(2R,5S)-2-(5-((benzyloxy)methyl)-2,5-dihydro-5-methylfuran-2-yl)propan-2-ol | 1138139-05-5

• 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: (2R,5S)-2-(5-((benzyloxy)methyl)-2,5-dihydro-5-methylfuran-2-yl)propan-2-ol
• 英文别名: 2-[(2R,5S)-5-methyl-5-(phenylmethoxymethyl)-2H-furan-2-yl]propan-2-ol
• CAS: 1138139-05-5
• 化学式: C₁₆H₂₂O₃
• 分子量: 262.349
• InChiKey: KLBNLFWOXZJMSJ-ZBFHGGJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,5S)-2-(5-((benzyloxy)methyl)-2,5-dihydro-5-methylfuran-2-yl)propan-2-ol 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 18.0h， 以81%的产率得到(2R,5S)-2-(tetrahydro-5-(hydroxymethyl)-5-methylfuran-2-yl)propan-2-ol
  参考文献：
  名称：

  Gold catalysis in stereoselective natural product synthesis: (+)-linalool oxide, (−)-isocyclocapitelline, and (−)-isochrysotricine

  摘要：

  A stereoselective synthesis of the tetrahydrofuran-containing natural products (2S,5R)-(+)-linalool oxide (1), (-)-isocyclocapitelline (2), and (-)-isochrysotricine (3) is reported. Key steps are the copper-mediated S(N)2'-substitution of propargyl oxiranes 7 and the gold-catalyzed cycloisomerization of dihydroxyallenes 8/17, resulting in a highly efficient center-to-axis-to-center chirality transfer. The enantioselective total synthesis of (-)-isocyclocapitelline (2) and (-)-isochrysotricine (3) allowed the elucidation of the absolute configuration of these beta-carboline natural products. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.11.104
• 作为产物：
  描述：

  (2R,5S)-(5-((benzyloxy)methyl)-2,5-dihydro-5-methylfuran-2-yl)ethanone 、 甲基氯化镁 在 水 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以88%的产率得到(2R,5S)-2-(5-((benzyloxy)methyl)-2,5-dihydro-5-methylfuran-2-yl)propan-2-ol
  参考文献：
  名称：

  Gold catalysis in stereoselective natural product synthesis: (+)-linalool oxide, (−)-isocyclocapitelline, and (−)-isochrysotricine

  摘要：

  A stereoselective synthesis of the tetrahydrofuran-containing natural products (2S,5R)-(+)-linalool oxide (1), (-)-isocyclocapitelline (2), and (-)-isochrysotricine (3) is reported. Key steps are the copper-mediated S(N)2'-substitution of propargyl oxiranes 7 and the gold-catalyzed cycloisomerization of dihydroxyallenes 8/17, resulting in a highly efficient center-to-axis-to-center chirality transfer. The enantioselective total synthesis of (-)-isocyclocapitelline (2) and (-)-isochrysotricine (3) allowed the elucidation of the absolute configuration of these beta-carboline natural products. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.11.104