8-[fluoro-methyl-[methyl(diphenyl)silyl]silyl]-N,N-dimethylnaphthalen-1-amine | 223432-69-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 8-[fluoro-methyl-[methyl(diphenyl)silyl]silyl]-N,N-dimethylnaphthalen-1-amine
• CAS: 223432-69-7
• 化学式: C₂₆H₂₈FNSi₂
• 分子量: 429.684
• InChiKey: FJLZWDDMFOTOGS-UHFFFAOYSA-N

物化性质

• 沸点：
  472.8±27.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.63
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-[fluoro-methyl-[methyl(diphenyl)silyl]silyl]-N,N-dimethylnaphthalen-1-amine 在 四(三苯基膦)钯 、 二苯基乙炔 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以76%的产率得到二苯基甲基硅烷氟
  参考文献：
  名称：

  Synthesis, structure, and reactivity of 1,ω-bis(pseudo-pentacoordinated) 1,ω-difluoro-oligosilanes bearing 8-(dimethylamino)-1-naphthyl groups

  摘要：

  1,omega-Bis[8-(dimethylamino)-1-naphthyl]-1,omega-difluorotrisilane 1 (omega = 3) and tetrasilane 2 (omega = 4) have been prepared. The X-ray crystallography of dl-1 and meso-1 shows unsymmetrical structures having different coordination modes at the two terminal silicons. The unsymmetrical nature of the structure of 1 can also be observed by solid state CP/MAS NMR spectroscopy. Trisilane 1 is thermochemically labile and undergoes facile degradation at 145 degrees C, but is photochemically stable under irradiation of its benzene solution with a 6 W-low pressure mercury lamp, making a sharp contrast to the behavior of their tetracoordinate counterparts containing naphthyl groups which are thermochemically stable but photochemically active. Tetrasilane 2 undergoes a Pd(0)-catalyzed alpha-elimination of a fluorosilane moiety at the two pseudo-pentacoordinated silicon atoms to form the 1,2-difluorodisilane, which is trapped with diphenylacetylene as a double-silylation product. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(98)00973-5
• 作为产物：
  描述：

  [1-(二甲氨基)-8-萘基]锂 、 1,1-difluoro-1,2-dimethyl-2,2-diphenyldisilane 生成 8-[fluoro-methyl-[methyl(diphenyl)silyl]silyl]-N,N-dimethylnaphthalen-1-amine
  参考文献：
  名称：

  表现为 Sila-Ylides 的分子内碱基配位亚甲硅烷

  摘要：

  带有 8-氨基-或 8-膦基-1-萘基的二价硅物质已被证明在二苯乙炔存在下表现为亲核硅-叶立德，以提供含有烯基阴离子和铵或鏻阳离子部分的两性离子中间体。这些齐特离子中间体的反应途径已被阐明高度依赖于阳离子中心的特性，如 N 和 P。

  DOI：

  10.1080/10426500212275

文献信息

• Thermolysis of bis(pentacoordinate) silicon compound bearing two 1-fluorodisilanyl units at 4- and 8-positions on 1,5-bis(dimethylamino)naphthalene ring: construction of disilapyrene skeleton and cyclophane-shaped siloxane dimer
  作者：Tomoyuki Saeki、Akio Toshimitsu、Kohei Tamao

  DOI：10.1016/s0022-328x(03)00376-0

  日期：2003.11

  The thermolysis of a bis(pentacoordinate) silicon compound having two pentacoordinate silicon units at the 4- and 8-positions on the 1,5-bis(dimethylamino)naphthalene ring in the presence of diphenylacetylene affords a 1,6-dihydro-1,6-disilapyrene derivative. This reaction might proceed through a two-site silylene trapping with two acetylene molecules accompanied by an amino group migration from the

  在二苯乙炔的存在下，对在1,5-双（二甲基氨基）萘环的4和8位具有两个五配位硅单元的双（五配位）硅化合物进行热解可得到1,6-二氢-1， 6-二硅吡re衍生物。该反应可通过用两个乙炔分子捕获两个位点的甲硅烷基进行，伴随着一个氨基从萘基碳原子迁移到硅原子的迁移。每个硅原子上的二甲基氨基都可以轻松转换成各种官能团。二硅吡re衍生物之一，双（硅烷醇），通过使用二环己基碳二亚胺的脱氢缩合反应而二聚，以76％的收率形成环烷形分子。
• Wurtz-type Coupling Reaction of<i>Pseudo</i>-pentacoordinate Halodisilanes Using Magnesium: Enhanced Reactivity of the Silicon-Halogen Bond by Intramolecular Amine-coordination to Silicon
  作者：Kohei Tamao、Masahiro Asahara、Tomoyuki Saeki、Akio Toshimitsu

  DOI：10.1246/cl.1999.335

  日期：1999.4

  A 2,3-bis(pseudo-pentacoordinate) tetrasilane was obtained by the reductive dimerization of 1-[8-(dimethylamino)-1-naphthyl]-1-chlorodisilane using magnesium, and also from the analogous 1-fluorodisilane using a mixture of magnesium and magnesium bromide.

  通过镁还原二聚化1-[8-(二甲基氨基)-1-萘基]-1-氯二硅烷，以及通过镁和溴化镁的混合物还原二聚化类似的1-氟二硅烷，可以得到2,3-双（伪五元）四硅烷。