3-[difluoro(trimethylsilyl)methyl]-N,N-dimethylaniline | 1355722-41-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-[difluoro(trimethylsilyl)methyl]-N,N-dimethylaniline
• 英文别名: 1-[difluoro(trimethylsilyl)methyl]-3-(dimethylamino)benzene
• CAS: 1355722-41-6
• 化学式: C₁₂H₁₉F₂NSi
• 分子量: 243.372
• InChiKey: PTACACBMUIKMPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[difluoro(trimethylsilyl)methyl]-N,N-dimethylaniline 、 N,N-二乙基-4-溴苯甲酰胺 在 bis(η3-allyl-μ-chloropalladium(II)) 、 di-tert-butyl(2,4-dimethoxyphenyl)phosphine 、 cesium fluoride 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以85%的产率得到4-{difluoro[3-(N,N-dimethylamino)phenyl]methyl}-N,N-diethylbenzamide
  参考文献：
  名称：

  钯催化的芳基卤化物与芳基二氟甲基三甲基硅烷的芳基二氟甲基化

  摘要：

  钯催化的芳基卤化物与芳基二氟甲基三甲基硅烷的偶联被证明可形成二芳基二氟甲烷。钯的简单二烷基（二甲氧基苯基）膦配体在还原消除过程中稳定了钯和二氟苄基配体之间的π相互作用，并且钴催化的硅烷合成使该反应能够形成多种产物，包括具有生物活性的产物。

  DOI：

  10.1002/anie.202208204
• 作为产物：
  描述：

  三甲基氯硅烷 、 N,N-二甲基-3-(三氟甲基)苯胺 在 magnesium 、 copper(l) chloride 作用下， 反应 15.0h， 以32%的产率得到3-[difluoro(trimethylsilyl)methyl]-N,N-dimethylaniline
  参考文献：
  名称：

  Mg–Cu bimetal system for selective CF bond activation

  摘要：

  Bimetal system of Mg-CuCl I in DMI for selective C-F and C-Cl bonds activation has been examined. This article involves (1) a short overview of bimetal system of Mg-metals for selective C-F bond activation, (2) C-F bond activation of alkyl trifluoroacetates leading to alkyl difluoro(trimethylsilyl)acetates via difluoroketene silyl acetal, (3) selective C-Cl bond activation of 3- and 4-chloropentafluoroethylbenzenes, (4) C-F bond activation of substituted benzotrifluorides and (5) microscopic observation of an active site of magnesium surface formed in Mg-CuCl system and elucidation of reaction mechanism of C-Cl and C-F bond activation at the active site. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2013.02.001

文献信息

• Cu-deposits on Mg metal surfaces promote electron transfer reactions
  作者：Shinya Utsumi、Toshimasa Katagiri、Kenji Uneyama

  DOI：10.1016/j.tet.2011.11.082

  日期：2012.1

  The enhancement of the electron transfer processes in the Grignard reagent formation-type ring silylation and the defluorination-silylation of perfluoroalkyl benzenes by Cu(0)-deposited Mg metal were confirmed. Microscopic analysis and substituent effects implied a different reduction process in the presence of Cu-deposited Mg metal than in the presence of bare Mg metal. (C) 2011 Elsevier Ltd. All rights reserved.
• Mg–Cu bimetal system for selective CF bond activation
  作者：Shinya Utsumi、Toshimasa Katagiri、Kenji Uneyama

  DOI：10.1016/j.jfluchem.2013.02.001

  日期：2013.8

  Bimetal system of Mg-CuCl I in DMI for selective C-F and C-Cl bonds activation has been examined. This article involves (1) a short overview of bimetal system of Mg-metals for selective C-F bond activation, (2) C-F bond activation of alkyl trifluoroacetates leading to alkyl difluoro(trimethylsilyl)acetates via difluoroketene silyl acetal, (3) selective C-Cl bond activation of 3- and 4-chloropentafluoroethylbenzenes, (4) C-F bond activation of substituted benzotrifluorides and (5) microscopic observation of an active site of magnesium surface formed in Mg-CuCl system and elucidation of reaction mechanism of C-Cl and C-F bond activation at the active site. (C) 2013 Elsevier B.V. All rights reserved.
• Palladium‐Catalyzed Aryldifluoromethylation of Aryl Halides with Aryldifluoromethyl Trimethylsilanes
  作者：Kyoungmin Choi、Michael G. Mormino、Eric D. Kalkman、John Park、John F. Hartwig

  DOI：10.1002/anie.202208204

  日期：2022.10.10

  Palladium-catalyzed coupling of aryl halides with aryldifluoromethyl trimethylsilanes is shown to form diaryl difluoromethanes. A simple dialkyl(dimethoxyphenyl)phosphine ligand for palladium, stabilizing π-interactions between palladium and the difluorobenzyl ligand during reductive elimination, and a cobalt-catalyzed synthesis of the silanes enabled the reaction to form diverse products, including

  钯催化的芳基卤化物与芳基二氟甲基三甲基硅烷的偶联被证明可形成二芳基二氟甲烷。钯的简单二烷基（二甲氧基苯基）膦配体在还原消除过程中稳定了钯和二氟苄基配体之间的π相互作用，并且钴催化的硅烷合成使该反应能够形成多种产物，包括具有生物活性的产物。