5-(2-呋喃基)-3,4-二氢-2H-吡咯 | 104704-31-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 中文名称: 5-(2-呋喃基)-3,4-二氢-2H-吡咯
• 中文别名: 5-呋喃-2-基-3,4-二氢-2H-吡咯
• 英文名称: 5-(furan-2-yl)-3,4-dihydro-2H-pyrrole
• 英文别名: -(2-furyl)-1-pyrroline；5-[2]furyl-3,4-dihydro-2H-pyrrole；5-[2]Furyl-3,4-dihydro-2H-pyrrol
• CAS: 104704-31-6
• 化学式: C₈H₉NO
• mdl: MFCD09749693
• 分子量: 135.166
• InChiKey: RSWIYWDWUHQXIZ-UHFFFAOYSA-N

物化性质

• 保留指数：
  1780

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.375
• 拓扑面积：
  25.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  5-(2-呋喃基)-3,4-二氢-2H-吡咯 、 (三氟甲基)三甲基硅烷 在 二氟化氢钾 、 三氟乙酸 作用下， 以 乙腈 为溶剂， 以60%的产率得到2-(2-furanyl)-2-(trifluoromethyl)-pyrrolidine
  参考文献：
  名称：

  The reaction of cyclic imines with the Ruppert–Prakash reagent. Facile approach to α-trifluoromethylated nornicotine, anabazine, and homoanabazine

  摘要：

  We have demonstrated that the Ruppert-Prakash reagent is able to react with a number of cyclic imines under acidic condition to afford the corresponding alpha-trifluoromethyl derivatives of nitrogen heterocycles. 5-7-Membered cyclic imines bearing various alkyl, aryl or heterocyclic group were successfully involved in this transformation. Novel trifluoromethylated analogues of nicotine, anabasine, and homoanabasine alkaloids were synthesized. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.11.032
• 作为产物：
  描述：

  4-(2-呋喃)-4-氧丁腈 在 镍 作用下， 生成 5-(2-呋喃基)-3,4-二氢-2H-吡咯
  参考文献：
  名称：

  46. β -Cycloylpropionitriles。第三部分 还原成2-环基-Δ 2个-pyrrolines和2- cyclylpyrrolidines

  摘要：

  DOI：

  10.1039/jr9480000186

文献信息

• New method of preparation of C2F5Li and its reactions with cyclic imines and lactims: Synthesis of α-pentafluoroethyl proline
  作者：Nikolay E. Shevchenko、Valentine G. Nenajdenko、Gerd-Volker Röschenthaler

  DOI：10.1016/j.jfluchem.2008.01.013

  日期：2008.5

  Addition of pentafluoroethyllithium to cyclic imines leads to pentafluoroethyl substituted pyrrolidines, piperidines and azepanes while reaction of cyclic lactims gives rise to 2-pentafluoroethyl imines. Oxidative cleavage of 2-furyl-2-pentafluoroethyl pyrrolidine has been found to be an effective method for the preparation of a racemic α-pentafluoroethyl proline.

  在环亚胺上添加五氟乙基锂会产生五氟乙基取代的吡咯烷，哌啶和氮杂环庚烷，而环内酰胺的反应会生成2-五氟乙基亚胺。已经发现2-呋喃基-2-五氟乙基吡咯烷的氧化裂解是制备外消旋α-五氟乙基脯氨酸的有效方法。
• Diastereoselective synthesis of cyclic 1,3-aminoalcohols bearing CF3(CCl3)-groups
  作者：Nikolay E. Shevchenko、Gerd-Volker Röschenthaler、Alexander S. Mitiaev、Enno Lork、Valentine G. Nenajdenko

  DOI：10.1016/j.jfluchem.2008.05.005

  日期：2008.7

  β-Hydroxymethyl substituted cyclic imines or imidates are formed as a result of the reaction. The reduction of the prepared imines leads stereoselectively to the cyclic 1,3-aminoalcohols. Application of methyl trifluoropyruvate in this transformation opens an opportunity for the synthesis of γ-aminoacids derivatives which contain pyrrolidine moiety.

