(3'aR,5S,7'S,7'aR)-7'-[tert-butyl(dimethyl)silyl]oxy-2',2'-dimethyl-3-(2-nitrophenyl)spiro[1,3-oxazolidine-5,6'-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran]-2-one | 501347-42-8

• 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: (3'aR,5S,7'S,7'aR)-7'-[tert-butyl(dimethyl)silyl]oxy-2',2'-dimethyl-3-(2-nitrophenyl)spiro[1,3-oxazolidine-5,6'-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran]-2-one
• CAS: 501347-42-8
• 化学式: C₂₂H₃₂N₂O₈Si
• 分子量: 480.59
• InChiKey: DGVOPGXNCMLLDZ-QLDGJZPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.19
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3'aR,5S,7'S,7'aR)-7'-[tert-butyl(dimethyl)silyl]oxy-2',2'-dimethyl-3-(2-nitrophenyl)spiro[1,3-oxazolidine-5,6'-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran]-2-one 在 重铬酸吡啶 、 溶剂黄146 、 triethylamine tris(hydrogen fluoride) 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 144.0h， 生成 (3'aR,5S,7'aR)-2',2'-dimethyl-3-(2-nitrophenyl)spiro[1,3-oxazolidine-5,6'-4,7a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyran]-2,7'-dione
  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
• 作为产物：
  描述：

  1-氟-2-硝基苯 、 (3'aR,5S,7'S,7'aR)-7'-[tert-butyl(dimethyl)silyl]oxy-2',2'-dimethylspiro[1,3-oxazolidine-5,6'-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran]-2-one 在 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以56%的产率得到(3'aR,5S,7'S,7'aR)-7'-[tert-butyl(dimethyl)silyl]oxy-2',2'-dimethyl-3-(2-nitrophenyl)spiro[1,3-oxazolidine-5,6'-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran]-2-one
  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 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.