4-[3-(3-ethoxycarbonyl-3-methylbutoxy)propoxy]-2,2-dimethylbutyric acid ethyl ester | 787619-72-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-[3-(3-ethoxycarbonyl-3-methylbutoxy)propoxy]-2,2-dimethylbutyric acid ethyl ester
• 英文别名: Ethyl 4-[3-(4-ethoxy-3,3-dimethyl-4-oxobutoxy)propoxy]-2,2-dimethylbutanoate
• CAS: 787619-72-1
• 化学式: C₁₉H₃₆O₆
• 分子量: 360.491
• InChiKey: BWCOZKRHMBSBCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-[3-(3-ethoxycarbonyl-3-methylbutoxy)propoxy]-2,2-dimethylbutyric acid ethyl ester 在 lithium aluminium tetrahydride 作用下， 以 various solvent(s) 为溶剂， 反应 2.0h， 以91%的产率得到4-[3-(4-hydroxy-3,3-dimethylbutoxy)propoxy]-2,2-dimethylbutan-1-ol
  参考文献：
  名称：

  Long Hydrocarbon Chain Ether Diols and Ether Diacids That Favorably Alter Lipid Disorders in Vivo

  摘要：

  Long hydrocarbon chain ethers with bis-terminal hydroxyl or carboxyl groups have been synthesized and evaluated for their potential to favorably alter lipid disorders including metabolic syndrome. Compounds were assessed for their effects on the de novo incorporation of radiolabeled acetate into lipids in primary cultures of rat hepatocytes as well as for their effects on lipid and glycemic variables in female obese Zucker fatty rats following 1 and 2 weeks of daily oral administration. The most active compounds were found to be symmetrical with four to five methylene groups separating the central ether functionality and the gem dimethyl or methyl/aryl substituents. Biological activity was found to be greatest for tetramethyl-substituted ether diols (e.g., 28 and 31), while bis(arylmethyl) derivatives (e.g., 10, 11, and 27), diethers (e.g., 49, 50, and 56), and diphenyl ethers (e.g., 35 and 36) were the least active. For the most biologically active compound 28, we observed as much as a 346% increase in serum HDL-cholesterol and a 71% reduction in serum triglycerides at the highest dose administered (100 mg/kg) after 2 weeks of treatment. For compound 31 we observed a 69% reduction in non-HDL-cholesterol, accompanied by a 131% increase in HDL-cholesterol and an 84% reduction in serum triglycerides under the same treatment conditions.

  DOI：

  10.1021/jm0400395
• 作为产物：
  描述：

  3,7-二氧杂-1,9-壬二醇 在 吡啶 、 1,3,4-trimethylimidazolidin-2-one 、 三溴化磷 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.0h， 生成 4-[3-(3-ethoxycarbonyl-3-methylbutoxy)propoxy]-2,2-dimethylbutyric acid ethyl ester
  参考文献：
  名称：

  Long Hydrocarbon Chain Ether Diols and Ether Diacids That Favorably Alter Lipid Disorders in Vivo

  摘要：

  Long hydrocarbon chain ethers with bis-terminal hydroxyl or carboxyl groups have been synthesized and evaluated for their potential to favorably alter lipid disorders including metabolic syndrome. Compounds were assessed for their effects on the de novo incorporation of radiolabeled acetate into lipids in primary cultures of rat hepatocytes as well as for their effects on lipid and glycemic variables in female obese Zucker fatty rats following 1 and 2 weeks of daily oral administration. The most active compounds were found to be symmetrical with four to five methylene groups separating the central ether functionality and the gem dimethyl or methyl/aryl substituents. Biological activity was found to be greatest for tetramethyl-substituted ether diols (e.g., 28 and 31), while bis(arylmethyl) derivatives (e.g., 10, 11, and 27), diethers (e.g., 49, 50, and 56), and diphenyl ethers (e.g., 35 and 36) were the least active. For the most biologically active compound 28, we observed as much as a 346% increase in serum HDL-cholesterol and a 71% reduction in serum triglycerides at the highest dose administered (100 mg/kg) after 2 weeks of treatment. For compound 31 we observed a 69% reduction in non-HDL-cholesterol, accompanied by a 131% increase in HDL-cholesterol and an 84% reduction in serum triglycerides under the same treatment conditions.

  DOI：

  10.1021/jm0400395

文献信息

• Long Hydrocarbon Chain Ether Diols and Ether Diacids That Favorably Alter Lipid Disorders in Vivo
  作者：Ralf Mueller、Jing Yang、Caiming Duan、Emil Pop、Lian Hao Zhang、Tian-Bao Huang、Anna Denisenko、Olga V. Denisko、Daniela C. Oniciu、Charles L. Bisgaier、Michael E. Pape、Catherine Delaney Freiman、Brian Goetz、Clay T. Cramer、Krista L. Hopson、Jean-Louis H. Dasseux

  DOI：10.1021/jm0400395

  日期：2004.10.1

  Long hydrocarbon chain ethers with bis-terminal hydroxyl or carboxyl groups have been synthesized and evaluated for their potential to favorably alter lipid disorders including metabolic syndrome. Compounds were assessed for their effects on the de novo incorporation of radiolabeled acetate into lipids in primary cultures of rat hepatocytes as well as for their effects on lipid and glycemic variables in female obese Zucker fatty rats following 1 and 2 weeks of daily oral administration. The most active compounds were found to be symmetrical with four to five methylene groups separating the central ether functionality and the gem dimethyl or methyl/aryl substituents. Biological activity was found to be greatest for tetramethyl-substituted ether diols (e.g., 28 and 31), while bis(arylmethyl) derivatives (e.g., 10, 11, and 27), diethers (e.g., 49, 50, and 56), and diphenyl ethers (e.g., 35 and 36) were the least active. For the most biologically active compound 28, we observed as much as a 346% increase in serum HDL-cholesterol and a 71% reduction in serum triglycerides at the highest dose administered (100 mg/kg) after 2 weeks of treatment. For compound 31 we observed a 69% reduction in non-HDL-cholesterol, accompanied by a 131% increase in HDL-cholesterol and an 84% reduction in serum triglycerides under the same treatment conditions.