4(S)-Hydroxyperoxy-2(E)-nonenal | 150654-75-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4(S)-Hydroxyperoxy-2(E)-nonenal
• 英文别名: (E,4S)-4-hydroperoxynon-2-enal
• CAS: 150654-75-4
• 化学式: C₉H₁₆O₃
• 分子量: 172.224
• InChiKey: TVNYLRYVAZWBEH-IWGCBNPKSA-N

物化性质

• 沸点：
  316.6±35.0 °C(Predicted)
• 密度：
  0.999±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4(S)-Hydroxyperoxy-2(E)-nonenal 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (3S,6S)-3,6-Dihydro-6-pentyl-1,2-dioxin-3-ol 、 (3R,6S)-3,6-Dihydro-6-pentyl-1,2-dioxin-3-ol
  参考文献：
  名称：

  An organometallic approach to peroxy ketals

  摘要：

  A new method for peroxyketal synthesis is presented based upon formation of carbon-carbon bonds in the presence of a protected hydroperoxide. The 2-methoxypropyl perketal of 4(S)-hydroperoxy-2(E)-nonenal (2) undergoes reaction with a variety of metal hydrides and organometallic reagents to produce 4-peroxy 2-enols in good to excellent yields via chemoselective addition to the carbonyl carbon. Oxidation of the allylic alcohol to the 4-peroxy 2-enone is followed by deprotection to furnish a single enantiomer of a 4-hydroxyperoxy 2(E)-enone. Photochemical isomerization by the method of Snider induces spontaneous cyclization to epimeric 3-hydroxy-1,2-dioxins (hydroxy endoperoxides). Acidic methanolysis furnishes readily separable diastereomeric perketals as single enantiomers.

  DOI：

  10.1021/jo00072a032
• 作为产物：
  描述：

  Methyl 13(S)-<(1-methoxy-1-methylethyl)dioxy>-9(Z),11(E)-octadecadienoate 在 氧气 、 臭氧 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.58h， 生成 4(S)-Hydroxyperoxy-2(E)-nonenal
  参考文献：
  名称：

  An organometallic approach to peroxy ketals

  摘要：

  A new method for peroxyketal synthesis is presented based upon formation of carbon-carbon bonds in the presence of a protected hydroperoxide. The 2-methoxypropyl perketal of 4(S)-hydroperoxy-2(E)-nonenal (2) undergoes reaction with a variety of metal hydrides and organometallic reagents to produce 4-peroxy 2-enols in good to excellent yields via chemoselective addition to the carbonyl carbon. Oxidation of the allylic alcohol to the 4-peroxy 2-enone is followed by deprotection to furnish a single enantiomer of a 4-hydroxyperoxy 2(E)-enone. Photochemical isomerization by the method of Snider induces spontaneous cyclization to epimeric 3-hydroxy-1,2-dioxins (hydroxy endoperoxides). Acidic methanolysis furnishes readily separable diastereomeric perketals as single enantiomers.

  DOI：

  10.1021/jo00072a032