1-(trimethyltin)-8-dimethylaminonaphthalene | 89333-62-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(trimethyltin)-8-dimethylaminonaphthalene
• 英文别名: N,N-dimethyl-8-trimethylstannylnaphthalen-1-amine
• CAS: 89333-62-0
• 化学式: C₁₅H₂₁NSn
• 分子量: 334.048
• InChiKey: PZZWKGSYJUMHIE-UHFFFAOYSA-N

物化性质

• 沸点：
  348.4±34.0 °C(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：

  1-(trimethyltin)-8-dimethylaminonaphthalene 、 三甲基氯化锡 生成 四甲基锡
  参考文献：
  名称：

  JASTRZEBSKI, J. T. B. H.;KNAAP, C. T.;KOTEN, G., J. ORGANOMET. CHEM., 1983, 255, N 3, 287-293

  摘要：

  DOI：
• 作为产物：
  描述：

  三甲基氯化锡 、 [1-(二甲氨基)-8-萘基]锂 以 乙醚 为溶剂， 以76%的产率得到1-(trimethyltin)-8-dimethylaminonaphthalene
  参考文献：
  名称：

  Intramolecular penta- and hexacoordinate tetraorganotin compounds containing the 8-(dimethylamino)-1-naphthyl ligand

  摘要：

  A series of novel tetraorganotin compounds, Sn[(8-Me2N)C10H6-1]RR'R'', containing the 8-(dimethyl-amino)-1-naphthyl group, has been synthesized and characterized. For one of these compounds (R = R' = R'' = Ph) the molecular structure in the solid state has been determined by X-ray diffraction methods: C30H27NSn, monoclinic, space group P2(1/a), and a = 24.8365 (7) angstrom, b = 12.3785 (4) angstrom, c = 17.1997 (6) angstrom, beta = 109.102 (3)-degrees, and Z = 8; final R = 0.031 for 7920 observed reflections. The tin center has a distorted trigonal-bipyramidal coordination geometry with the nitrogen atom (Sn-N = 2.884 (3) angstrom) and one of the phenyl groups at approximately axial positions. The structure of this tetraorganotin compound was compared with that of [8-(dimethylamino)-1-naphthyl]methylphenyltin bromide, for which the structure in the solid state has been determined by X-ray diffraction methods: C19H20BrNSn, monoclinic, space group P2(1/a), with a = 16.356 (3) angstrom, b = 13.922 (4) angstrom, c = 8.082 (2) angstrom, beta = 102.91 (2); and Z = 4; final R = 0.042 for 2804 observed reflections. The tin center has a trigonal-bipyramidal coordination geometry in which the organic ligands occupy the equatorial sites, while the more electronegative Br and N ligands are in the axial positions. H-1, C-13, and Sn-119 NMR spectra of the tetraorganotin compounds show that, most likely as a result of the fixed orientation of the nitrogen atom with respect to the tin atom, also in solution these species are pentacoordinate. This may be concluded from the observations that (i) the H-1 and C-13 NMR spectra of chiral [8-(dimethylamino)-1-naphthyl]methylphenylneopentyltin show two resonances for the diastereotopic NMe2 group, indicating that pyramidal inversion of the nitrogen atom is blocked, and (ii) the increase of the 1J(Sn-119-C-13(1)naphthyl) values compared to those of unsubstituted naphthyltin compounds points to a coordination number larger than 4. Moreover, the tetraorganotin compounds show an enhanced reactivity in redistribution reactions, which may be the result of the labilization of the Sn-C bond in a trans position with respect to the coordinating nitrogen atom.

  DOI：

  10.1021/om00050a025

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
• Intramolecular penta- and hexacoordinate tetraorganotin compounds containing the 8-(dimethylamino)-1-naphthyl ligand
  作者：Johann T. B. H. Jastrzebski、Jaap Boersma、Peter M. Esch、Gerard Van Koten

  DOI：10.1021/om00050a025

  日期：1991.4

  A series of novel tetraorganotin compounds, Sn[(8-Me2N)C10H6-1]RR'R'', containing the 8-(dimethyl-amino)-1-naphthyl group, has been synthesized and characterized. For one of these compounds (R = R' = R'' = Ph) the molecular structure in the solid state has been determined by X-ray diffraction methods: C30H27NSn, monoclinic, space group P2(1/a), and a = 24.8365 (7) angstrom, b = 12.3785 (4) angstrom, c = 17.1997 (6) angstrom, beta = 109.102 (3)-degrees, and Z = 8; final R = 0.031 for 7920 observed reflections. The tin center has a distorted trigonal-bipyramidal coordination geometry with the nitrogen atom (Sn-N = 2.884 (3) angstrom) and one of the phenyl groups at approximately axial positions. The structure of this tetraorganotin compound was compared with that of [8-(dimethylamino)-1-naphthyl]methylphenyltin bromide, for which the structure in the solid state has been determined by X-ray diffraction methods: C19H20BrNSn, monoclinic, space group P2(1/a), with a = 16.356 (3) angstrom, b = 13.922 (4) angstrom, c = 8.082 (2) angstrom, beta = 102.91 (2); and Z = 4; final R = 0.042 for 2804 observed reflections. The tin center has a trigonal-bipyramidal coordination geometry in which the organic ligands occupy the equatorial sites, while the more electronegative Br and N ligands are in the axial positions. H-1, C-13, and Sn-119 NMR spectra of the tetraorganotin compounds show that, most likely as a result of the fixed orientation of the nitrogen atom with respect to the tin atom, also in solution these species are pentacoordinate. This may be concluded from the observations that (i) the H-1 and C-13 NMR spectra of chiral [8-(dimethylamino)-1-naphthyl]methylphenylneopentyltin show two resonances for the diastereotopic NMe2 group, indicating that pyramidal inversion of the nitrogen atom is blocked, and (ii) the increase of the 1J(Sn-119-C-13(1)naphthyl) values compared to those of unsubstituted naphthyltin compounds points to a coordination number larger than 4. Moreover, the tetraorganotin compounds show an enhanced reactivity in redistribution reactions, which may be the result of the labilization of the Sn-C bond in a trans position with respect to the coordinating nitrogen atom.
• JASTRZEBSKI, J. T. B. H.;KNAAP, C. T.;KOTEN, G., J. ORGANOMET. CHEM., 1983, 255, N 3, 287-293
  作者：JASTRZEBSKI, J. T. B. H.、KNAAP, C. T.、KOTEN, G.

  DOI：——

  日期：——