(2R)-2-((1S)-1-(3-methoxyphenyl)-2-nitroethyl)pentanal | 1203648-33-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2R)-2-((1S)-1-(3-methoxyphenyl)-2-nitroethyl)pentanal
• 英文别名: (R)-2-((S)-1-(3-methoxyphenyl)-2-nitroethyl)pentanal；(2R,3S)-2-propyl-4-nitro-3-(3-methoxyphenyl)butanal；(2R)-2-[(1S)-1-(3-methoxyphenyl)-2-nitroethyl]pentanal
• CAS: 1203648-33-2
• 化学式: C₁₄H₁₉NO₄
• 分子量: 265.309
• InChiKey: YYEQAOFJASBLIW-GXTWGEPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  正戊醛 、 1-methoxy-3-(2-nitro-vinyl)-benzene 在 N,N-dimethylbenzylamine prolinol trimethylsilyl ether 、 苯甲酸 作用下， 以 水 为溶剂， 反应 12.0h， 以96%的产率得到(2R)-2-((1S)-1-(3-methoxyphenyl)-2-nitroethyl)pentanal
  参考文献：
  名称：

  二芳基脯氨醇甲硅烷基醚盐作为新型、高效、水溶性和可回收的有机催化剂，用于在水中进行不对称迈克尔加成

  摘要：

  已经开发了一种用于醛与硝基烯烃在水中催化不对称迈克尔加成的新策略，并提供了具有优异非对映选择性和对映选择性的迈克尔加合物。这些有机催化剂的一个显着特点是它们可以循环使用六次以上，而不会显着降低催化活性和立体化学控制。此外，所提出的合成程序简单、实用且对环境无害。

  DOI：

  10.1021/ja9093583

文献信息

• A Novel Recyclable Organocatalytic System for the Highly Asymmetric Michael Addition of Aldehydes to Nitroolefins in Water
  作者：Allan Headley、Bukuo Ni、Dhruba Sarkar、Ramesh Bhattarai

  DOI：10.1055/s-0030-1260465

  日期：2011.6

  for the asymmetric Michael addition of aldehydes to nitroolefins with a catalytic system of organocatalyst 1 in combination with ionic-liquid-supported (ILS) benzoic acid in water has been developed. The Michael adducts of this system give excellent diastereo- and enantioselectivities. A notable feature of this organocatalytic system is that the catalyst can be recycled more than 12 times without significant

  已开发出一种新的策略，该策略是在有机催化剂1与离子液体负载的（ILS）苯甲酸组合的水中，将醛不对称地迈克尔加成到硝基烯烃中。该体系的迈克尔加合物具有出色的非对映选择性和对映选择性。该有机催化体系的显着特征是催化剂可以循环使用12次以上，而对映选择性没有明显损失。另外，提出的综合方法简单，实用且对环境无害。 醛-不对称催化-绿色化学-离子液体-迈克尔加成
• 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。
• Ionic Liquid-Supported (ILS) (S)-Pyrrolidine Sulfonamide for Asymmetric Michael Addition Reactions of Aldehydes with Nitroolefins
  作者：Emmy M. Omar、Kritanjali Dhungana、Allan D. Headley、Mohd Basyaruddin Abdul Rahman

  DOI：10.2174/157017811795038395

  日期：2011.3.1

  supported (ILS) (S)-pyrrolidine sulfonamide organocatalyst (1c), which was developed earlier in our lab, has been applied to a wider range of Michael addition reaction, involving various aryl-substituted nitroolefins and a series of aldehydes. Catalyst 1c catalyzes Michael additions in which only 2 equivalents of aldehydes to each equivalent of nitroolefin are required. With 10 mol% of ILS catalyst

  本实验室较早开发的一类离子液体负载型（ILS）（S）-吡咯烷磺酰胺有机催化剂（1c）已应用于更广泛的迈克尔加成反应，涉及各种芳基取代的硝基烯烃和一系列醛类。催化剂1c催化迈克尔加成，其中每当量硝基烯烃仅需要2当量醛。使用 10 mol% 的 ILS 催化剂 1c 负载，获得了中等至优异的产率（51-98%），具有中等对映选择性（28-83% ee）和高非对映选择性（syn/anti 比率高达 97/3）。此外，催化剂1c可以很容易地回收和重复使用至少5次，而活性略有降低。
• Asymmetric Michael reactions catalyzed by a highly efficient and recyclable quaternary ammonium ionic liquid-supported organocatalyst in aqueous media
  作者：Subrata K. Ghosh、Yupu Qiao、Bukuo Ni、Allan D. Headley

  DOI：10.1039/c3ob27398a

  日期：——

  developed and successfully applied to the asymmetric Michael reaction in the presence of a newly developed ionic liquid-supported (ILS) benzoic acid as co-catalyst. For the reactions studied, in which various aldehydes and nitroolefins were examined, excellent diastereo- and enantioselectivities were obtained with low catalyst loading. Also, the catalyst could be recycled for ten times without significant

  最近开发了一种新型的包含季铵离子部分的离子液体载体有机催化剂，并在存在新开发的离子液体载体（ILS）的情况下成功地将其应用于不对称迈克尔反应 苯甲酸作为助催化剂。对于所研究的反应，其中检查了各种醛和硝基烯烃，在低催化剂负载下获得了优异的非对映选择性和对映选择性。同样，该催化剂可以循环使用十次而不会显着损失对映选择性。
• Application of l-prolinamides as highly efficient organocatalysts for the asymmetric Michael addition of unmodified aldehydes to nitroalkenes
  作者：Hayriye Nevin Naziroglu、Mustafa Durmaz、Selahattin Bozkurt、Ayhan Sitki Demir、Abdulkadir Sirit

  DOI：10.1016/j.tetasy.2012.01.008

  日期：2012.1

  The asymmetric Michael addition of aldehydes to nitroolefins was investigated using a combination of L-prolinamide derivatives and various acidic additives. (S)-1,1'-Bi-2-naphthol was found to be the most effective co-catalyst and afforded the nitroaldehyde products with excellent yields (up to 95%), enantiomeric excesses (up to 99%) and diastereoselectivity ratios (up to 99:1). (C) 2012 Elsevier Ltd. All rights reserved.