(Z)-(+)-cyclohexyl nitronic ester of (4S^*,5R)-4-(1'-nitro-1'-carbethoxymethyl)-5-((1R)-menthyloxy)-3,4-dihydro-2(5H)-furanone

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (Z)-(+)-cyclohexyl nitronic ester of (4S^*,5R)-4-(1'-nitro-1'-carbethoxymethyl)-5-((1R)-menthyloxy)-3,4-dihydro-2(5H)-furanone
• 英文别名: N-cyclohexyloxy-2-ethoxy-1-[(2R,3S)-2-[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]oxy-5-oxooxolan-3-yl]-2-oxoethanimine oxide
• 化学式: C₂₄H₃₉NO₇
• 分子量: 453.576
• InChiKey: QDFYHEYFUWDAMX-AEDREYMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  99.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (5R)-(L-menthyloxy)-2(5H)-furanone 在 sodium ethanolate 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 (Z)-(+)-cyclohexyl nitronic ester of (4S^*,5R)-4-(1'-nitro-1'-carbethoxymethyl)-5-((1R)-menthyloxy)-3,4-dihydro-2(5H)-furanone
  参考文献：
  名称：

  Synthesis and Characterization of Chiral Nitronic Esters via O-Alkylation of (4S*,5R)-(+)-4-(1‘-Nitro-1‘-carbethoxymethyl)- 5-[(1R)-menthyloxy]-3,4-dihydro-2(5H)-furanone with Alkyl Halides

  摘要：

  A series of stable and enantiomerically pure alkyl nitronic esters are synthesized in good to excellent yields via O-alkylation of (4S*,5R)-(+)-4-(1'-nitro-1'-carbethoxymethyl)-5-[(1R)-menthyloxy] -3,4-dihydro-2(5H)-furanone (4a) with alkyl halides in the presence of K2CO3 and DMF at room temperature. Thus, nitronic esters are obtained for the first time from the alkali metal salt of a nitro compound and various alkyl halides, which refutes the traditionally held view that the reaction of alkyl halides with alkali metal derivatives of nitro compounds gives a carbonyl compound and an oxime, rather than a nitronic ester. Secondary alkyl nitronic esters are found to partially decompose into O-alkyloximes. The configurations of the nitronic esters and O-alkyloximes were assigned to be Z on the basis of the NOE experiments. The synthesis of the nitro furanone 4a and its enolization to form a six-membered intramolecular hydrogen bond structure are described.

  DOI：

  10.1021/jo951902z

文献信息

• Synthesis and Characterization of Chiral Nitronic Esters via <i>O</i>-Alkylation of (4<i>S</i>*,5<i>R</i>)-(+)-4-(1‘-Nitro-1‘-carbethoxymethyl)- 5-[(1<i>R</i>)-menthyloxy]-3,4-dihydro-2(5<i>H</i>)-furanone with Alkyl Halides
  作者：Fu-An Kang、Cheng-Lie Yin、Shi-Wang She

  DOI：10.1021/jo951902z

  日期：1996.1.1

  A series of stable and enantiomerically pure alkyl nitronic esters are synthesized in good to excellent yields via O-alkylation of (4S*,5R)-(+)-4-(1'-nitro-1'-carbethoxymethyl)-5-[(1R)-menthyloxy] -3,4-dihydro-2(5H)-furanone (4a) with alkyl halides in the presence of K2CO3 and DMF at room temperature. Thus, nitronic esters are obtained for the first time from the alkali metal salt of a nitro compound and various alkyl halides, which refutes the traditionally held view that the reaction of alkyl halides with alkali metal derivatives of nitro compounds gives a carbonyl compound and an oxime, rather than a nitronic ester. Secondary alkyl nitronic esters are found to partially decompose into O-alkyloximes. The configurations of the nitronic esters and O-alkyloximes were assigned to be Z on the basis of the NOE experiments. The synthesis of the nitro furanone 4a and its enolization to form a six-membered intramolecular hydrogen bond structure are described.