9-azidononanal | 298691-04-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 9-azidononanal
• 英文别名: 9-Azidononanal
• CAS: 298691-04-0
• 化学式: C₉H₁₇N₃O
• 分子量: 183.253
• InChiKey: XELAGZRWNULUTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  13
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9-azidononanal 在 三苯基膦 、 lithium hexamethyldisilazane 作用下， 以 乙腈 为溶剂， 生成 methyl (5S,6E,8Z,11Z)-20-amino-5-[tert-butyl(diphenyl)silyl]oxyicosa-6,8,11-trienoate
  参考文献：
  名称：

  The design and synthesis of a 5-HETE affinity chromatography ligand for 5-hydroxyeicosanoid dehydrogenase

  摘要：

  The first total synthesis of an omega-amino 5-HETE derivative 27 has been accomplished by a new counterclockwise strategy, in which C-1 is constructed first and C-20 last. The omega-amino 5-HETE derivative was transformed to an affinity chromatography ligand, the biotinylated 5-HETE 30. This affinity chromatography ligand is aimed at purifying the 5-hydroxyeicosanoid dehydrogenase enzyme, which is responsible for the conversion of 5-HETE to 5-oxo-ETE, a potent eosinophil chemotactic factor. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00971-0
• 作为产物：
  描述：

  9-溴-1-壬醇 在 sodium azide 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 生成 9-azidononanal
  参考文献：
  名称：

  The design and synthesis of a 5-HETE affinity chromatography ligand for 5-hydroxyeicosanoid dehydrogenase

  摘要：

  The first total synthesis of an omega-amino 5-HETE derivative 27 has been accomplished by a new counterclockwise strategy, in which C-1 is constructed first and C-20 last. The omega-amino 5-HETE derivative was transformed to an affinity chromatography ligand, the biotinylated 5-HETE 30. This affinity chromatography ligand is aimed at purifying the 5-hydroxyeicosanoid dehydrogenase enzyme, which is responsible for the conversion of 5-HETE to 5-oxo-ETE, a potent eosinophil chemotactic factor. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00971-0

文献信息

• Fluorinated triazole-containing sphingosine analogues. Syntheses and<i>in vitro</i>evaluation as SPHK inhibitors
  作者：Margarita Escudero-Casao、Adrià Cardona、Raúl Beltrán-Debón、Yolanda Díaz、M. Isabel Matheu、Sergio Castillón

  DOI：10.1039/c8ob01867g

  日期：——

  Sphingosine analogues with a rigid triazole moiety in the aliphatic chain and systematic modifications in the polar head and different degrees of fluorination at the terminus of the alkylic chain were synthesized from a common alkynyl aziridine key synthon. This key synthon was obtained by enantioselective organocatalyzed aziridination and it was subsequently ring opened in a regioselective manner

  从常见的炔基氮丙啶关键合成子合成了在脂肪族链中具有刚性三唑部分，在极性头上的系统修饰以及在烷基链末端具有不同氟化度的鞘氨醇类似物。该关键的合成子通过对映选择性的有机催化的叠氮化而获得，随后在酸性介质中以区域选择性的方式开环。以直接的方式制备了多达16种鞘氨醇类似物。在体外所获得的产品作为SPHK1和SPHK2抑制剂的活性进行评估，显示相当的活性到DMS的。