4-((4R,5R)-5-Decyl-2,2-dioxo-2λ6-[1,3,2]dioxathiolan-4-yl)-butyric acid methyl ester | 188576-31-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机硫酸及其衍生物
• 英文名称: 4-((4R,5R)-5-Decyl-2,2-dioxo-2λ6-[1,3,2]dioxathiolan-4-yl)-butyric acid methyl ester
• CAS: 188576-31-0
• 化学式: C₁₇H₃₂O₆S
• 分子量: 364.503
• InChiKey: LQNZDOTUKXALHV-HZPDHXFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.89
• 重原子数：
  24.0
• 可旋转键数：
  13.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  78.9
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-((4R,5R)-5-Decyl-2,2-dioxo-2λ6-[1,3,2]dioxathiolan-4-yl)-butyric acid methyl ester 在 吡啶 、 lithium hydroxide 、 硫酸 作用下， 反应 36.0h， 生成 6-acetoxy-5-hexadecanolide
  参考文献：
  名称：

  Intramolecular SN2 ring opening of a cyclic sulfate: synthesis of erythro-(−)-6-acetoxy-5-hexadecanolide—a major component of mosquito oviposition attractant pheromone

  摘要：

  Methyl trans-hexa-5-decenoate is dihydroxylated using AD-mix-alpha followed by treatment with thionyl chloride to furnish cyclic sulfite 8 as the major product. The cyclic sulfite 8 is oxidized to the cyclic sulfate 2. Highly regio- and stereospecific ring opening of (4S, 5S)-carboxybutyl-5-decylcyclic sulfate generated in situ by the hydrolysis of 2 furnished (5R,6S)-6-hydroxy-5-hexadecanolide 9 in high yield. Acetylation of 9 afforded natural oviposition attractant pheromone 1 in good yield. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00011-6
• 作为产物：
  描述：

  4-((4R,5R)-5-Decyl-2-oxo-2λ4-[1,3,2]dioxathiolan-4-yl)-butyric acid methyl ester 在 ruthenium trichloride 、 sodium periodate 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 反应 2.0h， 以85%的产率得到4-((4R,5R)-5-Decyl-2,2-dioxo-2λ6-[1,3,2]dioxathiolan-4-yl)-butyric acid methyl ester
  参考文献：
  名称：

  Intramolecular SN2 ring opening of a cyclic sulfate: synthesis of erythro-(−)-6-acetoxy-5-hexadecanolide—a major component of mosquito oviposition attractant pheromone

  摘要：

  Methyl trans-hexa-5-decenoate is dihydroxylated using AD-mix-alpha followed by treatment with thionyl chloride to furnish cyclic sulfite 8 as the major product. The cyclic sulfite 8 is oxidized to the cyclic sulfate 2. Highly regio- and stereospecific ring opening of (4S, 5S)-carboxybutyl-5-decylcyclic sulfate generated in situ by the hydrolysis of 2 furnished (5R,6S)-6-hydroxy-5-hexadecanolide 9 in high yield. Acetylation of 9 afforded natural oviposition attractant pheromone 1 in good yield. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00011-6