Ethyl 4,4-diphenyl-5,6-dihydrosilolo[3,2-b]furan-2-carboxylate | 1430235-59-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: Ethyl 4,4-diphenyl-5,6-dihydrosilolo[3,2-b]furan-2-carboxylate
• 英文别名: ethyl 4,4-diphenyl-5,6-dihydrosilolo[3,2-b]furan-2-carboxylate
• CAS: 1430235-59-8
• 化学式: C₂₁H₂₀O₃Si
• 分子量: 348.474
• InChiKey: RFPYXCXEOYCBTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.48
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  Ethyl 5-(2-diphenylsilylethyl)furan-2-carboxylate 在 降冰片烯 、 1,10-菲罗啉 、 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以88%的产率得到Ethyl 4,4-diphenyl-5,6-dihydrosilolo[3,2-b]furan-2-carboxylate
  参考文献：
  名称：

  Fused Heteroaromatic Dihydrosiloles: Synthesis and Double-Fold Modification

  摘要：

  An efficient method for the synthesis of fused heteroaromatic dihydrosiloles via Ni-catalyzed hydrosilylation/intramolecular Ir-catalyzed dehydrogenative coupling of the Si-H bond with the heteroaromatic C-H bond has been developed. The method is efficient for both electron-deficient and -rich heterocycles. It exhibits high functional group tolerance and good regioselectivity. Fused heteroaromatic dihydrosiloles can be smoothly halogenated and then oxidized or arylated. Application of these transformations allows obtaining highly functionallzed heteroaromatic structures. A gram-scale synthesis of dihydropyridinosilole has also been accomplished using reduced amounts of Ni- and Ir-catalysts.

  DOI：

  10.1021/ol400977r

文献信息

• Fused Heteroaromatic Dihydrosiloles: Synthesis and Double-Fold Modification
  作者：Alexey Kuznetsov、Yoshiharu Onishi、Yoshihiro Inamoto、Vladimir Gevorgyan

  DOI：10.1021/ol400977r

  日期：2013.5.17

  An efficient method for the synthesis of fused heteroaromatic dihydrosiloles via Ni-catalyzed hydrosilylation/intramolecular Ir-catalyzed dehydrogenative coupling of the Si-H bond with the heteroaromatic C-H bond has been developed. The method is efficient for both electron-deficient and -rich heterocycles. It exhibits high functional group tolerance and good regioselectivity. Fused heteroaromatic dihydrosiloles can be smoothly halogenated and then oxidized or arylated. Application of these transformations allows obtaining highly functionallzed heteroaromatic structures. A gram-scale synthesis of dihydropyridinosilole has also been accomplished using reduced amounts of Ni- and Ir-catalysts.