(5aRS,6RS,9aSR)-1,3,5a,6,7,8,9,9a-octahydro-6-(1-methylethyl)-9-methylene-1-oxo-2-benzoxepin-4-carboxaldehyde | 116700-86-8

• 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: (5aRS,6RS,9aSR)-1,3,5a,6,7,8,9,9a-octahydro-6-(1-methylethyl)-9-methylene-1-oxo-2-benzoxepin-4-carboxaldehyde
• 英文别名: 6-isopropyl-9-methylene-1-oxo-1,3,5a,6,7,8,9,9a-octahydrobenzo[c]oxepine-4-carbaldehyde；(5aS,6R,9aS)-9-methylidene-1-oxo-6-propan-2-yl-3,5a,6,7,8,9a-hexahydro-2-benzoxepine-4-carbaldehyde
• CAS: 116700-86-8
• 化学式: C₁₅H₂₀O₃
• 分子量: 248.322
• InChiKey: GMNCDJMDWBBFHT-MGPQQGTHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5aRS,6RS,9aSR)-1,3,5a,6,7,8,9,9a-octahydro-6-(1-methylethyl)-9-methylene-1-oxo-2-benzoxepin-4-carboxaldehyde 在 叔丁基过氧化氢 、 sodium chlorite 、 hexacarbonyl molybdenum 作用下， 生成 (+)-萜烯七脂酸
  参考文献：
  名称：

  EPC synthesis of (+)-heptelidic acid

  摘要：

  An EPC (enantiomerically pure compound) synthesis of the antibiotic natural product (+)-heptelidic acid (1) is presented. Key step of the synthesis is a conjugate addition of the acetal protected vinyl cuprate 4 to the auxiliary shielded enoate 5n which gives the adduct 7n as a single diastereomer. After cleavage of the acetal protecting group and of the chiral auxiliary the enantiomerically pure beta-ketoester 12 has been obtained which has been transformed to the title compound 1 (11 steps starting from 5n, 10.6% overall yield).

  DOI：

  10.1007/bf00807894
• 作为产物：
  描述：

  methyl (5R,6S)-6-[3-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]prop-1-enyl]-2-diethoxyphosphoryloxy-5-propan-2-ylcyclohexene-1-carboxylate 在 bis(acetylacetonate)nickel(II) chromium(VI) oxide 、 sodium hydroxide 、 bis(2-oxo-1,3-oxazolidin-3-yl)phosphinous chloride 、 三氯化铁 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 114.12h， 生成 (5aRS,6RS,9aSR)-1,3,5a,6,7,8,9,9a-octahydro-6-(1-methylethyl)-9-methylene-1-oxo-2-benzoxepin-4-carboxaldehyde
  参考文献：
  名称：

  EPC synthesis of (+)-heptelidic acid

  摘要：

  An EPC (enantiomerically pure compound) synthesis of the antibiotic natural product (+)-heptelidic acid (1) is presented. Key step of the synthesis is a conjugate addition of the acetal protected vinyl cuprate 4 to the auxiliary shielded enoate 5n which gives the adduct 7n as a single diastereomer. After cleavage of the acetal protecting group and of the chiral auxiliary the enantiomerically pure beta-ketoester 12 has been obtained which has been transformed to the title compound 1 (11 steps starting from 5n, 10.6% overall yield).

  DOI：

  10.1007/bf00807894

文献信息

• EPC synthesis of (+)-heptelidic acid
  作者：G. Riehs、E. Urban

  DOI：10.1007/bf00807894

  日期：1997.3

  An EPC (enantiomerically pure compound) synthesis of the antibiotic natural product (+)-heptelidic acid (1) is presented. Key step of the synthesis is a conjugate addition of the acetal protected vinyl cuprate 4 to the auxiliary shielded enoate 5n which gives the adduct 7n as a single diastereomer. After cleavage of the acetal protecting group and of the chiral auxiliary the enantiomerically pure beta-ketoester 12 has been obtained which has been transformed to the title compound 1 (11 steps starting from 5n, 10.6% overall yield).