4-benzylamino-2(5H)-furanone | 38470-54-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-benzylamino-2(5H)-furanone
• 英文别名: 4-benzylamino-5H-furan-2-one；N-benzyl tetronamide；4-(benzylamino)furan-2(5H)-one；3-(benzylamino)-2H-furan-5-one
• CAS: 38470-54-1
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: JVDKXMKPYLYITQ-UHFFFAOYSA-N

物化性质

• 熔点：
  137-139 °C(Solv: benzene (71-43-2))
• 沸点：
  396.9±41.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-benzylamino-2(5H)-furanone 在 palladium on activated charcoal 氢氧化钾 、 氢气 、 sodium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 苯 为溶剂， 66.0 ℃ 、101.33 kPa 条件下， 反应 3.0h， 生成 (5S,6S)-5-Acetyl-1-benzyl-6-benzyloxymethyl-piperidin-2-one
  参考文献：
  名称：

  Construction of Hydroxylated Alkaloids (.+-.)-Mannonolactam, (.+-.)-Deoxymannojirimycin, and (.+-.)-Prosopinine through Aza-Annulation

  摘要：

  The aza-annulation of beta enamino carbonyl substrates with acrylate derivatives provides an efficient and convenient route for the regioselective construction of delta-lactams. This two-step ring-forming sequence involved initial generation of the benzyl enamine through either a condensation or conjugate addition reaction with BnNH(2), followed by aza-annulation with acryloyl chloride or acrylic anhydride. Controlled by the rigid framework of the intermediate lactam, introduction of ring substituents was accomplished with high relative stereoselectivity. The carbonyl functionality, which was necessary to direct the regioselectivity of the aza-annulation reaction, was then transformed into a protected hydroxyl substituent through Baeyer-Villiger oxidation. The resultant delta-lactam product was used as a valuable intermediate in the synthesis of three natural products. Subsequent modification of this delta-lactam gave the naturally occurring alpha-mannosidase inhibitors (+/-)-mannonolactam and (+/-)deoxymannojirimycin, while synthesis of the alkaloid (+/-)-prosopinine was accomplished through homologation of the lactam carbonyl.

  DOI：

  10.1021/jo00092a015
• 作为产物：
  描述：

  dimethyl 3-(benzylamino)pent-2-enedioate 在 N-溴代丁二酰亚胺(NBS) 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 生成 4-benzylamino-2(5H)-furanone
  参考文献：
  名称：

  N-Bromosuccinimide-Promoted Cyclization of β-Carboxymethyl Enamino Esters; Synthesis of Functionalized 4-Amino-2(5H)-Furanones

  摘要：

  介绍了一种简单的两步法制备各种 5-羧甲基-2(5H)-呋喃酮的方法。详细研究了 δ-羧甲基烯氨基酯与 N-溴代丁二酰亚胺的反应。

  DOI：

  10.1055/s-0030-1260132

文献信息

• A Novel and Highly Stereoselective Approach to Aza-Spirocycles. A Short Total Synthesis of 2-<i>epi</i>-(±)-Perhydrohistrionicotoxin and an Unprecedented Decarboxylation of 2-Pyrones
  作者：Michael J. McLaughlin、Richard P. Hsung、Kevin P. Cole、Juliet M. Hahn、Jiashi Wang

  DOI：10.1021/ol020052o

  日期：2002.6.1

  [reaction: see text] A novel and highly stereoselective synthesis of aza-spirocycles is described. An application of this methodology is illustrated as a short and concise total synthesis of 2-epi-(+/-)-perhydrohistrionicotoxin with high diastereomeric control at the aza-spirocenter. An unprecedented decarboxylation of the 2-pyrone ring is observed in this total synthesis effort.

