(5R,6S)-(-)-erythro-6-hydroxy-5-dodecanolide | 114811-18-6

• 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-hydroxy-5-dodecanolide
• 英文别名: (5R,6S)-6-hydroxydodecano-5-lactone；(6R)-6-[(1S)-1-hydroxyheptyl]oxan-2-one
• CAS: 114811-18-6
• 化学式: C₁₂H₂₂O₃
• 分子量: 214.305
• InChiKey: MLEMQFJGWFYWOE-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.41
• 重原子数：
  15.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (5R,6S)-(-)-erythro-6-hydroxy-5-dodecanolide 、 乙酸酐 生成 (5R,6S)-(-)-erythro-6-acetoxy-5-dodecanolide
  参考文献：
  名称：

  SALA, LUIS F.;CRAVERO, RAQUEL M.;SIGNORRELLA, SANDRA R.;GONZALEZ-SIERRA, +, SYNTH. COMMUN., 17,(1987) N 11, 1287-1297

  摘要：

  DOI：
• 作为产物：
  描述：

  在 sodium hydroxide 作用下， 以 乙醇 、 甲苯 、 苯 为溶剂， 反应 17.0h， 生成 (5R,6S)-(-)-erythro-6-hydroxy-5-dodecanolide
  参考文献：
  名称：

  Enzymes in organic synthesis. 27. Lipase-Catalyzed Synthesis of (5R,6S)-6-Acetoxyalkan-5-olides - homologues of the mosquito oviposition attractant pheromone

  摘要：

  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.

  DOI：

  10.1002/prac.19973390176

文献信息

• Metabolism of Deuterated<i>erythro</i>‐Dihydroxy Fatty Acids in<i>Saccharomyces cerevisiae</i>: Enantioselective Formation and Characterization of Hydroxylactones
  作者：Leif‐A. Garbe、Katja Morgenthal、Katrin Kuscher、Roland Tressl

  DOI：10.1002/hlca.200890129

  日期：2008.6

  Epoxides of fatty acids are hydrolyzed by epoxide hydrolases (EHs) into dihydroxy fatty acids which are of particular interest in the mammalian leukotriene pathway. In the present report, the analysis of the configuration of dihydroxy fatty acids via their respective hydroxylactones is described. In addition, the biotransformation of (±)-erythro-7,8- and -3,4-dihydroxy fatty acids in the yeast Saccharomyces

  脂肪酸的环氧化合物被环氧水解酶（EHs）水解为二羟基脂肪酸，这在哺乳动物白三烯途径中特别重要。在本报告中，描述了通过其各自的羟基内酯对二羟基脂肪酸构型的分析。另外，通过GC / EI-MS分析表征了酵母酿酒酵母中（±）-赤型-7，8-和-3，4-二羟基脂肪酸的生物转化。化学合成的（±）的生物转化-赤-7,8-二羟基（7,8- 2 ħ 2）十四烷酸（（±） -赤- 1）在酵母酿酒酵母导致形成5,6-二羟基（5,6- 2 H 2）十二酸（6），将其内酯化为（5 S，6 R）-6-羟基（5,6- 2 H 2）十二酸具有86％ee的-5-内酯（（5 S，6 R）-4）进入赤型-5-羟基（5,6- 2 H 2）十二烷-6-内酯（erythro - 8）。另外，该α -ketols 7-羟基-8-氧代（7- 2 ħ 1）十四烷酸（图9a）和8-羟基-7-氧代（8- 2检测到H 1）十四烷酸（9b）作为中间体。6的进一步代谢产生3
• Sala, Luis F.; Cravero, Raquel M.; Signorella, Sandra R., Synthetic Communications, 1987, vol. 17, # 11, p. 1287 - 1298
  作者：Sala, Luis F.、Cravero, Raquel M.、Signorella, Sandra R.、Gonzalez-Sierra, Manuel、Ruveda, Edmundo A.

  DOI：——

  日期：——