(S)-3-(1-(furan-2-yl)-2-nitroethyl)pentane-2,4-dione | 1073917-23-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-3-(1-(furan-2-yl)-2-nitroethyl)pentane-2,4-dione
• 英文别名: 3-[(1S)-1-(furan-2-yl)-2-nitroethyl]pentane-2,4-dione
• CAS: 1073917-23-3
• 化学式: C₁₁H₁₃NO₅
• 分子量: 239.228
• InChiKey: NNPRUNPCDSRXQP-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  93.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-(2-糠酰)-2-硝基乙烯 、 乙酰丙酮 在 1-[3,5-bis(trifluoromethyl)phenyl]-3-[(2S)-dimethylamino-(1S)-phenylpropyl]thiourea 作用下， 以 乙醚 为溶剂， 反应 42.0h， 以83%的产率得到(S)-3-(1-(furan-2-yl)-2-nitroethyl)pentane-2,4-dione
  参考文献：
  名称：

  麻黄碱和伪麻黄碱衍生的硫脲在酮酯和二酮与硝基烯烃的不对称迈克尔加成中

  摘要：

  麻黄碱衍生的双功能硫脲已被合成并用作有机催化剂，用于 1,3-二羰基化合物与硝基烯烃的迈克尔加成反应。

  DOI：

  10.1055/s-0029-1219582

文献信息

• Novel bifunctional chiral squaramide-amine catalysts for highly enantioselective addition of mono and diketones to nitroalkenes
  作者：Ze Dong、Xiaoqing Jin、Pengcheng Wang、Chang Min、Jin Zhang、Zhe Chen、Hai-Bing Zhou、Chune Dong

  DOI：10.3998/ark.5550190.0012.927

  日期：——

  Novel bifunctional chiral squaramide–amine organocatalysts have been developed by rational combination of pyrrolidine and a cinchona alkaloid. The catalysts promoted the enantioselective Michael addition of both mono- and diketones to a broad range of nitroalkenes providing the corresponding products in moderate to high yields with excellent enantioselectivities and diastereoselectivities (up to 96%

  通过吡咯烷和金鸡纳生物碱的合理组合开发了新型双功能手性方酸酰胺-胺有机催化剂。该催化剂促进了单酮和二酮对广泛范围的硝基烯烃的对映选择性迈克尔加成，以中等至高产率提供相应的产物，具有优异的对映选择性和非对映选择性（产率高达 96%，96% ee，98:2 dr）。条件温和。这些结果表明，将两个手性特权骨架、吡咯烷和辛可宁与方酸酰胺连接器组装在一起是实现更广泛底物范围、高反应效率和对映选择性的有用策略。嵌入催化剂的两个主链之间手性的匹配对于提高对映选择性也很关键。
• A Polystyrene-Supported, Highly Recyclable Squaramide Organocatalyst for the Enantioselective Michael Addition of 1,3-Dicarbonyl Compounds to β-Nitrostyrenes
  作者：Pinar Kasaplar、Paola Riente、Caroline Hartmann、Miquel A. Pericàs

  DOI：10.1002/adsc.201200526

  日期：2012.11.12

  A chiral squaramide has been supported onto a polystyrene (PS) resin through a copper-catalyzed azide–alkyne cycloaddition (CuAAC) reaction and used as a very active, easily recoverable and highly reusable organocatalyst for the asymmetric Michael addition of 1,3-dicarbonyl compounds to β-nitrostyrenes. The PS-supported squaramide could be recycled up to 10 times.

  通过铜催化的叠氮化物-炔烃环加成（CuAAC）反应，将手性方酰胺被负载在聚苯乙烯（PS）树脂上，并用作非常活泼，易于回收和高度可重复使用的有机催化剂，用于1,3-二羰基不对称迈克尔加成反应β-硝基苯乙烯的化合物。PS支撑的方胺最多可回收10次。
• Chiral Squaramide Derivatives are Excellent Hydrogen Bond Donor Catalysts
  作者：Jeremiah P. Malerich、Koji Hagihara、Viresh H. Rawal

  DOI：10.1021/ja805693p

  日期：2008.11.5

  dominant platform for hydrogen bond promoted asymmetric catalysts. A large number of reactions, reported in scores of publications, have been successfully promoted by chiral thioureas. The present paper reports the use of squaramides as a highly effective new scaffold for the development of chiral hydrogen bond donor catalysts. Squaramide catalysts are very simple to prepare. The (-)-cinchonine modified

  硫脲代表了氢键促进的不对称催化剂的主要平台。手性硫脲已经成功地促进了大量反应，在许多出版物中都有报道。本论文报道了使用方酸酰胺作为开发手性氢键供体催化剂的高效新型支架。方酸酰胺催化剂的制备非常简单。(-)-辛可宁改性方酸酰胺 (5) 很容易通过方酸甲酯通过两步法制备，即使在催化剂负载量低至 0.1 mol% 的情况下，对于 1 的共轭加成反应也显示出是一种有效的催化剂。 ,3-二羰基化合物转化为 β-硝基苯乙烯。以高产率和优异的对映选择性获得加成产物。
• Sugar-Derived Bifunctional Thiourea Organocatalyzed Asymmetric Michael Addition of Acetylacetone to Nitroolefins
  作者：Peng Gao、Chungui Wang、Yang Wu、Zhenghong Zhou、Chuchi Tang

  DOI：10.1002/ejoc.200800555

  日期：2008.9

  A bifunctional chiral thiourea organocatalyst bearing a glycosyl scaffold and a tertiary amino group proved to be an effective organocatalyst for the asymmetric Michael addition of acetylacetone to nitroolefins. The corresponding adducts were obtained in good to excellent yields with excellent enantioselectivities (up to 96 % ee). (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

  带有糖基支架和叔氨基的双功能手性硫脲有机催化剂被证明是乙酰丙酮与硝基烯烃不对称迈克尔加成的有效有机催化剂。相应的加合物以良好到极好的收率获得，具有极好的对映选择性（高达 96% ee）。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• Highly efficient and enantioselective Michael addition of acetylacetone to nitroolefins catalyzed by chiral bifunctional organocatalyst bearing multiple hydrogen-bonding donors
  作者：Xin Shi、Wei He、Hua Li、Xu Zhang、Shengyong Zhang

  DOI：10.1016/j.tetlet.2011.04.043

  日期：2011.6

  efficient catalyst system for the asymmetric addition of acetylacetone to nitroolefins using a chiral bifunctional organocatalyst bearing multiple hydrogen-bonding donors was developed. When using the organocatalyst 2c derived from natural cinchona alkaloid in optimal conditions, up to 98% chemical yield and 98% ee were observed with a variety of aromatic nitroolefins.

  开发了一种新的高效催化剂体系，该体系使用带有多个氢键供体的手性双官能有机催化剂将乙酰丙酮不对称加成到硝基烯烃中。当在最佳条件下使用衍生自天然金鸡纳生物碱的有机催化剂2c时，使用多种芳族硝基烯烃可观察到高达98％的化学收率和98％ee。