11-(tetradecylselenyl)undecanoic acid | 7740-61-6

• 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: 11-(tetradecylselenyl)undecanoic acid
• 英文别名: 12-Selena-hexacosansaeure
• CAS: 7740-61-6
• 化学式: C₂₅H₅₀O₂Se
• 分子量: 461.631
• InChiKey: WZRWOOFBNRZXNY-UHFFFAOYSA-N

物化性质

• 熔点：
  64-65.5 °C
• 沸点：
  539.1±23.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.82
• 重原子数：
  28.0
• 可旋转键数：
  24.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R)-2-azido-3,4-O-isopropylidene-1,3,4-octadecanetriol 、 11-(tetradecylselenyl)undecanoic acid 在 N-甲基吗啉 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以45%的产率得到1-O-α-D-galactopyranosyl-2-N-(11-tetradecylselenoundecanoyl)-2S,3S,4R-phytosphingosine
  参考文献：
  名称：

  Synthesis and Th1-immunostimulatory activity of α-galactosylceramide analogues bearing a halogen-containing or selenium-containing acyl chain

  摘要：

  A novel series of CD1d ligand alpha-galactosylceramides (alpha-GalCers) were synthesized by incorporation of the heavy atoms Br and Se in the acyl chain backbone of alpha-galactosyl-N-cerotoylphytosphingosine. The synthetic analogues are potent CD1d ligands and stimulate mouse invariant natural killer T (iNKT) cells to selectively enhance Th1 cytokine production. These synthetic analogues would be efficient X-ray crystallographic probes to disclose precise atomic positions of alkyl carbons and lipid-protein interactions in KRN7000/CD1d complexes. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.06.007
• 作为产物：
  描述：

  溴代十四烷 在 selenium 、 sodium tetrahydroborate 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 1.0h， 生成 11-(tetradecylselenyl)undecanoic acid
  参考文献：
  名称：

  Synthesis and Th1-immunostimulatory activity of α-galactosylceramide analogues bearing a halogen-containing or selenium-containing acyl chain

  摘要：

  A novel series of CD1d ligand alpha-galactosylceramides (alpha-GalCers) were synthesized by incorporation of the heavy atoms Br and Se in the acyl chain backbone of alpha-galactosyl-N-cerotoylphytosphingosine. The synthetic analogues are potent CD1d ligands and stimulate mouse invariant natural killer T (iNKT) cells to selectively enhance Th1 cytokine production. These synthetic analogues would be efficient X-ray crystallographic probes to disclose precise atomic positions of alkyl carbons and lipid-protein interactions in KRN7000/CD1d complexes. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.06.007