N,N-dimethyl-8-(trimethylsilyl)naphthalen-1-amine | 89333-63-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N,N-dimethyl-8-(trimethylsilyl)naphthalen-1-amine
• 英文别名: N,N-dimethyl-8-trimethylsilylnaphthalen-1-amine
• CAS: 89333-63-1
• 化学式: C₁₅H₂₁NSi
• 分子量: 243.424
• InChiKey: RKFJLKDBUDJAEF-UHFFFAOYSA-N

物化性质

• 沸点：
  325.7±17.0 °C(Predicted)
• 密度：
  0.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N-dimethyl-8-(trimethylsilyl)naphthalen-1-amine 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 为溶剂， 以91 %的产率得到2,4-dibromo-N,N-dimethyl-8-(trimethylsilyl)naphthalen-1-amine
  参考文献：
  名称：

  邻溴-N,N-二甲基苯胺及相关萘中卤素-锂交换的“支撑效应”

  摘要：

  介绍了“支撑效应”的表现——第三基团的存在导致两个取代基之间的间接相互作用——及其对溴-锂交换的容易性和选择性以及所形成的芳基锂的反应性的影响。在带有两个溴的萘底物中，证明了对反应区域选择性的影响。

  DOI：

  10.1002/chem.202303956
• 作为产物：
  描述：

  1-fluoro-1,1-bis(8-dimethylamino-1-naphthyl)-2,2,2-trimethyldisilane 在 四(三苯基膦)钯 二苯基乙炔 作用下， 以 xylene 为溶剂， 反应 48.0h， 以89%的产率得到N,N-dimethyl-8-(trimethylsilyl)naphthalen-1-amine
  参考文献：
  名称：

  Synthesis, structure, and reactivity of disilanes containing one neutral [4+2]-coordinate silicon center

  摘要：

  [4+2]-Coordinate disilanes containing two 8-dimethylamino-1-naphthyl (8-Me2N-1-Np) groups on the same silicon atom, (8-Me2N-1-Np)(2)XSi-SiMe3, where X = F, OH, OEt. and H, are prepared. The X-ray structures of the two derivatives, X = F and OH, show that one of the coordinated dimethylamino groups is anti to the electronegative X group, while the other is anti to the trimethylsilyl group. The [4 + 2]-coordinate disilanes (X = F or OEt) are found to be thermally stable under these conditions such that the corresponding (4 + 1]-coordinate disilanes (8-Me2N-1-Np)XMeSi-SiMePh2 (X = F or OEt) readily undergo degradation. In the presence of Pd(PPh3)(4) as a catalyst, the [4 + 2]-coordinate disilane (X = F) undergoes degradation to generate naphthylsilane (8-Me2N-1-Np)-SiMe3, the reaction pathway being different from that of the [4 + 1]-coordinate disilane (X = F) which affords the fluorosilane, F-SiMePh2. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(01)01385-7

文献信息

• Pentacoordinate [8-(dimethylamino)naphthyl]diorganotin halides containing a rigid, flat chelate ring. An unexpected redistribution reaction between [8-(dimethylamino)naphthyl]trimethyltin and trimethyltin halide
  作者：Johann T.B.H. Jastrzebski、Christopher T. Knaap、Gerard van Koten

  DOI：10.1016/s0022-328x(00)99320-3

  日期：1983.10

  The tetraorgano- and triorgano-halotin compounds Me3(8-Me2NC10H6)Sn and RR′(8-Me2NC10H6)SnX (R = R′ = Me or Ph, X = Cl or Br and R = Me, R′ = Ph, X = Br) have been obtained from the reaction of 8-dimethylamino-1-naphthyl-lithium (8-Me2NC10H6Li) with the relevant organotin halide (Me3SnCl or RR′SnX2). On the basis of the 1H NMR data a trigonal bipyramidal structure with intramolecular Sn-N coordination

  四有机和三有机卤代化合物Me 3（8-Me 2 NC 10 H 6）Sn和RR'（8-Me 2 NC 10 H 6）SnX（R = R'= Me或Ph，X = Cl或Br R = Me，R'= Ph，X = Br）是由8-二甲基氨基-1-萘基锂（8-Me 2 NC 10 H 6 Li）与相关的有机卤化锡（Me 3 SnCl）反应制得的或RR'SnX 2）。基于1 H NMR数据，提出了一种用于RR'（8-Me 2 NC 10 H）分子内Sn-N配位的三角双锥体结构6）SnX化合物，其中有机配体占据赤道，N和X原子位于轴向位置。手性MePh（8-Me 2 NC 10 H 6）SnBr中的Sn中心具有相当大的构型稳定性（至少在NMR时标上为60 MHz）：配位的NMe 2基团的Me基在至少120°时仍保持对位异构C。这种较高的稳定性归因于分别连接到扁平萘基环的1位和8位的Sn和N原子的固定位置。Me
• Sterically facilitated meta-lithiation of arenes, containing electron-donating groups
  作者：Alexander S. Antonov、Victor G. Bardakov、Valeriia V. Mulloyarova

  DOI：10.1016/j.jorganchem.2019.121068

  日期：2020.1

  The influence of the bulky trimethylsilyl substituent on the selectivity of metallation of dimethylaniline, anisole and 1-dimethylaminonaphthalene is studied. The neighboring SiMe3 group forces dimethylamino and methoxy groups to occupy a conformation with an unshared electron pair turned towards silicon atom. This forced conformation prevents NMe2 and OMe groups from providing the DOM-effect, thus facilitating meta-metallation with the use of bulky LiCKOR. While the inverted NMe2 group completely suppresses ortho-metallation, the less bulky and more electron withdrawing OMe group demonstrates more rotation freedom allowing selective ortho-metallation with smaller reagents such as n-BuLi or tert-BuLi. (C) 2019 Elsevier B.V. All rights reserved.