(8S,5R)-8-<(1-Methoxy-1-methylethyl)dioxy>-6(E)-tridecan-5-ol | 150592-56-6

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机氧化物
• 英文名称: (8S,5R)-8-<(1-Methoxy-1-methylethyl)dioxy>-6(E)-tridecan-5-ol
• 英文别名: (E,5R,8S)-8-(2-methoxypropan-2-ylperoxy)tridec-6-en-5-ol
• CAS: 150592-56-6
• 化学式: C₁₇H₃₄O₄
• 分子量: 302.455
• InChiKey: GPZBZJSVNAPPIA-WVJKRLJDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-(+)-α-甲氧基-α-(三氟甲基)苯乙酸 、 (8S,5R)-8-<(1-Methoxy-1-methylethyl)dioxy>-6(E)-tridecan-5-ol 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (E)-(1R,4S)-1-butyl-4-(1-methoxy-1-methyl-ethylperoxy)-non-2-enyl ester
  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 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 6.08h， 生成 (8S,5R)-8-<(1-Methoxy-1-methylethyl)dioxy>-6(E)-tridecan-5-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