3-[5-(tetrahydropyran-2-yloxy)-pent-2-(E)-enoyl]-oxazolidin-2-one | 711029-02-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 3-[5-(tetrahydropyran-2-yloxy)-pent-2-(E)-enoyl]-oxazolidin-2-one
• 英文别名: 3-[(E)-5-(oxan-2-yloxy)pent-2-enoyl]-1,3-oxazolidin-2-one
• CAS: 711029-02-6
• 化学式: C₁₃H₁₉NO₅
• 分子量: 269.298
• InChiKey: NMTDEQKJSMHRCN-ORCRQEGFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-[5-(tetrahydropyran-2-yloxy)-pent-2-(E)-enoyl]-oxazolidin-2-one 在 三乙基硼 、 氧气 1,1-di{(3aS,8aR)-indano[1,2-d][1,3]oxazolin-2-yl}cyclopropan 、 三正丁基氢锡 、 magnesium iodide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 acetic acid 7-chloro-4,4-dimethyl-3-[2-oxo-2-(2-oxo-oxazolidin-3-yl)-ethyl]-heptyl ester
  参考文献：
  名称：

  Application of Enantioselective Radical Reactions:  Synthesis of (+)-Ricciocarpins A and B

  摘要：

  Enantioselective synthesis of (+)-ricciocarpins A and B has been achieved in 41 and 45% overall yields, respectively, starting from a beta-substituted oxazolidinone. The key steps in the strategy are an enantioselective conjugate radical addition and the addition of a furyl organometallic to a key aldehyde intermediate.

  DOI：

  10.1021/ol0495772
• 作为产物：
  描述：

  3-(2-tetrahydropyranyloxy)propanal 、 diethyl (2-oxo-2-(2-oxooxazolidin-3-yl)ethyl)phosphonate 在 N,N-二异丙基乙胺 、 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以71%的产率得到3-[5-(tetrahydropyran-2-yloxy)-pent-2-(E)-enoyl]-oxazolidin-2-one
  参考文献：
  名称：

  Application of Enantioselective Radical Reactions:  Synthesis of (+)-Ricciocarpins A and B

  摘要：

  Enantioselective synthesis of (+)-ricciocarpins A and B has been achieved in 41 and 45% overall yields, respectively, starting from a beta-substituted oxazolidinone. The key steps in the strategy are an enantioselective conjugate radical addition and the addition of a furyl organometallic to a key aldehyde intermediate.

  DOI：

  10.1021/ol0495772

文献信息

• Application of Enantioselective Radical Reactions:  Synthesis of (+)-Ricciocarpins A and B
  作者：Mukund P. Sibi、Liwen He

  DOI：10.1021/ol0495772

  日期：2004.5.1

  Enantioselective synthesis of (+)-ricciocarpins A and B has been achieved in 41 and 45% overall yields, respectively, starting from a beta-substituted oxazolidinone. The key steps in the strategy are an enantioselective conjugate radical addition and the addition of a furyl organometallic to a key aldehyde intermediate.