1-氯-1-(4-甲氧基苯基)硅杂环丁烷 | 251453-07-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 1-氯-1-(4-甲氧基苯基)硅杂环丁烷
• 中文别名: 1-(4-甲氧基苯基)-1-氯硅基环丁烷；1-(4-甲氧基苯基)-1-氯硅杂环丁烷
• 英文名称: 1-chloro-1-(4'-methoxyphenyl)silacyclobutane
• 英文别名: 1-(4-Methoxyphenyl)-1-chlorosilacyclobutane；1-chloro-1-(4-methoxyphenyl)siletane
• CAS: 251453-07-3
• 化学式: C₁₀H₁₃ClOSi
• mdl: MFCD09910002
• 分子量: 212.751
• InChiKey: AAWBPQWOJOCPHO-UHFFFAOYSA-N

物化性质

• 沸点：
  100°C/0/1mmHg
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.89
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• TSCA：
  No
• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  1-氯-1-(4-甲氧基苯基)硅杂环丁烷 在 allyl(cyclopentadiene)palladium(II) 、 20% palladium hydroxide on charcoal 、 (11bS)-N,N-bis((S)-1-Phenylethyl)-8,9,10,11,12,13,14,15-octahydrodinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-amine 、 氢气 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 35.0 ℃ 、101.33 kPa 条件下， 反应 98.5h， 生成 dimethyl (1R,2S,3S)-1-(4-methoxyphenyl)-1-methylsilinane-2,3-dicarboxylate
  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
• 作为产物：
  描述：

  1，1-二氯硅基环丁烷 、 4-甲氧基苯基溴化镁 以 四氢呋喃 、 乙醚 为溶剂， 生成 1-氯-1-(4-甲氧基苯基)硅杂环丁烷
  参考文献：
  名称：

  Palladium-Catalyzed Enantioselective Desymmetrization of Silacyclobutanes: Construction of Silacycles Possessing a Tetraorganosilicon Stereocenter

  摘要：

  A palladium-catalyzed desymmetrization of alkyne-tethered silacyclobutanes to give silacycles possessing a tetraorganosilicon stereocenter has been developed, and high chemo- and enantioselectivities have been achieved by the use of a newly synthesized chiral phosphoramidite ligand.

  DOI：

  10.1021/ja208621x

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.