(R)-3-(2-chlorophenyl)-2,2-dimethyl-4-nitrobutanal

• 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-chlorophenyl)-2,2-dimethyl-4-nitrobutanal
• 英文别名: (3R)-3-(2-chlorophenyl)-2,2-dimethyl-4-nitrobutanal
• 化学式: C₁₂H₁₄ClNO₃
• 分子量: 255.701
• InChiKey: UENAIURQSOHLFG-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-chloro-2-(2-nitrovinyl)benzene 、 异丁醛 在 N-(3-((S)-1-(D-prolyl)pyrrolidin-2-yl)propyl)-1,1,1-trifluoromethanesulfonamide 作用下， 以 甲苯 为溶剂， 反应 72.0h， 以80%的产率得到(R)-3-(2-chlorophenyl)-2,2-dimethyl-4-nitrobutanal
  参考文献：
  名称：

  d-Prolyl-2-（三氟甲基磺酰胺基丙基）吡咯烷：常温条件下醛向β-硝基烯烃的不对称迈克尔加成反应的有机催化剂

  摘要：

  制备了四个2-（三氟甲基磺酰胺基烷基）吡咯烷及其d-脯氨酰胺，并筛选出在室温下且不使用添加剂的情况下，醛与β-硝基烯烃的迈克尔加成反应的有机催化剂。发现d -Prolyl-2-（三氟甲基磺酰胺基丙基）吡咯烷是所研究分子中最好的，它以非常高的产率（高达95％），高的非对映选择性（高达> 99：1）和高的非对映选择性产生γ-硝基醛。具有高达97％的ee。

  DOI：

  10.1021/acs.joc.8b02945

文献信息

• Highly enantioselective Michael addition of aldehydes to nitroolefins catalyzed by primary amine thiourea organocatalysts
  作者：Jia-Rong Chen、You-Quan Zou、Liang Fu、Fan Ren、Fen Tan、Wen-Jing Xiao

  DOI：10.1016/j.tet.2010.05.056

  日期：2010.7

  Asymmetric Michael addition reactions of aldehydes to nitroolefins have been successfully initiated by a series of primary amine thiourea bifunctional catalysts, with high enantioselectivities (90–98% ee) and excellent yields (80–96%). The privileged quinine scaffold was found to be essential to the reaction efficiency and enantioselectivity.

  一系列伯胺硫脲双功能催化剂具有高对映选择性（90-98％ee）和优异的收率（80-96％），已成功地引发了醛与硝基烯烃的迈克尔不对称迈克尔加成反应。发现特权的奎宁支架对于反应效率和对映选择性是必不可少的。
• Asymmetric Conjugate Addition of α,α-Disubstituted Aldehydes to Nitroalkenes Organocatalyzed by Chiral Monosalicylamides from trans-Cyclohexane-1,2-Diamines
  作者：José Martínez-Guillén、Jesús Flores-Ferrándiz、Cecilia Gómez、Enrique Gómez-Bengoa、Rafael Chinchilla

  DOI：10.3390/molecules23010141

  日期：——

  Primary amine-salicylamides derived from chiral trans-cyclohexane-1,2-diamines are used as organocatalysts for the enantioselective conjugate addition of α,α-disubstituted aldehydes to arylated and heteroarylated nitroalkenes. The reaction is performed in the presence of 4-dimethylaminopyridine as an additive in dichloromethane as a solvent at room temperature. The corresponding enantioenriched γ-nitroaldehydes

  衍生自手性反式-环己烷-1,2-二胺的伯胺-水杨酰胺用作有机催化剂，用于将 α,α-二取代醛对映选择性共轭加成到芳基化和杂芳基化硝基烯烃。该反应在作为添加剂的4-二甲氨基吡啶存在下在作为溶剂的二氯甲烷中在室温下进行。以高达 95% 的对映选择性获得相应的对映体富集的 γ-硝基醛。理论计算用于证明立体感应的原因。
• 一种高效负载催化剂不对称催化Michael加成的 方法
  申请人：台州学院

  公开号：CN104610003B

  公开（公告）日：2016-07-06

  本发明涉及一种高效、环境友好的手性负载催化剂，以水做溶剂室温反应条件下实现异丁醛与硝基烯烃不对称Michael加成方法。所述方法包括以超顺磁纳米颗粒负载、“离子气氛”修饰的手性小分子为催化剂，N,N-二甲基吡啶(DMAP)为促进剂、25℃、常压下异丁醛与硝基烯烃进行立体选择性Michael加成反应，负载催化剂重复使用5次，未发现反应收率和ee值明显下降。该法操作简单、催化剂立体选择性好、回收简单、催化反应体系可重复使用性好、反应条件温和，易于实现规模化生产。
• In search of diamine analogs of the α,α-diphenyl prolinol privileged chiral organocatalyst. Synthesis of diamine derivatives of α,α-diphenyl-(S)-prolinol and their application as organocatalysts in the asymmetric Michael and Mannich reactions
  作者：Gloria Reyes-Rangel、Jorge Vargas-Caporali、Eusebio Juaristi

  DOI：10.1016/j.tet.2015.11.032

  日期：2016.1

  This paper describes improved reaction conditions for the substitution of the hydroxyl group in (S)-diphenyl(pyrrolidin-2-yl)methanol by the azide group, which was then reduced to the diamine derivative. We examined two protecting groups (N-Bn and N-Boc) on the pyrrolidine nitrogen in order to functionalize the primary amino group into various amide, alkylated amine, sulfonamide, thiourea and triazole derivatives. Notably, carefully controlled conditions were required to generate the desired derivatives from the sterically hindered benzhydrylamine moiety. Unexpectedly, upon removal of the N-protecting group in derivatives containing electrophilic polar double bonds (C=S, C=O) cyclization took place, affording products such as amidines. The target compounds were evaluated as bifunctional organocatalysts in the asymmetric Michael and Mannich addition reactions. (S)-2-(Azidodiphenylmethyl) pyrrolidine (S)-7 was identified as the most efficient organocatalyst among the various diamine derivatives of alpha,alpha-diphenyl-(S)-prolinol prepared in this work. (C) 2015 Elsevier Ltd. All rights reserved.
• <scp>d</scp>-Prolyl-2-(trifluoromethylsulfonamidopropyl)pyrrolidine: An Organocatalyst for Asymmetric Michael Addition of Aldehydes to β-Nitroalkenes at Ambient Conditions
  作者：Amol B. Gorde、Ramesh Ramapanicker

  DOI：10.1021/acs.joc.8b02945

  日期：2019.2.1

  yrrolidines and their d-prolinamides were prepared and screened as organocatalysts for the Michael addition reaction of aldehydes with β-nitroalkenes at rt and without the use of additives. d-Prolyl-2-(trifluoromethylsulfonamidopropyl)pyrrolidine was found to be the best among the molecules studied, which yielded γ-nitro aldehydes in very high yields (up to 95%), with high diastereoselectivity (up

  制备了四个2-（三氟甲基磺酰胺基烷基）吡咯烷及其d-脯氨酰胺，并筛选出在室温下且不使用添加剂的情况下，醛与β-硝基烯烃的迈克尔加成反应的有机催化剂。发现d -Prolyl-2-（三氟甲基磺酰胺基丙基）吡咯烷是所研究分子中最好的，它以非常高的产率（高达95％），高的非对映选择性（高达> 99：1）和高的非对映选择性产生γ-硝基醛。具有高达97％的ee。