(R)-2-(1-(2-methoxyphenyl)-2,5-dioxopyrrolidin-3-yl)-2-methylpropanal | 1352335-26-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (R)-2-(1-(2-methoxyphenyl)-2,5-dioxopyrrolidin-3-yl)-2-methylpropanal
• 英文别名: 2-[(3R)-1-(2-methoxyphenyl)-2,5-dioxopyrrolidin-3-yl]-2-methylpropanal
• CAS: 1352335-26-2
• 化学式: C₁₅H₁₇NO₄
• 分子量: 275.304
• InChiKey: PQYATUIFMIMZME-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(2-甲氧基苯基)-吡咯-2,5-二酮 、 异丁醛 在 C₂₆H₄₃N₃OS 作用下， 以 甲苯 为溶剂， 以93%的产率得到(R)-2-(1-(2-methoxyphenyl)-2,5-dioxopyrrolidin-3-yl)-2-methylpropanal
  参考文献：
  名称：

  新型双萜衍生的双功能硫脲催化剂促进的高对映选择性迈克尔加成反应：手性琥珀酰亚胺衍生物的双立体控制方法

  摘要：

  描述了双立体控制的有机催化不对称迈克尔加成取代琥珀酰亚胺的合成。从醛和马来酰亚胺开始，将两种特殊的手性双萜衍生的双官能硫脲分别用作丁二酰亚胺时，琥珀酰亚胺的两种对映异构体均可以高至优异的收率（高达98％）和对映选择性（高达99％）获得。催化剂。而且，这些催化剂可以有效地用于大规模催化合成，且产率和对映选择性相同。手性00：000–000，2014年。©2014 Wiley Periodicals，Inc.

  DOI：

  10.1002/chir.22279

文献信息

• Enantioselective Michael addition of aldehydes to maleimides organocatalysed by chiral 1,2-diamines: an experimental and theoretical study
  作者：Angel Avila、Rafael Chinchilla、Enrique Gómez-Bengoa、Carmen Nájera

  DOI：10.1016/j.tetasy.2013.10.001

  日期：2013.12

  commercially available chiral 1,2-diamines were used as organocatalysts for the enantioselective conjugate addition of aldehydes, including α,α-disubstituted, to maleimides. The reaction was carried out in the presence of hexanedioic acid as an additive in aqueous solvents at room temperature. By employing (1S,2S)- and (1R,2R)-cyclohexane-1,2-diamine as organocatalysts, the corresponding Michael adducts bearing

  简单且可商购的手性1,2-二胺用作有机催化剂，用于将包括α，α-二取代的醛的对映选择性共轭加成至马来酰亚胺。反应在室温下在水性溶剂中在己二酸作为添加剂存在下进行。通过使用（1 S，2 S）-和（1 R，2 R）-环己烷-1,2-二胺作为有机催化剂，可以高产率或定量产率获得相应的带有新立体中心的迈克尔加合物，其对映选择性高达92％ ，而使用（1 S，2 S）-1,2-二苯乙烷-1,2-二胺的ee值要低得多。理论计算被用来证明所观察到的立体感应的意义。
• Enantioselective Synthesis of Succinimides by Michael Addition of Aldehydes to Maleimides Organocatalyzed by Chiral Primary Amine-Guanidines
  作者：Angel Avila、Rafael Chinchilla、Enrique Gómez-Bengoa、Carmen Nájera

  DOI：10.1002/ejoc.201300492

  日期：2013.8

  The authors thank the Spanish Ministerio de Economia y Competitividad (MEC) (projects CTQ2010-20387, CTQ2010-21263-C02, and Consolider Ingenio 2010, CSD2007-00006), the Fondos Europeos para el Desarrollo Regional (FEDER), the COST Action CM0905 “Organocatalysis”, the Generalitat Valenciana (Prometeo/2009/039), the Basque Government (GV grant IT-291-07), the University of Alicante, and the University

  作者感谢西班牙经济与竞争部长 (MEC)（项目 CTQ2010-20387、CTQ2010-21263-C02 和 Consolider Ingenio 2010、CSD2007-00006）、Fondos Europeos para el Desarrollo、CM05 “Organocatalysis”、Generalitat Valenciana (Prometeo/2009/039)、巴斯克政府（GV grant IT-291-07）、阿利坎特大学和巴斯克地区大学的财政支持。
• Solvent-Induced Reversal of Enantioselectivity in the Synthesis of Succinimides by the Addition of Aldehydes to Maleimides Catalysed by Carbamate-Monoprotected 1,2-Diamines
  作者：Jesús Flores-Ferrándiz、Béla Fiser、Enrique Gómez-Bengoa、Rafael Chinchilla

  DOI：10.1002/ejoc.201403415

  日期：2015.2

  The authors are grateful for the financial support from the Spanish Ministerio de Economia y Competitividad (MEC) (project number CTQ2011-24151), Fondos Europeos para el Desarrollo Regional (FEDER), the COST Action CM0905 “Organocatalysis”, the FP7 Marie Curie Action of the European Commission via the ITN ECHONET Network (FP7-MCITN-2012-316379), the University of Alicante and the University of the

  作者感谢西班牙经济与竞争部长 (MEC)（项目编号 CTQ2011-24151）、欧洲基金会（FEDER）、COST 行动 CM0905“有机催化”、FP7 玛丽居里行动的财政支持欧盟委员会通过 ITN ECHONET 网络 (FP7-MCITN-2012-316379)、阿利坎特大学和巴斯克大学。
• Organocatalytic enantioselective conjugate addition of aldehydes to maleimides in deep eutectic solvents
  作者：Jesús Flores-Ferrándiz、Rafael Chinchilla

  DOI：10.1016/j.tetasy.2016.12.009

  日期：2017.2

  The conjugate enantioselective addition of aldehydes, mainly alpha,alpha-disubstituted, to maleimides leading to enantioenriched succinimides, has been achieved in recyclable deep eutectic solvents at room temperature. Enantiomerically pure carbamate-monoprotected trans-cyclohexane-1,2-diamines are used as organocatalysts, affording high yields and up to 94% ee of the final succinimides. The product can be extracted from the deep eutectic solvent, which retains the chiral organocatalyst, allowing both the solvent and catalyst to be reused. (C) 2016 Elsevier Ltd. All rights reserved.
• A highly efficient large-scale asymmetric Michael addition of isobutyraldehyde to maleimides promoted by a novel multifunctional thiourea
  作者：Zhi-wei Ma、Yu-xia Liu、Pan-li Li、Hang Ren、Yu Zhu、Jing-chao Tao

  DOI：10.1016/j.tetasy.2011.10.002

  日期：2011.10

  A novel class of chiral multifunctional thioureas bearing a chiral lipophilic beyerane scaffold and a primary amino group were designed and prepared. The thioureas were proven to be effective for catalyzing the asymmetric Michael addition between isobutyraldehyde and maleimides with only 0.5 mol% catalyst loading, and exhibited double asymmetric induction. Both of the catalysts afforded the corresponding adduct with high to excellent yields (up to 98%) and excellent enantioselectivities (up to 99%). Furthermore, this catalytic system can be used efficiently in large-scale reactions with the yields and enantioselectivities being maintained at the same level. (C) 2011 Elsevier Ltd. All rights reserved.