4-(5'-t-Butyldimetylsilyl-1'-hydroxy-2'-phenylsulfonylpent-2'-(E)-en-4'-ynyl)-1,2-methylenedioxabenzene | 144797-10-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 4-(5'-t-Butyldimetylsilyl-1'-hydroxy-2'-phenylsulfonylpent-2'-(E)-en-4'-ynyl)-1,2-methylenedioxabenzene
• 英文别名: (E)-2-(benzenesulfonyl)-1-(1,3-benzodioxol-5-yl)-5-[tert-butyl(dimethyl)silyl]pent-2-en-4-yn-1-ol
• CAS: 144797-10-4
• 化学式: C₂₄H₂₈O₅SSi
• 分子量: 456.635
• InChiKey: OVEWCZYCLOAHDE-WSDLNYQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.86
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  81.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-(tert-butyldimethylsilyl)-2-propynal 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 0.66h， 生成 4-(5'-t-Butyldimetylsilyl-1'-hydroxy-2'-phenylsulfonylpent-2'-(E)-en-4'-ynyl)-1,2-methylenedioxabenzene
  参考文献：
  名称：

  A stereoselective cis-enyne synthesis using vinyl sulfone chemistry

  摘要：

  The trans-sulfonyl enyne 8 was deprotonated using lithium diisopropylamide to provide a cis-enyne anion which was coupled with a variety of carbonyl compounds to provide, in high yields, a range of silyl-protected phenylsulfonyl enynes. These were desulfonylated in good yields to provide silyl protected terminal cis-enynes. Both these processes were shown to proceed with very good cis-selectivity.

  DOI：

  10.1016/s0040-4020(01)80456-7

文献信息

• A stereoselective cis-enyne synthesis using vinyl sulfone chemistry
  作者：Andrew B. Holmes、Guy R. Pooley

  DOI：10.1016/s0040-4020(01)80456-7

  日期：1992.1

  The trans-sulfonyl enyne 8 was deprotonated using lithium diisopropylamide to provide a cis-enyne anion which was coupled with a variety of carbonyl compounds to provide, in high yields, a range of silyl-protected phenylsulfonyl enynes. These were desulfonylated in good yields to provide silyl protected terminal cis-enynes. Both these processes were shown to proceed with very good cis-selectivity.