3-(furan-2-yl)-2-methyl-4-nitrobutanal | 1214939-13-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 3-(furan-2-yl)-2-methyl-4-nitrobutanal
• 英文别名: (2S,3S)-3-(furan-2-yl)-2-methyl-4-nitrobutanal
• CAS: 1214939-13-5
• 化学式: C₉H₁₁NO₄
• 分子量: 197.191
• InChiKey: YOSNSWPGMRDLKO-HTQZYQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  76
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(2-糠酰)-2-硝基乙烯 、 丙醛 在 (R,S)-α,α-diphenyl-2-pyrrolidinemethanol tert-butyldimethylsilyl ether 作用下， 以 二氯甲烷 为溶剂， 生成 3-(furan-2-yl)-2-methyl-4-nitrobutanal
  参考文献：
  名称：

  聚苯乙烯支持的二芳基脯氨醇醚是迈克尔型反应的高效有机催化剂

  摘要：

  锚固在聚苯乙烯树脂上的α，α-二苯基脯氨醇甲基和三甲基甲硅烷基醚是通过铜催化的叠氮化物-炔烃环加成反应（CuAAC）制备的。O显示的催化活性和对映选择性三甲基甲硅烷基衍生物与最著名的均相催化剂表现出的可比性相当，后者可将醛加成到硝基烯烃中，将丙二酸酯或硝基甲烷加成到α，β-不饱和醛上。当有机催化的反应通过烯胺机制进行时，催化单元，三唑连接基和聚合物基体的组合可提供前所未有的底物选择性，有利于线性短链醛。通过亚胺离子中间体进行的反应具有很高的通用性。还通过不对称迈克尔加成反应评估了聚苯乙烯负载的α，α-二苯基脯氨醇甲醚的催化行为。通常，将二芳基脯氨醇醚固定在不溶性聚苯乙烯树脂上的CuAAC具有重要的操作优势，例如高催化活性，

  DOI：

  10.1002/chem.201101730

文献信息

• NOVEL TRICYCLIC CHIRAL COMPOUNDS AND THEIR USE IN ASYMMETRIC CATALYSIS
  申请人：Loh Teck Peng

  公开号：US20110269972A1

  公开（公告）日：2011-11-03

  The present invention relates to a compound of general Formula (XX), its formation and its use in asymmetric catalysis. In Formula (XX) R and R 31 are independently —COOR 3 , —R 4 COOR 3 , —R 4 CHO, —R 4 COR 3 , —R 4 CONR 5 R 6 , —R 4 COX, —R 4 OP(═O)(OH) 2 , —R 4 P(═O)(OH) 2 ), —R 4 C(O)C(R 3 )CR 5 R 6 and —R 4 CO 2 COR 3 . In addition, R 31 may also be hydrogen. R 3 , R 5 and R 6 are independently hydrogen, an aliphatic group with a main chain having 1 to about 20 carbon atoms, an alicyclic group, an aromatic group, an arylaliphatic group or an arylalicyclic group, comprising 0 to about 3 heteroatoms independently selected from the group consisting of N, O, S, Se and Si. R 4 an aliphatic bridge with a main chain having 1 to about 20 carbon atoms, an alicyclic bridge, an aromatic bridge, an arylaliphatic bridge or an arylalicyclic bridge, comprising 0 to about 3 heteroatoms independently selected from the group consisting of N, O, S, Se and Si, and X is halogen. In Formula (XX) R 30 is —C(OH)R 1 R 2 or —COOR 14 , wherein R 1 , R 2 and R 14 are independently hydrogen, an aliphatic group with a main chain having 1 to about 20 carbon atoms, an alicyclic group, an aromatic group, an arylaliphatic group or an arylalicyclic group, comprising 0 to about 3 heteroatoms independently selected from the group consisting of N, O, S, Se and Si.

