2,2-difluoro-1-phenyl-2-(phenylselanyl)ethanol | 868761-04-0

• 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: 2,2-difluoro-1-phenyl-2-(phenylselanyl)ethanol
• 英文别名: 2,2-difluoro-1-phenyl-2-phenylselanyl-ethanol；2,2-difluoro-2-phenylseleno-1-phenylethanol；2,2-Difluoro-1-phenyl-2-phenylselanylethanol
• CAS: 868761-04-0
• 化学式: C₁₄H₁₂F₂OSe
• 分子量: 313.205
• InChiKey: ZYPNPPVLTXYRGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.34
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2-difluoro-1-phenyl-2-(phenylselanyl)ethanol 在 indium(III) chloride 、 氢氧化钾 、 sodium tetrahydroborate 、 四丁基溴化铵 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Reductive Radical Reaction of gem-Difluorinated Organoselenium Compounds with an Indium(III) Chloride-Sodium Borohydride System

  摘要：

  对于宝石二氟苯基硒化合物，通过 InCl3 和 NaBH4 之间的反金属化作用原位生成的氢化铟被认为是一种方便的自由基试剂，可以替代氢化三丁基锡。NaBH4/InCl3 系统除了在分子内环化和自由基脱硒化反应中表现出色外，在有机硒化合物与苯乙烯的分子间自由基加成中也取得了成功。

  DOI：

  10.1055/s-2006-926420
• 作为产物：
  描述：

  苯硒酚 在 sodium tetrahydroborate 、 4 A molecular sieve 、 四丁基氟化铵 、 sodium hydride 、 magnesium 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.83h， 生成 2,2-difluoro-1-phenyl-2-(phenylselanyl)ethanol
  参考文献：
  名称：

  Synthesis and Transformation of [Difluoro(phenylseleno)methyl]- trimethylsilane

  摘要：

  [GRAPHIC]A novel and efficient strategy was developed to synthesize [difluoro(phenylseleno)methyl]trimethylsilane (PhSeCF2-TMS, 2), which was further utilized as a nucleophilic difluoromethylating reagent to incorporate the difluoro(phenylseleno)methyl (PhSeCF2) group into carbonyl compounds in good yields. The resulting PhSeCF2-containing alcohols 3 could be conveniently converted into corresponding difluoromethyl alcohols 4 by a radical deselenylation.

  DOI：

  10.1021/jo051119z

文献信息

• Lewis acid-catalyzed tri- and difluoromethylation reactions of aldehydes
  作者：Satoshi Mizuta、Norio Shibata、Shinichi Ogawa、Hiroyuki Fujimoto、Shuichi Nakamura、Takeshi Toru

  DOI：10.1039/b603041f

  日期：——

  The first Lewis acid-catalyzed trifluoromethylation reactions of aldehydes with Me3SiCF3 under TiF4/DMF, Ti(OiPr)4/DMF and Cu(OAc)2/dppp/toluene conditions are described. We have successfully applied this methodology to the difluoromethylation of aldehydes using Me3SiCF2SePh, Me3SiCF2P(O)OEt2 and Me3SiCF2SPh.

  首次报道了在TiF4/DMF、Ti(OiPr)4/DMF和Cu(OAc)2/dppp/甲苯条件下，三甲基硅基三氟甲基（Me3SiCF3）与醛的Lewis酸催化三氟甲基化反应。我们还成功地应用这种方法，使用Me3SiCF2SePh、Me3SiCF2P(O)OEt2和Me3SiCF2SPh实现了醛的双氟甲基化。
• Difluoro(phenylchalcogen)methylation of aldehydes, ketones, and imines with S-, Se-, and Te-containing reagents PhXCF2H (X=S, Se, Te)
  作者：Mingyou Hu、Fei Wang、Yanchuan Zhao、Zhengbiao He、Wei Zhang、Jinbo Hu

  DOI：10.1016/j.jfluchem.2011.08.007

  日期：2012.3

  prepared, and their relative reactivity towards aldehydes, ketones, and imines was investigated. Compared to the former developed (phenylchalcogen)difluoromethylation reagents, these reagents are relatively easily available and more atom-economical in fluoroalkylation reactions. It was found that the efficient nucleophilic (phenylchalcogen)difluoromethylation of aldehydes, ketones, and imines could be

  制备了一系列含硫，硒和碲的（苯基硫属元素）二氟甲基化试剂PhSCF 2 H（1a），PhSeCF 2 H（1b）和PhTeCF 2 H （1c），它们对醛，酮，对亚胺进行了调查。与以前开发的（苯基硫属元素化物）二氟甲基化试剂相比，这些试剂相对容易获得，并且在氟代烷基化反应中更经济。发现用1a - 1c可以实现醛，酮和亚胺的有效亲核性（苯硫族元素）二氟甲基化。试剂1a和1b与羰基化合物和亚胺的反应活性比1c高，并且PhOCF 2 H（1d）无法进行类似的氟烷基化反应。
• Synthesis and Transformation of [Difluoro(phenylseleno)methyl]- trimethylsilane
  作者：Ying-Ying Qin、Xiao-Long Qiu、Yan-Yan Yang、Wei-Dong Meng、Feng-Ling Qing

  DOI：10.1021/jo051119z

  日期：2005.10.1

  [GRAPHIC]A novel and efficient strategy was developed to synthesize [difluoro(phenylseleno)methyl]trimethylsilane (PhSeCF2-TMS, 2), which was further utilized as a nucleophilic difluoromethylating reagent to incorporate the difluoro(phenylseleno)methyl (PhSeCF2) group into carbonyl compounds in good yields. The resulting PhSeCF2-containing alcohols 3 could be conveniently converted into corresponding difluoromethyl alcohols 4 by a radical deselenylation.
• Reductive Radical Reaction of <i>gem</i>-Difluorinated Organoselenium Compounds with an Indium(III) Chloride-Sodium Borohydride System
  作者：Feng-Ling Qing、Ying-Ying Qin、Yan-Yan Yang、Xiao-Long Qiu

  DOI：10.1055/s-2006-926420

  日期：2006.5

  As for gem-difluorinated phenylseleno compounds, indium hydride, in situ generated by transmetallation between InCl3 and NaBH4, was found to be a convenient radical reagent as an alternative to tributyltin hydride. Besides its excellent performance in intramolecular cyclization and radical deselenylation, the NaBH4/InCl3 system also succeeded in intermolecular radical addition between organoselenium compounds and styrene.

  对于宝石二氟苯基硒化合物，通过 InCl3 和 NaBH4 之间的反金属化作用原位生成的氢化铟被认为是一种方便的自由基试剂，可以替代氢化三丁基锡。NaBH4/InCl3 系统除了在分子内环化和自由基脱硒化反应中表现出色外，在有机硒化合物与苯乙烯的分子间自由基加成中也取得了成功。