Methyl-(5-phenylcarbamoyl-pentyl)-phosphinic acid ethyl ester | 606092-26-6

• 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: Methyl-(5-phenylcarbamoyl-pentyl)-phosphinic acid ethyl ester
• 英文别名: 6-[ethoxy(methyl)phosphoryl]-N-phenylhexanamide
• CAS: 606092-26-6
• 化学式: C₁₅H₂₄NO₃P
• 分子量: 297.334
• InChiKey: AYBFLFOFMQTIOK-UHFFFAOYSA-N

物化性质

• 密度：
  1.107±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methyl-(5-phenylcarbamoyl-pentyl)-phosphinic acid ethyl ester 在 lithium hydroxide 作用下， 以 甲醇 为溶剂， 反应 10.0h， 生成
  参考文献：
  名称：

  Phosphorus-Based SAHA Analogues as Histone Deacetylase Inhibitors

  摘要：

  graphicThree analogues of suberoyl anilide hydroxamic acid (SAHA) with phosphorus metal-chelating functionalities were synthesized as inhibitors of histone deacetylases (HDACs). The compounds showed weak activity for HeLa nuclear extracts (IC50 = 0.57-6.1 mM), HDAC8 (IC50 = 0.28-0.41 mM), and histone-deacetylase-like protein (HDLP, IC50 = 0.33-1.9 mM), suggesting that the transition state of HDAC is not analogous to zinc proteases. Anti proliferative activity against A2780 cancer cells (IC50 = 0.11-0.12 mM), comparable to SAHA (0.15 mM), was observed.

  DOI：

  10.1021/ol035056n
• 作为产物：
  描述：

  6-溴己酰氯 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 生成 Methyl-(5-phenylcarbamoyl-pentyl)-phosphinic acid ethyl ester
  参考文献：
  名称：

  Phosphorus-Based SAHA Analogues as Histone Deacetylase Inhibitors

  摘要：

  graphicThree analogues of suberoyl anilide hydroxamic acid (SAHA) with phosphorus metal-chelating functionalities were synthesized as inhibitors of histone deacetylases (HDACs). The compounds showed weak activity for HeLa nuclear extracts (IC50 = 0.57-6.1 mM), HDAC8 (IC50 = 0.28-0.41 mM), and histone-deacetylase-like protein (HDLP, IC50 = 0.33-1.9 mM), suggesting that the transition state of HDAC is not analogous to zinc proteases. Anti proliferative activity against A2780 cancer cells (IC50 = 0.11-0.12 mM), comparable to SAHA (0.15 mM), was observed.

  DOI：

  10.1021/ol035056n

文献信息

• Metal‐Free Synthesis of <i>N</i> ‐Aryl Amides using Organocatalytic Ring‐Opening Aminolysis of Lactones
  作者：Wusheng Guo、José Enrique Gómez、Luis Martínez‐Rodríguez、Nuno A. G. Bandeira、Carles Bo、Arjan W. Kleij

  DOI：10.1002/cssc.201700415

  日期：2017.5.9

  Catalytic ring‐opening of bio‐sourced non‐strained lactones with aromatic amines can offer a straightforward, 100 % atom‐economical, and sustainable pathway towards relevant N‐aryl amide scaffolds. Herein, the first general, metal‐free, and highly efficient N‐aryl amide formation is reported from poorly reactive aromatic amines and non‐strained lactones under mild operating conditions using an organic

  生物来源的非应变内酯与芳族胺的催化开环可以提供一种直接的，100％原子经济且可持续的通往相关N芳基酰胺支架的途径。在此，据报道，在温和的操作条件下，使用有机双环胍催化剂，由反应性较差的芳族胺和非应变的内酯首次形成了无金属且高效的N-芳基酰胺。该协议具有很高的应用潜力，例如与药物相关的分子的形式合成。