(R)-2-[(S)-1-(4-chlorophenyl)-2-nitroethyl]pentanal | 1271248-69-1

• 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)-2-[(S)-1-(4-chlorophenyl)-2-nitroethyl]pentanal
• 英文别名: (2R)-2-[(1S)-1-(4-chlorophenyl)-2-nitroethyl]pentanal
• CAS: 1271248-69-1
• 化学式: C₁₃H₁₆ClNO₃
• 分子量: 269.728
• InChiKey: XADJYMNPTQSOMT-WCQYABFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  正戊醛 、 1-nitro-2-(4-chlorophenyl)ethylene 在 (2S,4R)-4-(tert-butyldimethylsilanyloxy)-2-[(S)-methyl-(1-phenylethyl)carbamoyl]pyrrolidine-1-carboxylic acid tert-butyl ester 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以98%的产率得到(R)-2-[(S)-1-(4-chlorophenyl)-2-nitroethyl]pentanal
  参考文献：
  名称：

  醛与硝基烯烃不对称迈克尔加成反应中简单的4-羟基脯氨酰胺有机催化剂的结构反应性研究

  摘要：

  合成了一系列简单的4-羟基脯氨酰胺，发现它们可以作为有机催化剂，以极高的收率（98％），全非对映选择性（99：1，syn：anti）和对映选择性（98）将醛不对称共轭加成至硝基烯烃。％ee，代表syn）。此外，实现了低催化剂负载量（5mol％）和低醛摩尔过量（1.5当量）的使用。

  DOI：

  10.1002/adsc.201100028

文献信息

• Michael addition of carbonyl compounds to nitroolefins under the catalysis of new pyrrolidine-based bifunctional organocatalysts
  作者：A. Castán、R. Badorrey、J. A. Gálvez、P. López-Ram-de-Víu、M. D. Díaz-de-Villegas

  DOI：10.1039/c7ob02798b

  日期：——

  the asymmetric Michael addition of carbonyl compounds to nitroolefins have been synthesised from homoallylamines, which are easily obtained from (R)-glyceraldehyde as a chiral precursor. Under optimal reaction conditions, these bifunctional organocatalysts showed a high catalytic efficiency (almost quantitative yield in most cases) and stereoselectivity in the Michael addition reactions of a variety

  已经从高烯丙基胺合成了用于羰基化合物不对称迈克尔加成到硝基烯烃的新型双官能吡咯烷基有机催化剂，其很容易从作为手性前体的（R）-甘油醛获得。在最佳反应条件下，这些双功能有机催化剂在多种醛（高达98：2 dr和97％ee）和酮（高达5％）的迈克尔加成反应中显示出高催化效率（在大多数情况下几乎是定量产率）和立体选择性。 98：2 dr和99％ee）转化为硝基烯烃。
• Diphenylprolinol silyl ether-derived thioureas as highly efficient catalysts for the asymmetric Michael addition of aldehydes to nitroalkenes
  作者：Chunyan He、Xiaochen Ren、Yingle Feng、Yonghai Chai、Shengyong Zhang、Weiping Chen

  DOI：10.1016/j.tetlet.2015.04.119

  日期：2015.6

  This Letter described the synthesis of the first diarylprolinol silyl ether-derived bifunctional thiourea organocatalysts. The catalysts were applied to the asymmetric Michael addition of aldehydes to nitroalkenes to give the desired adducts in good yields (up to 99%) with excellent enantioselectivities (up to 99% ee) and excellent diastereoselectivities (up to 99:1). The spatial placement of C-4 substituent

  这封信描述了第一种由二芳基脯氨醇甲硅烷基醚衍生的双官能硫脲有机催化剂的合成。将催化剂应用于醛与硝基烯烃的不对称迈克尔加成反应，以良好的收率（高达99％ee）和出色的非对映选择性（高达99：1）以良好的收率（高达99％）得到所需的加合物。C-4取代基的空间位置对反应活性和立体选择性很重要。
• Synthesis of new pyrrolidine-based organocatalysts and study of their use in the asymmetric Michael addition of aldehydes to nitroolefins
  作者：Alejandro Castán、Ramón Badorrey、José A Gálvez、María D Díaz-de-Villegas

  DOI：10.3762/bjoc.13.59

  日期：——

  pyrrolidine-based organocatalysts with a bulky substituent at C2 were synthesized from chiral imines derived from (R)-glyceraldehyde acetonide by diastereoselective allylation followed by a sequential hydrozirconation/iodination reaction. The new compounds were found to be effective organocatalysts for the Michael addition of aldehydes to nitroolefins and enantioselectivities up to 85% ee were achieved

  通过衍生自非对映选择性烯丙基化，随后进行顺序的加氢锆化/碘化反应，由（R）-甘油醛丙酮化物衍生的手性亚胺合成了在C2具有较大取代基的新型吡咯烷基有机催化剂。发现新化合物是醛向硝基烯烃的迈克尔加成反应的有效有机催化剂，对映选择性高达85％ee。
• Structure–reactivity relationships of l-proline derived spirolactams and α-methyl prolinamide organocatalysts in the asymmetric Michael addition reaction of aldehydes to nitroolefins
  作者：Fintan Kelleher、Sinead Kelly、John Watts、Vickie McKee

  DOI：10.1016/j.tet.2010.03.002

  日期：2010.5

  l-Proline derived spirolactams and α-methyl prolinamides act as organocatalysts for the asymmetric conjugate addition of aldehydes to nitroolefins in excellent yields, with good diastereoselectivity and enantioselectivity. Furthermore, low catalyst loadings (5 mol %) and a low aldehyde molar excess (1.5 M equiv) were achieved.

  1-脯氨酸衍生的螺内酰胺和α-甲基脯氨酰胺可作为有机催化剂，以优异的收率，良好的非对映选择性和对映选择性将醛不对称共轭加成至硝基烯烃。此外，获得了低的催化剂负载量（5mol％）和低的醛摩尔过量（1.5M当量）。
• Self-assembled proline-amino thioureas as efficient organocatalysts for the asymmetric Michael addition of aldehydes to nitroolefins
  作者：Wan-Hui Wang、Takeshi Abe、Xiang-Bo Wang、Koichi Kodama、Takuji Hirose、Guang-You Zhang

  DOI：10.1016/j.tetasy.2010.11.025

  日期：2010.12

  A small co-catalyst library of amino thioureas has been established from chiral 1,3-diamines. These bifunctional thioureas can form assemblies with proline to cooperatively catalyze the asymmetric Michael addition of aldehydes to nitroolefins. Both the reaction rate (up to 98% yield for 18 h) and the enantioselectivity (up to 94% ee) were significantly improved upon in less polar solvents. (C) 2010 Elsevier Ltd. All rights reserved.