(R)-(-)-4-(4'-methyl-2'-oxocyclohex-3'-en-1'-yl)butyraldehyde | 176980-42-0

• 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
• 英文别名: 3-Cyclohexene-1-butanal, 4-methyl-2-oxo-, (R)-；4-[(1R)-4-methyl-2-oxocyclohex-3-en-1-yl]butanal
• CAS: 176980-42-0
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: ZGGJVBDAMOHRGC-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-(-)-4-(4'-methyl-2'-oxocyclohex-3'-en-1'-yl)butyraldehyde 在 甲醇 、 lithium aluminium tetrahydride 、 samarium diiodide 、 sodium hexamethyldisilazane 、 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.75h， 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 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 以98%的产率得到(R)-(-)-4-(4'-methyl-2'-oxocyclohex-3'-en-1'-yl)butyraldehyde
  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).