  在温和条件下，没有任何催化剂的情况下，环亚胺和环内酰胺与通过吸电子三氟甲基或三氯甲基基团活化的羰基化合物的醛醇缩合反应得以进行。反应的结果是形成β-羟甲基取代的环状亚胺或酰亚胺。制备的亚胺的还原立体选择性地产生环状的1，3-氨基醇。在该转化中三氟丙酮酸甲酯的应用为合成包含吡咯烷部分的γ-氨基酸衍生物提供了机会。
• Convenient synthesis of melatonin analogues: 2- and 3-substituted -N-acetylindolylalkylamines
  作者：Valentine G. Nenajdenko、Eugene P. Zakurdaev、Eugene V. Prusov、Elizabeth S. Balenkova

  DOI：10.1016/j.tet.2004.10.006

  日期：2004.12

  A new method for the synthesis of 2- and 3-substituted indolylalkylamides, derivatives of melatonin, from arylhydrazines and amidoketones by the Fischer reaction was elaborated. The amidoketones can be easily prepared from cyclic imines by reaction with acylpyridinium chloride. This method is a one-step synchronous creation of the selected alkylamide fragment and the indole core. Variation of the arylhydrazines

  阐述了一种通过费歇尔反应从芳基肼和酰胺酮合成褪黑激素衍生物的2-和3-取代的吲哚基烷基酰胺的新方法。通过与酰化吡啶鎓氯化物反应，可以容易地由环状亚胺制备酰胺酮。该方法是一步一步同步创建所选的烷基酰胺片段和吲哚核。的芳基肼的变化创造indolylalkylamides和酰胺酮的合适的选择可以直接酰胺烷基链的吲哚的2位或3位的碳环所需的取代基。
• Conjugate Additions, Aza-Cope, and Dissociative Rearrangements and Unexpected Electrocyclic Ring Closures in the Reactions of 2-(2-Pyrrolidinyl)-Substituted Heteroaromatic Systems with Acetylenic Sulfones
  作者：Mitchell H. Weston、Masood Parvez、Thomas G. Back

  DOI：10.1021/jo101030b

  日期：2010.8.6

  sulfones proceeded via two pathways. The first involves conjugate addition of the pyrrolidine to the acetylenic sulfone to afford a zwitterion, followed by dissociation of the C−N bond and recombination of the resulting carbocation and vinyl anion to afford the corresponding azepine derivative. The second comprises a cascade of conjugate addition, aza-Cope rearrangement and anionic 6π electrocyclic ring-closure

  2-杂芳基取代的吡咯烷与炔属砜的反应通过两个途径进行。第一个涉及将吡咯烷共轭添加到炔属砜中以提供两性离子，然后将C-N键解离，然后将所得的碳正离子和乙烯基阴离子重组以提供相应的氮杂环庚烷衍生物。第二步包括级联共轭加成，氮杂-Cope重排和阴离子6π电环闭合步骤。由CN裂解形成的碳正离子中间体的稳定性决定了主要途径。
• Synthesis of Pyrrolo[2,1-<i>a</i>]isoquinolinium Salts from 1-Pyrrolines and Alkynes via Rhodium-Catalyzed C–H Functionalization/N-Annulation Tandem Reaction
  作者：Dmitrii A. Shabalin、Maxim K. Kazak、Igor’ A. Ushakov、Alexander V. Vashchenko、Elena Yu. Schmidt

  DOI：10.1021/acs.joc.2c00555

  日期：2022.5.20

  A convenient synthesis of pyrrolo[2,1-a]isoquinolinium salts from 1-pyrrolines and alkynes through rhodium-catalyzed C–H functionalization/N-annulation tandem reaction is described. The protocol features a good substrate tolerance, mild reaction conditions, and high yields of target products. Exploration of the alkyne scope unexpectedly revealed a novel labile functional group-promoted rhodium-catalyzed

  描述了通过铑催化的 C-H 官能化/N-环化串联反应从 1-吡咯啉和炔烃方便合成吡咯并[2,1 - a ] 异喹啉盐。该方案具有良好的底物耐受性、温和的反应条件和高收率的目标产物。炔烃范围的探索出人意料地揭示了一种新的不稳定官能团促进的铑催化的 C-H 官能化/C-环化/消除 1-吡咯啉与缺电子炔烃的级联反应。