(1aR,3aR,7S,7aR,7bS)-7-(2-Hydroxy-ethyl)-1a-methyl-octahydro-1-oxa-cyclopropa[a]naphthalen-7a-ol | 176980-46-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1aR,3aR,7S,7aR,7bS)-7-(2-Hydroxy-ethyl)-1a-methyl-octahydro-1-oxa-cyclopropa[a]naphthalen-7a-ol
• 英文别名: (1aR,3aR,7S,7aR,7bS)-7-(2-hydroxyethyl)-1a-methyl-2,3,3a,4,5,6,7,7b-octahydronaphtho[1,2-b]oxiren-7a-ol
• CAS: 176980-46-4
• 化学式: C₁₃H₂₂O₃
• 分子量: 226.316
• InChiKey: LRDCASGMPXBKLJ-NZEXEKPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  53
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-methoxytrifluoromethylphenylacetyl chloride 、 (1aR,3aR,7S,7aR,7bS)-7-(2-Hydroxy-ethyl)-1a-methyl-octahydro-1-oxa-cyclopropa[a]naphthalen-7a-ol 生成 3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid 2-((1aR,3aR,7S,7aR,7bS)-7a-hydroxy-1a-methyl-decahydro-1-oxa-cyclopropa[a]naphthalen-7-yl)-ethyl ester
  参考文献：
  名称：

  Asymmetric Reductive Cyclization. Total Synthesis of (−)-C₁₀-Desmethyl Arteannuin B

  摘要：

  An efficient total synthesis of (-)-C-10-desmethyl arteannuin B (5) has been achieved. The sequence features the use of a chiral auxiliary to introduce absolute asymmetry at an early stage and a stereoselective, chelation-controlled reductive cyclization of 8, using samarium diiodide as the reducing agent. The methodology promises to be applicable to the synthesis of a wide range of analogs capable of being converted to potent antimalarial agents related to artemisinin (1).

  DOI：

  10.1021/jo9600417
• 作为产物：
  描述：

  (R)-(-)-4-(4'-methyl-2'-oxocyclohex-3'-en-1'-yl)butyraldehyde dimethyl acetal 在 甲醇 、 lithium aluminium tetrahydride 、 samarium diiodide 、 sodium hexamethyldisilazane 、 potassium carbonate 、 间氯过氧苯甲酸 、 三氟乙酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 4.75h， 生成 (1aR,3aR,7S,7aR,7bS)-7-(2-Hydroxy-ethyl)-1a-methyl-octahydro-1-oxa-cyclopropa[a]naphthalen-7a-ol
  参考文献：
  名称：

  Asymmetric Reductive Cyclization. Total Synthesis of (−)-C₁₀-Desmethyl Arteannuin B

  摘要：

  An efficient total synthesis of (-)-C-10-desmethyl arteannuin B (5) has been achieved. The sequence features the use of a chiral auxiliary to introduce absolute asymmetry at an early stage and a stereoselective, chelation-controlled reductive cyclization of 8, using samarium diiodide as the reducing agent. The methodology promises to be applicable to the synthesis of a wide range of analogs capable of being converted to potent antimalarial agents related to artemisinin (1).

  DOI：

  10.1021/jo9600417