tetrakis(2-stannylethyl)silane | 314727-95-2

• 分子结构分类: 有机化合物 - 有机盐 - 有机金属盐
• 英文名称: tetrakis(2-stannylethyl)silane
• 英文别名: tetrakis(2-stannylethylene)silane
• CAS: 314727-95-2
• 化学式: C₈H₂₈SiSn₄
• 分子量: 627.236
• InChiKey: SNMUNHBOTFAPLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.43
• 重原子数：
  13.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  tetrakis(2-stannylethyl)silane 、 N-(2-tert-butyldimethylsiloxyethyl)acrylamide 在 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile 作用下， 以 甲苯 为溶剂， 以76%的产率得到tetrakis(2-[tris(2-[N-(2-tert-butyldimethylsiloxyethyl)carbamido]ethyl)stannyl]ethyl)silane
  参考文献：
  名称：

  Synthesis and Characterization of Water-Soluble Tin-Based Metallodendrimers

  摘要：

  Introduction of ionic or nonionic hydrophilic terminal groups into the hydrophobic dendritic backbone Si(CH(2)CH(2)Sn)(4) led to a variety of first-generation water-soluble tin-based dendrimers. Functionalization of the hydridotin dendrimer Si(CH(2)CH(2)SnH(3))(4) (1) via 12-fold hydrostannation reaction of acrylic acid derivatives served as the key step. 1 reacts with methyl acrylate to give Si[CH(2)CH(2)Sn(CH(2)CH(2)COOCH(3))(3)](4) (2), which by means of alkaline hydrolysis was converted into the water-soluble carboxylate-terminated dendrimers Si[CH(2)CH(2)Sn(CH(2)CH(2)COOM)(3)](4) [M = Na (3), K (4)]. Reduction of 2 afforded the dendritic polyalcohol Si[CH(2)CH(2)Sn(CH(2)CH(2)CH(2)OH)(3)](4) (5). A clearly enhanced water solubility due to nonionic surface functionalization of 2 was obtained by its reaction with 2-aminoethanol, formally yielding Si[CH(2)CH(2)Sn(CH(2)CH(2)CONHCH(2)CH(2)OH)(2.5)(CH(2)CH(2)COOCH(3))(0.5)](4) (6). The hydrostannation. of O-protected N-(2-hydroxyethyl)acrylamides by 1, however, gave the monodisperse derivatives Si[CH(2)CH(2)Sn(CH(2)CH(2)CONHCH(2)CH(2)OR)(3)](4) [R = CO(2)(t)Bu (7), SiMe(2)(t)Bu (8)]; deprotection of 8 with tetra-n-butylammonium fluoride yielded the water-soluble Si[CH(2)CH(2)Sn(CH(2)CH(2)CONHCH(2)CH(2)OH)(3)](4) (9). Also via hydrostannation reaction by 1, the ester-substituted analogue Si[CH(2)CH(2)Sn(CH(2)CH(2)COOCH(2)CH(2)OH)(3)](4) (10), showing a clearly lower hydrolytic stability, and the homologous amide-substituted dendrimer Si[CH(2)CH(2)Sn(CH(2)CH(2)CONHCH(2)CH(2)OCH(2)CH(2)OH)(3)](4) (11) were synthesized. The new organotin dendrimers were characterized by elemental analysis, multinuclear NMR spectroscopy ((1)H, (13)C, (119)Sn), and mass spectrometry (MALDI-TOF, ESI). With respect to the potential use of water-soluble tin-based metallodendrimers as X-ray contrast agents, 6 was studied in vivo in mice, roughly estimating its LD(50) to 3 mmol Sn/kg body weight.

  DOI：

  10.1021/om021011z
• 作为产物：
  描述：

  tetrakis[2-(tribromostannyl)ethyl]silane 在 LiAlH₄ 作用下， 以 乙醚 为溶剂， 以90%的产率得到tetrakis(2-stannylethyl)silane
  参考文献：
  名称：

  Si(CH2CH2SnH3)4—a unique organotin hydride featuring 12 SnH units in a dendritic molecule. Single-crystal X-ray structures of tetrakis(2-stannylethylene)silane and tetrakis[2-(triphenylstannyl)ethylene]silane

  摘要：

  Fourfold hydrostannation of tetravinylsilane affords the first generation metallodendrimer Si(CH2CH2SnPh3)(4) (1). Selective bromination yields Si(CH2CH2SnBr3)(4) (2), which can be reduced by LiAlH4 to give Si(CH2CH2SnH3)(4) (3), containing 12 reactive Sn-H bonds. These novel dendritic organotin compounds were characterized by elemental analysis, spectroscopic studies (H-1-, C-13-, Sn-119-NMR; IR) and by single-crystal X-ray structure determination. The molecular structures of 1 and 3 reveal increased conformational constraint in 1; the average Sn-H bond length in 3 is 1.60(7) Angstrom. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(00)00188-1