  [反应：见正文]描述了氮杂螺环化合物的新颖且高度立体选择性的合成。该方法的应用举例说明了在aza-spirocenter上具有高非对映异构体控制的2-epi-（+/-）-perhydrohistrionicotoxin的简短合成。在该总合成过程中观察到了2-吡喃酮环的空前脱羧。
• Tetronamides as Latent Acyclic Vinylogous Amides in Formal <i>Aza</i>-[3 + 3] Cycloaddition Reactions with α,β-Unsaturated Iminium Salts. An Unexpected Rearrangement and an Approach to Synthesis of Substituted Piperidines
  作者：Nadiya Sydorenko、Richard P. Hsung、Ossama Saleh Darwish、Juliet M. Hahn、Jia Liu

  DOI：10.1021/jo049108d

  日期：2004.10.1

  A detailed account regarding formal aza-[3 + 3] cycloaddition reactions of tetronamides with α,β-unsaturated iminium salts is described here. This investigation uncovers regioisomeric cycloadducts that were not found in previous studies involving this formal cycloaddition and an unexpected rearrangement that led to pyridines and dihydropyridines. Both stereochemical and regiochemical issues raised

  在此描述有关四酰胺与α，β-不饱和亚胺盐的形式氮杂-[3 + 3]的正式氮杂-[3 + 3]环加成反应的详细说明。这项研究发现了以前的研究中未发现的区域异构体环加合物，该研究涉及这种正式的环加成反应以及导致吡啶和二氢吡啶的意外重排。这项研究中提出的立体化学和区域化学问题都为该环加成反应提供了进一步的机械学见解。通过小心地控制反应温度，获得了所需的形式的环加合物。随后将这些环加合物转化为官能化的哌啶，确立了将四氨酰胺用作潜在的无环乙烯基酰胺类化合物的形式，用于形式的氮杂-[3 + 3]环加成反应。
• METHOD FOR PRODUCING 4-AMINOBUT-2-ENOLIDES
  申请人：Lui Norbert

  公开号：US20100204480A1

  公开（公告）日：2010-08-12

  The present invention relates to a process for preparing 4-aminobut-2-enolides and also corresponding intermediates and starting compounds which are passed through or used in the process according to the invention.

  本发明涉及一种制备4-氨基丁-2-烯醇酰胺的方法，以及通过本发明的方法经过或使用的相应中间体和起始化合物。
• N-Substituted Tetronamides as Ambident Nucleophilic Building Blocks for the Synthesis of New 4-Aza-2,3-didehydropodophyllotoxins
  作者：David Madec、Giovanni Poli、Francesco Mingoia、Guillaume Prestat

  DOI：10.1055/s-2008-1078429

  日期：2008.6

  Aza-analogues of podophyllotoxin were synthesized in two steps from N-substituted tetronamides. The acid-mediated benz­hydrylation of N-substituted tetronamides with a suitably functionalized benzhydrol quantitatively afforded the cyclization precursors. The target pentacyclic 4-aza-2,3-didehydropodo-phyllotoxins were next obtained via an intramolecular copper-mediated Ullmann-type N-arylation.

  通过两个步骤，从 N-取代的四酰胺中合成了 Podophyllotoxin 的氮杂类似物。酸介导的 N-取代四酰胺与适当官能化的二苯甲酰基苯甲基化反应定量地得到了环化前体。接下来，通过分子内铜介导的乌尔曼型 N-芳基化反应，获得了目标五环 4-氮杂-2,3-二脱氢吡咯烷毒素。
• Unexpected Knoevenagel self-condensation reaction of tetronic acid: synthesis of a new class of organic heterocyclic salts
  作者：Ahmad Shaabani、Afshin Sarvary、Sajjad Keshipour、Ali Hossein Rezayan、Rahim Ghadari

  DOI：10.1016/j.tet.2010.01.009

  日期：2010.3

  A new class of pyridinium, quinolinium, isoquinolinum, and N-methylimidazolium-3-(2,5-dihydro-5-oxofuran-3-yl)-4-hydroxyfuran-2(5H)-one salts have been prepared in high yields by reacting pyridine, quinoline, isoquinoline, N-methylimidazole, 1,4-diazabicyclo[2.2.2]octane, and their derivatives with tetronic acid in CH2Cl2.

  新型的吡啶鎓，喹啉鎓，异喹啉鎓和N-甲基咪唑-3-（2,5-二氢5-呋喃呋喃3-基）-4-羟基呋喃2（5 H）-通过使吡啶，喹啉，异喹啉，N-甲基咪唑，1,4-二氮杂双环[2.2.2]辛烷及其衍生物与tetronic酸在CH 2 Cl 2中反应来合成。