(2R,3S)-3-(4-fluorophenyl)-2-isopropyl-4-nitrobutanal | 1229238-50-9

• 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: (2R,3S)-3-(4-fluorophenyl)-2-isopropyl-4-nitrobutanal
• 英文别名: (2R,3S)-3-(4-fluorophenyl)-4-nitro-2-propan-2-ylbutanal
• CAS: 1229238-50-9
• 化学式: C₁₃H₁₆FNO₃
• 分子量: 253.273
• InChiKey: COWOMWXKLBOMOH-CHWSQXEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 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：
  62.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(4-氟苯基)-2-硝基乙烯 、 异戊醛 在 (2S)-N-tritylpyrrolidine-2-carboxamide 、 苯甲酸 作用下， 以 甲苯 为溶剂， 反应 24.5h， 以90%的产率得到(2R,3S)-3-(4-fluorophenyl)-2-isopropyl-4-nitrobutanal
  参考文献：
  名称：

  Aromatic l-prolinamide-catalyzed asymmetric Michael addition of aldehydes to nitroalkenes

  摘要：

  Two chiral aromatic L-prolinamides were synthesized in high overall yield (95%) from N-Boc-L-proline and served as organocatalysts in asymmetric Michael reactions of aldehydes to nitroalkenes. Under the optimized reaction conditions, (S)-N-tritylpyrrolidine-2-carboxamide 4 was found to be a highly efficient organocatalyst for the Michael addition, and the corresponding Michael adducts were obtained in good yields (up to 94%), with excellent enantioselectivities (up to 99% ee) and diastereoselectivities (up to 99:1 dr). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.11.006

文献信息

• Efficient and Highly Enantioselective Michael Addition of Aldehydes to Nitroalkenes Catalyzed by a Surfactant-type Organocatalyst in the Presence of Water
  作者：Feng Hu、Chang-Shan Guo、Jin Xie、Hai-Liang Zhu、Zhi-Zhen Huang

  DOI：10.1246/cl.2010.412

  日期：2010.4.5

  silyl ether organocatalyst bearing a long chain only in 2 mol % loading could catalyze the asymmetric Michael reaction of various aldehydes with trans-nitroalkenes at room temperature in the presence of water, giving the desired adducts in excellent yields with high diastereoselectivities and excellent enantioselectivities (up to >99% ee).

  发现在20 mol % HCOOH存在下，只有2 mol %负载量的长链(S)-脯氨醇甲硅烷基醚有机催化剂在室温下可以催化各种醛与反硝基烯烃的不对称迈克尔反应。水，以优异的收率提供所需的加合物，具有高非对映选择性和优异的对映选择性（高达> 99％ee）。
• Aromatic l-prolinamide-catalyzed asymmetric Michael addition of aldehydes to nitroalkenes
  作者：Yongchao Wang、Jun Lin、Kun Wei

  DOI：10.1016/j.tetasy.2014.11.006

  日期：2014.12

  Two chiral aromatic L-prolinamides were synthesized in high overall yield (95%) from N-Boc-L-proline and served as organocatalysts in asymmetric Michael reactions of aldehydes to nitroalkenes. Under the optimized reaction conditions, (S)-N-tritylpyrrolidine-2-carboxamide 4 was found to be a highly efficient organocatalyst for the Michael addition, and the corresponding Michael adducts were obtained in good yields (up to 94%), with excellent enantioselectivities (up to 99% ee) and diastereoselectivities (up to 99:1 dr). (C) 2014 Elsevier Ltd. All rights reserved.