1,1,1,3,3,3-hexafluoropropan-2-yl (R)-4-(1,3-dioxolan-2-yl)-5-phenylpentanoate | 1400943-32-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子
• 英文名称: 1,1,1,3,3,3-hexafluoropropan-2-yl (R)-4-(1,3-dioxolan-2-yl)-5-phenylpentanoate
• 英文别名: 1,1,1,3,3,3-hexafluoropropan-2-yl (4R)-4-(1,3-dioxolan-2-yl)-5-phenylpentanoate
• CAS: 1400943-32-9
• 化学式: C₁₇H₁₈F₆O₄
• 分子量: 400.318
• InChiKey: ZLGDEQJGBRNXOW-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1,1,1,3,3,3-hexafluoropropan-2-yl (R)-4-(1,3-dioxolan-2-yl)-5-phenylpentanoate 、 苯酚 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以70%的产率得到phenyl (R)-4-(1,3-dioxolan-2-yl)-5-phenylpentanoate
  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
• 作为产物：
  描述：

  1,1,1,3,3,3-六氟异丙基丙烯酸酯 在 [8-(hydroxydiphenylmethyl)-1,11-dimethoxy-6,7-dihydro-5H-dibenzo[c,e]azepin-4-yl]diphenylmethanol 、 对甲苯磺酸 作用下， 以 乙醚 为溶剂， 反应 36.0h， 生成 1,1,1,3,3,3-hexafluoropropan-2-yl (R)-4-(1,3-dioxolan-2-yl)-5-phenylpentanoate
  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