dimethyl[2-((dimethylamino)methyl)phenyl]tin chloride | 148980-19-2

• 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: dimethyl[2-((dimethylamino)methyl)phenyl]tin chloride
• 英文别名: 1-[2-[chloro(dimethyl)stannyl]phenyl]-N,N-dimethylmethanamine
• CAS: 148980-19-2
• 化学式: C₁₁H₁₈ClNSn
• 分子量: 318.434
• InChiKey: KDJKVWVMPXLMRM-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 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′-(diphenylphosphino)ferrocene-1-carboxylic acid 、 dimethyl[2-((dimethylamino)methyl)phenyl]tin chloride 、 potassium tert-butylate 以 二氯甲烷 为溶剂， 以91%的产率得到dimethyl[2-((dimethylamino)methyl)phenyl]stannyl 1'-(diphenylphosphino)-1-ferrocenecarboxylate
  参考文献：
  名称：

  Preparation and structural characterization of simple and donor-substituted triorganostannyl 1′-(diphenylphosphino)-1-ferrocenecarboxylates and their P-chalcogenide derivatives

  摘要：

  Triorganotin chlorides Me3SnCl and (L-NC)Me2SnCl (LNC = 2-[(dimethylamino)methyl]phenyl) reacted with potassium 1'-(diphenylphosphino)-1-ferrocenecarboxylate to give the respective carboxylates, Ph(2)PfcCO(2)SnMe(3) (1) and Ph(2)PfcCO(2)SnMe(2)(LNC) (2; fc = ferrocene-1,1'-diyl), while the analogous triphenylstannyl derivative 3 resulted by condensation of Ph3SnOH with 1'-(diphenylphosphino)-1-ferrocenecarboxylic acid (Hdpf). Compounds 1 and 2 were smoothly oxidized with hydrogen peroxide or elemental sulfur to afford the corresponding P-chalcogen derivatives (P-oxides 1a and 2a; P-sulfides 1b and 2b). All compounds were characterized by multinuclear NMR, IR and mass spectroscopy, and the solid-state structures of 1, 1a, 2, 2a and 2b were determined by single-crystal X-ray diffraction. In the crystal structures of 1 and 1a, the tin atoms were found with distorted trigonal bipyramidal coordination environments completed by the C=O or P=O oxygens, respectively, from adjacent molecules, which in turn resulted in the formation of infinite linear assemblies. Tin atoms in 2, 2a, and 2b were found with trigonal bipyramidal surrounding as well, though with the donor substituent LNC assuming one of the axial donor sites. Compounds 2 and 2a crystallized as stoichiometric hydrates (2.1/2H(2)O, 2a.H2O), in which the water molecules served as hydrogen bond donors for the polar groups (C=O and P=O) and thus aided the formation of closed H-bonded assemblies; the structure of 2b was essentially molecular. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2009.09.042

文献信息

• Preparation and structural characterization of simple and donor-substituted triorganostannyl 1′-(diphenylphosphino)-1-ferrocenecarboxylates and their P-chalcogenide derivatives
  作者：Petr Štěpnička、Ivana Císařová、Aleš Růžička

  DOI：10.1016/j.jorganchem.2009.09.042

  日期：2010.1

  Triorganotin chlorides Me3SnCl and (L-NC)Me2SnCl (LNC = 2-[(dimethylamino)methyl]phenyl) reacted with potassium 1'-(diphenylphosphino)-1-ferrocenecarboxylate to give the respective carboxylates, Ph(2)PfcCO(2)SnMe(3) (1) and Ph(2)PfcCO(2)SnMe(2)(LNC) (2; fc = ferrocene-1,1'-diyl), while the analogous triphenylstannyl derivative 3 resulted by condensation of Ph3SnOH with 1'-(diphenylphosphino)-1-ferrocenecarboxylic acid (Hdpf). Compounds 1 and 2 were smoothly oxidized with hydrogen peroxide or elemental sulfur to afford the corresponding P-chalcogen derivatives (P-oxides 1a and 2a; P-sulfides 1b and 2b). All compounds were characterized by multinuclear NMR, IR and mass spectroscopy, and the solid-state structures of 1, 1a, 2, 2a and 2b were determined by single-crystal X-ray diffraction. In the crystal structures of 1 and 1a, the tin atoms were found with distorted trigonal bipyramidal coordination environments completed by the C=O or P=O oxygens, respectively, from adjacent molecules, which in turn resulted in the formation of infinite linear assemblies. Tin atoms in 2, 2a, and 2b were found with trigonal bipyramidal surrounding as well, though with the donor substituent LNC assuming one of the axial donor sites. Compounds 2 and 2a crystallized as stoichiometric hydrates (2.1/2H(2)O, 2a.H2O), in which the water molecules served as hydrogen bond donors for the polar groups (C=O and P=O) and thus aided the formation of closed H-bonded assemblies; the structure of 2b was essentially molecular. (C) 2009 Elsevier B.V. All rights reserved.