(S)-3-(2-nitro-1-(2-nitrophenyl)ethyl)pentane-2,4-dione | 1372797-63-1

• 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: (S)-3-(2-nitro-1-(2-nitrophenyl)ethyl)pentane-2,4-dione
• 英文别名: 3-[(1S)-2-nitro-1-(2-nitrophenyl)ethyl]pentane-2,4-dione
• CAS: 1372797-63-1
• 化学式: C₁₃H₁₄N₂O₆
• 分子量: 294.264
• InChiKey: YTGZIUMHDCBDAB-LLVKDONJSA-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：

  Β,2-二硝基苯乙烯 、 乙酰丙酮 在 (2-aminoethyl)polystyrene-supported chiral bifunctional squaramide 作用下， 以 neat (no solvent) 为溶剂， 反应 1.5h， 以88%的产率得到(S)-3-(2-nitro-1-(2-nitrophenyl)ethyl)pentane-2,4-dione
  参考文献：
  名称：

  受支持和不受支持的手性方酰胺作为有机催化剂用于立体选择性迈克尔加成反应：对映体纯的二茂铁和螺并铬烷的合成

  摘要：

  从衍生自天然氨基酸的二胺和可商购的氨基烷基聚苯乙烯树脂开始，已经容易地制备了新型的负载性手性双官能方酸酰胺。在室温下的纯净条件下，这些麦角酰胺在不同的迈克尔添加量下均表现为出色的立体选择性可回收有机催化剂。以2-（2-硝基乙烯基）苯酚为亲电试剂，以优异的收率和对映选择性，反应生成易于转化为4 H-色烯和螺并二氢吡喃酮的中间体。

  DOI：

  10.1021/acs.joc.7b01177

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。
• Ferrocene Analogues of Hydrogen-Bond-Donor Catalysts: An Investigative Study on Asymmetric Michael Addition of 1,3-Dicarbonyl Compounds to Nitroalkenes
  作者：Rajiv Trivedi、Kadiyala Rao、M. Kantam

  DOI：10.1055/s-0034-1379491

  日期：——

  moieties. A stepwise sequential route was used to assemble the various components of these ferrocene derivatives. The resulting bifunctional catalysts were used successfully in asymmetric Michael additions of 1,3-dicarbonyl compounds to β-nitrostyrenes. The corresponding products were obtained in high yields and in good to excellent enantioselectivities and diastereoselectivities under mild conditions by

  本报告描述了含有金鸡纳生物碱部分的基于方酸酰胺或硫脲的双功能催化剂的八种二茂铁衍生物的合成。使用逐步顺序路线来组装这些二茂铁衍生物的各种组分。所得双功能催化剂成功用于 1,3-二羰基化合物与 β-硝基苯乙烯的不对称迈克尔加成反应。通过使用 1 mol% 的催化剂，在温和条件下以高收率和良好到优异的对映选择性和非对映选择性获得了相应的产物。
• Novel Chiral Bifunctional L-Thiazoline-Thiourea Derivatives: Design and Application in EnantioselectiveMichael Reactions
  作者：Qi Lai、Yang Li、Zhiyong Gong、Qingwen Liu、Chiyu Wei、Zhiguang Song

  DOI：10.1002/chir.22540

  日期：2015.12

  Several novel chiral bifunctional L‐thiazoline‐thiourea derivatives were easily synthesized from commercially available L‐cysteine in high yield. These catalysts were subsequently applied to the enantioselective Michael addition of acetylacetone to β‐nitrostyrenes. The products with S configuration were obtained in 98% enantiomeric excess (ee) when the L‐thiazoline‐thiourea derivatives were used. A

  从市售L-半胱氨酸可以轻松地高收率地合成几种新颖的手性双功能L-噻唑啉-硫脲衍生物。这些催化剂随后用于将乙酰丙酮的对映选择性迈克尔加成至β-硝基苯乙烯。当使用L-噻唑啉-硫脲衍生物时，具有98％对映体过量（ee）的产品具有S构型。提出了一个合理的过渡态模型来解释观察到的对映选择性。手性27：979–988，2015。©2015 Wiley Periodicals，Inc.
• Fast, solvent-free and hydrogen-bonding-mediated asymmetric Michael addition in a ball mill
  作者：Yi-Feng Wang、Ru-Xiang Chen、Ke Wang、Bin-Bin Zhang、Zhao-Bo Li、Dan-Qian Xu

  DOI：10.1039/c2gc16521j

  日期：——

  The chiral squaramide derivatives as hydrogen bonding catalyst for the Michael addition reactions of 1,3-dicarbonyl compounds to nitroolefins under solvent-free conditions was developed using a planetary ball mill. High yields, high enantioselectivities and shorter reaction times were achieved with low catalyst loading.

  手性方酰胺衍生物作为氢键 催化剂 1,3-二羰基化合物的迈克尔加成反应 硝基烯烃 在下面 溶剂使用行星式球磨机开发了无条件条件。低收率获得了高收率，高对映选择性和较短的反应时间催化剂 加载中。
• 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。