(±)-4-(furan-2-yl)-5-nitropentan-2-one | 98996-68-0

• 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: (±)-4-(furan-2-yl)-5-nitropentan-2-one
• 英文别名: 4-(furan-2-yl)-5-nitropentan-2-one；4-[2]furyl-5-nitro-pentan-2-one；4-[2]Furyl-5-nitro-pentan-2-on；4-(2-Furanyl)-5-nitro-2-pentanone
• CAS: 98996-68-0
• 化学式: C₉H₁₁NO₄
• 分子量: 197.191
• InChiKey: SNUYAOAXDQPONO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  (±)-4-(furan-2-yl)-5-nitropentan-2-one 在 盐酸 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  A Synthesis of Substituted Tetrahydro-2-pyranols

  摘要：

  DOI：

  10.1002/prac.199733901118
• 作为产物：
  描述：

  1-(2-糠酰)-2-硝基乙烯 、 丙酮 在 藜芦酸 、 (1R,2R)-反式-N-Boc-1,2-二氨基环己烷 、 (1S,2S)-BOC-1,2-环己二胺 作用下， 以 氯仿 为溶剂， 生成 (±)-4-(furan-2-yl)-5-nitropentan-2-one
  参考文献：
  名称：

  Enantioselective addition of aryl ketones and acetone to nitroalkenes organocatalyzed by carbamate-monoprotected cyclohexa-1,2-diamines

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2015.07.011

文献信息

• Lipase/Acetamide-Catalyzed Carbon-Carbon Bond Formations: A Mechanistic View
  作者：Xiao-Yang Chen、Guo-Jun Chen、Jun-Liang Wang、Qi Wu、Xian-Fu Lin

  DOI：10.1002/adsc.201201080

  日期：2013.3.25

  A lipase B from Candida antarctica (CALB)/acetamide‐catalyzed Michael addition of less‐activated ketones and aromatic nitroolefins has been developed, which is particularly interesting because neither CALB nor acetamide can independently catalyze the reaction to any appreciable extent. This co‐catalyst system was applicable to the Michael additions of cyclic and acyclic ketones to a series of aromatic

  已经开发了一种来自南极假丝酵母（CALB）/乙酰胺催化的Michael的活化程度较低的酮和芳族硝基烯烃的脂肪酶B ，这特别有趣，因为CALB和乙酰胺都无法独立地在任何明显的程度上催化该反应。该助催化剂体系适用于在一系列芳族和杂芳族硝基烯烃中将环状和无环酮进行迈克尔加成反应。实验事实证实了乙酰胺和环己酮之间的氢键可用于观察到的活化作用，并提供了有关CALB /乙酰胺共催化的新机理的见解。
• Highly Enantioselective Synthesis of γ-Nitro Heteroaromatic Ketones in a Doubly Stereocontrolled Manner Catalyzed by Bifunctional Thiourea Catalysts Based on Dehydroabietic Amine: A Doubly Stereocontrolled Approach to Pyrrolidine Carboxylic Acids
  作者：Xianxing Jiang、Yifu Zhang、Albert S. C. Chan、Rui Wang

  DOI：10.1021/ol8025268

  日期：2009.1.1

  class of dehydroabietic amine-substituted primary amine-thiourea bifunctional catalysts were designed and synthesized. The doubly stereocontrolled organocatalytic conjugate addition of a variety of heterocycles-bearing ketones to nitroalkenes was investigated for the first time, affording (S)- or (R)-γ-nitro heteroaromatic ketones with excellent enantioselectivities (up to ee >99%). Furthermore, the nearly

  设计并合成了一类新型的脱氢松香胺取代的伯胺-硫脲双功能催化剂。首次研究了将多种带有杂环的酮加到硝基烯烃中的双立体控制有机催化共轭加成反应，从而提供了具有出色对映选择性（高达ee> 99％）的（S）-或（R）-γ-硝基杂芳族酮。此外，几乎光学纯的γ-硝基杂芳族酮可以容易地转化为手性吡咯烷羧酸。
• Small Changes Result in Large Differences: Discovery of (−)-Incrustoporin Derivatives as Novel Antiviral and Antifungal Agents
  作者：Aidang Lu、Jinjin Wang、Tengjiao Liu、Jian Han、Yinhui Li、Min Su、Jianxin Chen、Hui Zhang、Lizhong Wang、Qingmin Wang

  DOI：10.1021/jf503060k

  日期：2014.9.3

  On the basis of the structure of natural product (-)-incrustoporin (1), a series of lactone compounds 4a-i and 5a-i were designed and synthesized from nitroolefin. The antiviral and antifungal activities of these compounds were evaluated in vitro and in vivo. The small changes between 4 and 5 at the 3,4-position result in large differences in bioactivities. Compounds 4 exhibited significantly higher antiviral activity against tobacco mosaic virus (TMV) than dehydro compounds 5. However, the antifungal activity of 4 is relatively lower than that of 5. Compounds 4a, 4c, and 4i with excellent in vivo anti-TMV activity emerged as new antiviral lead compounds. Compounds 5d-g showed superiority over the commercial fungicides chlorothalonil and carbendazim against Cercospora arachidicola Hor at 50 mg kg(-1). The present study provides fundamental support for the development and optimization of (-)-incrustoporin derivatives as potential inhibitors of plant virus and pathogenic fungi.
• Simple Cyclohexanediamine-Derived Primary Amine Thiourea Catalyzed Highly Enantioselective Conjugate Addition of Nitroalkanes to Enones
  作者：Kui Mei、Mei Jin、Shilei Zhang、Ping Li、Wenjing Liu、Xiaobei Chen、Fei Xue、Wenhu Duan、Wei Wang

  DOI：10.1021/ol9010322

  日期：2009.7.2

  A highly enantioselective conjugate addition of nitroalkanes to enones has been developed. The process is efficiently catalyzed by a simple chiral cyclohexanediamine-derived primary amine thiourea with a broad substrate scope.
• Koslow; Fink, Metodiceskij sbornik, 1956, # 21, p. 163,165
  作者：Koslow、Fink

  DOI：——

  日期：——