(2S,3R)-2-methyl-3-(naphthalen-1-yl)-4-nitrobutanal | 1214939-14-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2S,3R)-2-methyl-3-(naphthalen-1-yl)-4-nitrobutanal
• 英文别名: (2S,3R)-2-methyl-3-(1-naphthalenyl)-4-nitrobutanal；(2S,3R)-2-methyl-3-naphthalen-1-yl-4-nitrobutanal
• CAS: 1214939-14-6
• 化学式: C₁₅H₁₅NO₃
• 分子量: 257.289
• InChiKey: SNQAFNVYTMDHOS-IAQYHMDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 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-(2-硝基乙烯基)萘 、 丙醛 在 4-二甲氨基吡啶 、 8-ethoxycarbonyl (2S,3aR,8aS)-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-2-carboxylic acid 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 (2S,3R)-2-methyl-3-(naphthalen-1-yl)-4-nitrobutanal 、 2-methyl-3-(naphthalen-1-yl)-4-nitrobutanal
  参考文献：
  名称：

  化学酶：受天然产物启发的一类新型结构刚性三环两栖有机催化剂

  摘要：

  基于六氢吡咯并[2,3- b ]吲哚骨架作为新型的化学酶，合理设计了新型结构刚性的三环两性手性催化剂。这种新型的化学酶具有结构刚性的三环骨架和手性囊，为不对称诱导提供了组织良好的手性环境，以及疏水性囊，使有机催化反应在有机溶剂和水中均能顺利进行。

  DOI：

  10.1021/ol9029758

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。
• 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.。
• Highly Efficient and Modularly Tuned Bicyclic Organocatalyst for the Enantioselective Michael Addition of Aldehydes to Nitroalkenes
  作者：Teck-Peng Loh、Jian Xiao、Feng-Xia Xu、Yun-Peng Lu、Yan-Ling Liu

  DOI：10.1055/s-0030-1260527

  日期：2011.6

  type of bicyclic organocatalyst has been successfully applied to the asymmetric Michael addition of aldehydes to nitrostyrenes in good yields and good enantioselectivities by using a self-assembly strategy. The success of this reaction is attributed to good control of the geometry of the enamine and efficient face shielding. organocatalyst - bicyclic - enamine control - Michael addition

  一种新型的双环有机催化剂已成功地通过自组装策略成功地将醛不对称迈克尔加成至硝基苯乙烯，并具有良好的收率和良好的对映选择性。该反应的成功归因于对烯胺的几何形状的良好控制和有效的面部防护。 有机催化剂-双环-烯胺控制-迈克尔加成
• Tricyclic chiral compounds and their use in asymmetric catalysis
  申请人：Loh Teck Peng

  公开号：US09206090B2

  公开（公告）日：2015-12-08

  The present invention relates to a compound of general Formula (XX), its formation and its use in asymmetric catalysis. In Formula (XX) R and R31 are independently —COOR3, —R4COOR3, —R4CHO, —R4COR3, —R4CONR5R6, —R4COX, —R4OP(═O)(OH)2, —R4P(═O)(OH)2), —R4C(O)C(R3)CR5R6 and —R4CO2COR3. In addition, R31 may also be hydrogen. R3, R5 and R6 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. R4 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) R30 is —C(OH)R1R2 or —COOR14, wherein R1, R2 and R14 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.

  本发明涉及一种通式为（XX）的化合物，其形成和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1到约20个碳原子的主链的脂肪族基团、螺环烷基团、芳香基团、芳基脂肪族基团或芳基螺环基团，包括0到约3个独立选择自N、O、S、Se和Si的杂原子。R4为具有1到约20个碳原子的主链的脂肪族桥、螺环桥、芳香桥、芳基脂肪族桥或芳基螺环桥，包括0到约3个独立选择自N、O、S、Se和Si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1到约20个碳原子的主链的脂肪族基团、螺环烷基团、芳香基团、芳基脂肪族基团或芳基螺环基团，包括0到约3个独立选择自N、O、S、Se和Si的杂原子。