(1S,3R,4aR,8aS,)-1-hydroxymethyl-6-methyl-4a,5,8,8a-tetrahydro-1H-isochromen-4(3H)-one | 1221185-26-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (1S,3R,4aR,8aS,)-1-hydroxymethyl-6-methyl-4a,5,8,8a-tetrahydro-1H-isochromen-4(3H)-one
• CAS: 1221185-26-7
• 化学式: C₁₂H₁₈O₄
• 分子量: 226.273
• InChiKey: APWRWXHPEBKHNB-BTQIBKBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.89
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1S,3R,4aR,8aS,)-1-hydroxymethyl-6-methyl-4a,5,8,8a-tetrahydro-1H-isochromen-4(3H)-one 在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 以30%的产率得到(1S,5S,6S,8S,9S,10S)-6-hydroxymethyl-2-methyl-7-oxatricyclo[6.1.1.0^5,10]dec-2-ene-8,9-diol
  参考文献：
  名称：

  Reactions of stereocontrolled intramolecular carbocyclization of levoglucosenone adduct with isoprene

  摘要：

  An intramolecular carbocyclization was found of levoglucosenone adduct with isoprene providing a fused cyclobutane. The intramolecular oxacyclization of the adduct was performed under the treatment with I(2), H(3)PO(4), SOCl(2), and Pd/C leading to 1,4-epoxide. Methods were developed of radical and anionic (by Ferrier method) transformation of the adduct into chiral trans- and cis-decalins.

  DOI：

  10.1134/s1070428010020144
• 作为产物：
  描述：

  (1S,2S,7R,9R)-5-methyl-10,12-dioxatricyclo[7.2.1.0^2,7]dodec-4-en-8-one 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以57%的产率得到(1S,3R,4aR,8aS,)-1-hydroxymethyl-6-methyl-4a,5,8,8a-tetrahydro-1H-isochromen-4(3H)-one
  参考文献：
  名称：

  Cleavage of the 1,6-anhydro bridge in the levoglucosenone adduct with isoprene and its derivatives

  摘要：

  Methods of opening of the 1,6-anhydro bridge in levoglucosenone (ZnCl(2)-Ac(2)O), its adducts with isoprene (ZnCl(2)-Ac(2)O, HCl-MeOH), and hydroxy derivatives (H(3)PO(4)-Ac(2) (O)) were studied. Cleavage of the 1,6-anhydro bridge in anomeric acetoxy derivatives of levoglucosenone-isoprene adduct by the action of BF(3) center dot Et(2)O-Ac(2)O was accompanied by acetylation at the allylic C (6) position.

  DOI：

  10.1134/s1070428010010148