(1'R)-1-(1'-phenylethyl)-1H-pyrrole | 96360-64-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: (1'R)-1-(1'-phenylethyl)-1H-pyrrole
• 英文别名: (R)-1-(1-phenylethyl)-1H-pyrrole；1-(1-phenylethyl)-1H-pyrrole；(1r)-(-)-N-(1-phenylethyl) pyrrole；1-[(1R)-1-phenylethyl]pyrrole
• CAS: 96360-64-4
• 化学式: C₁₂H₁₃N
• 分子量: 171.242
• InChiKey: KEDQNBIZJNAJJP-LLVKDONJSA-N

物化性质

• 沸点：
  252.0±9.0 °C(Predicted)
• 密度：
  0.95±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (1'R)-1-(1'-phenylethyl)-1H-pyrrole 在 双氧水 作用下， 以 吡啶 为溶剂， 反应 192.0h， 以22%的产率得到(1'R)-1-(1'-phenylethyl)-1,5-dihydro-pyrrol-2-one
  参考文献：
  名称：

  A new asymmetric approach toward 5-substituted pyrrolidin-2-one derivatives

  摘要：

  The condensation between a chiral 2-silyloxypyrrole and either achiral or chiral formyl cation equivalents has been studied. The methodology has allowed to build-up 5-substituted pyrrolidin-2-one derivatives with a stereocontrol from good to excellent. The chiral auxiliary located on the silyloxypyrrole showed an intrinsic good level of diastereoface discrimination at C-5. However. the use of a 2-methoxy-3-tosyl-oxazolidine as chiral formylating agent allowed a total stereocontrol in the condensation. A rationale for the observed stereochemical outcome is presented. The stereoselective manipulation of these adducts provided new potentially interesting pyroglutamic aldehyde and prolinal derivatives. whereas treatment with TiCl4 triggered unexpectedly a Pomeranz-Fritsch type intramolecular condensation affording a benzocondensated indolizidinone. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00494-3
• 作为产物：
  描述：

  顺式-1,4-二氯-2-丁烯 、 R(+)-alpha-甲基苄胺 在 air 、 silica gel 、 三乙胺 作用下， 反应 0.03h， 以63%的产率得到(1'R)-1-(1'-phenylethyl)-1H-pyrrole
  参考文献：
  名称：

  New and clean synthesis of N-substituted pyrroles under microwave irradiation

  摘要：

  N-Substituted homochiral pyrrole derivatives were synthesized by the ring-closure reaction of cis-1,4-dichloro-2-butene with various amine compounds on a silica surface under microwave irradiation. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.07.013

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。
• Enantioselective Synthesis of <i>N</i>-Benzylic Heterocycles: A Nickel and Photoredox Dual Catalysis Approach
  作者：Cristofer Pezzetta、Davide Bonifazi、Robert W. M. Davidson

  DOI：10.1021/acs.orglett.9b03338

  日期：2019.11.15

  Reported herein is a dual nickel- and photoredox-catalyzed modular approach for the preparation of enantioenriched N-benzylic heterocycles. α-Heterocyclic carboxylic acids, easily obtainable from common commercial material, are reported as suitable substrates for a decarboxylative strategy in conjunction with a chiral pyridine–oxazoline (PyOx) ligand, providing quick access to enantioenriched drug-like

  本文报道了用于制备对映体富集的N-苄基杂环的双重镍和光氧化还原催化的模块化方法。据报道，很容易从常见的商业原料中获得的α-杂环羧酸与手性吡啶-恶唑啉（PyOx）配体一起用作脱羧策略的合适底物，可快速获得对映体富集的类药物产品。已表明在杂环部分上存在指导基团是有益的，在许多情况下提供了改进的立体选择性。
• Synthesis and Characterization of Chiral Conducting Polymers Based on Polypyrrole
  作者：Fang Chen、Parveen Akhtar、Leon A. P. Kane-Maguire、Gordon G. Wallace

  DOI：10.1071/c96189

  日期：——

  A range of optically active pyrrole monomers have been synthesized in which a chiral sub- stituent is covalently bonded either to the pyrrole N or C3 ring position, namely (–)-(1R)-4-methyl-N-(1-phenylethyl)pyrrole-3-carboxamide, (+)-(1S)-4-methyl-N-(1-phenylethyl)pyrrole-3-carboxamide, (–)-(1R)-4-methyl-N-(1-naphthylethyl)pyrrole-3-carboxamide, (+)-(1S)-4-methyl-N-(1-naphthylethyl)pyrrole-3-carboxamide, (+)-(2S)-2-(1H-pyrrol-1-yl)propionic acid, (+)-(1S)-N-(1-phenyl-ethyl)pyrrole, and (–)-(1R)-N-(1-phenylethyl)pyrrole. Their chiroptical properties have been established by circular dichroism spectroscopy. Electropolymerization of the three N-substituted pyrrole monomers provided films of chiral conducting polymers, whose electrical and spectroscopic properties are described. Although oxidation of the C3 substituted pyrrole monomers was also facile, electrodeposition was poor and films of the associated polymers could not be obtained.

  我们合成了一系列具有光学活性的吡咯单体，其中的 手性副基质共价键合到吡咯 N 环或 C3 环位置上。 位上共价键合，即 (-)-(1R)-4-甲基-N-(1-苯基乙基)吡咯-3-甲酰胺、 (+)-(1S)-4-甲基-N-(1-苯基乙基)吡咯-3-甲酰胺、 (-)-(1R)-4-甲基-N-(1-萘乙基)吡咯-3-甲酰胺、 (+)-(1S)-4-甲基-N-(1-萘乙基)吡咯-3-甲酰胺、 (+)-(2S)-2-(1H-pyrrol-1-yl)propionic 酸、 (+)-(1S)-N-(1-苯基乙基)吡咯、 和 (-)-(1R)-N-(1-苯基乙基)吡咯。 它们的光电性质已通过圆二色性 光谱法确定了它们的光电性质。这三种 N 取代的吡咯单体的电聚合提供了手性导电聚合物薄膜。 导电聚合物薄膜。 介绍。虽然 C3 取代的吡咯单体也很容易氧化，但电沉积效果不佳。 虽然 C3 取代的吡咯单体也很容易氧化，但电沉积效果不佳，无法获得相关聚合物薄膜。 薄膜。
• 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。