1,3,5,7-tetramethyl-1,3,5,7-tetrasilaadamantane | 17995-33-4

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 1,3,5,7-tetramethyl-1,3,5,7-tetrasilaadamantane
• 英文别名: 1,3,5,7-Tetramethyl-tetrasila-adamantan；1,3,5,7-Tetramethyl-1,3,5,7-tetrasila-adamantan；1,3,5,7-tetramethyl-1,3,5,7-tetrasilatricyclo[3.3.1.13,7]decane
• CAS: 17995-33-4
• 化学式: C₁₀H₂₄Si₄
• 分子量: 256.643
• InChiKey: XMNIPURNPMVXKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.58
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,3,5,7-tetramethyl-1,3,5,7-tetrasilaadamantane 在 一氯化碘 作用下， 以 二氯甲烷 为溶剂， 反应 45.0h， 生成 trifluoro-methanesulfonic acid 3,5-dimethyl-7-trifluoromethanesulfonyloxy-1,3,5,7-tetrasila-tricyclo[3.3.1.1^3,7]dec-1-yl ester
  参考文献：
  名称：

  1-Triflato-3,5,7-trimethyl-1,3,5,7-tetrasilaadamantane and 1,3-bis-triflato-5,7-dimethyl-1,3,5,7-tetrasilaadamantane; synthesis, complexation study and X-ray structure of 1-hydroxy-3,5,7-trimethyl-1,3,5,7-tetrasilaadamantane

  摘要：

  The symmetrical 1,3,5,7-tetramethyl-1,3,5,7-tetrasilaadamantane (1) reacts with 1.5 molar equivalents of ICl-AgOTf at room temperature to furnish the hitherto unknown 1-triflato-3,5,7-trimethyl-1,3,5,7-tetrasilaadamantane (9) chemoselectively, in near quantitative yields. The treatment of 9 with 2 mol equivalents of ICl-AgOTf affords the bis-triflate 10 in high yields. Control experiments showed that reaction of 1 with ICl (1 mol equivalents) -CCl4 is sluggish, giving 18% conversion to 1-chloro-3,5,7-trimethyl-1,3,5,7-tetrasilaadamantane (2) after 23 h at room temperature. Addition of AlBr3 catalyzes the process, allowing 73%, conversion after 21 h at room temperature. The ICI-AgOTf reagent eliminates the need to prepare and isolate 2 as an intermediate for the synthesis of 9. In silicon NMR spectra, the Si-29 Si-OTf resonance of 10 is slightly upfield compared with that of 9. Treatment of 9 with a saturated solution of B(C6F5)(3) in CH2Cl2 at room temperature shows only minor deshielding at silicon as determined by Si-29-NMR spectroscopy. Attempts to generate donor-acceptor complexes by treatment of 9 with AI(OTf)(3)-CD3CN and with liquid BCl3 gave no notable changes in the Si-OTf NMR chemical shift. In attempts to grow crystals from 9 and 10, white crystals suitable for X-ray analysis were obtained from a sample of 9, the molecular structure of which was shown to be 1-hydroxy-3,5,7-trimethyl-1,3,5,7-tetra-silaadamantane (11), generated by hydrolysis of the Si-OTf bond. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(02)01642-x
• 作为产物：
  描述：

  四甲基硅烷 生成 1,3,5,7-tetramethyl-1,3,5,7-tetrasilaadamantane
  参考文献：
  名称：

  Fritz,G. et al., Angewandte Chemie, 1970, vol. 82, p. 445 - 446

  摘要：

  DOI：

文献信息

• Fritz, Gerhard, Angewandte Chemie, 1987, vol. 99, # 11, p. 1150 - 1171
  作者：Fritz, Gerhard

  DOI：——

  日期：——
• Kovacs, Ilona; Magull, Joerg; Fritz, Gerhard, Bulletin de la Societe Chimique de France, 1995, vol. 132, p. 585 - 589
  作者：Kovacs, Ilona、Magull, Joerg、Fritz, Gerhard

  DOI：——

  日期：——
• Reactivity studies of bridgehead organosilicon compounds with nucleophilic reagents
  作者：G. D. Homer、L. H. Sommer

  DOI：10.1021/ja00804a026

  日期：1973.11
• FRITZ, G.;NEUTZNER, J.;VOLK, H., Z. ANORG. UND ALLG. CHEM., 1983, 497, N 2, 21-55
  作者：FRITZ, G.、NEUTZNER, J.、VOLK, H.

  DOI：——

  日期：——
• FRITZ, G.;HONOLD, J., Z. ANORG. UND ALLG. CHEM., 556,(1988) N 1, 23-56
  作者：FRITZ, G.、HONOLD, J.

  DOI：——

  日期：——

表征谱图