2-hydroxyoctadec-3-enoic acid | 853569-77-4

• 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: 2-hydroxyoctadec-3-enoic acid
• 英文别名: (E)-2-hydroxyoctadec-3-enoic Acid
• CAS: 853569-77-4
• 化学式: C₁₈H₃₄O₃
• 分子量: 298.466
• InChiKey: DFXJNNLDXLLTOL-FOCLMDBBSA-N

物化性质

• 熔点：
  96.0-96.2 °C(Solv: acetone (67-64-1))
• 沸点：
  440.3±25.0 °C(Predicted)
• 密度：
  0.957±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  21
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 乙酸乙烯酯 、 2-hydroxyoctadec-3-enoic acid 在 Amano PS 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 96.0h， 以40%的产率得到methyl (2'R,3'E)-2'-hydroxyoctadec-3'-enoate
  参考文献：
  名称：

  Chemo-enzymatic short-step total synthesis of symbioramide

  摘要：

  A concise synthesis of symbiorarnide, a marine-origin ceramide from a common starting material, methyl (+/-)-trans-2,3epoxyoctadecanoate, in a convergent manner was achieved. The key step is the direct lipase-catalyzed coupling reaction between methyl (2R,3E)-2-hydroxy-3-octadecenoate and non-protected (+/-)-erythro-dihydrosphingosine, giving natural (2S,3R,2 ' R)-symbioramide and its (2R,3S,2 ' R)-isomer in 38% and 37% yield, respectively. The optically active beta,gamma-unsaturated alpha-hydroxyester was prepared by Mg(ClO4)(2)-inediated isomerization of epoxide and the subsequent lipase PS-catalyzed kinetic resolution. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.03.093
• 作为产物：
  描述：

  methyl (+/-)-trans-2,3-epoxyoctadecanoate 在 magnesium(II) perchlorate 、 Chirazyme L-2 、 3 Angstroem MS 、 L-Selectride 作用下， 以 phosphate buffer 、 乙醚 、 正己烷 、 甲苯 为溶剂， 反应 36.0h， 生成 2-hydroxyoctadec-3-enoic acid
  参考文献：
  名称：

  Chemo-enzymatic short-step total synthesis of symbioramide

  摘要：

  A concise synthesis of symbiorarnide, a marine-origin ceramide from a common starting material, methyl (+/-)-trans-2,3epoxyoctadecanoate, in a convergent manner was achieved. The key step is the direct lipase-catalyzed coupling reaction between methyl (2R,3E)-2-hydroxy-3-octadecenoate and non-protected (+/-)-erythro-dihydrosphingosine, giving natural (2S,3R,2 ' R)-symbioramide and its (2R,3S,2 ' R)-isomer in 38% and 37% yield, respectively. The optically active beta,gamma-unsaturated alpha-hydroxyester was prepared by Mg(ClO4)(2)-inediated isomerization of epoxide and the subsequent lipase PS-catalyzed kinetic resolution. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.03.093

文献信息

• Chemo-enzymatic short-step total synthesis of symbioramide
  作者：Tsukasa Takanami、Hiroki Tokoro、Dai-ichiro Kato、Shigeru Nishiyama、Takeshi Sugai

  DOI：10.1016/j.tetlet.2005.03.093

  日期：2005.5

  A concise synthesis of symbiorarnide, a marine-origin ceramide from a common starting material, methyl (+/-)-trans-2,3epoxyoctadecanoate, in a convergent manner was achieved. The key step is the direct lipase-catalyzed coupling reaction between methyl (2R,3E)-2-hydroxy-3-octadecenoate and non-protected (+/-)-erythro-dihydrosphingosine, giving natural (2S,3R,2 ' R)-symbioramide and its (2R,3S,2 ' R)-isomer in 38% and 37% yield, respectively. The optically active beta,gamma-unsaturated alpha-hydroxyester was prepared by Mg(ClO4)(2)-inediated isomerization of epoxide and the subsequent lipase PS-catalyzed kinetic resolution. (c) 2005 Elsevier Ltd. All rights reserved.