(R)-3-(4-chlorophenyl)-2,2-dimethyl-4-nitrobutanal | 1134192-78-1

• 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: (R)-3-(4-chlorophenyl)-2,2-dimethyl-4-nitrobutanal
• 英文别名: (R)-2,2-dimethyl-4-nitro-3-(4-chlorophenyl)butanal；(3R)-3-(4-chlorophenyl)-2,2-dimethyl-4-nitrobutanal
• CAS: 1134192-78-1
• 化学式: C₁₂H₁₄ClNO₃
• 分子量: 255.701
• InChiKey: VGCIWHFYGKEJIG-LLVKDONJSA-N

物化性质

• 沸点：
  365.6±37.0 °C(Predicted)
• 密度：
  1.211±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 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-(4-氯苯基)-2-硝基乙烯 、 异丁醛 在 (S)-N,N-dimethyl-1,1-diphenyl-1-(pyrrolidin-2-yl)methanamine 、 苯甲酸 作用下， 以 异丙醇 为溶剂， 反应 24.0h， 以95%的产率得到(R)-3-(4-chlorophenyl)-2,2-dimethyl-4-nitrobutanal
  参考文献：
  名称：

  使用α,α-二苯基-(S)-脯氨醇衍生的手性二胺催化剂异丁醛与硝基烯烃的不对称迈克尔加成

  摘要：

  通过使用α,α-二苯基-(S)-脯氨醇衍生的手性二胺催化剂1b，实现了异丁醛对硝基烯烃类似物的对映选择性迈克尔加成。在该协议中，催化剂...

  DOI：

  10.1246/bcsj.20200078

文献信息

• One-Pot Asymmetric Synthesis of γ-Nitroaldehydes from Aldehydes and Nitroalkanes through a Catalytic Tandem Reaction Using an Amino Acid Lithium Salt
  作者：Masanori Yoshida、Naoki Kitamikado、Hiroto Ikehara、Shoji Hara

  DOI：10.1021/jo102570p

  日期：2011.4.1

  One-pot asymmetric synthesis of γ-nitroaldehydes from aldehydes and nitroalkanes was achieved by a catalytic tandem reaction using a primary amino acid lithium salt, O-tert-butyldiphenylsilyl l-tyrosine lithium salt, as a catalyst. Various aryl, alkenyl, and alkyl aldehydes were converted into γ-nitroaldehydes via in situ generation of nitroalkenes.

  从醛和硝基烷烃γ-nitroaldehydes的一锅不对称合成，通过使用一级氨基酸锂盐，催化串联反应实现ø -叔-butyldiphenylsilyl升-酪氨酸锂盐，作为催化剂。各种芳基，烯基和烷基醛通过原位生成硝基烯烃转化为γ-硝基醛。
• ORGANOCATALYST
  申请人：Chen Kwunmin

  公开号：US20110040104A1

  公开（公告）日：2011-02-17

  The present invention provides an organocatalyst of formula (I), wherein R 1 is —H, —OH, —O—Si(R 4 )(R 5 )(R 6 ) or C 1-6 alkoxy, in which R 4 , R 5 and R 6 are identical or different and independently selected from the group consisting of C 1-6 alkyl, phenyl and phenyl substituted with C 1-6 alkyl; R 2 is —OH or ═O; X 1 is one selected from the group consisting of —NH—, —S— and X 2 is one selected from the group consisting of —C(═O)—, —CH 2 — and and X 1 is different from X 2 . The high yield and enantioselectivity of an addition reaction are obtained by using the organocatalyst of the present invention.

  本发明提供了一种式(I)的有机催化剂，其中R1为—H，—OH，—O—Si(R4)(R5)(R6)或C1-6烷氧基，其中R4、R5和R6相同或不同，并且独立地选自由C1-6烷基、苯基和苯基上取代的C1-6烷基的群；R2为—OH或═O；X1为从—NH—、—S—中选择的一种；X2为从—C(═O)—、—CH2—中选择的一种；X1与X2不同。通过使用本发明的有机催化剂，可以获得加成反应的高产率和对映选择性。
• Asymmetric Michael Addition Organocatalyzed by α,β-Dipeptides under Solvent-Free Reaction Conditions
  作者：C. Gabriela Avila-Ortiz、Lenin Díaz-Corona、Erika Jiménez-González、Eusebio Juaristi

  DOI：10.3390/molecules22081328

  日期：——

  α,β-dipeptides as chiral organocatalysts in the asymmetric Michael addition reaction between enolizable aldehydes and N-arylmaleimides or nitroolefins is described. With N-arylmaleimides as substrates, the best results were achieved with dipeptide 2 as a catalyst in the presence of aq. NaOH. Whereas dipeptides 4 and 6 in conjunction with 4-dimethylaminopyridine (DMAP) and thiourea as a hydrogen bond

  描述了六种新的α，β-二肽作为手性有机催化剂在可烯化醛与N-芳基马来酰亚胺或硝基烯烃之间的不对称迈克尔加成反应中的应用。以N-芳基马来酰亚胺为底物，在水溶液中存在二肽2作为催化剂可获得最佳结果。氢氧化钠 而二肽4和6与4-二甲基氨基吡啶（DMAP）和作为氢键供体的硫脲结合，被证明是异丁醛与各种硝基烯烃之间对映选择性反应中的高效有机催化体系。
• Highly enantioselective Michael addition of α,α-disubstituted aldehydes to nitroolefins
  作者：Xing-Tao Guo、Feng Sha、Xin-Yan Wu

  DOI：10.1007/s11164-016-2468-0

  日期：2016.7

  A highly enantioselective Michael addition reaction of α,α-disubstituted aldehydes to β-nitrostyrenes has been developed. In the presence of rosin-based chiral primary amine-thiourea, γ-nitroaldehydes were afforded in excellent enantioselectivities (up to 99 % ee) with up to 99 % yield.

  已经开发出α，α-二取代醛对β-硝基苯乙烯的高度对映选择性迈克尔加成反应。在基于松香的手性伯胺-硫脲的情况下，以极高的对映选择性（高达99％ee）提供了γ-硝基醛，产率高达99％。
• Highly enantioselective Michael addition of aldehydes to nitroolefins catalyzed by primary amine thiourea organocatalysts
  作者：Jia-Rong Chen、You-Quan Zou、Liang Fu、Fan Ren、Fen Tan、Wen-Jing Xiao

  DOI：10.1016/j.tet.2010.05.056

  日期：2010.7

  Asymmetric Michael addition reactions of aldehydes to nitroolefins have been successfully initiated by a series of primary amine thiourea bifunctional catalysts, with high enantioselectivities (90–98% ee) and excellent yields (80–96%). The privileged quinine scaffold was found to be essential to the reaction efficiency and enantioselectivity.

  一系列伯胺硫脲双功能催化剂具有高对映选择性（90-98％ee）和优异的收率（80-96％），已成功地引发了醛与硝基烯烃的迈克尔不对称迈克尔加成反应。发现特权的奎宁支架对于反应效率和对映选择性是必不可少的。