(1R,3S,5S,7S,8R,9S,11S)-3-ethoxy-6,6-dimethoxy-11-methyl-2-oxatetracyclo[6.3.0.0^3,7.0^5,9]undecane | 949596-88-7

• 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: (1R,3S,5S,7S,8R,9S,11S)-3-ethoxy-6,6-dimethoxy-11-methyl-2-oxatetracyclo[6.3.0.0^3,7.0^5,9]undecane
• CAS: 949596-88-7
• 化学式: C₁₅H₂₄O₄
• 分子量: 268.353
• InChiKey: PKLRPAZSQHWIAR-LHWOPQQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.03
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1R,3S,5S,7S,8R,9S,11S)-3-ethoxy-6,6-dimethoxy-11-methyl-2-oxatetracyclo[6.3.0.0^3,7.0^5,9]undecane 在 咪唑 、 盐酸 、 lithium aluminium tetrahydride 、 samarium diiodide 、 四丁基氟化铵 、 碘 、 仲丁基锂 、 potassium carbonate 、 戴斯-马丁氧化剂 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 二氯甲烷 、 环己烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.92h， 生成 (1R,2S,6S,7S,8S)-2-(2,4-dioxapentyl)-8-methylbicyclo[4.3.0]non-3-en-7-ol
  参考文献：
  名称：

  Towards EPC-syntheses of the structural class of cochleamycins and macquarimicins. Part 1: EPC-synthesis of the hydrindene subunit of the cochleamycins

  摘要：

  A racemic as well as an EPC-synthesis of the cis-hydrindene subunit of the cochleamycins, physiologically active microbial secondary metabolites, are reported. The five stereogenic centres of this subunit are introduced in high stereoselectivity in a short sequence by intermolecular Diels-Alder reaction, stereoselective methylation and hydride reduction. Cyclisation via nucleophilic addition, acidic fragmentation, regioselective Shapiro reaction and inversion of a secondary alcohol are the further key steps of these syntheses. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.092
• 作为产物：
  描述：

  (1S,2S,4S,6S,7R)-1,7,8,9-tetrachloro-10,10-dimethoxy-4-methyltricyclo[5.2.1.0^2,6]dec-8-en-3-one 在 sodium tetrahydroborate 、 sodium 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 (1R,3S,5S,7S,8R,9S,11S)-3-ethoxy-6,6-dimethoxy-11-methyl-2-oxatetracyclo[6.3.0.0^3,7.0^5,9]undecane
  参考文献：
  名称：

  Towards EPC-syntheses of the structural class of cochleamycins and macquarimicins. Part 1: EPC-synthesis of the hydrindene subunit of the cochleamycins

  摘要：

  A racemic as well as an EPC-synthesis of the cis-hydrindene subunit of the cochleamycins, physiologically active microbial secondary metabolites, are reported. The five stereogenic centres of this subunit are introduced in high stereoselectivity in a short sequence by intermolecular Diels-Alder reaction, stereoselective methylation and hydride reduction. Cyclisation via nucleophilic addition, acidic fragmentation, regioselective Shapiro reaction and inversion of a secondary alcohol are the further key steps of these syntheses. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.092