(Z)-1-Bromo-pentadec-2-ene | 172994-83-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机溴化物
• 英文名称: (Z)-1-Bromo-pentadec-2-ene
• CAS: 172994-83-1
• 化学式: C₁₅H₂₉Br
• 分子量: 289.299
• InChiKey: KDKYCDCYRXECRE-YPKPFQOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.25
• 重原子数：
  16.0
• 可旋转键数：
  12.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  (Z)-1-Bromo-pentadec-2-ene 在 苯基锂 作用下， 反应 0.67h， 生成 3-(tert-butyloxycarbonyl)-2,2-dimethyl-4(R)-<1(Z),3(Z)-hexadecadienyl>oxazolidine
  参考文献：
  名称：

  Structure Determination of an Endogenous Sleep-Inducing Lipid, cis-9-Octadecenamide (Oleamide):  A Synthetic Approach to the Chemical Analysis of Trace Quantities of a Natural Product

  摘要：

  The pursuit of endogenous sleep-inducing substances has been the focus of an extensive, complicated body of research. Several compounds, including Delta-sleep-inducing peptide and prostaglandin D-2, have been suggested to play a role in sleep induction, and yet, the molecular mechanisms of this physiological process remain largely unknown. In recent efforts, the cerebrospinal fluid of deep-deprived cats was analyzed in search of compounds that accumulated during sleep deprivation. An agent with the chemical formula C18H35NO was found to cycle with sleep-wake patterns, increasing in concentration with sleep deprivation and decreasing in amount upon recovery sleep. Since the material was generated in minute quantities and only under the special conditions of sleep deprivation, efforts to isolate sufficient material for adequate characterization, structure identification, and subsequent detailed evaluation of its properties proved unrealistic. With the trace amounts of the impure endogenous compound available, extensive MS studies on the agent were completed, revealing key structural features of the molecule including two degrees of unsaturation, a long alkyl chain, and a nitrogen substituent capable of fragmenting as ammonia. Additionally, HPLC traces suggested a weak UV absorbance for the unknown material. With this data in hand and encouraged by the relatively small size of the molecule, MW = 281, a synthetic approach toward the structural identification of the natural compound was initiated. Herein, we report the full details of the synthesis and comparative characterization of candidate structures for this endogenous agent that led to the unambiguous structural correlation with synthetic cis-9-octadecenamide.

  DOI：

  10.1021/ja9532345
• 作为产物：
  描述：

  (pentadec-2-yn-1-yloxy)tetrahydro-2H-pyran 在 甲醇 、 sodium tetrahydroborate 、 氢气 、 nickel(II) acetate tetrahydrate 、 三溴化磷 、 乙二胺 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 28.0h， 生成 (Z)-1-Bromo-pentadec-2-ene
  参考文献：
  名称：

  通过同源混合物的组合合成构建挥发性化合物的化学文库：Alk-4-en-1-ols、Alk-4-enals 和 Methyl Alk-4-enoates

  摘要：

  包含 66 个线性化合物的化合物库，六个分子家族的 11 个代表：( E )- 和 ( Z )-alk-4-en-1-ols、alk-4-enals 和甲基 alk-4-enoates 的异构体, 是通过组合合成制备的, 以允许创建直接可用于在 GC/MS 分析中识别它们的质谱数据库。我们在这里证明化合物库可以通过使用长线性合成序列的组合合成来制备，即。即，在 4-enals 的情况下为八步。由此产生的同系物混合物仍然可以完美地用于提供所需的信息，例如干净的质谱和良好的气相色谱保留指数。

  DOI：

  10.1002/cbdv.202200817