史氏环氧化恶唑烷酮甲基催化剂 | 403501-30-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 中文名称: 史氏环氧化恶唑烷酮甲基催化剂
• 英文名称: Shi Epoxidation Oxazolidinone Methyl Catalyst
• 英文别名: (3'aR,5S,7'aR)-2',2'-dimethyl-3-(4-methylphenyl)spiro[1,3-oxazolidine-5,6'-4,7a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyran]-2,7'-dione
• CAS: 403501-30-4
• 化学式: C₁₇H₁₉NO₆
• 分子量: 333.341
• InChiKey: WFKGDVVGAWYPFR-XNJGSVPQSA-N

物化性质

• 熔点：
  149-154 °C

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• WGK Germany：
  3

制备方法与用途

用途：不对称环氧化有机催化剂。

反应信息

• 作为产物：
  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

文献信息

• A practical synthesis of N-aryl-substituted oxazolidinone-containing ketone catalysts for asymmetric epoxidation
  作者：Mei-Xin Zhao、David Goeddel、Kai Li、Yian Shi

  DOI：10.1016/j.tet.2006.06.020

  日期：2006.8

  N-Aryl-substituted oxazolidinone-containing ketone catalysts for the asymmetric epoxidation of olefins can be efficiently prepared from d-glucose and anilines.

  可以由d-葡萄糖和苯胺有效地制备用于烯烃的不对称环氧化的含N-芳基取代的含恶唑烷酮的酮催化剂。
• Asymmetric Epoxidation Catalyzed by N-Aryl-Substituted Oxazolidinone-Containing Ketones:  Further Evidence for Electronic Effects
  作者：Lianhe Shu、Pingzhen Wang、Yonghong Gan、Yian Shi

  DOI：10.1021/ol020229e

  日期：2003.2.1

  [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.
• Effective Asymmetric Epoxidation of Styrenes by Chiral Dioxirane
  作者：David Goeddel、Lianhe Shu、Yi Yuan、O. Andrea Wong、Bin Wang、Yian Shi

  DOI：10.1021/jo0520285

  日期：2006.2.1

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