1,1-di-tert-butyl-2-(4-tolylimino)-trans-3,4-dimethylsilacyclobutane

• 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: 1,1-di-tert-butyl-2-(4-tolylimino)-trans-3,4-dimethylsilacyclobutane
• 英文别名: (3R,4R)-1,1-ditert-butyl-3,4-dimethyl-N-(4-methylphenyl)siletan-2-imine
• 化学式: C₂₀H₃₃NSi
• 分子量: 315.574
• InChiKey: PJZUCPOTYWGUIG-HZPDHXFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,1-di-tert-butyl-2-(4-tolylimino)-trans-3,4-dimethylsilacyclobutane 以 苯 为溶剂， 反应 192.0h， 以98%的产率得到1,1-di-tert-butyl-2--3,4-dimethylsilacyclobut-2-ene
  参考文献：
  名称：

  Stereospecific and Regioselective Isocyanide Insertions into Siliranes and Reactions of the Resulting Iminosilacyclobutanes

  摘要：

  The insertions of p-tolyl and tert-butyl isocyanide into siliranes yielded iminosilacyclobutanes with stereospecific retention of configuration. Monosubstituted siliranes underwent insertion into the more substituted Si-C bond of the ring, although this regioselectivity was eroded as substitution increased on the silirane ring. The iminosilacyclobutane products tautomerized thermally or in the presence of a palladium catalyst to yield the thermodynamically more stable aminosilacyclobutenes. Ring-expansion reactions of iminosilacyclobutanes were promoted by acids: treatment with aqueous copper sulfate produced an oxasilacyclopentane in high yield, whereas with trifluoroacetic acid, oxasilacyclohexanes were formed.

  DOI：

  10.1021/jo9816257
• 作为产物：
  描述：

  4-甲苯基异腈 、 trans-1,1-Di-tert-butyl-2,3-dimethylsiliran 以 苯 为溶剂， 反应 0.25h， 以86%的产率得到1,1-di-tert-butyl-2-(4-tolylimino)-trans-3,4-dimethylsilacyclobutane
  参考文献：
  名称：

  Stereospecific and Regioselective Isocyanide Insertions into Siliranes and Reactions of the Resulting Iminosilacyclobutanes

  摘要：

  The insertions of p-tolyl and tert-butyl isocyanide into siliranes yielded iminosilacyclobutanes with stereospecific retention of configuration. Monosubstituted siliranes underwent insertion into the more substituted Si-C bond of the ring, although this regioselectivity was eroded as substitution increased on the silirane ring. The iminosilacyclobutane products tautomerized thermally or in the presence of a palladium catalyst to yield the thermodynamically more stable aminosilacyclobutenes. Ring-expansion reactions of iminosilacyclobutanes were promoted by acids: treatment with aqueous copper sulfate produced an oxasilacyclopentane in high yield, whereas with trifluoroacetic acid, oxasilacyclohexanes were formed.

  DOI：

  10.1021/jo9816257

文献信息

• Stereospecific and Regioselective Isocyanide Insertions into Siliranes and Reactions of the Resulting Iminosilacyclobutanes
  作者：Phuc T. Nguyen、Wylie S. Palmer、K. A. Woerpel

  DOI：10.1021/jo9816257

  日期：1999.3.1

  The insertions of p-tolyl and tert-butyl isocyanide into siliranes yielded iminosilacyclobutanes with stereospecific retention of configuration. Monosubstituted siliranes underwent insertion into the more substituted Si-C bond of the ring, although this regioselectivity was eroded as substitution increased on the silirane ring. The iminosilacyclobutane products tautomerized thermally or in the presence of a palladium catalyst to yield the thermodynamically more stable aminosilacyclobutenes. Ring-expansion reactions of iminosilacyclobutanes were promoted by acids: treatment with aqueous copper sulfate produced an oxasilacyclopentane in high yield, whereas with trifluoroacetic acid, oxasilacyclohexanes were formed.