dimethyl 1-<2-(1,3-dioxolan-2-yl)ethyl>-2-(4-fluorophenyl)-5-(1-methylethyl)-1H-pyrrole-3,4-dicarboxylate | 104568-72-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: dimethyl 1-<2-(1,3-dioxolan-2-yl)ethyl>-2-(4-fluorophenyl)-5-(1-methylethyl)-1H-pyrrole-3,4-dicarboxylate
• 英文别名: dimethyl 1-[2-(1,3-dioxolan-2-yl)ethyl]-2-(4-fluorophenyl)-5-propan-2-ylpyrrole-3,4-dicarboxylate
• CAS: 104568-72-1
• 化学式: C₂₂H₂₆FNO₆
• 分子量: 419.45
• InChiKey: JGAHQOOXSGSIGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  75.99
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  dimethyl 1-<2-(1,3-dioxolan-2-yl)ethyl>-2-(4-fluorophenyl)-5-(1-methylethyl)-1H-pyrrole-3,4-dicarboxylate 在 水 、 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 反应 48.0h， 生成 2-(4-Fluoro-phenyl)-1-[2-((2R,4R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-5-isopropyl-1H-pyrrole-3,4-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Inhibitors of cholesterol biosynthesis. 3. Tetrahydro-4-hydroxy-6-[2-(1H-pyrrol-1-yl)ethyl]-2H-pyran 2-one inhibitors of HMG-CoA reductase. 2. Effects of introducing substituents at positions three and four of the pyrrole nucleus

  摘要：

  A series of trans-tetrahydro-4-hydroxy-6-[2-(2,3,4,5-substituted-1H-pyrrol-1-yl)ethyl]-2H-pyran-2-ones and their dihydroxy acids were prepared and tested for their ability to inhibit the enzyme HMG-CoA reductase in vitro. Inhibitory potency was found to increase substantially when substituents were introduced into positions three and four of the pyrrole ring. A systematic exploration of structure-activity relationships at these two positions led to the identification of a compound ((+)-33, (+)-(4R)-trans-2-(4-fluorophenyl)-5-(1-methylethyl)-N,3-diphenyl-1-[(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1H-pyrrole-4-carboxamide) with five times the inhibitory potency of the fungal metabolite compactin.

  DOI：

  10.1021/jm00105a056
• 作为产物：
  描述：

  (+/-)-methyl N-(4-fluorobenzoyl)-N-<2-(2-ethyl)-1,3-dioxolanyl>valine 在 sodium hydroxide 、 乙酸酐 作用下， 以 甲醇 、 水 为溶剂， 反应 5.0h， 生成 dimethyl 1-<2-(1,3-dioxolan-2-yl)ethyl>-2-(4-fluorophenyl)-5-(1-methylethyl)-1H-pyrrole-3,4-dicarboxylate
  参考文献：
  名称：

  Inhibitors of cholesterol biosynthesis. 3. Tetrahydro-4-hydroxy-6-[2-(1H-pyrrol-1-yl)ethyl]-2H-pyran 2-one inhibitors of HMG-CoA reductase. 2. Effects of introducing substituents at positions three and four of the pyrrole nucleus

  摘要：

  A series of trans-tetrahydro-4-hydroxy-6-[2-(2,3,4,5-substituted-1H-pyrrol-1-yl)ethyl]-2H-pyran-2-ones and their dihydroxy acids were prepared and tested for their ability to inhibit the enzyme HMG-CoA reductase in vitro. Inhibitory potency was found to increase substantially when substituents were introduced into positions three and four of the pyrrole ring. A systematic exploration of structure-activity relationships at these two positions led to the identification of a compound ((+)-33, (+)-(4R)-trans-2-(4-fluorophenyl)-5-(1-methylethyl)-N,3-diphenyl-1-[(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1H-pyrrole-4-carboxamide) with five times the inhibitory potency of the fungal metabolite compactin.

  DOI：

  10.1021/jm00105a056

文献信息

• Visible-Light-Induced Formal [3+2] Cycloaddition for Pyrrole Synthesis under Metal-Free Conditions
  作者：Jun Xuan、Xu-Dong Xia、Ting-Ting Zeng、Zhu-Jia Feng、Jia-Rong Chen、Liang-Qiu Lu、Wen-Jing Xiao

  DOI：10.1002/anie.201400602

  日期：2014.5.26

  A photocatalytic formal [3+2] cycloaddition of 2H‐azirines with alkynes has been achieved under irradiation by visible light in the presence of organic dye photocatalysts. This transformation provides efficient access to highly functionalized pyrroles in good yields and has been applied to the synthesis of drug analogues. A primary trial of photocascade catalysis merging energy transfer and redox neutral

  在有机染料光催化剂的存在下，在可见光照射下，已实现了2 H H叠氮基与炔烃的光催化形式[3 + 2]环加成反应。这种转化提供了以高收率高效获得高度官能化吡咯的途径，并已应用于药物类似物的合成。光级联催化合并能量转移和氧化还原中性反应的初步试验显示是成功的。
• ROTH, B. D.;BLANKLEY, C. J.;CHUCHOLOWSKI, A. W.;FERGUSON, E.;HOEFLE, M. L+, J. MED. CHEM., 34,(1991) N, C. 357-366
  作者：ROTH, B. D.、BLANKLEY, C. J.、CHUCHOLOWSKI, A. W.、FERGUSON, E.、HOEFLE, M. L+

  DOI：——

  日期：——
• ——
  作者：HOEFLE M. L.、 ROTH B. D.、 STRATTON C. D.

  DOI：——

  日期：——