4-(4-bromophenyl)-5-nitropentan-2-one | 923002-19-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(4-bromophenyl)-5-nitropentan-2-one
• 英文别名: (±)-4-(4-bromophenyl)-5-nitropentan-2-one
• CAS: 923002-19-1
• 化学式: C₁₁H₁₂BrNO₃
• 分子量: 286.125
• InChiKey: OXMTWLYQHOHPJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.79
• 重原子数：
  16.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  60.21
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-(4-bromophenyl)-5-nitropentan-2-one 在 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.25h， 生成
  参考文献：
  名称：

  Small Changes Result in Large Differences: Discovery of (−)-Incrustoporin Derivatives as Novel Antiviral and Antifungal Agents

  摘要：

  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.

  DOI：

  10.1021/jf503060k
• 作为产物：
  描述：

  对溴苯甲醛 在 L-脯氨酸 、 sodium hydroxide 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 0.25h， 生成 4-(4-bromophenyl)-5-nitropentan-2-one
  参考文献：
  名称：

  通过 10 元环环状过渡态作用的双功能 B,N 基不对称催化硝基苯乙烯-迈克尔加成

  摘要：

  B,N-双功能催化剂高硼脯氨酸已应用于催化不对称硝基烯烃-迈克尔加成到 β-硝基苯乙烯类似物，显示出广泛的底物耐受性、高转化率和中等至良好的不对称诱导。homoboroproline的充当基于所述仲胺的烯胺形成一种有效的催化剂，加上分子内的能力路易斯硝基功能的-酸螯合，在非FLP方式，以实现高效和对映选择性催化通过所提议的大10 -元环过渡态是显着的，并通过理论计算得到加强。

  DOI：

  10.1002/hlca.202100199

文献信息

• Concentration Effect in the Asymmetric Michael Addition of Acetone to β-Nitrostyrenes Catalyzed by Primary Amine Thioureas
  作者：Ciril Jimeno、Miquel Pericàs、Z. Günler、Ignacio Alfonso

  DOI：10.1055/s-0036-1589408

  日期：——

  yield and ee of the Michael­ addition products. Bifunctional primary amine thiourea (PAT) organocatalysts show remarkable improvement in enantioselectivity and catalytic activity (turnover frequency) in the asymmetric Michael addition of acetone to β-nitrostyrenes upon dilution. Mechanistic investigations indicate that this behavior corresponds to the inhibition of off-cycle catalyst deactivation at low

  献给教授迪特尔·恩德斯在他70之际个生日 抽象的 双功能伯胺硫脲（PAT）有机催化剂在稀释后将丙酮不对称迈克尔加成至β-硝基苯乙烯中时，对映选择性和催化活性（转化频率）均得到显着改善。机理研究表明，这种行为对应于在低浓度下抑制循环外催化剂失活，而不是在高浓度下发生聚集现象。低浓度反应（在β-硝基苯乙烯中≤0.2M）导致催化剂失活最小化，从而使迈克尔加成产物的收率和ee最优化。 双功能伯胺硫脲（PAT）有机催化剂在稀释后将丙酮不对称迈克尔加成至β-硝基苯乙烯中时，对映选择性和催化活性（转化频率）均得到显着改善。机理研究表明，这种行为对应于在低浓度下抑制循环外催化剂失活，而不是在高浓度下发生聚集现象。低浓度反应（在β-硝基苯乙烯中≤0.2M）导致催化剂失活最小化，从而使迈克尔加成产物的收率和ee最优化。
• 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.
• METHOD FOR PREPARING CHIRAL NITRO DERIVATIVES USING ORGANIC CHIRAL CATALYST COMPOUNDS AND ECO-FRIENDLY SOLVENTS
  申请人：KOREA UNIVERSITY RESEARCH AND BUSINESS FOUNDATION

  公开号：US20240076263A1

  公开（公告）日：2024-03-07

  Provided are a method for preparing chiral nitro derivatives using organic chiral catalyst compounds and water as an eco-friendly solvent, and the like. The catalyst is an organic catalyst based on (R,R)-1,2-diphenylethylenediamine (DPEN), and can prepare nitro derivatives having enantioselectivity and diastereoselectivity in excellent yield through a hydrophobic hydration effect. In particular, the preparation method of the present disclosure can stabilize a transition state through an interfacial reaction between the catalyst and water. In addition, indole derivatives can be synthesized using the chiral nitro derivatives prepared according to the present disclosure to be usefully used for the prevention or treatment of brain-nervous system diseases including depression and muscular diseases including cachexia.