(1S,5R)-1,4,4-trimethyl-3,8-dioxabicyclo[3.2.1]octan-2-one | 1138139-07-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1S,5R)-1,4,4-trimethyl-3,8-dioxabicyclo[3.2.1]octan-2-one
• CAS: 1138139-07-7
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: SEKNWXSVSHGQFU-MUWHJKNJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,5R)-1,4,4-trimethyl-3,8-dioxabicyclo[3.2.1]octan-2-one 在 二异丁基氢化铝 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 0.08h， 以85%的产率得到(1S,5R)-1,4,4-trimethyl-3,8-dioxabicyclo[3.2.1]octan-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)-2-(tetrahydro-5-(hydroxymethyl)-5-methylfuran-2-yl)propan-2-ol 在 2-碘酰基苯甲酸 作用下， 以 二甲基亚砜 为溶剂， 反应 18.0h， 以82%的产率得到(1S,5R)-1,4,4-trimethyl-3,8-dioxabicyclo[3.2.1]octan-2-one
  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

文献信息

• Gold catalysis in stereoselective natural product synthesis: (+)-linalool oxide, (−)-isocyclocapitelline, and (−)-isochrysotricine
  作者：Frank Volz、Sipke H. Wadman、Anja Hoffmann-Röder、Norbert Krause

  DOI：10.1016/j.tet.2008.11.104

  日期：2009.2

  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.