tert-butyl methyl (2-(tert-butyldimethylsiloxy)methyl-2-propen-1-yl)(2-methylphenyl)malonate | 1181693-05-9

• 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: tert-butyl methyl (2-(tert-butyldimethylsiloxy)methyl-2-propen-1-yl)(2-methylphenyl)malonate
• CAS: 1181693-05-9
• 化学式: C₂₅H₄₀O₅Si
• 分子量: 448.675
• InChiKey: GHYZAMSLJZSRBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.72
• 重原子数：
  31.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  tert-butyl methyl (2-(tert-butyldimethylsiloxy)methyl-2-propen-1-yl)(2-methylphenyl)malonate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 9.5h， 以68%的产率得到tert-butyl 5-methylene-2-oxo-3-(o-tolyl)tetrahydro-2H-pyran-3-carboxylate
  参考文献：
  名称：

  Stereoselective Synthesis of Spirooxindoles by Palladium-Catalyzed Decarboxylative Cyclization of γ-Methylidene-δ-valerolactones with Isatins

  摘要：

  A new synthetic method of spirooxindole derivatives has been developed by way of a palladium-catalyzed decarboxylative cyclization of gamma-methylidene-delta-valerolactones with isatins. By employing a newly prepared phosphoramidite ligand, the reaction proceeds smoothly with excellent diastereoselectivity. Preliminary results of its application to asymmetric catalysis using a chiral phosphoramidite ligand are also described.

  DOI：

  10.1021/ol901348f
• 作为产物：
  描述：

  tert-butyl methyl 2-methylphenylmalonate 、 2-(tert-butyldimethylsiloxy)methyl-2-propen-1-yl methanesulfonate 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 、 N,N-二甲基甲酰胺 为溶剂， 反应 86.33h， 以84%的产率得到tert-butyl methyl (2-(tert-butyldimethylsiloxy)methyl-2-propen-1-yl)(2-methylphenyl)malonate
  参考文献：
  名称：

  Stereoselective Synthesis of Spirooxindoles by Palladium-Catalyzed Decarboxylative Cyclization of γ-Methylidene-δ-valerolactones with Isatins

  摘要：

  A new synthetic method of spirooxindole derivatives has been developed by way of a palladium-catalyzed decarboxylative cyclization of gamma-methylidene-delta-valerolactones with isatins. By employing a newly prepared phosphoramidite ligand, the reaction proceeds smoothly with excellent diastereoselectivity. Preliminary results of its application to asymmetric catalysis using a chiral phosphoramidite ligand are also described.

  DOI：

  10.1021/ol901348f