1-t-Butyldimethylsilylundec-3-(Z)-en-1-yn-5-ol | 144797-13-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-t-Butyldimethylsilylundec-3-(Z)-en-1-yn-5-ol
• 英文别名: (Z)-1-[tert-butyl(dimethyl)silyl]undec-3-en-1-yn-5-ol
• CAS: 144797-13-7
• 化学式: C₁₇H₃₂OSi
• 分子量: 280.526
• InChiKey: XRGSXWMELCMGLU-KAMYIIQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.93
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-(tert-butyldimethylsilyl)-2-propynal 在 4-二甲氨基吡啶 、 正丁基锂 、 sodium dithionite 、 碳酸氢钠 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 8.08h， 生成 1-t-Butyldimethylsilylundec-3-(Z)-en-1-yn-5-ol
  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.