rac-methyl 8-hydroxytetradec-6-ynoate | 1352403-93-0

• 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: rac-methyl 8-hydroxytetradec-6-ynoate
• CAS: 1352403-93-0
• 化学式: C₁₅H₂₆O₃
• 分子量: 254.37
• InChiKey: MTKNOFHKLAUUJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.05
• 重原子数：
  18.0
• 可旋转键数：
  9.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  rac-methyl 8-hydroxytetradec-6-ynoate 在 吡啶 作用下， 以 正己烷 、 二氯甲烷 、 异丙醇 为溶剂， 反应 4.0h， 生成 (-)-(S)-14-methoxy-14-oxotetradec-8-yn-7-yl benzoate
  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
• 作为产物：
  描述：

  2H-吡喃,2-(6-庚炔-1-氧基)四氢 在 甲醇 、 sodium tetrahydroborate 、 Jones reagent 、 正丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 hexanes 、 乙醚 、 丙酮 为溶剂， 反应 55.58h， 生成 rac-methyl 8-hydroxytetradec-6-ynoate
  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.