  本发明涉及一种一般式（XX）的化合物，其形成以及在不对称催化中的应用。在式（XX）中，R和R31独立地为—COOR3，—R4COOR3，—R4CHO，—R4COR3，—R4CONR5R6，—R4COX，—R4OP(═O)(OH)2，—R4P(═O)(OH)2，—R4C(O)C(R3)CR5R6和—R4CO2COR3。此外，R31也可以是氢。R3、R5和R6独立地为氢，具有主链含有1至约20个碳原子的脂肪基团，脂环基团，芳香基团，芳基脂基团或芳基脂环基团，包括0至约3个从N、O、S、Se和Si组成的杂原子。R4为具有主链含有1至约20个碳原子的脂肪桥，脂环桥，芳香桥，芳基脂桥或芳基脂环桥，包括0至约3个从N、O、S、Se和Si组成的杂原子，X为卤素。在式（XX）中，R30为—C(OH)R1R2或—COOR14，其中R1、R2和R14独立地为氢，具有主链含有1至约20个碳原子的脂肪基团，脂环基团，芳香基团，芳基脂基团或芳基脂环基团，包括0至约3个从N、O、S、Se和Si组成的杂原子。
• Superparamagnetic Nanoparticle-Supported (S)-Diphenyl- prolinol Trimethylsilyl Ether as a Recyclable Catalyst for Asymmetric Michael Addition in Water
  作者：Bang Gen Wang、Bao Chun Ma、Qiong Wang、Wei Wang

  DOI：10.1002/adsc.201000508

  日期：2010.11.22

  A new superparamagnetic nanoparticle-supported (S)-diphenylprolinol trimethylsilyl ether (Jørgensen–Hayashi catalyst) was synthesized and applied for the asymmetric Michael addition of aldehydes to nitroalkenes in water, which gives products in moderate to good yields (up to 96%), good enantioselectivity (up to 90% ee) and diastereoselectivities (up to 99:1). The immobilized catalyst could be easily

  合成了一种新的超顺磁性纳米粒子负载的（S）-二苯基脯氨醇三甲基甲硅烷基醚（Jrrgensen–Hayashi催化剂），并将其用于醛在水中硝基苯的不对称迈克尔加成反应，从而使产品收率适中至良好（最高96％），良好的对映选择性（高达90％ee）和非对映选择性（高达99：1）。固定的催化剂可以容易地通过外部磁体与反应分离，并循环四次而不会显着降低催化效率。
• Enantioselective Michael Addition of Aldehydes to β-Nitrostyrenes Catalyzed by (S)-<i>N</i> -(D-Prolyl)-1-triflicamido-3-phenylpropan-2-amine
  作者：Amol B. Gorde、Ramesh Ramapanicker

  DOI：10.1002/ejoc.201900719

  日期：2019.8.7

  A D‐prolinamide containing a triflicamide group as the H‐bond donor was developed to catalyze the asymmetric Michael addition of β‐nitroalkenes with aldehydes. Very high enantioselectivity and yields are achieved using 10 mol% of the catalyst at r.t. in toluene.

  含有三氟甲酰胺基团作为氢键供体的AD-脯氨酰胺被开发用于催化β-硝基烯烃与醛的不对称迈克尔加成反应。在室温下使用10mol％的催化剂在甲苯中获得非常高的对映选择性和产率。
• Asymmetric Michael reaction of aldehydes with β-nitroalkenes catalyzed by pyrrolidine-camphor derived organocatalysts bearing hydrogen-bond donors
  作者：Jiang Weng、Hui-Bing Ai、Ren-Shi Luo、Gui Lu

  DOI：10.1002/chir.21991

  日期：2012.4

  derived organocatalysts were designed and synthesized. These organocatalysts were used for direct Michael reaction of aldehydes with nitroalkenes to give the desired γ‐nitrocarbonyl compounds in high yields (up to 99%), high diastereoselectivities (syn:anti up to 92:8), and good to excellent enantioselectivities (up to 94% ee). Possible transition‐state model was also proposed for this asymmetric transformation

  设计并合成了几种吡咯烷-樟脑衍生的有机催化剂。这些有机催化剂用于醛与硝基烯烃的直接迈克尔反应，以高收率（高达99％），高非对映选择性（合成：抗高达92：8）和良好至优异的对映选择性（高达90 ％）提供所需的γ-硝基羰基化合物。到94％ee）。还为这种不对称转化提出了可能的过渡态模型，该模型可能涉及原位形成的亲核烯胺和硝基烯烃之间的氢键相互作用。手性，2012年。©2012 Wiley Periodicals，Inc.。
• <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。