4-[3,5-Ditert-butyl-2-(2-methylprop-2-enoxy)phenyl]-2-methylbut-3-yn-2-ol | 936856-60-9

• 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: 4-[3,5-Ditert-butyl-2-(2-methylprop-2-enoxy)phenyl]-2-methylbut-3-yn-2-ol
• 英文别名: 4-[3,5-ditert-butyl-2-(2-methylprop-2-enoxy)phenyl]-2-methylbut-3-yn-2-ol
• CAS: 936856-60-9
• 化学式: C₂₃H₃₄O₂
• 分子量: 342.522
• InChiKey: HFFSTDSDEBQYPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-[3,5-Ditert-butyl-2-(2-methylprop-2-enoxy)phenyl]-2-methylbut-3-yn-2-ol 、 alkaline earth salt of/the/ methylsulfuric acid 以 甲苯 为溶剂， 反应 5.0h， 以75%的产率得到6,8-di-tert-butyl-1-(1-hydroxy-1-methylethyl)-3a-methyl-3a,4-dihydro-3H-cyclopenta[c]chromen-2-one
  参考文献：
  名称：

  Steric buttressing in the Pauson–Khand reactions of aryl enynes

  摘要：

  A variety of aryl enynes have been constructed from o-iodophenol derivatives containing ortho-tert-butyl groups via O-alkylation and a Sonogashira cross-coupling reaction. These substrates undergo efficient thermal and oxidative intramolecular Pauson-Khand reactions leading to the formation of sterically congested cyclopentenones, as well as the formation of medium-sized rings, although in the latter case with unusual regioselectivity. Incorporation of a TMS moiety on the alkyne group in a higher homolog led to cyclization via the normal mode, albeit in relatively low yield. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.03.131
• 作为产物：
  描述：

  2,4-二叔丁基苯酚 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide N-碘代丁二酰亚胺 、 potassium carbonate 、 三乙胺 、 sodium iodide 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 4-[3,5-Ditert-butyl-2-(2-methylprop-2-enoxy)phenyl]-2-methylbut-3-yn-2-ol
  参考文献：
  名称：

  Steric buttressing in the Pauson–Khand reactions of aryl enynes

  摘要：

  A variety of aryl enynes have been constructed from o-iodophenol derivatives containing ortho-tert-butyl groups via O-alkylation and a Sonogashira cross-coupling reaction. These substrates undergo efficient thermal and oxidative intramolecular Pauson-Khand reactions leading to the formation of sterically congested cyclopentenones, as well as the formation of medium-sized rings, although in the latter case with unusual regioselectivity. Incorporation of a TMS moiety on the alkyne group in a higher homolog led to cyclization via the normal mode, albeit in relatively low yield. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.03.131