3-methylene-1,1-diphenylsilacyclobutane | 172946-14-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 3-methylene-1,1-diphenylsilacyclobutane
• 英文别名: 3-Methylidene-1,1-diphenylsiletane
• CAS: 172946-14-4
• 化学式: C₁₆H₁₆Si
• 分子量: 236.389
• InChiKey: JSJPCRYZNXHBQT-UHFFFAOYSA-N

物化性质

• 沸点：
  310.0±35.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.82
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  5-oxohexanal 、 3-methylene-1,1-diphenylsilacyclobutane 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以32%的产率得到1-Methyl-3-methylidene-8-oxabicyclo[3.2.1]octane
  参考文献：
  名称：

  Preparation of 3-Methylenesilacyclobutane and its Use in Organic Synthesis

  摘要：

  Treatment of 3-methylene-1,1-diphenylsilacyclobutane (1a) with dihalo-methyllithium provided ring expanded 2-halo-4-methylenesilacyclopentane. Heating a mixture of In and carbonyl compound such as phCHO or PHCOMe at reflux in 1,2-dichloroethane afforded S-methylene-1,1-diphenyl-2-oxa-1-silacyclohexane which was converted into 3-methylene-15-alkanediol monomethyl ether upon treatment with dimethyl acetal in the presence of Lewis acid catalyst Treatment of ketoaldehyde (PhCOCH(2)CH(2)CHO) with 1a under BF3 . OEt(2) catalysis gave 3-methylene-1-phenyl-8-oxabicyclo[3.2.1]octane in one pot.

  DOI：

  10.1016/0040-4039(95)01710-y
• 作为产物：
  描述：

  3-氯-2-氯甲基丙烯 、 苯基溴化镁 在 碘 、 溴化乙啶 、 magnesium 作用下， 生成 3-methylene-1,1-diphenylsilacyclobutane
  参考文献：
  名称：

  Preparation of 3-Methylenesilacyclobutane and its Use in Organic Synthesis

  摘要：

  Treatment of 3-methylene-1,1-diphenylsilacyclobutane (1a) with dihalo-methyllithium provided ring expanded 2-halo-4-methylenesilacyclopentane. Heating a mixture of In and carbonyl compound such as phCHO or PHCOMe at reflux in 1,2-dichloroethane afforded S-methylene-1,1-diphenyl-2-oxa-1-silacyclohexane which was converted into 3-methylene-15-alkanediol monomethyl ether upon treatment with dimethyl acetal in the presence of Lewis acid catalyst Treatment of ketoaldehyde (PhCOCH(2)CH(2)CHO) with 1a under BF3 . OEt(2) catalysis gave 3-methylene-1-phenyl-8-oxabicyclo[3.2.1]octane in one pot.

  DOI：

  10.1016/0040-4039(95)01710-y

文献信息

• Preparation of 3-Methylenesilacyclobutane and its Use in Organic Synthesis
  作者：Kenji Okada、Kozo Matsumoto、Koichiro Oshima、Kiitiro Utimoto

  DOI：10.1016/0040-4039(95)01710-y

  日期：1995.10

  Treatment of 3-methylene-1,1-diphenylsilacyclobutane (1a) with dihalo-methyllithium provided ring expanded 2-halo-4-methylenesilacyclopentane. Heating a mixture of In and carbonyl compound such as phCHO or PHCOMe at reflux in 1,2-dichloroethane afforded S-methylene-1,1-diphenyl-2-oxa-1-silacyclohexane which was converted into 3-methylene-15-alkanediol monomethyl ether upon treatment with dimethyl acetal in the presence of Lewis acid catalyst Treatment of ketoaldehyde (PhCOCH(2)CH(2)CHO) with 1a under BF3 . OEt(2) catalysis gave 3-methylene-1-phenyl-8-oxabicyclo[3.2.1]octane in one pot.