1-α-naphthyl-1-silacyclobutane

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-α-naphthyl-1-silacyclobutane
• 英文别名: 1-naphthalen-1-ylsiletane
• 化学式: C₁₃H₁₄Si
• 分子量: 198.34
• InChiKey: MHJATRLUUZUBMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.68
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 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：

  1-α-naphthyl-1-silacyclobutane 、 2,3-苯并-1,1-二苯基-1-硅杂-2-环丁烯 在 bis(1,5-cyclooctadiene)nickel (0) 、 tris(3,5-dimethoxyphenyl)phosphine 作用下， 以 甲苯 为溶剂， 以97 %的产率得到1-(naphthalen-1-yl)-5,5-diphenyl-1,2,3,4,5,6-hexahydrobenzo[b][1,5]disilocine
  参考文献：
  名称：

  Ring Expansion toward Disila‐carbocycles via Highly Selective C−Si/C−Si Bond Cross‐Exchange

  摘要：

  Herein, we successfully inhibited the preferential homodimerization and C−Si/Si−H bond cross‐exchange of benzosilacyclobutenes and monohydro‐silacyclobutanes and achieved the first highly selective C−Si/C−Si bond cross‐exchange reaction by deliberately tuning the Ni‐catalytic system, which constitutes a powerful and atom‐economical ring expansion method for preparing medium‐sized cyclic compounds bearing two silicon atoms at the ring junction, which are otherwise inaccessible. The DFT calculation explicitly elucidated the pivotal role of Si−H bond at silacyclobutanes and the high ring strain of two substrates in realizing the two C−Si bonds cleavage and reformation in the catalytic cycle.

  DOI：

  10.1002/anie.202319187
• 作为产物：
  描述：

  1-α-naphthyl-1-chloro-1-silacyclobutane 在 环己氯化镁 作用下， 反应 4.0h， 以33%的产率得到1-cyclohexyl-1-(α-naphthyl)silacyclobutane
  参考文献：
  名称：

  Anomalous reaction of sterically hindered grignard reagents with 1-?-naphthyl-1-chloro-1-silacyclobutane

  摘要：

  DOI：

  10.1007/bf00952935

文献信息

• BERTRAND, G.;DUBAC, J.;MAZEROLLES, P.;ANCELLE, J., NOUV. J. CHIM., 1982, 6, N 7-8, 381-386
  作者：BERTRAND, G.、DUBAC, J.、MAZEROLLES, P.、ANCELLE, J.

  DOI：——

  日期：——
• USHAKOV, N. V.;PRITULA, N. A.;VDOVIN, V. M., IZV. AN CCCP. CEP. XIM., 1986, N 2, 434-437
  作者：USHAKOV, N. V.、PRITULA, N. A.、VDOVIN, V. M.

  DOI：——

  日期：——
• Anomalous reaction of sterically hindered grignard reagents with 1-?-naphthyl-1-chloro-1-silacyclobutane
  作者：N. V. Ushakov、N. A. Pritula、V. M. Vdovin

  DOI：10.1007/bf00952935

  日期：1986.2
• Ring Expansion toward Disila‐carbocycles via Highly Selective C−Si/C−Si Bond Cross‐Exchange
  作者：Min Liu、Nuo Yan、Haowen Tian、Bo Li、Dongbing Zhao

  DOI：10.1002/anie.202319187

  日期：2024.4.15

  Herein, we successfully inhibited the preferential homodimerization and C−Si/Si−H bond cross‐exchange of benzosilacyclobutenes and monohydro‐silacyclobutanes and achieved the first highly selective C−Si/C−Si bond cross‐exchange reaction by deliberately tuning the Ni‐catalytic system, which constitutes a powerful and atom‐economical ring expansion method for preparing medium‐sized cyclic compounds bearing two silicon atoms at the ring junction, which are otherwise inaccessible. The DFT calculation explicitly elucidated the pivotal role of Si−H bond at silacyclobutanes and the high ring strain of two substrates in realizing the two C−Si bonds cleavage and reformation in the catalytic cycle.