bromodifluoromethyl phenyl selenide | 868761-00-6

• 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: bromodifluoromethyl phenyl selenide
• 英文别名: [Bromo(difluoro)methyl]selanylbenzene
• CAS: 868761-00-6
• 化学式: C₇H₅BrF₂Se
• 分子量: 285.978
• InChiKey: WQOLBORSCNWCIR-UHFFFAOYSA-N

物化性质

• 沸点：
  199.1±40.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.96
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  bromodifluoromethyl phenyl selenide 在 4 A molecular sieve 、 四丁基氟化铵 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 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
• 作为产物：
  描述：

  苯硒酚 在 sodium tetrahydroborate 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.33h， 生成 bromodifluoromethyl phenyl selenide
  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

• A New Entry to Difluoromethylene Compounds; An Electrochemical Method
  作者：Hideki Asai、Kenji Uneyama

  DOI：10.1246/cl.1995.1123

  日期：1995.12

  Electroreduction of dibromodifluoromethane in the presence of diphenyldiselenide and olefins in a DMF-(Pt)-(Al) system provided adducts of in situ generated bromodifluoromethyl radical and phenylselenenyl group to olefins. One electron transfer from benzeneselenolate to CF2Br2 induces the formation of CF2Br· radical. This system is also useful for generation of ·CF2CO2Et radical from ethyl bromodifluoroacetate.

  在DMF-(Pt)-(Al)体系中，在二苯基二硒化物和烯烃的存在下，二溴二氟甲烷的电还原提供了原位产生的溴二氟甲基自由基和苯基硒基与烯烃的加合物。从苯硒酸盐到CF2Br2的一个电子转移诱导了CF2Br·自由基的形成。该系统还可用于从溴二氟乙酸乙酯生成·CF2CO2Et 自由基。
• 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。
• Perfluoroalkyl Selenoxides, Selenones and Selenoximines: General Preparation and Properties
  作者：Arnaud de Zordo‐Banliat、Kevin Grollier、Nicolas Vanthuyne、Sébastien Floquet、Thierry Billard、Guillaume Dagousset、Bruce Pégot、Emmanuel Magnier

  DOI：10.1002/anie.202300951

  日期：2023.3.13

  perfluoroalkyl selenoxides, selenones and selenoximines was possible through a selective oxidation of perfluoroalkyl selenoethers. Synthesis of perfluoroalkyl selenoxides was also described via a two-step one-pot reaction from selenocyanates. The perfluoroalkyl selenoximine family was synthesized. The Hansch-Leo parameters of the compounds were determined and some aryl perfluoroalkyl selenoxides were separated

  通过选择性氧化全氟烷基硒醚，可以获得全氟烷基硒氧化物、硒酮和硒肟。全氟烷基硒氧化物的合成也通过硒氰酸酯的两步一锅反应进行了描述。合成了全氟烷基硒肟家族。确定了化合物的 Hansch-Leo 参数，并通过手性 HPLC 分离了一些芳基全氟烷基硒氧化物。
• 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.