6-(3-((2,5-cis)-5-methyl-2-phenyl-1,3-dioxan-5-yl)-3-oxopropyl)cyclohex-2-enone | 1618091-72-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6-(3-((2,5-cis)-5-methyl-2-phenyl-1,3-dioxan-5-yl)-3-oxopropyl)cyclohex-2-enone
• CAS: 1618091-72-7
• 化学式: C₂₀H₂₄O₄
• 分子量: 328.408
• InChiKey: HZAMZTAWCGGGRP-DFVIVQSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.62
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  6-(3-((2,5-cis)-5-methyl-2-phenyl-1,3-dioxan-5-yl)-3-oxopropyl)cyclohex-2-enone 在 三氟甲磺酸三甲基硅酯 、 三苯基膦 、 二异丁基氢化铝 、 potassium carbonate 作用下， 以 二氯甲烷 、 正己烷 、 甲醇 为溶剂， 反应 1.5h， 以95%的产率得到6-(3-hydroxy-3-((2,5-cis)-5-methyl-2-phenyl-1,3-dioxan-5-yl)propyl)cyclohex-2-enone
  参考文献：
  名称：

  Selective Transformations of Carbonyl Functions in the Presence of α,β-Unsaturated Ketones: Concise Asymmetric Total Synthesis of Decytospolides A and B

  摘要：

  Enones selectively react with a combination of PPh3 and TMSOTf to produce phosphonium silyl enol ethers, which work as protective groups of enones during the reduction of other carbonyl functions and can be easily deprotected to regenerate parent enones at workup. Furthermore, the first ketone selective alkylations in the presence of enones were also accomplished. This in situ protection method was applied to concise asymmetric total syntheses of decytospolides A and B.

  DOI：

  10.1021/ol501463p
• 作为产物：
  描述：

  ethyl 4-(dodecylthio)-2-hydroxycyclohex-1-enecarboxylate 在 4-二甲氨基吡啶 、 甲酸 、 palladium diacetate 、 sodium hydride 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 15.0h， 生成 6-(3-((2,5-cis)-5-methyl-2-phenyl-1,3-dioxan-5-yl)-3-oxopropyl)cyclohex-2-enone
  参考文献：
  名称：

  Selective Transformations of Carbonyl Functions in the Presence of α,β-Unsaturated Ketones: Concise Asymmetric Total Synthesis of Decytospolides A and B

  摘要：

  Enones selectively react with a combination of PPh3 and TMSOTf to produce phosphonium silyl enol ethers, which work as protective groups of enones during the reduction of other carbonyl functions and can be easily deprotected to regenerate parent enones at workup. Furthermore, the first ketone selective alkylations in the presence of enones were also accomplished. This in situ protection method was applied to concise asymmetric total syntheses of decytospolides A and B.

  DOI：

  10.1021/ol501463p