2-[(2R,5R)-5-methyl-5-[(2S)-oxiran-2-yl]oxolan-2-yl]propan-2-ol | 157008-60-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: 2-[(2R,5R)-5-methyl-5-[(2S)-oxiran-2-yl]oxolan-2-yl]propan-2-ol
• CAS: 157008-60-1
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: QZRANJWXTXXQQC-KHQFGBGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[(2R,5R)-5-methyl-5-[(2S)-oxiran-2-yl]oxolan-2-yl]propan-2-ol 在 咪唑 、 copper(l) iodide 作用下， 以 四氢呋喃 为溶剂， 反应 1.17h， 生成
  参考文献：
  名称：

  Synthesis of 15,28-Dideoxy-15,28-didehydrothyrsenol

  摘要：

  The tetracyclic skeleton of thyrsenols A and B has been assembled, with the construction of ring A by exo-selective oxacyclization of an epoxybromohydrin, B ring formation by exo-selective oxacyclization of hydroxyepoxide followed by solvolytic ring expansion of a tetrahydrofuran to tetrahydropyran, C ring closure by tungsten-promoted endo-selective oxacyclization of a hydroxyalkyne, and D ring preparation by asymmetric dihydroxylation of an epoxyalkene accompanied by exo-selective oxacyclization. A modified Stille coupling linked two fragments at C-14-C-15 to directly provide the tetracyclic dienylether.

  DOI：

  10.3987/com-12-s(n)51
• 作为产物：
  描述：

  Toluene-4-sulfonic acid <3-methyl-3-(4-methylpent-3-enyl)oxiran-2-yl>methyl ester 在 甲基磺酰胺 、 AD-mix β 、 camphor-10-sulfonic acid 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 0.42h， 生成 2-[(2R,5R)-5-methyl-5-[(2S)-oxiran-2-yl]oxolan-2-yl]propan-2-ol
  参考文献：
  名称：

  Synthesis of 15,28-Dideoxy-15,28-didehydrothyrsenol

  摘要：

  The tetracyclic skeleton of thyrsenols A and B has been assembled, with the construction of ring A by exo-selective oxacyclization of an epoxybromohydrin, B ring formation by exo-selective oxacyclization of hydroxyepoxide followed by solvolytic ring expansion of a tetrahydrofuran to tetrahydropyran, C ring closure by tungsten-promoted endo-selective oxacyclization of a hydroxyalkyne, and D ring preparation by asymmetric dihydroxylation of an epoxyalkene accompanied by exo-selective oxacyclization. A modified Stille coupling linked two fragments at C-14-C-15 to directly provide the tetracyclic dienylether.

  DOI：

  10.3987/com-12-s(n)51

文献信息

• Synthesis of 15,28-Dideoxy-15,28-didehydrothyrsenol
  作者：Frank E. McDonald、Mary A. Smart

  DOI：10.3987/com-12-s(n)51

  日期：——

  The tetracyclic skeleton of thyrsenols A and B has been assembled, with the construction of ring A by exo-selective oxacyclization of an epoxybromohydrin, B ring formation by exo-selective oxacyclization of hydroxyepoxide followed by solvolytic ring expansion of a tetrahydrofuran to tetrahydropyran, C ring closure by tungsten-promoted endo-selective oxacyclization of a hydroxyalkyne, and D ring preparation by asymmetric dihydroxylation of an epoxyalkene accompanied by exo-selective oxacyclization. A modified Stille coupling linked two fragments at C-14-C-15 to directly provide the tetracyclic dienylether.