2-(3-hydroxy-3-methylbut-1-ynyl)-4-methyl-6-(tert-butyldimethylsilyloxy)-N,N-diethylbenzamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(3-hydroxy-3-methylbut-1-ynyl)-4-methyl-6-(tert-butyldimethylsilyloxy)-N,N-diethylbenzamide
• 英文别名: 2-[tert-butyl(dimethyl)silyl]oxy-N,N-diethyl-6-(3-hydroxy-3-methylbut-1-ynyl)-4-methylbenzamide
• 化学式: C₂₃H₃₇NO₃Si
• 分子量: 403.637
• InChiKey: NMBRMRCJKIMABS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.98
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3-hydroxy-3-methylbut-1-ynyl)-4-methyl-6-(tert-butyldimethylsilyloxy)-N,N-diethylbenzamide 、 trimethoxonium tetrafluoroborate 在 disodium hydrogenphosphate 、 水 、 碳酸氢钠 作用下， 以 乙腈 为溶剂， 反应 36.0h， 以90%的产率得到methyl 2-(3-hydroxy-3-methylbut-1-ynyl)-4-methyl-6-hydroxybenzoate
  参考文献：
  名称：

  A Pauson−Khand Approach to the Hamigerans

  摘要：

  An intramolecular Pauson-Khand reaction has been used in the construction of the tricyclic core common to the hamigeran terpenes. For effective cyclization, it was necessary to tether the olefin-containing moiety to the aromatic framework to reduce its conformation mobility; this was accomplished using a silylene protecting group. Efficient construction of the aryl enyne from a salicylic acid derivative was accomplished via ortho lithiation and Sonogashira cross-coupling chemistry.

  DOI：

  10.1021/ol7018604
• 作为产物：
  描述：

  2-(tert-butyldimethylsilyloxy)-6-iodo-4-methyl-N,N-diethylbenzamide 、 2-甲基-3-丁炔-2-醇 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 三乙胺 作用下， 反应 5.0h， 以73%的产率得到2-(3-hydroxy-3-methylbut-1-ynyl)-4-methyl-6-(tert-butyldimethylsilyloxy)-N,N-diethylbenzamide
  参考文献：
  名称：

  A Pauson−Khand Approach to the Hamigerans

  摘要：

  An intramolecular Pauson-Khand reaction has been used in the construction of the tricyclic core common to the hamigeran terpenes. For effective cyclization, it was necessary to tether the olefin-containing moiety to the aromatic framework to reduce its conformation mobility; this was accomplished using a silylene protecting group. Efficient construction of the aryl enyne from a salicylic acid derivative was accomplished via ortho lithiation and Sonogashira cross-coupling chemistry.

  DOI：

  10.1021/ol7018604

文献信息

• A Pauson−Khand Approach to the Hamigerans
  作者：Christian E. Madu、Carl J. Lovely

  DOI：10.1021/ol7018604

  日期：2007.11.1

  An intramolecular Pauson-Khand reaction has been used in the construction of the tricyclic core common to the hamigeran terpenes. For effective cyclization, it was necessary to tether the olefin-containing moiety to the aromatic framework to reduce its conformation mobility; this was accomplished using a silylene protecting group. Efficient construction of the aryl enyne from a salicylic acid derivative was accomplished via ortho lithiation and Sonogashira cross-coupling chemistry.