Methyl-<1R-(1α,4aβ,5β,8aα)>-1,2,3,4,4a,5,8,8a-octahydro-6-hydroxymethyl-5-(3R-hydroxy-4-methylpentyl)-1,4a-dimethyl-5-naphthalene-1-carboxylate | 171963-28-3

• 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: Methyl-<1R-(1α,4aβ,5β,8aα)>-1,2,3,4,4a,5,8,8a-octahydro-6-hydroxymethyl-5-(3R-hydroxy-4-methylpentyl)-1,4a-dimethyl-5-naphthalene-1-carboxylate
• 英文别名: methyl (1R,4aR,5R,8aR)-6-(hydroxymethyl)-5-[(3R)-3-hydroxy-4-methylpentyl]-1,4a-dimethyl-2,3,4,5,8,8a-hexahydronaphthalene-1-carboxylate
• CAS: 171963-28-3
• 化学式: C₂₁H₃₆O₄
• 分子量: 352.514
• InChiKey: XSMLTWMTQUMTCP-QOLKULSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Methyl-<1R-(1α,4aβ,5β,8aα)>-1,2,3,4,4a,5,8,8a-octahydro-6-hydroxymethyl-5-(3R-hydroxy-4-methylpentyl)-1,4a-dimethyl-5-naphthalene-1-carboxylate 在 叔丁基过氧化氢 、 二叔丁基过氧化物 、 vanadyl acetylacetonate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以98%的产率得到Methyl-<1aR-(1aβ,2aβ,3β,6aα,7α,7aβ)>-decahydro-7a-hydroxymethyl-7-(3R-hydroxy-4-methylpentyl)-3,6a-dimethylnaphth<2,3-b>oxiran-1-carboxylate
  参考文献：
  名称：

  New chiral synthons from abietic acid: Oxidation of the C-ring and degradation of the carbon skeleton

  摘要：

  The C-ring of abietic acid (1) is selectively oxidized and cleaved. New chiral synthons for stereoselective synthesis of bi- and tricyclic sesqui- and diterpenes are described.

  DOI：

  10.1007/bf00811381
• 作为产物：
  描述：

  methyl 13β,14β-dihydroxyabieta-7-en-18-oate 在 sodium tetrahydroborate 、 sodium periodate 作用下， 以 乙醇 为溶剂， 反应 20.0h， 生成 Methyl-<1R-(1α,4aβ,5β,8aα)>-1,2,3,4,4a,5,8,8a-octahydro-6-hydroxymethyl-5-(3R-hydroxy-4-methylpentyl)-1,4a-dimethyl-5-naphthalene-1-carboxylate
  参考文献：
  名称：

  New chiral synthons from abietic acid: Oxidation of the C-ring and degradation of the carbon skeleton

  摘要：

  The C-ring of abietic acid (1) is selectively oxidized and cleaved. New chiral synthons for stereoselective synthesis of bi- and tricyclic sesqui- and diterpenes are described.

  DOI：

  10.1007/bf00811381