(1R,2S,6S,8S)-2-(2,4-dioxapentyl)-8-methylbicyclo[4.3.0]non-3-en-7-one | 949597-19-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2S,6S,8S)-2-(2,4-dioxapentyl)-8-methylbicyclo[4.3.0]non-3-en-7-one
• 英文别名: (2S,3aR,4S,7aS)-4-(methoxymethoxymethyl)-2-methyl-2,3,3a,4,7,7a-hexahydroinden-1-one
• CAS: 949597-19-7
• 化学式: C₁₃H₂₀O₃
• 分子量: 224.3
• InChiKey: HILPVRRDTIOTRR-WHOHXGKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,2S,6S,8S)-2-(2,4-dioxapentyl)-8-methylbicyclo[4.3.0]non-3-en-7-one 在 吡啶 、 4-二甲氨基吡啶 、 samarium diiodide 、 二甲基溴化硼 、 碘 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 10.5h， 生成 (1R,2S,6S,7S,8S)-7-acetoxy-8-methyl-2-hydroxymethylbicyclo[4.3.0]non-3-ene
  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：

  (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 、 四丁基氟化铵 、 仲丁基锂 、 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 、 N,N-二甲基甲酰胺 为溶剂， 反应 44.92h， 生成 (1R,2S,6S,8S)-2-(2,4-dioxapentyl)-8-methylbicyclo[4.3.0]non-3-en-7-one
  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

文献信息

• Towards EPC-syntheses of the structural class of cochleamycins and macquarimicins. Part 1: EPC-synthesis of the hydrindene subunit of the cochleamycins
  作者：A. Chrobok、E. Gössinger、E. Orglmeister、K. Pflugseder、J. Schwaiger、F. Wuggenig

  DOI：10.1016/j.tet.2007.05.092

  日期：2007.8

  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.