(1R,3S,5R,6R)-6-methyl-5-(4-methoxybenzyloxy)-7-oxabicyclo[4.1.0]heptan-3-ol | 1048013-57-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,3S,5R,6R)-6-methyl-5-(4-methoxybenzyloxy)-7-oxabicyclo[4.1.0]heptan-3-ol
• CAS: 1048013-57-5
• 化学式: C₁₅H₂₀O₄
• 分子量: 264.321
• InChiKey: ZJNMRSQVWYOAQK-MYPMTAMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.89
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  51.22
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1R,3S,5R,6R)-6-methyl-5-(4-methoxybenzyloxy)-7-oxabicyclo[4.1.0]heptan-3-ol 、 3-溴丙烯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以81%的产率得到(1R,2R,4S,6R)-4-allyloxy-1-methyl-2-(4-methoxybenzyloxy)-7-oxabicyclo[4.1.0]heptane
  参考文献：
  名称：

  An Improved Asymmetric Synthesis of Malyngamide U and Its 2′-Epimer

  摘要：

  An accelerated and improved asymmetric synthesis of malyngamide U (1) and its 2'-epimer (2'-epi-1) was accomplished from readily available n-hexanal, ethanolamine and (R)-(-)-carvone. The key steps involved a Johnson-Claisen rearrangement in the synthesis of an unsaturated carboxylic acid 4 and an aldol reaction in the construction of the skeleton of I and 2'-epi-1. There are 13 steps in the synthesis, with a 2.7% overall yield for 1 and a 0.4% yield for 2'-epi-1.

  DOI：

  10.1021/jo800876u
• 作为产物：
  描述：

  (1R,3S,5R,6R)-6-methyl-5-(4-methoxybenzyloxy)-7-oxabicyclo[4.1.0]heptan-3-yl acetate 在 甲醇 、 potassium carbonate 作用下， 反应 2.0h， 以95%的产率得到(1R,3S,5R,6R)-6-methyl-5-(4-methoxybenzyloxy)-7-oxabicyclo[4.1.0]heptan-3-ol
  参考文献：
  名称：

  An Improved Asymmetric Synthesis of Malyngamide U and Its 2′-Epimer

  摘要：

  An accelerated and improved asymmetric synthesis of malyngamide U (1) and its 2'-epimer (2'-epi-1) was accomplished from readily available n-hexanal, ethanolamine and (R)-(-)-carvone. The key steps involved a Johnson-Claisen rearrangement in the synthesis of an unsaturated carboxylic acid 4 and an aldol reaction in the construction of the skeleton of I and 2'-epi-1. There are 13 steps in the synthesis, with a 2.7% overall yield for 1 and a 0.4% yield for 2'-epi-1.

  DOI：

  10.1021/jo800876u