(+)-(6R)-(2E)-1-acetoxy-8-nitro-2,6-dimethyloct-2-ene | 141208-72-2

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (+)-(6R)-(2E)-1-acetoxy-8-nitro-2,6-dimethyloct-2-ene
• CAS: 141208-72-2
• 化学式: C₁₂H₂₁NO₄
• 分子量: 243.303
• InChiKey: PRNOSNJAYFOUSE-VUUNSECVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  17.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  69.44
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (+)-(6R)-(2E)-1-acetoxy-8-nitro-2,6-dimethyloct-2-ene 在 lithium hydroxide 、 对氯苯异氰酸酯 、 三乙胺 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 16.0h， 生成 [(6R)-3,6-dimethyl-4,5,6,7-tetrahydro-3aH-2,1-benzoxazol-3-yl]methanol
  参考文献：
  名称：

  Furanoterpene Synthesis via Intramolecular Nitrile Oxide Cycloaddition Reaction: A Total Synthesis of (+)-Menthofuran

  摘要：

  A fused furan assembling strategy based on an intramolecular [3+2] dipolar cycloaddition reaction of nitrile oxide has been applied to a total synthesis of perfumy furanomonoterpene (+)-menthofuran (1). The key cycloaddition substrates (9) and (1 2) are easily prepared via straightforward routes starting from (+)-citronellal and these are treated with sodium hypochlorite and p-chlorophenyl isocyanate, respectively. The cycloaddition reactions generate 10 : 1 mixture of diastereoisomeric isoxazolines (2a) and (2b) in good to excellent yields. The isoxazolines (2a,b) thus obtained are converted to (+)-menthofuran (1) by sequential reductive hydrolysis and alkaline hydrolysis (or vice versa) followed by acid treatment of the resulting beta,gamma-dihydroxy ketone (1 4).

  DOI：

  10.3987/com-92-6231
• 作为产物：
  描述：

  (+)-香茅醛 在 吡啶 、 咪唑 、 叔丁基过氧化氢 、 sodium tetrahydroborate 、 silver(I) nitrite 、 selenium(IV) oxide 、 四丁基氟化铵 、 N,N-二异丙基乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 85.5h， 生成 (+)-(6R)-(2E)-1-acetoxy-8-nitro-2,6-dimethyloct-2-ene
  参考文献：
  名称：

  Furanoterpene Synthesis via Intramolecular Nitrile Oxide Cycloaddition Reaction: A Total Synthesis of (+)-Menthofuran

  摘要：

  A fused furan assembling strategy based on an intramolecular [3+2] dipolar cycloaddition reaction of nitrile oxide has been applied to a total synthesis of perfumy furanomonoterpene (+)-menthofuran (1). The key cycloaddition substrates (9) and (1 2) are easily prepared via straightforward routes starting from (+)-citronellal and these are treated with sodium hypochlorite and p-chlorophenyl isocyanate, respectively. The cycloaddition reactions generate 10 : 1 mixture of diastereoisomeric isoxazolines (2a) and (2b) in good to excellent yields. The isoxazolines (2a,b) thus obtained are converted to (+)-menthofuran (1) by sequential reductive hydrolysis and alkaline hydrolysis (or vice versa) followed by acid treatment of the resulting beta,gamma-dihydroxy ketone (1 4).

  DOI：

  10.3987/com-92-6231

文献信息

• Total Synthesis of (+)-Menthofuran
  作者：Kozo Shishido、Takeshi Takata、Koji Umimoto、Masayuki Shibuya

  DOI：10.3987/com-91-s19

  日期：——

  Total synthesis of optically active menthofuran, a perfumy monoterpene, has been accomplished employing the intramolecular [3 + 2] cycloaddition-based methodology for the construction of fused furans.