4-phenyl-3-hydroxy-3,6-dihydro-2H-pyran-2-one | 914390-10-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 4-phenyl-3-hydroxy-3,6-dihydro-2H-pyran-2-one
• 英文别名: 5-Hydroxy-4-phenyl-2,5-dihydropyran-6-one；5-hydroxy-4-phenyl-2,5-dihydropyran-6-one
• CAS: 914390-10-6
• 化学式: C₁₁H₁₀O₃
• 分子量: 190.199
• InChiKey: AYWYBQHSSJRZLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-phenyl-3-hydroxy-3,6-dihydro-2H-pyran-2-one 在 正丁基锂 、 六甲基二硅氮烷 、 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 3.78h， 生成 5-(1,1-dimethylethyl)-4-phenyl-5,6-dihydropyran-2-one
  参考文献：
  名称：

  A Rapid Divergent Synthesis of Highly Substituted δ-Lactones

  摘要：

  Nucleophilic 1,2-addition of (Z)-gamma-silyloxyvinylzinc reagents to ethyl glyoxylate followed by desilylation and cyclization affords 3,6-dihydro-3-hydroxypyran-2-ones in good chemical yields. In situ formation of allylic phosphates followed by reaction with RCu(CN) Li reagents affords substituted 5,6-dihydropyran-2-ones. The parent compound, 3,6-dihydro-3-hydroxypyran-2-one, undergoes allylic phosphate formation, cuprate-mediated allylic substitution, and 1,4-conjugate addition to afford trans-4,5-disubstituted tetrahydropyran-2-ones in a one-pot process.

  DOI：

  10.1021/ol0617695
• 作为产物：
  描述：

  tert-butyl-[(Z)-3-iodo-3-phenylprop-2-enoxy]-dimethylsilane 在 六氟合硅酸 、 叔丁基锂 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 0.5h， 生成 4-phenyl-3-hydroxy-3,6-dihydro-2H-pyran-2-one
  参考文献：
  名称：

  A Rapid Divergent Synthesis of Highly Substituted δ-Lactones

  摘要：

  Nucleophilic 1,2-addition of (Z)-gamma-silyloxyvinylzinc reagents to ethyl glyoxylate followed by desilylation and cyclization affords 3,6-dihydro-3-hydroxypyran-2-ones in good chemical yields. In situ formation of allylic phosphates followed by reaction with RCu(CN) Li reagents affords substituted 5,6-dihydropyran-2-ones. The parent compound, 3,6-dihydro-3-hydroxypyran-2-one, undergoes allylic phosphate formation, cuprate-mediated allylic substitution, and 1,4-conjugate addition to afford trans-4,5-disubstituted tetrahydropyran-2-ones in a one-pot process.

  DOI：

  10.1021/ol0617695

文献信息

• A Rapid Divergent Synthesis of Highly Substituted δ-Lactones
  作者：R. Karl Dieter、Fenghai Guo

  DOI：10.1021/ol0617695

  日期：2006.10.1

  Nucleophilic 1,2-addition of (Z)-gamma-silyloxyvinylzinc reagents to ethyl glyoxylate followed by desilylation and cyclization affords 3,6-dihydro-3-hydroxypyran-2-ones in good chemical yields. In situ formation of allylic phosphates followed by reaction with RCu(CN) Li reagents affords substituted 5,6-dihydropyran-2-ones. The parent compound, 3,6-dihydro-3-hydroxypyran-2-one, undergoes allylic phosphate formation, cuprate-mediated allylic substitution, and 1,4-conjugate addition to afford trans-4,5-disubstituted tetrahydropyran-2-ones in a one-pot process.