(1S,5R)-5-methyl-6,8-dioxabicyclo<3.2.1>octane | 145211-94-5

• 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,5R)-5-methyl-6,8-dioxabicyclo<3.2.1>octane
• 英文别名: (1S,5R)-5-methyl-6,8-dioxabicyclo[3.2.1]octane
• CAS: 145211-94-5
• 化学式: C₇H₁₂O₂
• 分子量: 128.171
• InChiKey: IHCQDMADHYJQPF-NKWVEPMBSA-N

物化性质

• 沸点：
  162.9±8.0 °C(Predicted)
• 密度：
  1.069±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  庚-6-烯-2-酮 在 盐酸 、 (3a,9R,3'''a,4'"b,9'"R)-9,9'-[1,4-phthalazinediylbis(oxy)]bis[6'-(methyloxy)-10,11-dihydrocinchonan] 、 potassium osmate(VI) 、 potassium carbonate 、 potassium hexacyanoferrate(III) 作用下， 生成 (1S,5R)-5-methyl-6,8-dioxabicyclo<3.2.1>octane 、 6,8-Dioxabicyclo[3.2.1]octane, 5-methyl-, (1R)-
  参考文献：
  名称：

  Enantioselective synthesis of the 6,8-dioxabicyclo-[3.2.1]octane skeleton by asymmetric dihydroxylation

  摘要：

  Sharpless asymmetric dihydroxylation (AD) of 6-hepten-2-one with AD-mix-alpha(R) followed by acidification gives (1S,5R)-5-methyl-6.8-dioxabicyclo[3.2.1]octane in moderate ee. This methodology defines a two-pot enantioselective construction of the (-)-frontalin and brevicomin skeleton from the corresponding 2-alkyl-1,3-dithiane and 5-bromo-1-hexene derivatives.

  DOI：

  10.1016/s0040-4039(00)60985-1

文献信息

• Enantioselective synthesis of the 6,8-dioxabicyclo-[3.2.1]octane skeleton by asymmetric dihydroxylation
  作者：Joseph A. Turpin、Leland O. Weigel

  DOI：10.1016/s0040-4039(00)60985-1

  日期：1992.10

  Sharpless asymmetric dihydroxylation (AD) of 6-hepten-2-one with AD-mix-alpha(R) followed by acidification gives (1S,5R)-5-methyl-6.8-dioxabicyclo[3.2.1]octane in moderate ee. This methodology defines a two-pot enantioselective construction of the (-)-frontalin and brevicomin skeleton from the corresponding 2-alkyl-1,3-dithiane and 5-bromo-1-hexene derivatives.