1-Nitro-2-furyl-(2)-3-benzoyl-propan | 92200-34-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-Nitro-2-furyl-(2)-3-benzoyl-propan
• 英文别名: 3-(2'-furyl)-4-nitro-1-phenylbutan-1-one；3-furan-2-yl-4-nitro-1-phenyl-butan-1-one；3-[2]Furyl-4-nitro-1-phenyl-butan-1-on；3-(Furan-2-yl)-4-nitro-1-phenylbutan-1-one
• CAS: 92200-34-5
• 化学式: C₁₄H₁₃NO₄
• 分子量: 259.262
• InChiKey: CEWXGQBQQDITCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  76
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-Nitro-2-furyl-(2)-3-benzoyl-propan 在 锌 作用下， 以 溶剂黄146 为溶剂， 生成 4-Furyl-(2)-2-phenyl-Δ¹-pyrrolin
  参考文献：
  名称：

  Terent'ev,A.P. et al., Doklady Chemistry, 1961, vol. 140, p. 937 - 940

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(2-糠酰)-2-硝基乙烯 、 二苯甲酰基甲烷 在 乙醇 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 反应 2.0h， 以68%的产率得到1-Nitro-2-furyl-(2)-3-benzoyl-propan
  参考文献：
  名称：

  1,3-二芳基丙烷-1,3-二酮与硝基苯乙烯的顺序迈克尔加成/复古-克莱森缩合：4-硝基-1,3-二芳基丁烷-1-酮的一步合成

  摘要：

  摘要 描述了1，3-二芳基丙烷-1，3-二酮与硝基苯乙烯的顺序迈克尔加成/复古-克莱森缩合。在温和，无过渡金属的条件下，以高至高收率高效合成了4-Nitro-1,3-diarylbutan-1-one。涉及顺序碳-碳键形成和裂解的这一一步方法为合成各种（γ）-硝基酮提供了一个很好的选择。 图形概要描述了1，3-二芳基丙烷-1，3-二酮与硝基苯乙烯的顺序迈克尔加成/复古-克莱森缩合。在温和且无过渡金属的条件下，以高至高收率高效合成了4-Nitro-1,3-diarylbutan-1-one。

  DOI：

  10.1007/s12039-019-1603-z

文献信息

• Enamines in solid-phase: synthesis and reactivity towards electrophiles
  作者：Fernando Aznar、Carlos Valdés、Marı́a-Paz Cabal

  DOI：10.1016/s0040-4039(00)00946-1

  日期：2000.7

  are synthesized in solid-phase by amination of terminal acetylenes with a secondary amine attached to Wang resin in a process catalyzed by mercury(II) acetate. The enamines obtained react with electrophiles such as isocyanates and nitroolefins to give rise to the expected addition products, which can be released from the resin by hydrolysis of the enamine under mild acidic conditions.

  在乙酸汞（II）催化的过程中，末端乙炔与连接到Wang树脂上的仲胺胺化，在固相中合成烯胺。所获得的烯胺与亲电子试剂如异氰酸酯和硝基烯烃反应，生成预期的加成产物，可通过在温和的酸性条件下烯胺的水解从树脂中释放出预期的加成产物。
• Polystyryl-BEMP as an Efficient Recyclable Catalyst for the Nucleophilic Addition of Nitroalkanes to α,β-Unsaturated Carbonyl Compounds under Solvent-Free Conditions
  作者：R. Ballini、L. Barboni、L. Castrica、F. Fringuelli、D. Lanari、F. Pizzo、L. Vaccaro

  DOI：10.1002/adsc.200800117

  日期：2008.6.9

  3-dimethylperhydro-1,3,2-diazaphosphorine supported on polystyrene (PS-BEMP) is an efficient catalyst for the addition of nitroalkanes (1–1.5 equiv.) to α,β-unsaturated carbonyl compounds (1.0 equiv.) in the absence of a reaction medium (solvent-free conditions). The corresponding γ-nitro carbonyl compounds have been isolated in excellent yields but the catalyst can be satisfactorily recovered and used for only 3 times

  2叔-聚苯乙烯（PS-BEMP）上负载的Butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine（PS-BEMP）是一种有效的催化剂，可将α1-β-不饱和硝基烷烃加成（1-1.5当量）在没有反应介质的情况下（无溶剂条件）羰基化合物（1.0当量）。已经以优异的产率分离了相应的γ-硝基羰基化合物，但是由于磁力搅拌导致催化剂珠粒的碎裂从而阻碍了其完全回收，因此可以令人满意地回收该催化剂并且仅将其使用3次。为了优化催化剂的再利用并提高无溶剂条件的环境效率，已经建立了第一个无溶剂循环连续流反应器。
• Bifunctional chiral organocatalytic compound having excellent enantioselectivity, preparation method therefor, and method for producing non-natural gamma-amino acid from nitro compound by using same
  申请人：KOREA UNIVERSITY RESEARCH AND BUSINESS FOUNDATION

  公开号：US11465135B2

  公开（公告）日：2022-10-11

  The present invention relates to a bifunctional chiral organocatalytic compound having excellent enantioselectivity, a preparation method therefor, and a method for producing a non-natural gamma amino acid from a nitro compound by using the chiral organocatalytic compound. According to the present invention, the bifunctional chiral organocatalytic compound having excellent enantioselectivity can be easily synthesized, gamma-amino acids with high optical selectivity can be obtained at a high yield by an economical and convenient method using the chiral organocatalytic compound, and various (R)-configuration gamma-amino acids, which are not present in nature, can be produced with high optical purity in large quantities by using a small amount of a catalyst, and therefore, the present invention can be widely utilized in various industrial fields including the pharmaceutical industry.

  本发明涉及一种具有优异对映选择性的双功能手性有机催化化合物、其制备方法以及利用该手性有机催化化合物从硝基化合物制备非天然γ-氨基酸的方法。根据本发明，可以很容易地合成具有优异对映选择性的双功能手性有机催化化合物，并通过使用该手性有机催化化合物的经济、简便的方法高产率地获得具有高光学选择性的γ-氨基酸、而且只需使用少量催化剂，就能大量生产出自然界中不存在的各种(R)构型γ-氨基酸，且光学纯度高，因此本发明可广泛应用于包括制药业在内的各种工业领域。
• Enantioselective addition of aryl ketones and acetone to nitroalkenes organocatalyzed by carbamate-monoprotected cyclohexa-1,2-diamines
  作者：Jesús Flores-Ferrándiz、Alexander Stiven、Lia Sotorríos、Enrique Gómez-Bengoa、Rafael Chinchilla

  DOI：10.1016/j.tetasy.2015.07.011

  日期：2015.9

  Enantiomerically pure carbamate-monoprotected trans-cyclohexane-1,2-diamines are used as chiral organocatalysts for the addition of aryl ketones and acetone to nitroalkenes to give enantioenriched beta-substituted gamma-nitroketones. The reaction was performed in the presence of 3,4-dimethoxybenzoic acid as an additive, in chloroform as the solvent at room temperature, achieving enantioselectivities up to 96%. Theoretical calculations are used to justify the observed sense of the stereoinduction. (C) 2015 Elsevier Ltd. All rights reserved.
• SOME GAMMA-NITRO-BETA-FURYLBUTYROPHENONES¹
  作者：Nathan L. Drake、H. W. Gilbert

  DOI：10.1021/ja01375a046

  日期：1930.12