2-[2-nitro-1-(2-thienyl)ethyl]-1H-pyrrole | 1011711-88-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-[2-nitro-1-(2-thienyl)ethyl]-1H-pyrrole
• 英文别名: (S)-2-(2-nitro-1-(thiophen-2-yl)ethyl)-1H-pyrrole；2-(2-nitro-1-(thiophen-2-yl)ethyl)-1H-pyrrole；2-[(1S)-2-nitro-1-thiophen-2-ylethyl]-1H-pyrrole
• CAS: 1011711-88-8
• 化学式: C₁₀H₁₀N₂O₂S
• 分子量: 222.268
• InChiKey: XNRRGBRNIATCNM-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  89.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  吡咯 、 反式-2-(2-硝基乙烯基)噻吩 在 chiral dinuclear zinc catalyst 4 A molecular sieve 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以58%的产率得到2-[2-nitro-1-(2-thienyl)ethyl]-1H-pyrrole
  参考文献：
  名称：

  Asymmetric Friedel−Crafts Alkylation of Pyrroles with Nitroalkenes Using a Dinuclear Zinc Catalyst

  摘要：

  The catalytic enantioselective and atom economic Friedel-Crafts alkylation of pyrroles with nitroalkenes under mild reaction conditions using a dinuclear zinc catalyst is reported. The versatility of the reaction is demonstrated by the conversion of a number of differentially substituted nitroalkenes with differentially substituted pyrroles. Tandem addition reactions to form 2,5-disubstituted pyrroles are also demsonstrated. All pyrrole alkylations have been carried out without using N-protecting groups, which also enhances the efficiency by which substituted pyrroles may be synthesized. The reactions result in good yields and excellent enantioselectivities.

  DOI：

  10.1021/ja711080y

文献信息

• Asymmetric Friedel–Crafts reaction of N-heterocycles and nitroalkenes catalyzed by imidazoline–aminophenol–Cu complex
  作者：Naota Yokoyama、Takayoshi Arai

  DOI：10.1039/b904275j

  日期：——

  Catalytic asymmetric Friedel–Crafts reaction of pyrrole with nitroalkenes was smoothly catalyzed by newly synthesized nitro-substituted imidazoline–aminophenol (1b)–Cu complex to give the adduct with up to 92% ee.

  新合成的硝基取代咪唑啉–氨基苯酚 (1b)–铜复合物顺利催化了吡咯与硝基烯烃的催化不对称Friedel–Crafts反应，产物的对映体过量达到92%。
• Enantioselective Michael Addition of Pyrroles with Nitroalkenes in Aqueous Media Catalyzed by a Water-Soluble Catalyst
  作者：Yang Gui、Yanan Li、Jianan Sun、Zhenggen Zha、Zhiyong Wang

  DOI：10.1021/acs.joc.8b01141

  日期：2018.7.20

  A new water-soluble catalytic system was developed and used in an enantioselective Michael addition of pyrroles with nitroalkenes in water to afford nitroethylpyrrole derivatives with both excellent yields and ee values.

  开发了一种新的水溶性催化系统，并将其用于吡咯与硝基烯烃在水中的对映选择性迈克尔加成反应，从而获得具有优异收率和ee值的硝基乙基吡咯衍生物。
• Boosting Chemical Stability, Catalytic Activity, and Enantioselectivity of Metal–Organic Frameworks for Batch and Flow Reactions
  作者：Xu Chen、Hong Jiang、Bang Hou、Wei Gong、Yan Liu、Yong Cui

  DOI：10.1021/jacs.7b06459

  日期：2017.9.27

  5-bis(trifluoromethyl)-, bismethyl-, and bisfluoro-phenyl substituents at the 3,3'-position. For the first time, we show that not only chemical stability but also catalytic activity and stereoselectivity of the MOFs can be tuned by modifying the ligand structures. Particularly, the MOF incorporated with -CF3 groups on the pore walls exhibits enhanced tolerance to water, weak acid, and base compared with the MOFs with

  多相催化的一个关键挑战是设计和合成具有高催化活性、选择性和可回收性的多相催化剂。在这里，我们证明了可以通过使用配体设计策略从金属有机框架 (MOF) 平台设计高性能多相不对称催化剂。三个具有骨架式 [Mn2L(H2O)2] 的多孔手性 MOF 是由 1,1'-双酚的对映纯膦酰基羧酸配体制备的，该配体用 3,5-双（三氟甲基）-、双甲基-和双氟-官能化苯基取代基在 3,3'-位。我们首次表明，不仅可以通过修饰配体结构来调节 MOF 的化学稳定性，还可以调节其催化活性和立体选择性。特别，与具有 -F 和 -Me 基团的 MOF 相比，在孔壁上引入 -CF3 基团的 MOF 对水、弱酸和碱的耐受性更强。在间歇和流动反应系统下，含 CF3 的 MOF 表现出优异的反应性、选择性和可回收性，为吲哚和吡咯与一系列酮酯或硝基烯烃的烷基化提供高产率和对映选择性。相比之下，相应的均相催化剂在催化测试反应时的
• Asymmetric Friedel−Crafts Alkylation of Pyrroles with Nitroalkenes Using a Dinuclear Zinc Catalyst
  作者：Barry M. Trost、Christoph Müller

  DOI：10.1021/ja711080y

  日期：2008.2.1

  The catalytic enantioselective and atom economic Friedel-Crafts alkylation of pyrroles with nitroalkenes under mild reaction conditions using a dinuclear zinc catalyst is reported. The versatility of the reaction is demonstrated by the conversion of a number of differentially substituted nitroalkenes with differentially substituted pyrroles. Tandem addition reactions to form 2,5-disubstituted pyrroles are also demsonstrated. All pyrrole alkylations have been carried out without using N-protecting groups, which also enhances the efficiency by which substituted pyrroles may be synthesized. The reactions result in good yields and excellent enantioselectivities.