diethyl 1-(4-fluorophenyl)-3-(2-furyl)-5-oxopyrrolidine-2,2-dicarboxylate | 613686-80-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: diethyl 1-(4-fluorophenyl)-3-(2-furyl)-5-oxopyrrolidine-2,2-dicarboxylate
• 英文别名: Diethyl 1-(4-fluorophenyl)-3-(furan-2-yl)-5-oxopyrrolidine-2,2-dicarboxylate
• CAS: 613686-80-9
• 化学式: C₂₀H₂₀FNO₆
• 分子量: 389.38
• InChiKey: KDRVJPZZLLKTPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  86
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  diethyl 1-(4-fluorophenyl)-3-(2-furyl)-5-oxopyrrolidine-2,2-dicarboxylate 在 indium(III) chloride 、 sodium tetrahydroborate 作用下， 以 乙腈 为溶剂， 以79%的产率得到1-(4-fluorophenyl)-4-(furan-2-yl)-5-hydroxymethylpyrrolidin-2-one
  参考文献：
  名称：

  NaBH₄−InCl₃-Mediated One-Pot Chemo- and Stereoselective Decarboxylative Reduction of α-Aza gem-Dicarboxylic Esters to Monoalcohols

  摘要：

  graph The combination of NaBH4 and a catalytic amount of InCl3 provides a one-pot method for chemo- and stereoselective decarboxylative reduction of gem-dicarboxylic esters 1 to monoalcohols 2 in the presence of the lactam carbonyl in refluxing acetonitrile under inert atmosphere.

  DOI：

  10.1021/ol051453h
• 作为产物：
  描述：

  (E)-3-(2-呋喃)丙烯酰氯 、 diethyl 2-((4-fluorophenyl)amino)malonate 在 三乙胺 作用下， 以 苯 为溶剂， 生成 diethyl 1-(4-fluorophenyl)-3-(2-furyl)-5-oxopyrrolidine-2,2-dicarboxylate
  参考文献：
  名称：

  在硼氢化钠和碘的作用下，在宝石二羧酸盐存在下，内酰胺羰基的化学选择性还原：N-芳基三取代吡咯的轻松进入

  摘要：

  使用硼氢化钠-碘体系将几种N-芳基γ-内酰胺宝石二羧酸盐化学选择性还原为环状胺二酯。在所有情况下，在THF中回流后2.5小时内完成还原。在水性（酸性）后处理中分离出环状胺产物，收率很高。水解脱羧，然后脱氢产生N-芳基碳乙氧基吡咯。

  DOI：

  10.1016/j.tetlet.2003.09.085

文献信息

• NaBH4-I2 mediated chemoselective reduction of γ-lactam and thio-γ-lactam in presence of gem-dicarboxylates: An easy access to 1,3-diaryl pyrrolidines
  作者：Gopa Barman、Pranab Haldar、Neelanjan Dutta、Jayanta K. Ray

  DOI：10.1002/jhet.542

  日期：2011.3

  Substituted pyrrolidine derivatives were synthesized in high yield by NaBH4/I2 mediated chemoselective reduction of N‐aryl‐γ‐lactam and N‐aryl‐thio‐γ‐lactam‐2,2‐dicarboxylate. With excess NaBH4/I2, carbonyl functionality of the ester groups remained unchanged. J. Heterocyclic Chem., (2011).

  NaBH 4 / I 2介导的N-芳基-γ-内酰胺和N-芳基-硫代-γ-内酰胺-2,2-二羧酸酯的化学选择性还原以高收率合成了取代的吡咯烷衍生物。在过量的NaBH 4 / I 2下，酯基的羰基官能度保持不变。J.杂环化​​学。（2011）。
• Diethyl 1-(4-fluorophenyl)-3-(2-furyl)-5-oxopyrrolidine-2,2-dicarboxylate and diethyl 1-(3,4-dichlorophenyl)-3-(2-furyl)-5-oxopyrrolidine-2,2-dicarboxylate
  作者：Jayanta Kumar Ray、Pranab Haldar、M. Canle L.、J. A. Santaballa、Jose Mahía

  DOI：10.1107/s0108270103029111

  日期：2004.3.15

  The title compounds, C20H20FNO6 and C20H19Cl2NO6, respectively, may exhibit bioactivity. In these compounds, the pyrrolidine ring adopts a conformation intermediate between envelope and half-chair. Only one of the two ethoxycarbonyl side chains is nearly planar. Centrosymmetric pairs are formed, and the crystal structure is stabilized by weak C-H...O hydrogen bonds and van der Waals interactions.
• Chemoselective reduction of a lactam carbonyl group in the presence of a gem-dicarboxylate by sodium borohydride and iodine: a facile entry to N-aryl trisubstituted pyrroles
  作者：Pranab Haldar、Jayanta K Ray

  DOI：10.1016/j.tetlet.2003.09.085

  日期：2003.11

  Several N-aryl γ-lactam gem dicarboxylates were chemoselectively reduced to cyclic amine diesters by using sodium borohydride–iodine system. The reduction in all cases was completed within 2.5 h after refluxing in THF. The cyclic amine products were isolated after aqueous (acidic) workup in good yields. Hydrolytic decarboxylation followed by dehydrogenation produced N-aryl carboethoxy pyrroles.

  使用硼氢化钠-碘体系将几种N-芳基γ-内酰胺宝石二羧酸盐化学选择性还原为环状胺二酯。在所有情况下，在THF中回流后2.5小时内完成还原。在水性（酸性）后处理中分离出环状胺产物，收率很高。水解脱羧，然后脱氢产生N-芳基碳乙氧基吡咯。
• NaBH₄−InCl₃-Mediated One-Pot Chemo- and Stereoselective Decarboxylative Reduction of α-Aza <i>g</i><i>em</i>-Dicarboxylic Esters to Monoalcohols
  作者：Pranab Haldar、Jayanta K. Ray

  DOI：10.1021/ol051453h

  日期：2005.9.1

  graph The combination of NaBH4 and a catalytic amount of InCl3 provides a one-pot method for chemo- and stereoselective decarboxylative reduction of gem-dicarboxylic esters 1 to monoalcohols 2 in the presence of the lactam carbonyl in refluxing acetonitrile under inert atmosphere.