3,5-(CF3)2C6H3(Me3Si)NH | 1309826-25-2

• 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: 3,5-(CF3)2C6H3(Me3Si)NH
• 英文别名: (SiMe3)(3,5-(CF3)2C6H3)NH；N-(Trimethylsilyl)-3,5-bis(trifluoromethyl)aniline；3,5-bis(trifluoromethyl)-N-trimethylsilylaniline
• CAS: 1309826-25-2
• 化学式: C₁₁H₁₃F₆NSi
• 分子量: 301.307
• InChiKey: NUBAWDKCJBSXRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.97
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3,5-(CF3)2C6H3(Me3Si)NH 、 tin(ll) chloride 在 n-BuLi 作用下， 以 乙醚 为溶剂， 以53%的产率得到
  参考文献：
  名称：

  Reactions of CO2 and related heteroallenes with CF3-substituted aromatic silylamines of tin

  摘要：

  In this report we detail the synthesis and characterization of new Sn(II) complexes containing the -N[(SiMe3)(Ar-F)] ligand [Ar-F = 3,5-(CF3)(2)C6H3)], specifically designed to provide both an electron-withdrawing -Ar-F group as well as the -SiMe3 group required for migration to oxygen. As well, we have also examined the reaction of the LiN[(SiMe3)(Ar-F) precursor with CO2 and observed the formation of a bicyclic lithium carbamate consisting of two 8-membered rings characterized by single crystal X-ray crystallography. The desired starting complex Sn[N(SiMe3)(Ar-F)](2) could be prepared directly via a metathesis reaction, although X-ray quality crystals could not be grown. The reactions of this complex with CO2, OCS, and CS2 are described. Reaction with CO2 results in an unexpected insertion reaction quite dissimilar to those seen in the literature. A proposed route that explains the surprising CO2 reaction chemistry and products is given. Reactions of Sn[N(SiMe3)(Ar-F)](2) with OCS led to multiple products, while reaction with CS2 led to simple insertion to form a dithiocarbamate. Interestingly, an attempt to purify Sn[N(SiMe3)(Ar-F)](2) by distillation led to an unexpected cyclization reaction with activation of an aromatic H atom. This ortho-metallated product from this cyclization reaction was clearly identified via X-ray crystallography. (c) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2011.06.010
• 作为产物：
  描述：

  三甲基氯硅烷 、 间二(三氟甲基)苯胺 在 正丁基锂 作用下， 以 乙醚 、 正己烷 为溶剂， 以80%的产率得到3,5-(CF3)2C6H3(Me3Si)NH
  参考文献：
  名称：

  Reactions of CO2 and related heteroallenes with CF3-substituted aromatic silylamines of tin

  摘要：

  In this report we detail the synthesis and characterization of new Sn(II) complexes containing the -N[(SiMe3)(Ar-F)] ligand [Ar-F = 3,5-(CF3)(2)C6H3)], specifically designed to provide both an electron-withdrawing -Ar-F group as well as the -SiMe3 group required for migration to oxygen. As well, we have also examined the reaction of the LiN[(SiMe3)(Ar-F) precursor with CO2 and observed the formation of a bicyclic lithium carbamate consisting of two 8-membered rings characterized by single crystal X-ray crystallography. The desired starting complex Sn[N(SiMe3)(Ar-F)](2) could be prepared directly via a metathesis reaction, although X-ray quality crystals could not be grown. The reactions of this complex with CO2, OCS, and CS2 are described. Reaction with CO2 results in an unexpected insertion reaction quite dissimilar to those seen in the literature. A proposed route that explains the surprising CO2 reaction chemistry and products is given. Reactions of Sn[N(SiMe3)(Ar-F)](2) with OCS led to multiple products, while reaction with CS2 led to simple insertion to form a dithiocarbamate. Interestingly, an attempt to purify Sn[N(SiMe3)(Ar-F)](2) by distillation led to an unexpected cyclization reaction with activation of an aromatic H atom. This ortho-metallated product from this cyclization reaction was clearly identified via X-ray crystallography. (c) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2011.06.010

文献信息

• Four-Membered Lutetaheterocycles
  作者：Renita Thim、Cäcilia Maichle-Mössmer、Reiner Anwander

  DOI：10.1021/acs.organomet.8b00312

  日期：2018.8.13

  The four-membered metallacyclic lutetium complexes TptBu,MeLu[CH2(SiMe2)NR] were synthesized via protonolysis of TptBu,MeLuMe2 (TptBu,Me = hydrotris(3-methyl-5-tert-butylpyrazolyl)borato) with silylamines HN(SiMe3)R (R = SiMe3, C6H3(CF3)2-3,5 (ArCF3)). The sterically less demanding amine HN(SiHMe2)2 led to the isolation of the heteroleptic complex TptBu,MeLuMe[N(SiHMe2)2]. The accessibility of the

  通过对Tp t Bu，Me LuMe 2（Tp t Bu，Me = Hydrotris（3-methyl-5- tert）进行质子分解，合成了四元金属环配合物Tp t Bu，Me Lu [CH 2（SiMe 2）NR] -丁基吡唑基）硼酸酯）与甲硅烷基胺HN（SiMe 3）R（R = SiMe 3，C 6 H 3（CF 3）2 -3,5（Ar CF3））。空间上要求较低的胺HN（SiHMe 2）2导致了杂配物Tp t Bu，Me的分离LuMe [N（SiHMe 2）2 ]。利用HOCH 2 t Bu探索了配合物Tp t Bu，Me Lu [CH 2（SiMe 2）NAr CF3 ]分子内开环的可及性，从而提供了新五氧化二complex配合物Tp t Bu，Me Lu [N（SiMe 3）Ar CF 3 ]（OCH 2 t Bu）和Tp t Bu，Me Lu（OCH 2 t Bu）2。Tp t
• Reactions of CO2 and related heteroallenes with CF3-substituted aromatic silylamines of tin
  作者：Constantine A. Stewart、Diane A. Dickie、Bahram Moasser、Richard A. Kemp

  DOI：10.1016/j.poly.2011.06.010

  日期：2012.1

  In this report we detail the synthesis and characterization of new Sn(II) complexes containing the -N[(SiMe3)(Ar-F)] ligand [Ar-F = 3,5-(CF3)(2)C6H3)], specifically designed to provide both an electron-withdrawing -Ar-F group as well as the -SiMe3 group required for migration to oxygen. As well, we have also examined the reaction of the LiN[(SiMe3)(Ar-F) precursor with CO2 and observed the formation of a bicyclic lithium carbamate consisting of two 8-membered rings characterized by single crystal X-ray crystallography. The desired starting complex Sn[N(SiMe3)(Ar-F)](2) could be prepared directly via a metathesis reaction, although X-ray quality crystals could not be grown. The reactions of this complex with CO2, OCS, and CS2 are described. Reaction with CO2 results in an unexpected insertion reaction quite dissimilar to those seen in the literature. A proposed route that explains the surprising CO2 reaction chemistry and products is given. Reactions of Sn[N(SiMe3)(Ar-F)](2) with OCS led to multiple products, while reaction with CS2 led to simple insertion to form a dithiocarbamate. Interestingly, an attempt to purify Sn[N(SiMe3)(Ar-F)](2) by distillation led to an unexpected cyclization reaction with activation of an aromatic H atom. This ortho-metallated product from this cyclization reaction was clearly identified via X-ray crystallography. (c) 2011 Elsevier Ltd. All rights reserved.