1-chloro-1-(2'-methylphenyl)silacyclobutane | 272439-73-3

• 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-chloro-1-(2'-methylphenyl)silacyclobutane
• 英文别名: 1-Chloro-1-(2-methylphenyl)siletane
• CAS: 272439-73-3
• 化学式: C₁₀H₁₃ClSi
• 分子量: 196.752
• InChiKey: YHXFQEZELKDHTI-UHFFFAOYSA-N

物化性质

• 沸点：
  255.9±10.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.79
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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-chloro-1-(2'-methylphenyl)silacyclobutane 、 2-硝基碘苯 在 bis(η3-allyl-μ-chloropalladium(II)) 四丁基氟化铵 、 三叔丁基膦 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以77%的产率得到1-甲基-2-(2-硝基苯基)苯
  参考文献：
  名称：

  Synthesis of Unsymmetrical Biaryls from Arylsilacyclobutanes

  摘要：

  [GRAPHICS]Aryl(fluoro)silacyclobutanes and aryl(chloro)silacyclobutanes have been found to undergo cross-coupling reactions with aryl iodides. The rate of reaction and extent of homocoupling were dramatically affected by the addition of ligands for the palladium catalyst. With (t-Bu)(3)P a wide range of electronically and structurally diverse unsymmetrical biaryls have been prepared in good to excellent yields.

  DOI：

  10.1021/ol991054k
• 作为产物：
  描述：

  邻甲苯基溴化镁 、 1，1-二氯硅基环丁烷 以 四氢呋喃 、 乙醚 为溶剂， 反应 32.5h， 生成 1-chloro-1-(2'-methylphenyl)silacyclobutane
  参考文献：
  名称：

  Palladium-Catalyzed Desymmetrization of Silacyclobutanes with Alkynes: Enantioselective Synthesis of Silicon-Stereogenic 1-Sila-2-cyclohexenes and Mechanistic Considerations

  摘要：

  A palladium-catalyzed enantioselective desymmetrization of silacyclobutanes with alkynes has been developed to give silicon-stereogenic 1-sila-2-cyclohexenes with high enantioselectivity. The products thus obtained undergo further derivatizations with complete stereoselectivity, and a new catalytic cycle involving alkyne coordination (oxidative cyclization)-transmetalation (sigma-bond metathesis)-reductive elimination has also been proposed.

  DOI：

  10.1021/ol301191u

文献信息

• Synthesis of Unsymmetrical Biaryls from Arylsilacyclobutanes
  作者：Scott E. Denmark、Zhicai Wu

  DOI：10.1021/ol991054k

  日期：1999.11.1

  [GRAPHICS]Aryl(fluoro)silacyclobutanes and aryl(chloro)silacyclobutanes have been found to undergo cross-coupling reactions with aryl iodides. The rate of reaction and extent of homocoupling were dramatically affected by the addition of ligands for the palladium catalyst. With (t-Bu)(3)P a wide range of electronically and structurally diverse unsymmetrical biaryls have been prepared in good to excellent yields.
• Palladium-Catalyzed Desymmetrization of Silacyclobutanes with Alkynes: Enantioselective Synthesis of Silicon-Stereogenic 1-Sila-2-cyclohexenes and Mechanistic Considerations
  作者：Ryo Shintani、Kohei Moriya、Tamio Hayashi

  DOI：10.1021/ol301191u

  日期：2012.6.1

  A palladium-catalyzed enantioselective desymmetrization of silacyclobutanes with alkynes has been developed to give silicon-stereogenic 1-sila-2-cyclohexenes with high enantioselectivity. The products thus obtained undergo further derivatizations with complete stereoselectivity, and a new catalytic cycle involving alkyne coordination (oxidative cyclization)-transmetalation (sigma-bond metathesis)-reductive elimination has also been proposed.