3-hydroxy-3,6-dihydro-2H-pyran-2-one | 914390-08-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 3-hydroxy-3,6-dihydro-2H-pyran-2-one
• 英文别名: 3,6-dihydro-3-hydroxy-2H-pyran-2-one；5-Hydroxy-2,5-dihydropyran-6-one
• CAS: 914390-08-2
• 化学式: C₅H₆O₃
• 分子量: 114.101
• InChiKey: CUFAWDAVXLDRKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  3-hydroxy-3,6-dihydro-2H-pyran-2-one 在 正丁基锂 、 六甲基二硅氮烷 、 zinc dibromide 作用下， 以 四氢呋喃 为溶剂， 反应 4.03h， 生成 5-butyl-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：

  ethyl 2-hydroxy-1-[(1,1-dimethylethyl)dimethylsilyloxy]-3-pentenoate 在 六氟合硅酸 作用下， 以 甲醇 为溶剂， 以89%的产率得到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

• Efficient Construction of α-Spirocyclopropyl Lactones: Iridium-Salen-Catalyzed Asymmetric Cyclopropanation
  作者：Masami Ichinose、Hidehiro Suematsu、Tsutomu Katsuki

  DOI：10.1002/anie.200805527

  日期：2009.4.14

  carbene source, the seven‐membered rings upon subsequent hydrolysis and Cope rearrangement when 1,3‐dienes were used (see example). The α‐spirocyclopropyl lactones were formed with high E (trans) selectivity and high enantioselectivity, and cyclopropanation occurred at the terminal double bond in 1,3‐dienes with excellent regioselectivity.

  三元和七元环是通过末端烯烃与乙烯基重氮内酯作为卡宾源的标题反应而构建的，随后进行水解时的七元环和当使用1,3-二烯时的Cope重排（请参见示例）。α-螺环丙基内酯的形成具有高E（反式）选择性和高对映选择性，并且环丙烷化发生在1,3-二烯的末端双键上，具有良好的区域选择性。