Dimethyl-[8-(methyl-diphenyl-stannanyl)-naphthalen-1-yl]-amine | 133071-19-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Dimethyl-[8-(methyl-diphenyl-stannanyl)-naphthalen-1-yl]-amine
• 英文别名: N,N-dimethyl-8-[methyl(diphenyl)stannyl]naphthalen-1-amine
• CAS: 133071-19-9
• 化学式: C₂₅H₂₅NSn
• 分子量: 458.19
• InChiKey: WXTHUTBRDAZKMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.01
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  呋喃甲酰氯 、 Dimethyl-[8-(methyl-diphenyl-stannanyl)-naphthalen-1-yl]-amine 在 trans-Pd(Cl)[C(O)Ph](PPh3)2 作用下， 以 四氢呋喃 为溶剂， 以80%的产率得到2-呋喃基苯基酮
  参考文献：
  名称：

  钯催化交叉偶联中锡的芳基转移的分子内促进。

  摘要：

  有机锡试剂中相邻的叔氨基会加速钯催化的呋喃酰氯的芳基化作用一百倍。

  DOI：

  10.1039/c39920001440
• 作为产物：
  描述：

  苯基锂 、 {8-(dimethylamino)-1-naphthyl}methylphenyltin bromide 以 乙醚 为溶剂， 以91%的产率得到Dimethyl-[8-(methyl-diphenyl-stannanyl)-naphthalen-1-yl]-amine
  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

• 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.
• Intramolecular facilitation of aryl-transfer from tin in palladium-catalysed cross-coupling
  作者：John M. Brown、Mark Pearson、Johann T. B. H. Jastrzebski、Gerard van Koten

  DOI：10.1039/c39920001440

  日期：——

  A neighbouring tertiary amino-group in the organotin reagent accelerates the palladium-catalysed arylation of furoyl chloride by a hundredfold.

  有机锡试剂中相邻的叔氨基会加速钯催化的呋喃酰氯的芳基化作用一百倍。