(R)-(-)-4-(4'-methyl-2'-oxocyclohex-3'-en-1'-yl)butyraldehyde dimethyl acetal | 176980-51-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-(-)-4-(4'-methyl-2'-oxocyclohex-3'-en-1'-yl)butyraldehyde dimethyl acetal
• 英文别名: (6R)-6-(4,4-dimethoxybutyl)-3-methylcyclohex-2-en-1-one
• CAS: 176980-51-1
• 化学式: C₁₃H₂₂O₃
• 分子量: 226.316
• InChiKey: LRRGMRDDKUJLMZ-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• 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：

  (R)-(-)-4-(4'-methyl-2'-oxocyclohex-3'-en-1'-yl)butyraldehyde dimethyl acetal 在 sodium hexamethyldisilazane 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.25h， 生成 (E)-6-((R)-4-Methyl-2-oxo-cyclohex-3-enyl)-hex-2-enoic acid methyl 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：

  4-iodobutyraldehyde dimethyl acetal 在 正丁基锂 、 臭氧 、 二异丙胺 、 lithium chloride 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 生成 (R)-(-)-4-(4'-methyl-2'-oxocyclohex-3'-en-1'-yl)butyraldehyde dimethyl acetal
  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

文献信息

• Asymmetric Reductive Cyclization. Total Synthesis of (−)-C₁₀-Desmethyl Arteannuin B
  作者：Michael Schwaebe、R. Daniel Little

  DOI：10.1021/jo9600417

  日期：1996.1.1

  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).