4-hydroxy-6-(3-hydroxypropyl)-4-methyl-3,4,5,6-tetrahydro-2H-pyran-2-one | 158094-94-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 4-hydroxy-6-(3-hydroxypropyl)-4-methyl-3,4,5,6-tetrahydro-2H-pyran-2-one
• 英文别名: 4-Hydroxy-6-(3-hydroxypropyl)-4-methyloxan-2-one
• CAS: 158094-94-1
• 化学式: C₉H₁₆O₄
• 分子量: 188.224
• InChiKey: UAHOPWOWOIRSMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-hydroxy-6-(3-hydroxypropyl)-4-methyl-3,4,5,6-tetrahydro-2H-pyran-2-one 在 吡啶 、 tris(tetra-n-butylammonium) hydrogen pyrophosphate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 2.0h， 生成 3-(4-Hydroxy-4-methyl-6-oxooxan-2-yl)propyl phosphono hydrogen phosphate
  参考文献：
  名称：

  Bifunctional Inhibitors of Mevalonate Kinase and Mevalonate 5-Diphosphate Decarboxylase

  摘要：

  A bifunctional inhibitor of mevalonate kinase and mevalonate 5-diphosphate decarboxylase was synthesized. Both enzymes are in the cholesterol biosynthetic pathway and play an important role in regulating cholesterol biosynthesis. The molecule may become a useful lead compound for further development for treating cardiovascular disease and cancer. This study provides a novel example of a single inhibitor blocking two sequential steps simultaneously in the cholesterol biosynthetic pathway.

  DOI：

  10.1021/ol052573s
• 作为产物：
  描述：

  4,7-bis(tetrahydropyranyloxy)-2-heptanone 在 碘 、 对甲苯磺酸 、 锌 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 生成 4-hydroxy-6-(3-hydroxypropyl)-4-methyl-3,4,5,6-tetrahydro-2H-pyran-2-one
  参考文献：
  名称：

  Bifunctional Inhibitors of Mevalonate Kinase and Mevalonate 5-Diphosphate Decarboxylase

  摘要：

  A bifunctional inhibitor of mevalonate kinase and mevalonate 5-diphosphate decarboxylase was synthesized. Both enzymes are in the cholesterol biosynthetic pathway and play an important role in regulating cholesterol biosynthesis. The molecule may become a useful lead compound for further development for treating cardiovascular disease and cancer. This study provides a novel example of a single inhibitor blocking two sequential steps simultaneously in the cholesterol biosynthetic pathway.

  DOI：

  10.1021/ol052573s

文献信息

• Irreducible analogs of mevaldic acid coenzyme A hemithioacetal as potential inhibitors of HMG-CoA reductase. 2. Synthesis of a secondary alcohol analog of mevaldic acid pantetheine hemithioacetal and an amide analog of 3-hydroxy-3-methylglutaryl-S-pantetheine
  作者：Rajesh H. Turakhia、Gordon C. Fischer、Cary J. Morrow、Brian L. Maschhoff、Michael I. Toubbeh、JoAnn L. Zbur-Wilson

  DOI：10.1021/jo00361a003

  日期：1986.5
• Bifunctional Inhibitors of Mevalonate Kinase and Mevalonate 5-Diphosphate Decarboxylase
  作者：Yongge Qiu、Ding Li

  DOI：10.1021/ol052573s

  日期：2006.3.1

  A bifunctional inhibitor of mevalonate kinase and mevalonate 5-diphosphate decarboxylase was synthesized. Both enzymes are in the cholesterol biosynthetic pathway and play an important role in regulating cholesterol biosynthesis. The molecule may become a useful lead compound for further development for treating cardiovascular disease and cancer. This study provides a novel example of a single inhibitor blocking two sequential steps simultaneously in the cholesterol biosynthetic pathway.