(R)-3-[2-nitro-1-(2-nitrophenyl)ethyl]pentane-2,4-dione | 1073917-21-1

• 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: (R)-3-[2-nitro-1-(2-nitrophenyl)ethyl]pentane-2,4-dione
• 英文别名: 3-[2-nitro-1-(2-nitrophenyl)-ethyl]-pentane-2,4-dione；(R)-3-(1-(2-nitrophenyl)-2-nitroethyl)pentane-2,4-dione；3-[(1R)-2-nitro-1-(2-nitrophenyl)ethyl]pentane-2,4-dione
• CAS: 1073917-21-1
• 化学式: C₁₃H₁₄N₂O₆
• 分子量: 294.264
• InChiKey: YTGZIUMHDCBDAB-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  126
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-nitro-2-(2-nitrovinyl)benzene 、 乙酰丙酮 在 3-[[[3,5-二(三氟甲基)苯基]甲基]氨基]-4-[(9R)-奎宁-9-基氨基]-3-环丁烯-1,2-二酮 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以96%的产率得到(R)-3-[2-nitro-1-(2-nitrophenyl)ethyl]pentane-2,4-dione
  参考文献：
  名称：

  手性方酸酰胺衍生物是优异的氢键供体催化剂

  摘要：

  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。

  DOI：

  10.1021/ja805693p

文献信息

• Asymmetric Michael addition reactions catalyzed by a novel upper-rim functionalized calix[4]squaramide organocatalyst
  作者：Ke Yang、Zhiyan Ma、Hong-Xiao Tong、Xiao-Qiang Sun、Xiao-Yu Hu、Zheng-Yi Li

  DOI：10.1016/j.cclet.2020.02.057

  日期：2020.12

  Abstract A novel upper-rim functionalized calix[4]squaramide organocatalyst bearing bis-squaramide and cyclohexanediamine scaffolds was designed and prepared to catalyse a serial of asymmetric Michael addition of 1,3-dicarbonyl compounds to α,β-unsaturated carbonyl compounds in high yields (up to 99 %) and good to excellent enantiomeric excesses (up to 99% ee). The comparative experiments indicated

  摘要设计并制备了一种新型的带有双-方胺和环己二胺骨架的上边缘功能化杯[4]方酰胺有机催化剂，以高产率催化1,3-二羰基化合物向α，β-不饱和羰基化合物的一系列不对称迈克尔加成反应。 （最高99％）和良好至优异的对映体过量（最高99％ee）。对比实验表明，杯芳烃芳烃与手性催化中心之间的协同作用对该杯[4]方酰胺催化剂有促进作用。此外，该策略还提供了宝贵且容易获得的手性色烯，萘醌和乙酰丙酮衍生物，它们是生物和药物化合物中的重要骨架。
• Doubly stereocontrolled asymmetric Michael addition of acetylacetone to nitroolefins promoted by an isosteviol-derived bifunctional thiourea
  作者：Zhi-wei Ma、Yu-xia Liu、Li-juan Huo、Xiang Gao、Jing-chao Tao

  DOI：10.1016/j.tetasy.2012.03.020

  日期：2012.4

  A novel class of chiral bifunctional thioureas bearing a chiral lipophilic beyerane scaffold and a tertiary amino group was designed and prepared. The thioureas were proven to be effective for catalyzing the doubly stereocontrolled asymmetric Michael addition between acetylacetone and nitroolefins. The corresponding adducts were obtained in high yields (up to 95%) and with good to excellent enantioselectivities

  设计并制备了一类新型的手性双官能硫脲，该手性双官能硫脲带有手性亲脂性拜亚烷骨架和叔氨基。硫脲被证明可有效催化乙酰丙酮和硝基烯烃之间的双立体控制的不对称迈克尔加成反应。相应的加合物以高收率（最高95％）和良好至优异的对映选择性（最高97％）获得。此外，乙酰乙酸叔丁酯与反式-β-硝基苯乙烯的反应也顺利进行，具有良好的对映选择性。
• Ferrocene as a scaffold for effective bifunctional amine–thiourea organocatalysts
  作者：Wei Yao、Ming Chen、Xueying Liu、Ru Jiang、Shengyong Zhang、Weiping Chen

  DOI：10.1039/c4cy00199k

  日期：——

  This work demonstrates that ferrocene could be an excellent scaffold for chiral organocatalysts.

  这项工作表明，二茂铁可以作为手性有机催化剂的优秀支架。
• Novel chiral Tetraazacalix[4]arene[2]triazine-based derivatives as catalysts: enantioselective Michael reaction of nitroolefins and diketones
  作者：Hayriye Nevin Genc

  DOI：10.1007/s10847-023-01186-1

  日期：2023.6

  azine-based catalysts for enantioselective Michael addition reactions of nitroolefins and diketones were presented. Chiral moieties were connected to the heteroatom-bridged calix-triazin scaffold by reactions of (S)- or (R)-(+)-1-(1-Naphthyl)ethylamine with tetraazacalix[4]arene[2]triazine. To utilize the catalytic activity of the chiral catalysts, diketones reacted with a wide variety of trans-β-nitrostyrenes

  介绍了一种基于四氮杂杯[4]芳烃[2]三嗪的新型衍生物，用于硝基烯烃和二酮的对映选择性迈克尔加成反应。通过 ( S )- 或 ( R )-(+)-1-(1-萘基) 乙胺与四氮杂杯[4]芳烃[2]三嗪的反应，将手性部分连接到杂原子桥接的杯-三嗪支架上。为了利用手性催化剂的催化活性，二酮分别与甲苯中的各种反式-β-硝基苯乙烯反应，以优异的收率和对映体过量（高达 96% 的收率和 99% ee）获得迈克尔产品。 图形概要
• New class of bifunctional thioureas from l-proline: highly enantioselective Michael addition of 1,3-dicarbonyls to nitroolefins
  作者：Poopathy Vinayagam、Manjunatha Vishwanath、Venkitasamy Kesavan

  DOI：10.1016/j.tetasy.2014.02.011

  日期：2014.4

  A new class of bifunctional tertiary amine thiourea was synthesized from L-proline. The reported thiourea is amenable to steric and electronic modifications at the stereogenic center bearing a thiourea moiety. Excellent enantioselectivity was obtained in the Michael addition of 2,4-pentanedione to various nitro olefins using the new organocatalyst. The construction of contiguous stereocenters via the Michael reaction of substituted 1,3-dicarbonyls to nitro olefins was also carried out with very good yield, enantioselectivity, and diastereoselectivity. (C) 2014 Elsevier Ltd. All rights reserved.