(5R,6S)-(-)-erythro-6-acetoxy-5-dodecanolide | 97806-58-1

• 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: (5R,6S)-(-)-erythro-6-acetoxy-5-dodecanolide
• 英文别名: [(1S)-1-[(2R)-6-oxooxan-2-yl]heptyl] acetate
• CAS: 97806-58-1
• 化学式: C₁₄H₂₄O₄
• 分子量: 256.342
• InChiKey: ILSZUXUFHQCLAO-QWHCGFSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.98
• 重原子数：
  18.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  (2R)-2-[(2S,3S)-3-pentyloxiran-2-yl]-2,3-dihydropyran-6-one 在 镍 氢溴酸 、 氢气 、 calcium carbonate 作用下， 以 吡啶 、 乙醇 、 氯仿 为溶剂， 25.0 ℃ 、303.98 kPa 条件下， 反应 3.62h， 生成 (5R,6S)-(-)-erythro-6-acetoxy-5-dodecanolide
  参考文献：
  名称：

  Sala, Luis F.; Cravero, Raquel M.; Signorella, Sandra R., Synthetic Communications, 1987, vol. 17, # 11, p. 1287 - 1298

  摘要：

  DOI：

文献信息

• Enzymes in organic synthesis. 27. Lipase-Catalyzed Synthesis of (5R,6S)-6-Acetoxyalkan-5-olides - homologues of the mosquito oviposition attractant pheromone
  作者：B. Henkel、A. Kunath、Hans Schick

  DOI：10.1002/prac.19973390176

  日期：——

  Sixteen homologous (5R*,6S*)-6-hydroxyalkan-5-olides rac-5 and their acetoxy derivatives rac-6 were synthesized from the corresponding methyl (Z)-alk-5-enoates 3 by osmium(VIII) oxide catalyzed cis-hydroxylation to the dihydroxy esters rac-4 and hydrolysis of these esters followed by lactonization. Pancreatin-catalyzed lactonization of the dihydroxy esters rac-4 afforded enantiomerically enriched hydroxy lactones ent-5, five of which were obtained enantiomerically pure by recrystallization. Acetylation of the 6-hydroxyalkan-5-olides rac-5 by vinyl acetate catalyzed by the lipase SP 526 provided enantiomerically enriched 6-acetoxyalkan-5-olides 6 with an enantiomeric excess of more than 90% in nine cases. These compounds are known as mosquito oviposition attractant pheromone (6h) or its homologues.
• SALA, LUIS F.;CRAVERO, RAQUEL M.;SIGNORRELLA, SANDRA R.;GONZALEZ-SIERRA, +, SYNTH. COMMUN., 17,(1987) N 11, 1287-1297
  作者：SALA, LUIS F.、CRAVERO, RAQUEL M.、SIGNORRELLA, SANDRA R.、GONZALEZ-SIERRA, +

  DOI：——

  日期：——