: 2 Torr)
• 密度：
  1.243±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  二氟溴甲基三甲基硅烷 、 大茴香酸 在 potassium hydroxide 作用下， 以 水 、 乙腈 为溶剂， 反应 2.5h， 以82%的产率得到difluoromethyl 4-methoxybenzoate
  参考文献：
  名称：

  Aqueous Base Promoted O-Difluoromethylation of Carboxylic Acids with TMSCF₂Br: Bench-Top Access to Difluoromethyl Esters

  摘要：

  A method for the O-difluoromethylation of carboxylic acids using commercially available TMSCF2Br is disclosed. The devised benchtop reaction system is air-stable and offers mild reaction conditions while using readily available reagents and solvents. The method is applicable to both aliphatic and aromatic carboxylic acids while demonstrating compatibility with a range of commonly encountered functional groups. The difluoromethyl esters of FDA approved drugs and pharmaceutically relevant molecules are also presented, demonstrating the potential for late-stage functionalization.

  DOI：

  10.1021/acs.orglett.9b03604

文献信息

• Difluoromethylation and gem-difluorocyclopropenation with difluorocarbene generated by decarboxylation
  作者：Xiao-Yun Deng、Jin-Hong Lin、Jian Zheng、Ji-Chang Xiao

  DOI：10.1039/c5cc02736e

  日期：——

  Difluoromethylation of the activated X–H bond and aliphatic thiols, and gem-difluorocyclopropenation of alkynes with difluorocarbene generated by decarboxylation are described.

  激活的X-H键和脂肪硫醇的二氟甲基化，以及通过脱羧生成的二氟卡宾对炔烃的gem-二氟环丙烯化进行了描述。
• <i>ortho</i>-Dialkylamino arylboranes as efficient reagents for difluorocarbene trapping
  作者：Egor A. Ilin、Vladimir O. Smirnov、Alexander D. Volodin、Alexander A. Korlyukov、Alexander D. Dilman

  DOI：10.1039/d0cc02567d

  日期：——

  Compounds bearing ortho-oriented dialkylamino and boryl groups can serve as efficient reagents to trap difluorocarbene leading to zwitterionic ammonium borates featuring N-CF2-B fragments. The reagents are shelf-stable and can be used as mechanistic probes for reactions proceeding via difluorocarbene.

  带有邻位取向的二烷基氨基和硼烷基的化合物可以用作捕获二氟卡宾的有效试剂，从而导致形成具有N-CF 2 -B片段的两性离子硼酸铵。该试剂具有贮存稳定性，可用作通过二氟卡宾进行反应的机理探针。
• Perfluoro- and polyfluorosulfonic acids. 21. Synthesis of difluoromethyl esters using fluorosulfonyldifluoroacetic acid as a difluorocarbene precursor
  作者：Qingyun Chen、Shengwen Wu

  DOI：10.1021/jo00274a012

  日期：1989.6
• CHEN, QING-YUN;WU, SHENG-WEN, J. ORG. CHEM., 54,(1989) N3, C. 3023-3027
  作者：CHEN, QING-YUN、WU, SHENG-WEN

  DOI：——

  日期：——
• Aqueous Base Promoted <i>O</i>-Difluoromethylation of Carboxylic Acids with TMSCF₂Br: Bench-Top Access to Difluoromethyl Esters
  作者：Vinayak Krishnamurti、Colby Barrett、Xanath Ispizua-Rodriguez、Matthew Coe、G. K. Surya Prakash

  DOI：10.1021/acs.orglett.9b03604

  日期：2019.12.6

  A method for the O-difluoromethylation of carboxylic acids using commercially available TMSCF2Br is disclosed. The devised benchtop reaction system is air-stable and offers mild reaction conditions while using readily available reagents and solvents. The method is applicable to both aliphatic and aromatic carboxylic acids while demonstrating compatibility with a range of commonly encountered functional groups. The difluoromethyl esters of FDA approved drugs and pharmaceutically relevant molecules are also presented, demonstrating the potential for late-stage functionalization.