(5S,7R)-4,6,8-trioxadispiro[4.1.47.25]tridecane | 1859-25-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5S,7R)-4,6,8-trioxadispiro[4.1.47.25]tridecane
• CAS: 1859-25-2
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: NATQIANNYYCYKD-AOOOYVTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-(tert-butyldimethylsiloxy)-1-(dimethyl (phenyl)silyl)butan-1-one 、 6-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1-hexen-3-one 在 3-乙基-5-(2-羟乙基)-4-甲基噻唑溴化物 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 camphor-10-sulfonic acid 作用下， 以 四氢呋喃 、 异丙醇 为溶剂， 反应 36.0h， 以54%的产率得到
  参考文献：
  名称：

  Convergent Access to Bis-spiroacetals through a Sila-Stetter–Ketalization Cascade

  摘要：

  An NHC-catalyzed sila-Stetter reaction between aliphatic acylsilanes and vinylketones bearing silyl ether substituents affords functionalized 1,4-diketones, which upon treatment under acidic conditions leads to the corresponding bis-spiroacetals. The two-step sequence may also be carried out in a one-pot operation leading to high yields of the desired bis-spiroacetals.

  DOI：

  10.1021/ol402017x

文献信息

• Efficient One-Step Synthesis of Bis-Spiroketals from Diynediols by π-Lewis Acid-Catalyzed Hydroalkoxylation/Hydration
  作者：Ivan Volchkov、Kamlesh Sharma、Eun Jin Cho、Daesung Lee

  DOI：10.1002/asia.201100131

  日期：2011.8.1

  Spiroling out of control: An efficient one‐step synthesis of 5‐5‐5, 5‐5‐6, and 6‐5‐6 bis‐spiroketals from 4,6‐diyne‐1,n‐diols and 5,7‐diyne‐1,n‐diols has been developed with good yields. A mixture of cis‐ and trans‐bis‐spiroketals were generally obtained from each substrate and the isolated cis‐ and trans‐bis‐spiroketals undergo interconversion to reach their equilibrium composition (see scheme).

  失控旋转：由4,6-二炔-1，正二醇和5,7-二醇有效合成5-5-5、5-6和6-5-6双螺缩酮二炔-1，n-二醇的开发具有良好的收率。通常从每种底物中获得顺式和反式双螺酮混合物，分离出的顺式和反式双螺酮混合物进行相互转化以达到其平衡组成（参见方案）。
• Convergent Access to Bis-spiroacetals through a Sila-Stetter–Ketalization Cascade
  作者：Jessica Labarre-Lainé、Redouane Beniazza、Valérie Desvergnes、Yannick Landais

  DOI：10.1021/ol402017x

  日期：2013.9.20

  An NHC-catalyzed sila-Stetter reaction between aliphatic acylsilanes and vinylketones bearing silyl ether substituents affords functionalized 1,4-diketones, which upon treatment under acidic conditions leads to the corresponding bis-spiroacetals. The two-step sequence may also be carried out in a one-pot operation leading to high yields of the desired bis-spiroacetals.