2-(1H-吡咯-1-基甲基)吡啶 | 78210-51-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 2-(1H-吡咯-1-基甲基)吡啶
• 英文名称: 2-((1H-pyrrol-1-yl)methyl)pyridine
• 英文别名: 2-[(pyrrol-1-yl)methyl]pyridine；N-pyridin-2-ylmethyl-1H-pyrrole；2-(pyrrol-1-ylmethyl)pyridine；N-(pyridin-2-ylmethyl)pyrrole；2-(1H-pyrrol-1-ylmethyl)pyridine
• CAS: 78210-51-2
• 化学式: C₁₀H₁₀N₂
• mdl: MFCD00052628
• 分子量: 158.203
• InChiKey: YFGRUERUDFISJK-UHFFFAOYSA-N

物化性质

• 沸点：
  100°C/0.5mm
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  一氧化碳 、 2-(1H-吡咯-1-基甲基)吡啶 在 Cu(TFA)₂*xH₂O 、 palladium diacetate 、 三甲基乙酸 作用下， 以 甲苯 为溶剂， 110.0 ℃ 、101.33 kPa 条件下， 反应 6.0h， 以60%的产率得到11H,11'H-[5,5'-bipyrido[1,2-a]pyrrolo[1,2-d]pyrazine]-11,11'-dione
  参考文献：
  名称：

  Pd-Catalyzed C(sp²)–H carbonylation of 2-benzylpyridines for the synthesis of pyridoisoquinolinones

  摘要：

  通过Pd催化的2-苄基吡啶的羰基环化反应，成功合成了吡啶异喹啉酮。

  DOI：

  10.1039/c6cc07612b
• 作为产物：
  描述：

  2-[(1-吡咯烷基)甲基]吡啶 在 β-环糊精 、 2-碘酰基苯甲酸 作用下， 以 水 为溶剂， 反应 9.0h， 以79%的产率得到2-(1H-吡咯-1-基甲基)吡啶
  参考文献：
  名称：

  o-Iodoxybenzoic acid (IBX): a versatile reagent for the synthesis of N-substituted pyrroles mediated by β-cyclodextrin in water

  摘要：

  o-Iodoxybenzoic acid (IBX), a very mild and efficient hypervalent iodine(V) reagent, aromatizes diversely substituted 1-benzylpyrrolidines and N-substituted L-proline analogues to the corresponding substituted pyrroles in good to excellent yields under mild conditions mediated by beta-cyclodextrin in water at room temperature. To the best of our knowledge, this is the first report on IBX, promoting complete aromatization leading to N-benzylpyrroles from the corresponding saturated five membered heterocyclic derivatives in water medium. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.06.077

文献信息

• Organic synthesis via magnetic attraction: benign and sustainable protocols using magnetic nanoferrites
  作者：R. B. Nasir Baig、Rajender S. Varma

  DOI：10.1039/c2gc36455g

  日期：——

  Magnetic nano-catalysts have been prepared using simple modification of iron ferrites. The nm size range of these particles facilitates the catalysis process, as an increased surface area is available for the reaction; the easy separation of the catalysts by an external magnet and their recovery and reuse are additional beneficial attributes. Glutathione bearing nano-ferrites have been used as organocatalysts for the Paal–Knorr reaction and homocoupling of boronic acids. Nanoferrites, post-synthetically modified by ligands, were used to immobilize nanometals (Cu, Pd, Ru, etc.) which enabled the development of efficient, sustainable and green procedures for azide–alkynes-cycloaddition (AAC) reactions, C–S coupling, O-allylation of phenol, Heck-type reactions and hydration of nitriles.

  通过简单修饰铁氧体，已制备出磁性纳米催化剂。这些粒子处于纳米尺寸范围，有助于催化过程，因为反应可利用增加的表面积；外部磁铁易于分离催化剂，并可回收和重复使用，这些是额外的有益特性。负载谷胱甘肽的纳米铁氧体已用作有机催化剂，用于Paal-Knorr反应和硼酸的均偶联。通过配体后合成改性的纳米铁氧体，用于固定纳米金属（铜、钯、钌等），从而实现了高效、可持续和绿色的叠氮-炔烃环加成（AAC）反应、碳-硫偶联、酚的烯丙基化、 Heck型反应和腈的水合反应的方法发展。
• Magnetic nanoparticle-supported glutathione: a conceptually sustainable organocatalyst
  作者：Vivek Polshettiwar、Babita Baruwati、Rajender S. Varma

  DOI：10.1039/b900784a

  日期：——

  A conceptually novel nanoparticle-supported and magnetically recoverable organocatalyst has been developed, which is readily prepared from inexpensive starting materials in a truly sustainable manner; which catalyzes the Paal–Knorr reaction with high yield in pure aqueous medium that avoids the use of toxic organic solvents, even in the workup step.

