3-<5-(4-Hydroxy-3-methylpentyl)-1,4-cyclohexadien-1,5-yl>-1,2-propanediol | 137571-47-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-<5-(4-Hydroxy-3-methylpentyl)-1,4-cyclohexadien-1,5-yl>-1,2-propanediol
• 英文别名: (2S)-3-[5-[(3S,4R)-4-hydroxy-3-methylpentyl]cyclohexa-1,4-dien-1-yl]propane-1,2-diol
• CAS: 137571-47-2
• 化学式: C₁₅H₂₆O₃
• 分子量: 254.37
• InChiKey: ATXMASDAPBHGJP-ZOWXZIJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-<5-(4-Hydroxy-3-methylpentyl)-1,4-cyclohexadien-1,5-yl>-1,2-propanediol 生成 4-Oxo-8,9-dimethyl-1,7-dioxaspiro<5.5>undecane-2-methanol
  参考文献：
  名称：

  Asymmetric synthesis of the milbemycin .beta.3 spiroketal subunit

  摘要：

  The milbemycin beta(3) spiroketal subunit 2 has been prepared with a high degree of enantiomeric purity. This represents the first reagent-controlled asymmetric synthesis of this complex molecule starting from an achiral starting material. Key reactions include Sharpless epoxidation, asymmetric hydroboration, and the Birch reduction of a meta-substituted cinnamyl epoxide. The enantiomeric excess of 2 was determined to be > 95% by a chiral shift H-1 NMR experiment with both optically active and racemic 2. The overall yield was 1.2% from methyl m-toluate (3).

  DOI：

  10.1021/jo00029a033
• 作为产物：
  描述：

  (2R,3S)-5-[5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethyl)-cyclohexa-1,4-dienyl]-3-methyl-pentan-2-ol 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 生成 3-<5-(4-Hydroxy-3-methylpentyl)-1,4-cyclohexadien-1,5-yl>-1,2-propanediol
  参考文献：
  名称：

  Asymmetric synthesis of the milbemycin .beta.3 spiroketal subunit

  摘要：

  The milbemycin beta(3) spiroketal subunit 2 has been prepared with a high degree of enantiomeric purity. This represents the first reagent-controlled asymmetric synthesis of this complex molecule starting from an achiral starting material. Key reactions include Sharpless epoxidation, asymmetric hydroboration, and the Birch reduction of a meta-substituted cinnamyl epoxide. The enantiomeric excess of 2 was determined to be > 95% by a chiral shift H-1 NMR experiment with both optically active and racemic 2. The overall yield was 1.2% from methyl m-toluate (3).

  DOI：

  10.1021/jo00029a033