(-)-(6R)-(2E)-1-acetoxy-8-iodo-2,6-dimethyloct-2-ene | 147594-70-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (-)-(6R)-(2E)-1-acetoxy-8-iodo-2,6-dimethyloct-2-ene
• CAS: 147594-70-5
• 化学式: C₁₂H₂₁IO₂
• 分子量: 324.202
• InChiKey: IUOONGGMZYMYGD-VUUNSECVSA-N

物化性质

• 沸点：
  328.3±35.0 °C(Predicted)
• 密度：
  1.335±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.74
• 重原子数：
  15.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (-)-(6R)-(2E)-1-acetoxy-8-iodo-2,6-dimethyloct-2-ene 在 silver(I) nitrite 作用下， 以 乙醚 为溶剂， 反应 72.0h， 以72%的产率得到(+)-(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
• 作为产物：
  描述：

  (+)-(6R)-(2E)-1-acetoxy-8-tert-butyldimethylsilyloxy-2,6-dimethyloct-2-ene 在 四丁基氟化铵 、 N,N-二异丙基乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 8.0h， 生成 (-)-(6R)-(2E)-1-acetoxy-8-iodo-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.