1,3-bis(2,2-dimethyl-1,3-dioxan-5-yloxy)propan-2-yl 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropanoate | 1043468-87-6

• 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: 1,3-bis(2,2-dimethyl-1,3-dioxan-5-yloxy)propan-2-yl 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropanoate
• 英文别名: 1,3-Bis[(2,2-dimethyl-1,3-dioxan-5-yl)oxy]propan-2-yl 2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropanoate
• CAS: 1043468-87-6
• 化学式: C₃₂H₄₁ClO₁₀
• 分子量: 621.125
• InChiKey: PAZPSIDJVXCULU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  43
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1,3-bis(2,2-dimethyl-1,3-dioxan-5-yloxy)propan-2-yl 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropanoate 在 Amberlyst 15 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 24.0h， 以87%的产率得到1,3-bis(1,3-dihydroxypropan-2-yloxy)propan-2-yl 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropanoate
  参考文献：
  名称：

  Synthesis of highly water-soluble fibrate derivatives via BGLation

  摘要：

  Three water-soluble fibrates (fenofibrate, bezafibrate and chlofibrate) conjugated with a symmetrically branched glyceryl trimer (BGL003) were synthesized, and an evaluation of the fenofibrate-BGL003 conjugate as a candidate for anti-hyperlipemia drug was carried out using rats. The water-solubility of the fenofibrate-BGL003 conjugate was several thousand times greater than that of the original fenofibrate. The lipid-lowering effects of the fenofibrate-BGL003 conjugate were as strong as those of the same grams of fenofibrate. The actual active species of fenofibrate, fenofibric acid, was detected in rats' blood, but neither the fenofibrate-BGL003 conjugate nor fenofibrate was detected, probably due to enzymatic hydrolysis of the ester bond. The plasma concentration of fenofibric acid derived from the fenofibrate-BGL003 conjugate was five times higher than that derived from fenofibrate 4 h after administration. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.057
• 作为产物：
  描述：

  1,3-双[(2,2-二甲基-1,3-二恶烷-5-基)氧代]-2-丙醇 、 非诺贝特酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以96%的产率得到1,3-bis(2,2-dimethyl-1,3-dioxan-5-yloxy)propan-2-yl 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropanoate
  参考文献：
  名称：

  Synthesis of highly water-soluble fibrate derivatives via BGLation

  摘要：

  Three water-soluble fibrates (fenofibrate, bezafibrate and chlofibrate) conjugated with a symmetrically branched glyceryl trimer (BGL003) were synthesized, and an evaluation of the fenofibrate-BGL003 conjugate as a candidate for anti-hyperlipemia drug was carried out using rats. The water-solubility of the fenofibrate-BGL003 conjugate was several thousand times greater than that of the original fenofibrate. The lipid-lowering effects of the fenofibrate-BGL003 conjugate were as strong as those of the same grams of fenofibrate. The actual active species of fenofibrate, fenofibric acid, was detected in rats' blood, but neither the fenofibrate-BGL003 conjugate nor fenofibrate was detected, probably due to enzymatic hydrolysis of the ester bond. The plasma concentration of fenofibric acid derived from the fenofibrate-BGL003 conjugate was five times higher than that derived from fenofibrate 4 h after administration. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.057