(R)-3-(2-bromophenyl)-2,2-dimethyl-4-nitrobutanal | 1198362-10-5

• 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-bromophenyl)-2,2-dimethyl-4-nitrobutanal
• 英文别名: (S)-2,2-dimethyl-4-nitro-3-(2-bromophenyl)butanal；(3S)-3-(2-bromophenyl)-2,2-dimethyl-4-nitrobutanal
• CAS: 1198362-10-5
• 化学式: C₁₂H₁₄BrNO₃
• 分子量: 300.152
• InChiKey: IWFHGLRCCCKBST-SNVBAGLBSA-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-溴-2-(2-硝基乙烯基)苯 、 异丁醛 在 1-[(1R,2R)-2-aminocyclohexyl]-3-[3-[[27-[3-[[(1R,2R)-2-aminocyclohexyl]carbamothioylamino]propoxy]-5,11,17,23-tetratert-butyl-26,28-dihydroxy-25-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaenyl]oxy]propyl]thiourea 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以82%的产率得到(R)-3-(2-bromophenyl)-2,2-dimethyl-4-nitrobutanal
  参考文献：
  名称：

  基于杯芳烃的高效伯胺-硫脲有机催化剂用于醛与硝基苯乙烯的不对称迈克尔加成

  摘要：

  首次描述了从对叔丁基杯[4]芳烃合成基于杯[4]芳烃的手性双功能伯胺-硫脲催化剂。杯[4]芳烃基催化剂被成功应用于促进醛与硝基烯烃的迈克尔加成，优先提供（R）-或（S）-加合物的高产率（高达95%）和优异的对映选择性（高达99%） es）。

  DOI：

  10.1080/10610278.2013.773331

文献信息

• Asymmetric Michael Addition Organocatalyzed by α,β-Dipeptides under Solvent-Free Reaction Conditions
  作者：C. Gabriela Avila-Ortiz、Lenin Díaz-Corona、Erika Jiménez-González、Eusebio Juaristi

  DOI：10.3390/molecules22081328

  日期：——

  α,β-dipeptides as chiral organocatalysts in the asymmetric Michael addition reaction between enolizable aldehydes and N-arylmaleimides or nitroolefins is described. With N-arylmaleimides as substrates, the best results were achieved with dipeptide 2 as a catalyst in the presence of aq. NaOH. Whereas dipeptides 4 and 6 in conjunction with 4-dimethylaminopyridine (DMAP) and thiourea as a hydrogen bond

  描述了六种新的α，β-二肽作为手性有机催化剂在可烯化醛与N-芳基马来酰亚胺或硝基烯烃之间的不对称迈克尔加成反应中的应用。以N-芳基马来酰亚胺为底物，在水溶液中存在二肽2作为催化剂可获得最佳结果。氢氧化钠 而二肽4和6与4-二甲基氨基吡啶（DMAP）和作为氢键供体的硫脲结合，被证明是异丁醛与各种硝基烯烃之间对映选择性反应中的高效有机催化体系。
• Asymmetric Michael Addition of Isobutyraldehyde to Nitroolefins Using an <i>α</i>,<i>α</i>-Diphenyl-(<i>S</i>)-prolinol-Derived Chiral Diamine Catalyst
  作者：Wei Han、Takeshi Oriyama

  DOI：10.1246/bcsj.20200078

  日期：2020.8.15

  The enantioselective Michael addition of isobutyraldehyde to nitroolefin analogs was achieved by utilizing an α,α-diphenyl-(S)-prolinol-derived chiral diamine catalyst 1b. In this protocol, catalys...

  通过使用α,α-二苯基-(S)-脯氨醇衍生的手性二胺催化剂1b，实现了异丁醛对硝基烯烃类似物的对映选择性迈克尔加成。在该协议中，催化剂...
• Design, synthesis and application of chiral tetraoxacalix[2]arene[2]triazine‐based organocatalysts in asymmetric Michael addition reactions
  作者：Hayriye Nevin Genc、Ummu Ozgun、Abdulkadir Sirit

  DOI：10.1002/chir.23055

  日期：2019.4

  A novel type of oxacalix[2]arene[2]triazine‐based organocatalysts for asymmetric Michael reactions are reported for the first time. Chiral subunits were attached to the heteroatom‐bridged calixaromatic platform by a reaction of (R)‐ and (S)‐1‐aminotetraline with tetraoxacalix[2]arene[2]triazine in both enantiomeric forms. To evaluate the catalytic efficiency of the novel organocatalysts, isobutyraldehyde

  首次报道了用于不对称迈克尔反应的新型草酸二恶唑[2]芳烃[2]三嗪基有机催化剂。手性亚基通过（R）和（S）-1-氨基四环与两种对映体形式的四氧杂acalix [2]芳烃[2]三嗪的反应连接到杂原子桥联的杯芳烃平台上。为了评估新型有机催化剂的催化效率，异丁醛与各种取代的和未取代的芳族反式-β-硝基苯乙烯在四氢呋喃（THF）中反应，导致迈克尔加合物的收率和对映体选择性高（产率高达97％，ee高达99％）。
• Pyrrolidinyl-Camphor Derivatives as a New Class of Organocatalyst for Direct Asymmetric Michael Addition of Aldehydes and Ketones to β-Nitroalkenes
  作者：Ying-Fang Ting、Chihliang Chang、Raju Jannapu Reddy、Dhananjay R. Magar、Kwunmin Chen

  DOI：10.1002/chem.201000483

  日期：——

  Practical and convenient synthetic routes have been developed for the synthesis of a new class of pyrrolidinyl–camphor derivatives (7 a–h). These novel compounds were screened as catalysts for the direct Michael addition of symmetrical α,α‐disubstituted aldehydes to β‐nitroalkenes. When this asymmetric transformation was catalyzed by organocatalyst 7 f, the desired Michael adducts were obtained in

  已经开发了实用且方便的合成路线来合成新型的吡咯烷基-樟脑衍生物（7 a–h）。筛选出这些新型化合物作为催化剂，将对称的α，α-二取代醛直接迈克尔加成至β-硝基烯烃。当该非对称转变是由有机催化剂催化的7 F，在高的化学产率得到所需的迈克尔加合物，具有高至优良的立体选择性（高达98：2非对映比（DR）和99％对映体过量（EE））。催化体系的范围已扩大到涵盖各种醛和酮作为供体来源。合成的应用由（S）-香茅醛，具有高立体选择性。
• 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.