12-[3-Iodo-2-(2-methoxy-ethoxymethoxy)-5-nitro-benzyloxy]-1-(2-thioxo-thiazolidin-3-yl)-dodecan-1-one | 173912-60-2

• 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: 12-[3-Iodo-2-(2-methoxy-ethoxymethoxy)-5-nitro-benzyloxy]-1-(2-thioxo-thiazolidin-3-yl)-dodecan-1-one
• CAS: 173912-60-2
• 化学式: C₂₆H₃₉IN₂O₇S₂
• 分子量: 682.641
• InChiKey: AADCGNAGUZEOFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.48
• 重原子数：
  38.0
• 可旋转键数：
  21.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  100.37
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  12-[3-Iodo-2-(2-methoxy-ethoxymethoxy)-5-nitro-benzyloxy]-1-(2-thioxo-thiazolidin-3-yl)-dodecan-1-one 在 palladium on activated charcoal 氢气 、 三乙胺 、 cesium fluoride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 146.0h， 生成 1-tetradecanoic acid 3-({[(N,N,N-trimethylammonio)ethoxy]hydroxyphosphoryl}oxy)-2-({12-[(2-hydroxy-5-aminobenzyl)oxy]dodecanoyl}oxy)propyl ester
  参考文献：
  名称：

  Synthesis and Properties of Photoactivatable Phospholipid Derivatives Designed To Probe the Membrane-Associate Domains of Proteins

  摘要：

  The total syntheses of photoactivatable phospholipidic probes 1 and 2 are described. These probes contain either an aryldiazonium function at their polar head (probes la and Ib) or an diazocyclohexadienonyl group attached to the end of one fatty acid side chain (probe 2) and have been designed to probe the lipid/water interface and the hydrophobic core of the membrane, respectively. The synthetic schemes include the possibility of incorporating a radio-labeled atom (tritium) for further labeling investigations. Both probes were stable in the dark under physiological conditions and could be efficiently photodecomposed at wavelengths above 300 nm, leading to the generation of highly reactive species, aryl cations and cyclohexadienonyl carbene, respectively. In addition, these probes displayed UV-absorption spectra which are compatible with tryptophan-mediated energy transfer photoactivation, which can lead potentially to an efficient mapping of the membrane-associate protein domains.

  DOI：

  10.1021/jo951350k
• 作为产物：
  描述：

  12-((2-hydroxy-5-nitrobenzyl)oxy)dodecanoic acid ethyl ester 在 sodium hydroxide 、 2-氯-1-甲基吡啶碘化物 、 碳酸氢钠 、 N,N,N-trimethylbenzenemethanaminium dichloroiodate 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 乙二醇二甲醚 、 二氯甲烷 、 水 为溶剂， 反应 37.0h， 生成 12-[3-Iodo-2-(2-methoxy-ethoxymethoxy)-5-nitro-benzyloxy]-1-(2-thioxo-thiazolidin-3-yl)-dodecan-1-one
  参考文献：
  名称：

  Synthesis and Properties of Photoactivatable Phospholipid Derivatives Designed To Probe the Membrane-Associate Domains of Proteins

  摘要：

  The total syntheses of photoactivatable phospholipidic probes 1 and 2 are described. These probes contain either an aryldiazonium function at their polar head (probes la and Ib) or an diazocyclohexadienonyl group attached to the end of one fatty acid side chain (probe 2) and have been designed to probe the lipid/water interface and the hydrophobic core of the membrane, respectively. The synthetic schemes include the possibility of incorporating a radio-labeled atom (tritium) for further labeling investigations. Both probes were stable in the dark under physiological conditions and could be efficiently photodecomposed at wavelengths above 300 nm, leading to the generation of highly reactive species, aryl cations and cyclohexadienonyl carbene, respectively. In addition, these probes displayed UV-absorption spectra which are compatible with tryptophan-mediated energy transfer photoactivation, which can lead potentially to an efficient mapping of the membrane-associate protein domains.

  DOI：

  10.1021/jo951350k