6-(3-azidophenyl)-1-(dimethoxyphosphoryl)-2-hexanone | 140900-68-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-(3-azidophenyl)-1-(dimethoxyphosphoryl)-2-hexanone
• 英文别名: Dimethyl [6-(3-azidophenyl)-2-oxohexyl]phosphonate；6-(3-azidophenyl)-1-dimethoxyphosphorylhexan-2-one
• CAS: 140900-68-1
• 化学式: C₁₄H₂₀N₃O₄P
• 分子量: 325.304
• InChiKey: FCADAFGLPOUQBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  67
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-(3-azidophenyl)-1-(dimethoxyphosphoryl)-2-hexanone 在 palladium on activated charcoal sodium tetrahydroborate 、 cerium(III) chloride 、 氢气 、 sodium hydride 作用下， 以 甲醇 为溶剂， 反应 7.22h， 生成 5-{(3aS,5R,6R,6aS)-6-[(S)-7-(3-Amino-phenyl)-3-hydroxy-heptyl]-5-hydroxy-1,3a,4,5,6,6a-hexahydro-pentalen-2-yl}-pentanoic acid methyl ester
  参考文献：
  名称：

  An azido-functionalized isocarbacyclin analogue acting as an efficient photoaffinity probe for a prostacyclin receptor

  摘要：

  A stable prostacyclin analogue, (15S)-18c, having an azidophenyl, group as a photoaffinity labeling functionality has been synthesized. This compound has a sufficiently high affinity to the prostacyclin receptor protein in mastocytoma P-815 cells, exhibiting an IC50 value of 3 nM for the replacement of iloprost bound to the receptor protein. A photoaffinity probe compound, [H-3]-(15S)-18c, is obtainable by reduction of the ketone 16c with [H-3]NaBH4-CeCl3 followed by alkaline hydrolysis of the methyl ester.

  DOI：

  10.1016/s0040-4020(01)88526-4
• 作为产物：
  描述：

  methyl 5-(3-aminophenyl)pentanoate 在 吡啶 、 正丁基锂 、 sodium azide 、 水 、 溶剂黄146 、 sodium nitrite 作用下， 以 四氢呋喃 为溶剂， 生成 6-(3-azidophenyl)-1-(dimethoxyphosphoryl)-2-hexanone
  参考文献：
  名称：

  An azido-functionalized isocarbacyclin analogue acting as an efficient photoaffinity probe for a prostacyclin receptor

  摘要：

  A stable prostacyclin analogue, (15S)-18c, having an azidophenyl, group as a photoaffinity labeling functionality has been synthesized. This compound has a sufficiently high affinity to the prostacyclin receptor protein in mastocytoma P-815 cells, exhibiting an IC50 value of 3 nM for the replacement of iloprost bound to the receptor protein. A photoaffinity probe compound, [H-3]-(15S)-18c, is obtainable by reduction of the ketone 16c with [H-3]NaBH4-CeCl3 followed by alkaline hydrolysis of the methyl ester.

  DOI：

  10.1016/s0040-4020(01)88526-4

文献信息

• An azido-functionalized isocarbacyclin analogue acting as an efficient photoaffinity probe for a prostacyclin receptor
  作者：Masaaki Suzuki、Hiroshi Koyano、Ryoji Noyori、Hitoshi Hashimoto、Manabu Negishi、Atsushi Ichikawa、Seiji Ito

  DOI：10.1016/s0040-4020(01)88526-4

  日期：1992.3

  A stable prostacyclin analogue, (15S)-18c, having an azidophenyl, group as a photoaffinity labeling functionality has been synthesized. This compound has a sufficiently high affinity to the prostacyclin receptor protein in mastocytoma P-815 cells, exhibiting an IC50 value of 3 nM for the replacement of iloprost bound to the receptor protein. A photoaffinity probe compound, [H-3]-(15S)-18c, is obtainable by reduction of the ketone 16c with [H-3]NaBH4-CeCl3 followed by alkaline hydrolysis of the methyl ester.