(3aR,6R,7S,7aS)-2,2-Dimethyl-6-(p-tolylamino-methyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6,7-diol | 403501-13-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: (3aR,6R,7S,7aS)-2,2-Dimethyl-6-(p-tolylamino-methyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6,7-diol
• CAS: 403501-13-3
• 化学式: C₁₆H₂₃NO₅
• 分子量: 309.362
• InChiKey: NYUBEIYQFCKHNK-HGTKMLMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.01
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  80.18
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (3aR,6R,7S,7aS)-2,2-Dimethyl-6-(p-tolylamino-methyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6,7-diol 在 重铬酸吡啶 、 4 A molecular sieve 、 碳酸氢钠 、 溶剂黄146 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 6.0h， 生成 史氏环氧化恶唑烷酮甲基催化剂
  参考文献：
  名称：

  Effective Asymmetric Epoxidation of Styrenes by Chiral Dioxirane

  摘要：

  High enantio selectivity (80-92% enantiomeric excess (ee)) has been obtained for the epoxidation of various styrenes using an easily prepared ketone (4) catalyst.

  DOI：

  10.1021/jo0520285
• 作为产物：
  描述：

  D-葡萄糖 在 硫酸 、 溶剂黄146 、 原甲酸三甲酯 作用下， 以 水 为溶剂， 反应 27.0h， 生成 (3aR,6R,7S,7aS)-2,2-Dimethyl-6-(p-tolylamino-methyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6,7-diol
  参考文献：
  名称：

  Asymmetric Epoxidation Catalyzed by N-Aryl-Substituted Oxazolidinone-Containing Ketones:  Further Evidence for Electronic Effects

  摘要：

  [GRAPHICS]Ketones containing N-aryl-substituted oxazolidinones have been prepared and investigated for the epoxidation of cis-beta-methylstyrene, styrene, and 1-phenylcyclohexene. The attractive interaction between the phenyl group of the olefin and the oxazolidinone of the catalyst is enhanced by introducing an electron-withdrawing group onto the N-phenyl group of the catalyst. The information obtained gives a better understanding of the ketone-catalyzed epoxidation. In addition, the easy preparation of some of the ketones makes them good candidates for practical use.

  DOI：

  10.1021/ol020229e

文献信息

• Asymmetric Epoxidation of 1,1-Disubstituted Terminal Olefins by Chiral Dioxirane via a Planar-like Transition State
  作者：Bin Wang、O. Andrea Wong、Mei-Xin Zhao、Yian Shi

  DOI：10.1021/jo801576k

  日期：2008.12.19

  Various 1,1-disubstituted terminal olefins have been investigated for asymmetric epoxidation using chiral ketone catalysts. Up to 88% ee has been achieved with a lactam ketone, and a planar transition state is likely to be a major reaction pathway.

  各种 1,1-二取代末端烯烃已被研究用于使用手性酮催化剂的不对称环氧化。使用内酰胺酮可实现高达 88% ee，并且平面过渡态可能是主要反应途径。
• Asymmetric Epoxidation Catalyzed by α,α-Dimethylmorpholinone Ketone. Methyl Group Effect on Spiro and Planar Transition States
  作者：O. Andrea Wong、Bin Wang、Mei-Xin Zhao、Yian Shi

  DOI：10.1021/jo900739q

  日期：2009.8.21

  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.