(R)-5-benzyltetrahydro-2H-pyran-2-one | 1353991-05-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (R)-5-benzyltetrahydro-2H-pyran-2-one
• 英文别名: (5R)-5-benzyloxan-2-one
• CAS: 1353991-05-5
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: UZIJRUIEROQNJH-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  在 sodium tetrahydroborate 、 三乙胺 、 三氟乙酸 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 15.5h， 生成 (R)-5-benzyltetrahydro-2H-pyran-2-one
  参考文献：
  名称：

  Powerful Amino Diol Catalyst for Effecting the Direct Asymmetric Conjugate Addition of Aldehydes to Acrylates

  摘要：

  Di-tert-butyl methylenemalonate (1) could be employed as a reactive equivalent of a three-carbon Michael acceptor such as acrylate in a direct asymmetric conjugate addition of aldehydes catalyzed by an axially chiral amino diol (S)-3a. Furthermore, acrylate, an unexplored and challenging substrate in enamine catalysis, has also been successfully employed in asymmetric conjugate addition reaction. Relatively inert acrylate is doubly activated by polyfluoroalkyl group of 2 and the hydroxyl group on the axially chiral amino diol catalyst (S)-3b, giving corresponding conjugate adducts in high yield with excellent enantiomeric excess. The obtained conjugate addition products were readily converted to synthetically useful and important chiral building blocks.

  DOI：

  10.1021/ja307668b

文献信息

• Powerful Amino Diol Catalyst for Effecting the Direct Asymmetric Conjugate Addition of Aldehydes to Acrylates
  作者：Taichi Kano、Fumitaka Shirozu、Matsujiro Akakura、Keiji Maruoka

  DOI：10.1021/ja307668b

  日期：2012.9.26

  Di-tert-butyl methylenemalonate (1) could be employed as a reactive equivalent of a three-carbon Michael acceptor such as acrylate in a direct asymmetric conjugate addition of aldehydes catalyzed by an axially chiral amino diol (S)-3a. Furthermore, acrylate, an unexplored and challenging substrate in enamine catalysis, has also been successfully employed in asymmetric conjugate addition reaction. Relatively inert acrylate is doubly activated by polyfluoroalkyl group of 2 and the hydroxyl group on the axially chiral amino diol catalyst (S)-3b, giving corresponding conjugate adducts in high yield with excellent enantiomeric excess. The obtained conjugate addition products were readily converted to synthetically useful and important chiral building blocks.