  开发了一种概念上新颖的纳米粒子支持和可磁性回收的有机催化剂，该催化剂可以通过真正可持续的方式，利用廉价的原材料轻松制备。它在纯水相介质中催化Paal–Knorr反应，具有高产率，避免了使用有毒有机溶剂，甚至在后处理步骤中也不例外。
• Direct Arylation of Pyrrole Derivatives in Ionic Liquids
  作者：Olena Vakuliuk、Daniel T. Gryko

  DOI：10.1002/ejoc.201100004

  日期：2011.5

  An efficient methodology for the direct arylation of pyrrole derivatives has been developed. The reaction proceeds smoothly with a wide range of structurally diverse aryl iodides. Derivatives bearing an N,N-dimethylamino group at the 1-position and an aryl substituent at the 2-position were prepared for the first time. This protocol is more environmentally friendly than those previously reported because

  已开发出一种用于吡咯衍生物直接芳基化的有效方法。反应在结构多样的芳基碘化物的范围内顺利进行。首次制备了在1-位带有N,N-二甲氨基和在2-位带有芳基取代基的衍生物。该协议比以前报道的协议更环保，因为它不含过渡金属并使用离子液体而不是挥发性有机溶剂。
• Magnetic Nanoparticle-Supported Glutathione as a Sustainable Organocatalyst
  申请人：Varma Rajender S.

  公开号：US20110054180A1

  公开（公告）日：2011-03-03

  This invention relates to the use of nano-organocatalysts, and, more specifically, to the use of magnetic nanomaterial-supported organocatalysts. It is an object of the present invention to provide “green” catalysts and protocols. According to one embodiment of the invention, a nano-organocatalyst in the form of a magnetic nanomaterial-supported organocatalyst is provided. According to other embodiments of the invention, glutathione and cysteine are provided as organocatalysts and magnetic nanomaterial-supported glutathione and magnetic nanomaterial-supported cysteine are provided for use as nano-organocatalysts. According to another embodiment of the invention, a method of using a recyclable magnetic nanomaterial-supported organocatalyst using a totally benign aqueous protocol, without using any organic solvent in the reaction or during the workup, is provided. According to a further embodiment of the invention, a recyclable magnetic nanomaterial-supported organocatalyst for various organocatalytic reactions, including but not limited to Paal-Knorr reactions, aza-Michael addition and pyrazole synthesis, is provided.

  本发明涉及纳米有机催化剂的使用，更具体地涉及磁性纳米材料支撑的有机催化剂的使用。本发明的目的是提供“绿色”催化剂和方案。根据本发明的一个实施例，提供了一种磁性纳米材料支撑的有机催化剂的纳米有机催化剂。根据本发明的其他实施例，提供了谷胱甘肽和半胱氨酸作为有机催化剂，以及用作纳米有机催化剂的磁性纳米材料支撑的谷胱甘肽和磁性纳米材料支撑的半胱氨酸。根据本发明的另一个实施例，提供了一种使用可回收磁性纳米材料支撑的有机催化剂的方法，使用完全良性的水相方案，在反应过程中或处理过程中不使用任何有机溶剂。根据本发明的另一个实施例，提供了一种用于各种有机催化反应的可回收磁性纳米材料支撑的有机催化剂，包括但不限于Paal-Knorr反应、aza-Michael加成和吡唑合成。
• A new facile approach to N-alkylpyrroles from direct redox reaction of 4-hydroxy-l-proline with aldehydes
  作者：ZhiQin Zou、ZeJun Deng、XinHong Yu、ManMan Zhang、SiHan Zhao、Ting Luo、Xin Yin、Hui Xu、Wei Wang

  DOI：10.1007/s11426-011-4445-1

  日期：2012.1

  An unprecedented acetic acid-catalyzed efficient access to N-alkylpyrroles from reaction of 4-hydroxy-l-proline with a variety of aldehydes has been achieved in good to excellent yields under mild reaction conditions.

  在前所未有的醋酸催化下，4-羟基-l-脯氨酸与多种醛反应生成 N-烷基吡咯，反应条件温和，收率良好甚至极佳。

表征谱图