(2R,3S)-2-methyl-3-(naphthalen-2-yl)-4-nitrobutanal | 1191426-18-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2R,3S)-2-methyl-3-(naphthalen-2-yl)-4-nitrobutanal
• 英文别名: (2R,3S)-2-methyl-3-(2-naphthyl)-4-nitrobutanal；(2R,3S)-2-methyl-4-nitro-3-naphthylbutanal；(2R,3S)-2-methyl-3-naphthalen-2-yl-4-nitrobutanal
• CAS: 1191426-18-2
• 化学式: C₁₅H₁₅NO₃
• 分子量: 257.289
• InChiKey: QTZZYCHVFCQOFW-NHYWBVRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 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 、 丙醛 在 (2S,3aS,7aS)-(octahydro-indol-2-yl)-methanol 、 sodium chloride 作用下， 以 水 为溶剂， 反应 7.0h， 以91%的产率得到(2R,3S)-2-methyl-3-(naphthalen-2-yl)-4-nitrobutanal
  参考文献：
  名称：

  Indolinol-catalyzed asymmetric Michael reaction of aldehydes to nitroalkenes in brine

  摘要：

  (2S,3aS,7aS)-全氢吲哚醇能够促进一系列醛和硝基烯烃底物的反应，生成具有 excellent 对映选择性（高达98% ee）、优异的产率和高的区域选择性（顺式/反式高达99:1）的迈克尔加成产物。我们的研究结果表明，全氢吲哚醇类化合物在海水中亦是高效的不对称迈克尔反应的有机催化剂，同时具有良好的环境友好性。© 2016 Elsevier Ltd. 保留所有权利。

  DOI：

  10.1016/j.tetasy.2016.03.006

文献信息

• Highly efficient asymmetric Michael addition of aldehydes to nitroalkenes with 4,5-methano-l-proline as organocatalysts
  作者：Han Yu、Mouming Liu、Sheng Han

  DOI：10.1016/j.tet.2014.08.069

  日期：2014.11

  5-methano-l-prolines were used as chiral organocatalysts in asymmetric Michael addition of aldehydes to nitroolefins. These proline-like catalysts are unique for their rigid bicyclic structure with a cyclopropane and two H atoms attached to the bridgehead C atoms lying on the same side of the ring. They therefore showed high efficiency in asymmetric Michael addition of aldehydes to nitroolefins. Under the optimal conditions

  4,5-甲基-1-脯氨酸在醛与硝基烯烃的不对称迈克尔加成反应中用作手性有机催化剂。这些类似于脯氨酸的催化剂具有独特的刚性双环结构，具有环丙烷和两个H原子与位于环同一侧的桥头C原子相连。因此，它们显示出在醛到硝基烯烃的不对称迈克尔加成反应中的高效率。在最佳条件下，仅使用5摩尔％的催化剂负载量，即可获得一系列醛和硝基烯烃的高收率和优异的非对映选择性和对映选择性（高达97/3 dr和98％ee）。该方法具有易于获得的催化剂，高催化效率和环保程序的特点。
• Asymmetric Conjugate Addition of Unmodified Propionaldehyde to β- Nitrostyrenes Catalyzed by Readily Available Proline-Based Dipeptidols
  作者：Ren-Yong Yang、Chao-Shan Da、Lei Yi、Feng-Chun Wu、Hong Li

  DOI：10.2174/157017809787003061

  日期：2009.1.1

  Organocatalytic asymmetric additions of unmodified aldehydes to β-nitrostyrenes are important carbon-carbon bond formation reactions and have become very attractive recently, because they are metal-free and environmentally benign. This work employed a series of L-proline-based diphenyl dipeptidols to catalyze this reaction. The results showed that these dipeptidols were effective organocatalysts with the yield up to 99%. 3a was optimal with the highest enantioselectivity up to 75% and dr (syn/anti) up to 94/6. In addition, the mechanism of this asymmetric reaction is also discussed.

  未改性醛与β-硝基苯炔的有机催化不对称加成反应是重要的碳-碳键形成反应，由于不含金属且对环境无害，近来变得非常有吸引力。这项研究采用了一系列基于 L-脯氨酸的二苯基二肽醇来催化这一反应。结果表明，这些二肽醇是有效的有机催化剂，产率高达 99%。3a 的对映选择性最高，可达 75%，dr（同/反）高达 94/6。此外，还讨论了该不对称反应的机理。
• Highly efficient asymmetric Michael addition of aldehyde to nitroolefin using perhydroindolic acid as a chiral organocatalyst
  作者：Lina Zhao、Jiefeng Shen、Delong Liu、Yangang Liu、Wanbin Zhang

  DOI：10.1039/c2ob00003b

  日期：——

  intermediate, were used as chiral organocatalysts in asymmetric Michael addition reactions of aldehydes to nitroolefins. These proline-like catalysts are unique for their rigid bicyclic structure with two H atoms attached to the bridgehead C atoms lying on the opposite side of the ring. They therefore showed high efficiency in asymmetric Michael additions of aldehydes to nitroolefins. Under the optimal conditions

  全氢吲哚酸，是一种工业生产的trandolapril中间体，在醛与硝基烯烃的不对称迈克尔加成反应中用作手性有机催化剂。这些类似于脯氨酸的催化剂具有独特的刚性双环结构，其中两个H原子连接到位于环相反侧的桥头C原子上。因此，它们在醛向硝基烯烃的不对称迈克尔加成中显示出高效率。在最佳条件下，仅使用5摩尔％的催化剂负载量，即可获得一系列醛和硝基烯烃的高化学收率的优异非对映选择性和对映选择性（最高99/1 dr和98％ee）。该方法的特点是容易获得的催化剂，高催化效率和绿色环保的程序。
• Highly Efficient and Modularly Tuned Bicyclic Organocatalyst for the Enantioselective Michael Addition of Aldehydes to Nitroalkenes
  作者：Teck-Peng Loh、Jian Xiao、Feng-Xia Xu、Yun-Peng Lu、Yan-Ling Liu

  DOI：10.1055/s-0030-1260527

  日期：2011.6

  type of bicyclic organocatalyst has been successfully applied to the asymmetric Michael addition of aldehydes to nitrostyrenes in good yields and good enantioselectivities by using a self-assembly strategy. The success of this reaction is attributed to good control of the geometry of the enamine and efficient face shielding. organocatalyst - bicyclic - enamine control - Michael addition

  一种新型的双环有机催化剂已成功地通过自组装策略成功地将醛不对称迈克尔加成至硝基苯乙烯，并具有良好的收率和良好的对映选择性。该反应的成功归因于对烯胺的几何形状的良好控制和有效的面部防护。 有机催化剂-双环-烯胺控制-迈克尔加成