(-)-(6R)-(2E)-1-acetoxy-7-hydroxyimino-2,6-dimethylhept-2-ene | 141208-70-0

• 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-7-hydroxyimino-2,6-dimethylhept-2-ene
• CAS: 141208-70-0
• 化学式: C₁₂H₂₁NO₃
• 分子量: 227.304
• InChiKey: AXNIFBHDJYMRRM-KDKFBZNJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.76
• 重原子数：
  16.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  58.89
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (-)-(6R)-(2E)-1-acetoxy-7-hydroxyimino-2,6-dimethylhept-2-ene 在 lithium hydroxide 、 sodium hypochlorite 作用下， 以 二氯甲烷 为溶剂， 生成 [(3R,3aR,6R)-3,6-dimethyl-4,5,6,7-tetrahydro-3aH-2,1-benzoxazol-3-yl]methanol
  参考文献：
  名称：

  Total Synthesis of (+)-Menthofuran

  摘要：

  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.

  DOI：

  10.3987/com-91-s19
• 作为产物：
  描述：

  [(E,6R)-2,6-dimethyl-8-oxooct-2-enyl] acetate 在 盐酸羟胺 、 sodium acetate 作用下， 生成 (-)-(6R)-(2E)-1-acetoxy-7-hydroxyimino-2,6-dimethylhept-2-ene
  参考文献：
  名称：

  Total Synthesis of (+)-Menthofuran

  摘要：

  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.

  DOI：

  10.3987/com-91-s19

文献信息

• Furanoterpene Synthesis via Intramolecular Nitrile Oxide Cycloaddition Reaction: A Total Synthesis of (+)-Menthofuran
  作者：Kozo Shishido、Koji Umimoto、Takeshi Takata、Osamu Irie、Masayuki Shibuya

  DOI：10.3987/com-92-6231

  日期：——

  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).