di-t-butyl (S)-2-(3-cyclohexyl-2-(hydroxymethyl)propyl)malonate | 1353991-19-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: di-t-butyl (S)-2-(3-cyclohexyl-2-(hydroxymethyl)propyl)malonate
• CAS: 1353991-19-1
• 化学式: C₂₁H₃₈O₅
• 分子量: 370.53
• InChiKey: UZQRXBCMIYRKBU-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.26
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  72.83
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  在 sodium tetrahydroborate 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 0.5h， 以70%的产率得到di-t-butyl (S)-2-(3-cyclohexyl-2-(hydroxymethyl)propyl)malonate
  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