(3R)-3-(1-ethoxyethoxy)-4,4-dimethyloxolan-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3R)-3-(1-ethoxyethoxy)-4,4-dimethyloxolan-2-one
• 化学式: C₁₀H₁₈O₄
• 分子量: 202.251
• InChiKey: XCKWOXNXPRBXHF-MQWKRIRWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R)-3-(1-ethoxyethoxy)-4,4-dimethyloxolan-2-one 在 三氟甲磺酸三甲基硅酯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到(R)-(+)-O-vinyl pantolactone
  参考文献：
  名称：

  Novel Use of N-Benzoyl-N,O-acetals as N-Acylimine Equivalents in Asymmetric Heterocycloaddition:  An Extended Enantioselective Pathway to β-Benzamido Aldehydes

  摘要：

  For the first time, easily available N-(alpha-methoxyalkyl)amides were successfully used as synthetic equivalents of N-acylimines in an asymmetric heterocycloaddition process. The facial-controlled formation of 6-alkoxydihydrooxazines was thus achieved by SnCl4-promoted heterocycloaddition of (R)-O-vinyl pantolactone. By simple acidic hydrolysis of the crude heteroadducts, new beta-aryl- and beta-alkyl-substituted benzamido aldehydes were thus obtained in good overall yields with high enantioselectivities.

  DOI：

  10.1021/jo0203138
• 作为产物：
  描述：

  乙烯基乙醚 、 D-(-)-泛酰内酯 在 三氟乙酸 作用下， 生成 (3R)-3-(1-ethoxyethoxy)-4,4-dimethyloxolan-2-one
  参考文献：
  名称：

  An Improved Dienophile-Induced Access to Enantiopure 2,4-Dideoxysugar Lactones via Hetero Diels-Alder Reaction: Synthesis of the (+)-Lactone Moiety of Compactin

  摘要：

  DOI：

  10.1055/s-1998-4489

文献信息

• An Improved Dienophile-Induced Access to Enantiopure 2,4-Dideoxysugar Lactones via Hetero Diels-Alder Reaction: Synthesis of the (+)-Lactone Moiety of Compactin
  作者：Gilles Dujardin、Sandrine Rossignol、Eric Brown

  DOI：10.1055/s-1998-4489

  日期：1998.5
• Novel Use of <i>N</i>-Benzoyl-<i>N,O</i>-acetals as <i>N</i>-Acylimine Equivalents in Asymmetric Heterocycloaddition:  An Extended Enantioselective Pathway to β-Benzamido Aldehydes
  作者：Patricia Gizecki、Robert Dhal、Céline Poulard、Pascal Gosselin、Gilles Dujardin

  DOI：10.1021/jo0203138

  日期：2003.5.1

  For the first time, easily available N-(alpha-methoxyalkyl)amides were successfully used as synthetic equivalents of N-acylimines in an asymmetric heterocycloaddition process. The facial-controlled formation of 6-alkoxydihydrooxazines was thus achieved by SnCl4-promoted heterocycloaddition of (R)-O-vinyl pantolactone. By simple acidic hydrolysis of the crude heteroadducts, new beta-aryl- and beta-alkyl-substituted benzamido aldehydes were thus obtained in good overall yields with high enantioselectivities.