(S)-methyl 8-hydroxytetradecanoate | 1352404-24-0

• 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: (S)-methyl 8-hydroxytetradecanoate
• 英文别名: methyl (8S)-8-hydroxytetradecanoate
• CAS: 1352404-24-0
• 化学式: C₁₅H₃₀O₃
• 分子量: 258.401
• InChiKey: ATHQVZWTRMFEDJ-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2H-吡喃,2-(6-庚炔-1-氧基)四氢 在 吡啶 、 甲醇 、 sodium tetrahydroborate 、 Jones reagent 、 正丁基锂 、 5% Pd-BaSO4 、 氢气 、 对甲苯磺酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 hexanes 、 乙醚 、 正己烷 、 二氯甲烷 、 水 、 异丙醇 、 丙酮 为溶剂， 反应 59.58h， 生成 (S)-methyl 8-hydroxytetradecanoate
  参考文献：
  名称：

  Synthesis of highly enantioenriched hydroxy- and dihydroxy-fatty esters: substrate precursors for cytochrome P450BioI

  摘要：

  A series of highly enantioenriched hydroxy- and dihydroxy-fatty esters were required as part of our ongoing investigation into cytochrome P450(BioI). This mediates the biosynthesis of pimelic acid via C-C bond cleavage of long chain fatty acids within Bacillus subtilis. Herein we report the synthesis of various stereoisomers of methyl 7-hydroxytetradecanoate, methyl 8-hydroxytetradecanoate, and methyl 7,8-dihydroxytetradecanoate in highly enantioenriched form, using a combination of asymmetric synthesis and a preparative enantioselective HPLC is reported. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.08.027

文献信息

• Synthesis of highly enantioenriched hydroxy- and dihydroxy-fatty esters: substrate precursors for cytochrome P450BioI
  作者：Arti A. Singh、Siti N.A. Zulkifli、Michaela Meyns、Patricia Y. Hayes、James J. De Voss

  DOI：10.1016/j.tetasy.2011.08.027

  日期：2011.10

  A series of highly enantioenriched hydroxy- and dihydroxy-fatty esters were required as part of our ongoing investigation into cytochrome P450(BioI). This mediates the biosynthesis of pimelic acid via C-C bond cleavage of long chain fatty acids within Bacillus subtilis. Herein we report the synthesis of various stereoisomers of methyl 7-hydroxytetradecanoate, methyl 8-hydroxytetradecanoate, and methyl 7,8-dihydroxytetradecanoate in highly enantioenriched form, using a combination of asymmetric synthesis and a preparative enantioselective HPLC is reported. (C) 2011 Elsevier Ltd. All rights reserved.