(3a'R,5S,7'S,7a'S)-7'-hydroxy-3-(4-methoxyphenyl)-2',2'-dimethyltetrahydrospiro[oxazolidine-5,6'-[1,3]dioxolo[4,5-c]pyran]-2-one | 906371-66-2

• 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: (3a'R,5S,7'S,7a'S)-7'-hydroxy-3-(4-methoxyphenyl)-2',2'-dimethyltetrahydrospiro[oxazolidine-5,6'-[1,3]dioxolo[4,5-c]pyran]-2-one
• CAS: 906371-66-2
• 化学式: C₁₇H₂₁NO₇
• 分子量: 351.356
• InChiKey: UMONOUYJBWUTMJ-WVZRYYJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.26
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  86.69
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (3a'R,5S,7'S,7a'S)-7'-hydroxy-3-(4-methoxyphenyl)-2',2'-dimethyltetrahydrospiro[oxazolidine-5,6'-[1,3]dioxolo[4,5-c]pyran]-2-one 在 重铬酸吡啶 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 以36%的产率得到(3'aR,5S,7'aR)-3-(4-methoxyphenyl)-2',2'-dimethylspiro[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：

  D-葡萄糖 在 硫酸 、 碳酸氢钠 、 溶剂黄146 、 原甲酸三甲酯 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 26.75h， 生成 (3a'R,5S,7'S,7a'S)-7'-hydroxy-3-(4-methoxyphenyl)-2',2'-dimethyltetrahydrospiro[oxazolidine-5,6'-[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

• Highly Enantioselective CH Oxidation of <i>v</i><i>ic</i>-Diols with Shi's Oxazolidinone Dioxiranes
  作者：Kavitha Jakka、Cong-Gui Zhao

  DOI：10.1021/ol060904a

  日期：2006.7.1

  [reaction: see text] Through an analogical study of the transition states of CH oxidation and asymmetric epoxidation of terminal alkenes, the first dioxirane-mediated catalytic highly enantioselective CH oxidation method was realized with Shi's oxazolidinone ketone derivatives. Very good enantioselectivity (up to 92% ee) may be obtained for both asymmetrization of meso vic-diols and kinetic resolution

  [反应：参见正文]通过对CH氧化和末端烯烃不对称环氧化的过渡态的类似研究，使用Shi的恶唑烷酮酮衍生物实现了第一个二环氧乙烷烷介导的催化高对映选择性CH氧化方法。对于内消旋vic-二醇的不对称化和外消旋vic-二醇的动力学拆分，可以获得非常好的对映选择性（高达92％ee）。