3-(2-Hydroxyethoxy)-1-methylidenecyclohexane | 133620-97-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(2-Hydroxyethoxy)-1-methylidenecyclohexane
• 英文别名: 2-(3-Methylidenecyclohexyl)oxyethanol
• CAS: 133620-97-0
• 化学式: C₉H₁₆O₂
• 分子量: 156.225
• InChiKey: QWQGZGJHJCWKNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-[1-bromo-5-(phenylsulfanylmethyl)hex-5-en-3-yl]oxyethanol 在 六正丁基二锡 作用下， 以 苯 为溶剂， 以75%的产率得到3-(2-Hydroxyethoxy)-1-methylidenecyclohexane
  参考文献：
  名称：

  [3 + 3]通过连续两个电子和一个电子烯丙基化的环

  摘要：

  3-苯硫基-2-（三甲基甲硅烷基甲基）丙烯是通过[3 + 3]环合法制备亚甲基环己烷的方便的辅助试剂。三甲基甲硅烷基可促进路易斯酸催化的醛或乙缩醛的烯丙基化，而苯硫基可指导6-内-trig自由基环化反应。

  DOI：

  10.1016/s0040-4039(00)92100-2

文献信息

• [3+3] Annulation by sequential two electron and one electron allylation
  作者：Dale E. Ward、Brian F. Kaller

  DOI：10.1016/s0040-4039(00)92100-2

  日期：1991.2

  3-phenylthio-2-(trimethylsilymethyl)propene is a convenient conjunctive reagent for the preparation of methylenecyclohexanes via a [3+3] annulation. The trimethylsilyl group facilitates the Lewis acid catalyzed allylation of an aldehyde or acetal while the phenylthio group directs a 6-endo-trig radical cyclization reaction.

  3-苯硫基-2-（三甲基甲硅烷基甲基）丙烯是通过[3 + 3]环合法制备亚甲基环己烷的方便的辅助试剂。三甲基甲硅烷基可促进路易斯酸催化的醛或乙缩醛的烯丙基化，而苯硫基可指导6-内-trig自由基环化反应。
• [3 + 3] Annulation Based on 6-Endo-Trig Radical Cyclization: Regioselectivity and Diastereoselectivity
  作者：Dale E. Ward、Yuanzhu Gai、Brian F. Kaller

  DOI：10.1021/jo00129a024

  日期：1995.12

  The development of a [3 + 3] annulation strategy based on sequential ''two-electron'' and ''one-electron'' allylation of beta-substituted aldehydes and derivatives with the bifunctional isobutene conjunctive reagent 1 is described. The key step involves an unusual 6-endo-trig radical cyclization. Yields of 6-endo products are improved if the PhS group is oxidized to a PhSO(2) group prior to cyclization. The structural factors affecting the regioselectivity and stereoselectivity of the cyclization are examined. In general, the stereoselectivity of 6-endo-trig cyclization of 5-hexenyl radicals can be rationalized by conformational analysis of chairlike transition states and can be calculated effectively with an MM2 force field model, High 6-endo regioselectivity requires a strong driving force. Fragmentable allylic groups (R(3)Sn, PhSO(2), and to a lesser extent PhS) are shown to be sufficiently activating to achieve 6-endo regioselectivity.