(R)-3-hydroxyhexadecanoic acid ethyl ester | 245489-83-2

• 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: (R)-3-hydroxyhexadecanoic acid ethyl ester
• 英文别名: ethyl (3R)-3-hydroxyhexadecanoate
• CAS: 245489-83-2
• 化学式: C₁₈H₃₆O₃
• 分子量: 300.482
• InChiKey: LTSBJVJXSJSRRZ-QGZVFWFLSA-N

物化性质

• 沸点：
  403.4±18.0 °C(Predicted)
• 密度：
  0.918±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  21
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-3-hydroxyhexadecanoic acid ethyl ester 在 咪唑 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 39.0h， 生成 (R)-3-((tert-butyldimethylsilyl)oxy)hexadecanoic acid
  参考文献：
  名称：

  Enantioselective synthesis of natural biologically active ivaide A: 1,3-di-(R)-β-hydroxy-glyceride glycerol

  摘要：

  The natural 1,3-di-beta-hydroxy-glyceride glycerol ivaide A 1 from Ajuga iva has been synthesised by diacylation of dihydroxyacetone with 3-hydroxyhexadecanoic acid, followed by reduction to the corresponding glycerol derivative. The enantiomerically pure (R)-beta-hydroxyhexadecanoic ester intermediate 6 was obtained by a coupling reaction of an ethylacetoacetate dianion and the corresponding bromoalkyl, followed by the known reduction of the resulting beta-ketoester 5 by fermenting baker's yeast. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00222-0
• 作为产物：
  描述：

  ethyl 3-oxohexadecanoate 在 baker's yeast 、 蔗糖 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以43%的产率得到(R)-3-hydroxyhexadecanoic acid ethyl ester
  参考文献：
  名称：

  Enantioselective synthesis of natural biologically active ivaide A: 1,3-di-(R)-β-hydroxy-glyceride glycerol

  摘要：

  The natural 1,3-di-beta-hydroxy-glyceride glycerol ivaide A 1 from Ajuga iva has been synthesised by diacylation of dihydroxyacetone with 3-hydroxyhexadecanoic acid, followed by reduction to the corresponding glycerol derivative. The enantiomerically pure (R)-beta-hydroxyhexadecanoic ester intermediate 6 was obtained by a coupling reaction of an ethylacetoacetate dianion and the corresponding bromoalkyl, followed by the known reduction of the resulting beta-ketoester 5 by fermenting baker's yeast. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00222-0

文献信息

• Synthesis of Novel β-Lactone Inhibitors of Fatty Acid Synthase
  作者：Robyn D. Richardson、Gil Ma、Yatsandra Oyola、Manuel Zancanella、Lynn M. Knowles、Piotr Cieplak、Daniel Romo、Jeffrey W. Smith

  DOI：10.1021/jm800321h

  日期：2008.9.11

  Fatty acid synthase (FAS) is necessary for growth and survival of tumor cells and is a promising drug target for oncology. Here, we report oil the syntheses and activity of novel inhibitors of the thioesterase domain of FAS. Using the structure of orlistat as a starting point, which contains a beta-lactone as the central pharmacophore, 28 novel congeners were synthesized and examined. Structural features such as the length of the alpha- and beta-alkyl chains, their chemical composition, and arnino ester substitutions were altered and tile resulting compounds explored for inhibitory activity toward the thioesterase domain of FAS. Nineteen congeners show improved potency for FAS in biochemical assays relative to orlistat. Three of that subset, including the natural product valilactone, also display all increased potency in inducing tumor cell death and improved solubility compared to orlistat. These findings Support the idea that all orlistat congener can be optimized for use in a preclinical drug design and for clinical drug development.
• Enantioselective synthesis of natural biologically active ivaide A: 1,3-di-(R)-β-hydroxy-glyceride glycerol
  作者：H.B Jannet、A Al Mourabit、A Gateau-Olesker、C Marazano、Z Mighri

  DOI：10.1016/s0957-4166(99)00222-0

  日期：1999.6

  The natural 1,3-di-beta-hydroxy-glyceride glycerol ivaide A 1 from Ajuga iva has been synthesised by diacylation of dihydroxyacetone with 3-hydroxyhexadecanoic acid, followed by reduction to the corresponding glycerol derivative. The enantiomerically pure (R)-beta-hydroxyhexadecanoic ester intermediate 6 was obtained by a coupling reaction of an ethylacetoacetate dianion and the corresponding bromoalkyl, followed by the known reduction of the resulting beta-ketoester 5 by fermenting baker's yeast. (C) 1999 Elsevier Science Ltd. All rights reserved.