dimethyl (1S)-1-(4-methoxyphenyl)-1-methyl-3,4-dihydro-2H-siline-5,6-dicarboxylate | 1335224-94-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: dimethyl (1S)-1-(4-methoxyphenyl)-1-methyl-3,4-dihydro-2H-siline-5,6-dicarboxylate
• CAS: 1335224-94-6
• 化学式: C₁₇H₂₂O₅Si
• 分子量: 334.444
• InChiKey: YPJIGHFONCOBFU-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.96
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimethyl (1S)-1-(4-methoxyphenyl)-1-methyl-3,4-dihydro-2H-siline-5,6-dicarboxylate 在 20% palladium hydroxide on charcoal 、 氢气 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以79%的产率得到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-氯-1-(4-甲氧基苯基)硅杂环丁烷 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 四氢呋喃 、 乙醚 、 甲苯 为溶剂， 反应 52.5h， 生成 dimethyl (1S)-1-(4-methoxyphenyl)-1-methyl-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

文献信息

• 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.