3-(4-methoxyphenyl)-2,2-dimethyl-4-nitrobutanal | 1101901-05-6

• 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: 3-(4-methoxyphenyl)-2,2-dimethyl-4-nitrobutanal
• 英文别名: 3-(4-Methoxyphenyl)-2,2-dimethyl-4-nitrobutanal
• CAS: 1101901-05-6
• 化学式: C₁₃H₁₇NO₄
• 分子量: 251.282
• InChiKey: VKNZSJFUEBOTFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-甲氧基-β-硝基苯乙烯 、 异丁醛 在 4-二甲氨基吡啶 、 磺酰胺 、 聚甘氨酸 作用下， 以 甲苯 为溶剂， 反应 0.03h， 生成 3-(4-methoxyphenyl)-2,2-dimethyl-4-nitrobutanal
  参考文献：
  名称：

  Practical access to highly enantioenriched quaternary carbon Michael adducts using simple organocatalysts

  摘要：

  一种由氨基酸（OtBu-L-苏氨酸）、氢键供体（硫酰胺）和胺碱（DMAP）组成的三组分催化剂体系可使α-支链醛加成到硝基烯烃，产率高且ee值优异。重要的是，该催化剂的负载量（5.0 摩尔%）和醛的化学计量（1.2-2.0 等量）均达到了报告中的最低水平，而且在大多数情况下都能观察到最佳的当前产物曲线。

  DOI：

  10.1039/c0ob00822b

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。
• Primary amino acid lithium salt as a catalyst for asymmetric Michael addition of isobutyraldehyde with β-nitroalkenes
  作者：Atsushi Sato、Masanori Yoshida、Shoji Hara

  DOI：10.1039/b814804j

  日期：——

  Phenylalanine lithium salt was found to be an effective catalyst for asymmetric Michael addition of isobutyraldehyde with beta-nitroalkenes to give quaternary carbon-containing nitroalkanes.

  发现苯丙氨酸锂盐是异丁醛与β-硝基烯烃不对称迈克尔加成以生成含季碳的硝基链烷的有效催化剂。
• Highly enantioselective conjugate addition of aldehydes to nitroolefins catalyzed by chiral bifunctional sulfamides
  作者：Xue-jing Zhang、Sheng-ping Liu、Xue-ming Li、Ming Yan、Albert S. C. Chan

  DOI：10.1039/b818582d

  日期：——

  Chiral bifunctional sulfamides were found to be highly efficient organocatalysts for the conjugate addition of aldehydes to nitroolefins in the presence of base additives.

  手性双功能磺酰胺被发现是醛与亚硝烯在碱性添加剂存在下进行 conjugate 加成反应的高效有机催化剂。
• Chiral picolylamines for Michael and aldol reactions: probing substrate boundaries
  作者：Thomas C. Nugent、Ahtaram Bibi、Abdul Sadiq、Mohammad Shoaib、M. Naveed Umar、Foad N. Tehrani

  DOI：10.1039/c2ob26382c

  日期：——

  organocatalyst template, a vicinal chiral diamine based on a pyridine-primary amine motif. The addition of cyclohexanone to β-nitrostyrene has many catalyst solutions, but cyclopentanone and isobutyraldehyde additions continue to be challenging. PicAm-3 (10 mol%) readily allows the Michael addition of cyclopentanone or isobutyraldehyde (5.0 equiv.) to β-nitrostyrene derivatives. By contrast, PicAm-1 (7.0 mol%)

  在这里，我们报告了有关通过吡啶甲基胺有机催化剂模板（基于吡啶-伯胺基序的邻位手性二胺）增加底物宽度的研究。的加法环己酮 到 β-硝基苯乙烯 有很多催化剂溶液，但是 环戊酮异丁醛的添加仍然具有挑战性。PicAm- 3（10 mol％）允许迈克尔添加环戊酮 或者 异丁醛（5.0当量）β-硝基苯乙烯衍生物。相比之下，PicAm- 1（7.0 mol％）最适合催化Aldol反应环己酮 或者 环庚酮（3.3当量）与芳族醛。报告了18种产品，每种反应类型都报告了新产品（4b–d，9c）。通常注意到非常好的产率和立体选择性。需要酸添加剂的反应通过瞬时手性烯胺进行，并提出了双功能催化模型的机理实例。
• 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。