2-(2-azidoethyl)furan | 925688-04-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-(2-azidoethyl)furan
• CAS: 925688-04-6
• 化学式: C₆H₇N₃O
• 分子量: 137.141
• InChiKey: OMRPJERBNWURDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  27.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-azidoethyl)furan 以 甲苯 为溶剂， 反应 1.5h， 生成 2-[(2-ethylsulfanylacetyl)(2-furan-2-ylethyl)amino]cyclohex-1-enecarboxylic acid ethyl ester
  参考文献：
  名称：

  Acid-Promoted Cyclization Reactions of Tetrahydroindolinones. Model Studies for Possible Application in a Synthesis of Selaginoidine

  摘要：

  [GRAPHIC]The synthesis of various substituted bicyclic lactams by an acid-induced Pictet-Spengler reaction of tetrahydroindolinones bearing tethered heteroaromatic rings is presented. The outcome of the cyclization depends on the position of the furan tether, tether length, nature of the tethered heteroaromatic ring, and the substituent group present on the 5-position of the tethered heteroaryl group. A one-pot procedure was developed to efficiently prepare tetrahydroindolinones containing tethered furan rings. In a typical example, the reaction of furanyl azide 26 with n-Bu3P delivered iminophosphorane 27, which was allowed to react with a 1-alkyl-(2-oxocyclohexyl)acetic acid to provide the desired furanyl-substituted tetrahydroindolinone system 29. Treatment of 29 with trifluoroacetic acid afforded the tetracyclic lactam skeleton 30 found in the alkaloid (+/-)-selaginoidine.

  DOI：

  10.1021/jo0619783
• 作为产物：
  描述：

  β-2-呋喃基乙醇 在 sodium azide 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.5h， 生成 2-(2-azidoethyl)furan
  参考文献：
  名称：

  Acid-Promoted Cyclization Reactions of Tetrahydroindolinones. Model Studies for Possible Application in a Synthesis of Selaginoidine

  摘要：

  [GRAPHIC]The synthesis of various substituted bicyclic lactams by an acid-induced Pictet-Spengler reaction of tetrahydroindolinones bearing tethered heteroaromatic rings is presented. The outcome of the cyclization depends on the position of the furan tether, tether length, nature of the tethered heteroaromatic ring, and the substituent group present on the 5-position of the tethered heteroaryl group. A one-pot procedure was developed to efficiently prepare tetrahydroindolinones containing tethered furan rings. In a typical example, the reaction of furanyl azide 26 with n-Bu3P delivered iminophosphorane 27, which was allowed to react with a 1-alkyl-(2-oxocyclohexyl)acetic acid to provide the desired furanyl-substituted tetrahydroindolinone system 29. Treatment of 29 with trifluoroacetic acid afforded the tetracyclic lactam skeleton 30 found in the alkaloid (+/-)-selaginoidine.

  DOI：

  10.1021/jo0619783

文献信息

• METHOD FOR PREPARING ENAMIDE COMPOUND AND RUTHENIUM COMPLEX CATALYST USED THEREIN
  申请人：POSTECH ACADEMY-INDUSTRY FOUNDATION

  公开号：US20170291885A1

  公开（公告）日：2017-10-12

  Provided is a method for preparing an enamide compound, which includes reacting an organic azide compound having α-hydrogen and an anhydride by addition of a ruthenium complex catalyst in the presence of an ionic liquid, and a ruthenium complex catalyst used herein.

  提供了一种制备烯酰胺化合物的方法，包括在存在离子液体的情况下，通过向具有α-氢的有机叠氮化合物和酸酐添加钌配合物催化剂来反应，并且这里使用的是一种钌配合物催化剂。
• Synthesis of Enamides by Ruthenium-Catalyzed Reaction of Alkyl Azides with Acid Anhydrides in Ionic Liquid
  作者：Han Kyu Pak、Junghoon Han、Mina Jeon、Yongjin Kim、Yearang Kwon、Jin Yong Park、Young Ho Rhee、Jaiwook Park

  DOI：10.1002/cctc.201500935

  日期：2015.12

  Enamides were synthesized by a ruthenium‐catalyzed one‐pot, one‐step procedure from alkyl azides and acid anhydrides. The substrate scope includes not only secondary azides, but also primary aliphatic ones to give a wide range of enamides containing various functional groups. This one‐step procedure was based on the newly discovered activity of Severin's diruthenium complex ([Cp^RuCl2]2: Cp^=η5‐1‐methoxy‐2

  通过钌催化的一步法，一步法由烷基叠氮化物和酸酐合成酰胺。底物的范围不仅包括仲叠氮化物，而且还包括伯脂族伯酸，以得到各种包含各种官能团的酰胺。这种一步程序是基于塞韦林的二钌复合物（混合[Cp ^的RuCl的新发现的活性2 ] 2：的Cp ^ =η 5 -1-甲氧基-2,4-二-叔-丁基-3-新戊基环戊二烯基），用于将烷基叠氮化物转化为离子液体中相应的NH亚胺中间体。在Severin配合物与叠氮化物的化学计量反应中观察到钌四烯配合物的形成，烷基化叠氮化物充当了NH亚胺中间体的形成催化剂。
• An Aza-Wittig/π-Furan Cyclization Approach Toward the Homoerythrina Alkaloid (±)-Selaginoidine
  作者：Michael P. Cassidy、Ayse Daut Özdemir、Albert Padwa

  DOI：10.1021/ol0501323

  日期：2005.3.1

  react with 1-methyl-(2-oxocyclohexyl)acetic acid to give the desired hexahydroindolinone ring system. Further treatment with trifluoroacetic acid afforded the tetracyclic lactam skeleton found in the alkaloid (+/-)-selaginoidine.

  [反应：见正文]开发了一种一锅法，以有效地制备含有束缚的呋喃环的六氢吲哚满酮。呋喃基叠氮化物与Bu 3 P的反应得到亚氨基磷烷，使其与1-甲基-（2-氧代环己基）乙酸反应，得到所需的六氢吲哚酮环系统。用三氟乙酸进一步处理，得到在生物碱（+/-）-硒代嘧啶中发现的四环内酰胺骨架。