1-ethyl-1-(4-methoxyphenyl)silacyclobutane | 1379659-31-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-ethyl-1-(4-methoxyphenyl)silacyclobutane
• 英文别名: 1-ethyl-1-(4-methoxyphenyl)siletane
• CAS: 1379659-31-0
• 化学式: C₁₂H₁₈OSi
• 分子量: 206.36
• InChiKey: WRZIZPNFXSVUHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.77
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-ethyl-1-(4-methoxyphenyl)silacyclobutane 、 丁炔二酸二甲酯 在 allyl(cyclopentadiene)palladium(II) 、 10,16-dimethyl-N,N-bis[(1S)-1-phenylethyl]-12,14-dioxa-13-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3(8),9,16,18(23)-hexaen-13-amine 作用下， 以 甲苯 为溶剂， 反应 14.0h， 以90%的产率得到dimethyl (1S)-1-ethyl-1-(4-methoxyphenyl)-3,4-dihydro-2H-siline-5,6-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：

  4-甲氧基苯基溴化镁 以 四氢呋喃 、 乙醚 为溶剂， 反应 71.0h， 生成 1-ethyl-1-(4-methoxyphenyl)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

• Rhodium‐Catalyzed Intermolecular Silylation of C _sp −H by Silacyclobutanes
  作者：Tao He、Bin Li、Lichuan Liu、Wenpeng Ma、Wei He

  DOI：10.1002/chem.202100084

  日期：2021.3.26

  The signature reactivity of silacyclobutane (SCB) is their cycloaddition reactions with various π bonds. Recently, the first cases were disclosed where SCBs reacted with both Csp2−H and Csp3−H σ bonds in an intramolecular fashion. Herein, it is reported that SCB is also an efficient reagent for Csp−H bond silylation. Thus, rhodium‐catalyzed intermolecular reactions between SCBs and terminal alkynes

  硅环丁烷（SCB）的特征反应性是它们与各种π键的环加成反应。最近，公开了第一种情况，其中SCB以分子内方式与C sp2- H和C sp3- Hσ键反应。在此，据报道SCB也是用于C sp -H键甲硅烷基化的有效试剂。因此，SCB和末端炔烃之间的铑催化的分子间反应产生了一系列对称且不对称的带有C sp -Si功能的四有机硅。初步研究表明，该反应不涉及环加成途径，而是直接激活C sp -H键。