2-naphthyl chlorodifluoromethyl ketone | 141110-96-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-naphthyl chlorodifluoromethyl ketone
• 英文别名: 2-chloro-2,2-difluoro-1-(naphthalen-2-yl)ethanone；2-chloro-2,2-difluoro-1-(naphthalen-2-yl)ethan-1-one；2-Chloro-2,2-difluoro-1-naphthalen-2-yl-ethanone；2-chloro-2,2-difluoro-1-naphthalen-2-ylethanone
• CAS: 141110-96-5
• 化学式: C₁₂H₇ClF₂O
• 分子量: 240.637
• InChiKey: JMMRIMKVQGRGGO-UHFFFAOYSA-N

物化性质

• 沸点：
  313.7±37.0 °C(Predicted)
• 密度：
  1.356±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-naphthyl chlorodifluoromethyl ketone 在 二甲氨基三氟化硫 、 magnesium 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 生成 [1,1,2,2-tetrafluoro-2-(naphthalen-2-yl)ethyl](trimethyl)silane
  参考文献：
  名称：

  Cross-Coupling of [2-Aryl-1,1,2,2-tetrafluoroethyl](trimethyl)silanes with Aryl Halides

  摘要：

  The synthesis of arylCF(2)CF(2)SiMe(3) and their reactivity in cross-coupling reactions with aryl iodides and aryl bromides to afford a range of 1,1,2,2-tetrafluoro-1,2-aryl-ethanes is reported. The use of pyridine as an alternative to phenanthroline, and the ability to carry out the reaction at 60 degrees C or room temperature are the key features of this Cu-Ag mediated cross-coupling methodology. The chemistry is compatible with (hetero)aryl halides, offering a platform to develop products of interest in material and medicinal chemistry.

  DOI：

  10.1021/acs.orglett.5b01510
• 作为产物：
  描述：

  2,2,4,4,4-pentafluoro-3,3-dihydroxy-1-(naphthalen-2-yl)butan-1-one 在 N-氯代丁二酰亚胺 、 三乙胺 、 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以80%的产率得到2-naphthyl chlorodifluoromethyl ketone
  参考文献：
  名称：

  Synthesis of α-Halo-α,α-difluoromethyl Ketones by a Trifluoroacetate Release/Halogenation Protocol

  摘要：

  Three series of alpha-halo-alpha,alpha-difluoromethyl ketones are prepared from highly alpha-fluorinated gem-dials by exploiting the facile release of trifluoroacetate, followed by immediate trapping of the liberated alpha,alpha-difluoroenolate with an electrophilic chlorine, bromine, or iodine source. The products are typically isolated in good yields, even in the case of sensitive, alpha-iodo-alpha,alpha-difluoromethyl ketones. Also, we demonstrate that an alpha-iodo-alpha,alpha-difluoromethyl ketone will participate in a copper-promoted reaction to forge a new carbon-carbon bond.

  DOI：

  10.1021/jo2017179

文献信息

• Copper-mediated cascade radical cyclization of olefins with naphthalenyl iododifluoromethyl ketones
  作者：Peng Peng、Guo-zhi Huang、Ying-xin Sun、Xing Wang、Jing-jing Wu、Fan-hong Wu

  DOI：10.1039/c9ob00916g

  日期：——

  Copper-mediated radical cyclization of naphthalenyl iododifluoromethyl ketones with olefins was successfully developed to generate a series of unprecedented gem-difluorodihydrophenanthrenones, especially 2,2-difluoro-3,4-dihydrophenanthren-1(2H)-one derivatives. This strategy features the use of cheap copper powder and excellent regioselectivity and diastereoselectivity, thus providing a facile approach

  铜介导的萘二碘二氟甲基酮与烯烃的自由基自由基环化反应已成功开发，以生成一系列前所未有的gem-difluorodihydrophenanthrenones，尤其是2,2-difluoro-3,4-dihydrophenanthren-1（2H）-one衍生物。该策略的特点是使用廉价的铜粉，并具有出色的区域选择性和非对映选择性，从而为在药物发现和开发中的应用提供了一种简便的方法。初步的机理研究表明，二氟自由基中间体的参与。进行密度泛函理论（DFT）计算以提供区域选择性的进一步证据。
• Lin, Gialih; Liu, Hsiao-Chien; Wu, Fang-Chen, Journal of the Chinese Chemical Society, 1994, vol. 41, # 1, p. 103 - 108
  作者：Lin, Gialih、Liu, Hsiao-Chien、Wu, Fang-Chen、Chen, Show-Jane

  DOI：——

  日期：——
• Cross-Coupling of [2-Aryl-1,1,2,2-tetrafluoroethyl](trimethyl)silanes with Aryl Halides
  作者：Miriam O’Duill、Emmanuelle Dubost、Lukas Pfeifer、Véronique Gouverneur

  DOI：10.1021/acs.orglett.5b01510

  日期：2015.7.17

  The synthesis of arylCF(2)CF(2)SiMe(3) and their reactivity in cross-coupling reactions with aryl iodides and aryl bromides to afford a range of 1,1,2,2-tetrafluoro-1,2-aryl-ethanes is reported. The use of pyridine as an alternative to phenanthroline, and the ability to carry out the reaction at 60 degrees C or room temperature are the key features of this Cu-Ag mediated cross-coupling methodology. The chemistry is compatible with (hetero)aryl halides, offering a platform to develop products of interest in material and medicinal chemistry.
• Synthesis of α-Halo-α,α-difluoromethyl Ketones by a Trifluoroacetate Release/Halogenation Protocol
  作者：Jinu P. John、David A. Colby

  DOI：10.1021/jo2017179

  日期：2011.11.4

  Three series of alpha-halo-alpha,alpha-difluoromethyl ketones are prepared from highly alpha-fluorinated gem-dials by exploiting the facile release of trifluoroacetate, followed by immediate trapping of the liberated alpha,alpha-difluoroenolate with an electrophilic chlorine, bromine, or iodine source. The products are typically isolated in good yields, even in the case of sensitive, alpha-iodo-alpha,alpha-difluoromethyl ketones. Also, we demonstrate that an alpha-iodo-alpha,alpha-difluoromethyl ketone will participate in a copper-promoted reaction to forge a new carbon-carbon bond.