(2R,3S)-3-but-3'-enyloxy-2-vinyltetrahydropyran | 234111-41-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (2R,3S)-3-but-3'-enyloxy-2-vinyltetrahydropyran
• 英文别名: (2R,3S)-3-but-3-enoxy-2-ethenyloxane
• CAS: 234111-41-2
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: HRVOYQFRKWOLDL-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,3S)-3-but-3'-enyloxy-2-vinyltetrahydropyran 在 bis(tricyclohexylphosphine)benzylidine ruthenium(IV) di 、 盐酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (Z)-(4aS,9aR)-3,4,4a,6,7,9a-hexahydro-2H-1,5-dioxabenzocycloheptene
  参考文献：
  名称：

  Ring-Closing Metathesis in the Synthesis of Large and Medium-Sized Oxacycles. Application to the Synthesis of Polyoxygenated Macrocycles

  摘要：

  Ring-closing olefin metathesis (RCM) catalyzed by Grubbs's ruthenium benzylidene complex 1 is applied to the synthesis of unsaturated rings ranging in size from seven to thirteen members in trans-fused polyether systems. Reaction occurs with great efficiency in the cyclization of oxepene and oxocene rings, but as ring size increases, yields drop. The influence of the final double bond position is also studied. Better yields and milder reaction conditions are observed when an additional oxygen atom is introduced on the diene. This feature has promoted the application of this reaction to the synthesis of polyoxygenated macrocycles (with sizes ranging from 15 to 21 members), with excellent results.

  DOI：

  10.1021/jo9901438
• 作为产物：
  描述：

  (2R,3S)-2-hydroxymethyltetrahydropyran-3-ol 在 咪唑 、 正丁基锂 、 pyridine-SO3 complex 、 potassium tert-butylate 、 四丁基氟化铵 、 碘 、 四氯化钛 、 sodium cyanoborohydride 、 对甲苯磺酸 、 二甲基亚砜 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 、 苯 为溶剂， 反应 30.0h， 生成 (2R,3S)-3-but-3'-enyloxy-2-vinyltetrahydropyran
  参考文献：
  名称：

  Ring-Closing Metathesis in the Synthesis of Large and Medium-Sized Oxacycles. Application to the Synthesis of Polyoxygenated Macrocycles

  摘要：

  Ring-closing olefin metathesis (RCM) catalyzed by Grubbs's ruthenium benzylidene complex 1 is applied to the synthesis of unsaturated rings ranging in size from seven to thirteen members in trans-fused polyether systems. Reaction occurs with great efficiency in the cyclization of oxepene and oxocene rings, but as ring size increases, yields drop. The influence of the final double bond position is also studied. Better yields and milder reaction conditions are observed when an additional oxygen atom is introduced on the diene. This feature has promoted the application of this reaction to the synthesis of polyoxygenated macrocycles (with sizes ranging from 15 to 21 members), with excellent results.

  DOI：

  10.1021/jo9901438