(2S,3R)-2-isopropyl-3-(naphthalen-1-yl)-4-nitrobutanal

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2S,3R)-2-isopropyl-3-(naphthalen-1-yl)-4-nitrobutanal
• 英文别名: 2-isopropyl-3-naphthalen-1-yl-4-nitro butyraldehyde；(2S,3R)-3-naphthalen-1-yl-4-nitro-2-propan-2-ylbutanal
• 化学式: C₁₇H₁₉NO₃
• 分子量: 285.343
• InChiKey: HXAJZAVMLHJVPA-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 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 、 异戊醛 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 72.0h， 以87%的产率得到(2S,3R)-2-isopropyl-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。
• 4,4′-Disubstituted-L-proline Catalyzes the Direct Asymmetric Michael Addition of Aldehydes to Nitrostyrenes
  作者：Liu-qun Gu、Gang Zhao

  DOI：10.1002/adsc.200600640

  日期：2007.7.2

  In a search for small organic molecules as catalysts for the direct asymmetric Michael addition reaction of aldehydes to nitrostyrenes, 4,4′-di(naphthalene-1-ylmethyl)-L-proline 1c and a catalytic amount of 4-dimethylaminopyridine (DMAP) were found to be an efficient system for the Michael addition of aldehydes to nitrostyrenes with high diastereo- and enantioselectivity and broad substrate range.

  在寻找小的有机分子作为醛与硝基苯乙烯，4,4'-二（萘-1-基甲基）-L-脯氨酸1c和催化量的4-二甲基氨基吡啶（DMAP）直接不对称迈克尔加成反应的催化剂被发现是一种高效的体系，可将醛类迈克尔加成到硝基苯乙烯中，具有高非对映选择性和对映选择性，并且底物范围广。
• 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。
• Betancort, Juan M.; Sakthivel, Kandasamy; Thayumanavan, Rajeswari, Synthesis, 2004, # 9, p. 1509 - 1521
  作者：Betancort, Juan M.、Sakthivel, Kandasamy、Thayumanavan, Rajeswari、Tanaka, Fujie、Barbas III, Carlos F.

  DOI：——

  日期：——
• Catalytic Direct Asymmetric Michael Reactions:  Taming Naked Aldehyde Donors
  作者：Juan M. Betancort、Carlos F. Barbas

  DOI：10.1021/ol0167006

  日期：2001.11.1

  [GRAPHICS]Direct catalytic enantio- and diastereoselective Michael addition reactions of unmodified aldehydes to nitro olefins using (S)-2-(morpholinomethyl)-pyrrolidine as a catalyst are described. The reactions proceed in good yield (up to 96%) in a highly syn-selective manner (up to 98:2) with enantloselectivities approaching 80%. The resulting gamma -formyl nitro compounds are readily converted to chiral, nonracemic 3,4-disubstituted pyrrolidines.