Pentadecanoic acid 4-nitro-phenyl ester | 100825-43-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: Pentadecanoic acid 4-nitro-phenyl ester
• 英文别名: 4-Nitrophenyl pentadecanoate；(4-nitrophenyl) pentadecanoate
• CAS: 100825-43-2
• 化学式: C₂₁H₃₃NO₄
• 分子量: 363.497
• InChiKey: HZEBRHPDHWBCMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  26
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Pentadecanoic acid 4-nitro-phenyl ester 在 polymer bounded 4-(dialkylamino)pyridine phosphate buffer 作用下， 生成 对硝基苯酚 、 十五烷酸
  参考文献：
  名称：

  Ion-Induced Specificity Change in Polymer-Catalyzed Solvolyses ofp-Nitrophenyl Alkanoates

  摘要：

  DOI：

  10.1002/anie.199715431

文献信息

• Stereoselective Synthesis and Structure−Activity Relationship of Novel Ceramide Trafficking Inhibitors. (1<i>R</i>,3<i>R</i>)-<i>N</i>-(3-Hydroxy-1-hydroxymethyl-3-phenylpropyl)dodecanamide and Its Analogues
  作者：Yoshitaka Nakamura、Ryosuke Matsubara、Hidetoshi Kitagawa、Shū Kobayashi、Keigo Kumagai、Satoshi Yasuda、Kentaro Hanada

  DOI：10.1021/jm0300779

  日期：2003.8.1

  New ceramide trafficking inhibitors, (1R,3R)-N-(3-hydroxy-1-hydroxymethyl-3-phenylpropyl)dodecanamide (HPA-12) and a series of its analogues, were synthesized in diastereomerically and enantiomerically pure forms, and the structure-activity relationship was investigated. These analogues were stereoselectively synthesized via catalytic enantioselective Mannich-type reactions using a Cu(II)-chiral diamine 4 complex. Analysis of HPA-12 analogues having various lengths of the amide side chain showed that the optimal chain length for the inhibition of sphingomyelin biosynthesis is 13 with an IC50 of similar to50 nM. Masking of the hydroxy group at the 2'- or 3-position of HPA-12 was carried out by methylation, and it was revealed that these hydroxy groups were essential for the activity. Installation of another hydroxy group onto HPA-12 at the same position as that in the natural ceramide was also conducted, but no enhancement of the activity was observed.
• Ion-Induced Specificity Change in Polymer-Catalyzed Solvolyses ofp-Nitrophenyl Alkanoates
  作者：Guang-Jia Wang、Wilmer K. Fife

  DOI：10.1002/anie.199715431

  日期：1997.8.4