(1S,7R,10R,11S)-11-(hydroxymethyl)-7-methyl-10-(methylethyl)-4-oxatricyclo[5.3.1.0(2,6)]undec-2(6)-en-3-one | 405157-85-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S,7R,10R,11S)-11-(hydroxymethyl)-7-methyl-10-(methylethyl)-4-oxatricyclo[5.3.1.0(2,6)]undec-2(6)-en-3-one
• 英文别名: drechslerin B；Drechslerine B；(1S,7R,10R,11S)-11-(hydroxymethyl)-7-methyl-10-propan-2-yl-4-oxatricyclo[5.3.1.02,6]undec-2(6)-en-3-one
• CAS: 405157-85-9
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: MOVBLVLLDMOXTD-GOMXZESMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (1R,7S,8R)-1-methyl-5-oxo-8-(methylethyl)-4-oxa-tricyclo[5.3.1.0(2,6)]undec-2(6)-ene-11-carbaldehyde 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以44%的产率得到(1S,7R,10R,11S)-11-(hydroxymethyl)-7-methyl-10-(methylethyl)-4-oxatricyclo[5.3.1.0(2,6)]undec-2(6)-en-3-one
  参考文献：
  名称：

  First total syntheses of bicyclic marine sesquiterpenoids drechslerines A and B

  摘要：

  The first total syntheses of the bicyclic sesquiterpenoids drechslerines A (1) and B (2), which were isolated from the algicolous fungus Drechslera dematioidea in the marine red alga Liagora viscida, has been accomplished starting from (S)-carvone (13) via three palladium-catalyzed reactions, namely, diastereoselective allylation, conjugate reduction, and carbon monoxide insertion, as the key reactions. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.04.007