(R)-N-[2,3-Bis(hexadecyloxy)propyl]-2-hydroxyhexadecanamide | 321887-56-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-N-[2,3-Bis(hexadecyloxy)propyl]-2-hydroxyhexadecanamide
• CAS: 321887-56-3
• 化学式: C₅₁H₁₀₃NO₄
• 分子量: 794.383
• InChiKey: BQRAWLNRSMSQMQ-UCNWKSROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.92
• 重原子数：
  56.0
• 可旋转键数：
  49.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  67.79
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (R)-N-[2,3-Bis(hexadecyloxy)propyl]-2-hydroxyhexadecanamide 在 4-acetylamino-2,2,6,6-tetramethylpiperidine-N-oxyl sodium hypochlorite 、 碳酸氢钠 、 sodium bromide 作用下， 以 乙酸乙酯 、 甲苯 为溶剂， 反应 0.25h， 以84%的产率得到(R)-N-[2,3-Bis(hexadecyloxy)propyl]-2-oxohexadecanamide
  参考文献：
  名称：

  Synthesis of 2‐Oxo Amide Triacylglycerol Analogues and Study of Their Inhibition Effect on Pancreatic and Gastric Lipases

  摘要：

  A general method for the synthesis of chiral 2-ore amide triacylglycerol analogues, from (R)- or (S)-3-aminopropane-1,2-diol, was developed. These novel inhibitors of digestive lipases are analogues of the triacylglycerol molecule, a natural substrate of lipases, and they were designed to contain the Zero amide functionality in place of the scissile ester bond at the sn-1 or sn-3 position and nonhydrolysable ether bonds instead of ester bonds at the other two remaining positions. The 2-ore amide derivatives synthesised were tested for their ability to form stable monomolecular films at the air/water interface by recording their surface pressure/molecular area compression isotherms. The inhibition of porcine pancreatic and human gastric lipases by the 2-ore amides was studied by means of the monolayer technique with mixed films of 1,2-dicaprin and with variable proportions of each inhibitor. The alpha (50) values of these triacylglycerol analogues for PPL and HGL varied between 4.4 to 7.0% and 5.6 to 15.9%, respectively. The chirality at the sn-2 position of Zero amide triacylglycerol analogues affected the a,, value for HGL, but not for PPL.

  DOI：

  10.1002/1521-3765(20001117)6:22<4211::aid-chem4211>3.0.co;2-#
• 作为产物：
  描述：

  (R)-N-tert-Butoxycarbonyl-2,3-bis(hexadecyloxy)propanamine 在 盐酸 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (R)-N-[2,3-Bis(hexadecyloxy)propyl]-2-hydroxyhexadecanamide
  参考文献：
  名称：

  Synthesis of 2‐Oxo Amide Triacylglycerol Analogues and Study of Their Inhibition Effect on Pancreatic and Gastric Lipases

  摘要：

  A general method for the synthesis of chiral 2-ore amide triacylglycerol analogues, from (R)- or (S)-3-aminopropane-1,2-diol, was developed. These novel inhibitors of digestive lipases are analogues of the triacylglycerol molecule, a natural substrate of lipases, and they were designed to contain the Zero amide functionality in place of the scissile ester bond at the sn-1 or sn-3 position and nonhydrolysable ether bonds instead of ester bonds at the other two remaining positions. The 2-ore amide derivatives synthesised were tested for their ability to form stable monomolecular films at the air/water interface by recording their surface pressure/molecular area compression isotherms. The inhibition of porcine pancreatic and human gastric lipases by the 2-ore amides was studied by means of the monolayer technique with mixed films of 1,2-dicaprin and with variable proportions of each inhibitor. The alpha (50) values of these triacylglycerol analogues for PPL and HGL varied between 4.4 to 7.0% and 5.6 to 15.9%, respectively. The chirality at the sn-2 position of Zero amide triacylglycerol analogues affected the a,, value for HGL, but not for PPL.

  DOI：

  10.1002/1521-3765(20001117)6:22<4211::aid-chem4211>3.0.co;2-#