N,N-bis(phenylsilyl)propan-2-amine | 1414859-93-0

• 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: N,N-bis(phenylsilyl)propan-2-amine
• CAS: 1414859-93-0
• 化学式: C₁₅H₂₁NSi₂
• 分子量: 271.509
• InChiKey: KAJSZYYFHKVPLD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.52
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  苯硅烷 、 异丙胺 在 (1,3-bis(2,4,6-trimethylphenyl)-imidazol-2-ylidene)Yb[N(SiMe3)2]2 作用下， 以 苯 为溶剂， 反应 1.0h， 以75%的产率得到N,N-bis(phenylsilyl)propan-2-amine
  参考文献：
  名称：

  [（NHC）Yb {N（SiMe3）2} 2]-硅烷与胺的催化交叉脱氢偶联

  摘要：

  热门新闻：[（NHC）Yb {N（SiMe 3）2 } 2 ]加合物（NHC = N-杂环卡宾）是有效的催化剂，用于硅烷与一系列伯胺和仲胺的催化交叉脱氢偶联，从而制得在温和的反应条件下，收率很高（82–100％）。稀土金属甲硅烷基酰胺的催化活性和选择性是通过改变NHC的空间体积来调节的。

  DOI：

  10.1002/anie.201205317

文献信息

• [(NHC)Yb{N(SiMe₃)₂}₂]-Catalyzed Cross-Dehydrogenative Coupling of Silanes with Amines
  作者：Weilong Xie、Hongfan Hu、Chunming Cui

  DOI：10.1002/anie.201205317

  日期：2012.10.29

  cross‐dehydrogenative coupling of silanes with a range of primary and secondary amines to yield silylamines in high yields (82–100 %) under mild reaction conditions. The catalytic activity and selectivity of the rare‐earth‐metal silylamides are modulated by altering the steric bulk of the NHC.

  热门新闻：[（NHC）Yb N（SiMe 3）2 } 2 ]加合物（NHC = N-杂环卡宾）是有效的催化剂，用于硅烷与一系列伯胺和仲胺的催化交叉脱氢偶联，从而制得在温和的反应条件下，收率很高（82–100％）。稀土金属甲硅烷基酰胺的催化活性和选择性是通过改变NHC的空间体积来调节的。
• Homoleptic Divalent Dialkyl Lanthanide-Catalyzed Cross-Dehydrocoupling of Silanes and Amines
  作者：Aradhana Pindwal、Arkady Ellern、Aaron D. Sadow

  DOI：10.1021/acs.organomet.6b00138

  日期：2016.6.13

  The rare-earth bis(alkyl) compound SmC(SiHMe2)(3)}(2)THF2 (1b) is prepared by the reaction of samarium(II) iodide and 2 equiv of KC(SiHMe2)(3). This synthesis is similar to that of previously reported YbC(SiHMe2)(3)}2THF(2) (la), and compounds la,b are isostructural. Reactions of lb and 1 or 2 equiv of B(C6F5)(3) afford SmC(SiHMe2)(3)HB(C6F5)(3)THF2 (2b) or SmHB(C6F5)(3)}2THF(2) (3b), respectively, and 1,3-disilacyclobutane Me2Si-C(SiHMe2)(2)}(2) as a byproduct. Bands from 2300 to 2400 cm(-1) assigned to vBH in the IR spectra and highly paramagnetically shifted signals in the 1113 NMR spectra of 2b and 3b provided evidence for Sm-coordinated HB(C6F5)(3). Compounds la,b react with the bulky N-heterocyclic carbene (NHC) 1,3-di-tert-butylimidazol-2-ylidene (ImtBu) to displace both THF ligands and give three-coordinate monoadducts LnC(SiHMe2)(3)}(2)]mtBu (Ln = Yb (4a), Sm (4b)). Complexes 4a,b catalyze cross-dehydrocoupling of organosilanes with primary and secondary amines at room temperature to give silazanes and 112, whereas la,b are not effective catalysts under these conditions. Second-order plots of In[Et2NH]/[Ph2SiH2]} vs time for 4a-catalyzed dehydrocoupling are linear and indicate first-order dependences on silane and amine concentrations. However, changes in the experimental rate law with increased silane concentration or decreased amine concentration reveal inhibition by silane. In addition, excess ImtBu or THF inhibit the reaction rate. These data, along with the structures of 4a,b, suggest that the bulky carbene favors low coordination numbers, which is important for accessing the catalytically active species.