(3aR,6S,7S,7aS)-7-hydroxy-2,2,2',2'-tetramethyl-4'-(4-methylphenyl)spiro[3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6,6'-morpholine]-3'-one | 1177357-82-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: (3aR,6S,7S,7aS)-7-hydroxy-2,2,2',2'-tetramethyl-4'-(4-methylphenyl)spiro[3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6,6'-morpholine]-3'-one
• CAS: 1177357-82-2
• 化学式: C₂₀H₂₇NO₆
• 分子量: 377.437
• InChiKey: MHCZYPIDIMPMRL-DICRZQGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  77.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3aR,6S,7S,7aS)-7-hydroxy-2,2,2',2'-tetramethyl-4'-(4-methylphenyl)spiro[3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6,6'-morpholine]-3'-one 在 重铬酸吡啶 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以95%的产率得到(3aR,6S,7aR)-2,2,2',2'-tetramethyl-4'-(4-methylphenyl)spiro[4,7a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyran-6,6'-morpholine]-3',7-dione
  参考文献：
  名称：

  Asymmetric Epoxidation Catalyzed by α,α-Dimethylmorpholinone Ketone. Methyl Group Effect on Spiro and Planar Transition States

  摘要：

  Asymmetric epoxidation of olefins by using an alpha,alpha-dimethylmorpholinone-containing chiral ketone catalyst (4) has been investigated. This ketone, which has the combined features of several previously studied catalysts, is an effective catalyst for trans- and trisubstituted olefins, and up to 97% ee has been achieved. The alpha,alpha-dimethyl group has significant impact oil spiro and planar transition states.

  DOI：

  10.1021/jo900739q
• 作为产物：
  描述：

  2-溴-2-甲基丙酰溴 、 (3aR,6R,7S,7aS)-2,2-Dimethyl-6-(p-tolylamino-methyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6,7-diol 在 碳酸氢钠 、 sodium hydride 作用下， 以 二氯甲烷 、 四氢呋喃 、 mineral oil 为溶剂， 反应 16.5h， 以45%的产率得到(3aR,6S,7S,7aS)-7-hydroxy-2,2,2',2'-tetramethyl-4'-(4-methylphenyl)spiro[3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6,6'-morpholine]-3'-one
  参考文献：
  名称：

  Asymmetric Epoxidation Catalyzed by α,α-Dimethylmorpholinone Ketone. Methyl Group Effect on Spiro and Planar Transition States

  摘要：

  Asymmetric epoxidation of olefins by using an alpha,alpha-dimethylmorpholinone-containing chiral ketone catalyst (4) has been investigated. This ketone, which has the combined features of several previously studied catalysts, is an effective catalyst for trans- and trisubstituted olefins, and up to 97% ee has been achieved. The alpha,alpha-dimethyl group has significant impact oil spiro and planar transition states.

  DOI：

  10.1021/jo900739q