(S)-2,2-dimethyl-3-(naphthalen-2-yl)-4-nitrobutanal | 1214939-16-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-2,2-dimethyl-3-(naphthalen-2-yl)-4-nitrobutanal
• 英文别名: (S)-2,2-dimethyl-3-(naphthalene-2-yl)-4-nitrobutanal；2,2-dimethyl-3-(naphthalen-2-yl)-4-nitrobutanal；(3S)-2,2-dimethyl-3-naphthalen-2-yl-4-nitrobutanal
• CAS: 1214939-16-8
• 化学式: C₁₆H₁₇NO₃
• 分子量: 271.316
• InChiKey: IXHHRZVKHADYLF-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  2-[(E)-2-硝基乙烯基]萘 、 异丁醛 在 ethyl (1R,4S,5R,9S,10R,13S,14R)-14-[[2-[[(1S,2S)-2-aminocyclohexyl]amino]-3,4-dioxocyclobuten-1-yl]amino]-5,9,13-trimethyltetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate 作用下， 以 氯仿 为溶剂， 以81%的产率得到(S)-2,2-dimethyl-3-(naphthalen-2-yl)-4-nitrobutanal
  参考文献：
  名称：

  手性伯胺-方胺催化异丁醛向硝基烯烃的高对映选择性迈克尔加成反应

  摘要：

  摘要 迄今为止，手性伯胺-方酰胺在有机催化领域尚未得到广泛研究。本文开发了一种从天然产物甜菊糖苷衍生的新型手性方酸酰胺。通过使用这些方形酰胺催化剂将异丁醛与硝基烯烃进行迈克尔加成反应，可以生成一系列γ-硝基醛的两种对映异构体。该不对称反应进行得很好，以高产率（高达98％）和高至优异的对映选择性（高达99％ee）提供了所需的产物。 迄今为止，手性伯胺-方酰胺在有机催化领域尚未得到广泛研究。本文开发了一种从天然产物甜菊糖苷衍生的新型手性方酸酰胺。通过使用这些方形酰胺催化剂将异丁醛与硝基烯烃进行迈克尔加成反应，可以生成一系列γ-硝基醛的两种对映异构体。该不对称反应进行得很好，以高产率（高达98％）和高至优异的对映选择性（高达99％ee）提供了所需的产物。

  DOI：

  10.1055/s-0036-1588090

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。
• 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。
• Highly Enantioselective Michael Additions of Isobutyraldehyde to Nitroalkenes Promoted by Amphiphilic Bifunctional Primary Amine-Thioureas in Organic or Aqueous Medium
  作者：Zhi-Wei Ma、Yu-Xia Liu、Wen-Jing Zhang、Yan Tao、Yu Zhu、Jing-Chao Tao、Ming-Sheng Tang

  DOI：10.1002/ejoc.201101086

  日期：2011.11

  isobutyraldehyde and nitroalkenes. The chiral thiourea 1a furnished S enantiomers, whereas 1b afforded R enantiomers, both with high yields (up to 92 %) and high to excellent enantioselectivities (up to 98 %). Furthermore, the reactions proceeded smoothly both in organic solvents and in water under mild conditions.

  设计并合成了一类新的基于拜耳烷支架的手性两亲双功能硫脲，每个硫脲都含有伯氨基，从容易获得的天然产物异甜菊醇中合成。硫脲被证明可有效催化异丁醛和硝基烯烃之间的不对称迈克尔加成。手性硫脲 1a 提供 S 对映异构体，而 1b 提供 R 对映异构体，两者均具有高产率（高达 92 %）和高至极好的对映选择性（高达 98 %）。此外，反应在温和条件下在有机溶剂和水中均顺利进行。
• Enantioselective Michael addition of isobutyraldehyde to nitroalkenes organocatalyzed by chiral primary amine-guanidines
  作者：Angel Avila、Rafael Chinchilla、Béla Fiser、Enrique Gómez-Bengoa、Carmen Nájera

  DOI：10.1016/j.tetasy.2014.02.006

  日期：2014.3

  Primary amine-guanidines derived from trans-cyclohexane-1,2-diamines are used as organocatalysts for the enantioselective conjugate addition of isobutyraldehyde to arylated and heteroarylated nitroalkenes. The reaction was performed in the presence of imidazole as the additive in aqueous DMF as the solvent at 0 °C. The corresponding Michael adducts bearing a new stereocenter were obtained in high yields

  衍生自反式-环己烷-1，2-二胺的伯胺胍用作有机催化剂，用于将异丁醛对映选择性共轭加成到芳基化和杂芳基化的硝基烯烃上。该反应在咪唑作为添加剂存在下，在DMF水溶液中作为溶剂在0℃下进行。以高收率和高达80％的对映选择性获得了带有新的立体中心的相应的迈克尔加合物。理论计算用于证明所观察到的立体感。
• 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。