(2R,3S)-3-(4-chlorophenyl)-N-methyl-4-nitro-2-phenylbutanamide | 1457935-43-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (2R,3S)-3-(4-chlorophenyl)-N-methyl-4-nitro-2-phenylbutanamide
• CAS: 1457935-43-1
• 化学式: C₁₇H₁₇ClN₂O₃
• 分子量: 332.787
• InChiKey: VSPZTWDHBDGCPV-CVEARBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  dimethyl phenylacetylphosphonate 、 1-(4-氯苯基)-2-硝基乙烯 、 甲胺 在 1-(2,6-diisopropylphenyl)-3-((1S,2S)-2-(dimethylamino)cyclohexyl)thiourea 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 2.41h， 以73%的产率得到
  参考文献：
  名称：

  Organocatalyzed asymmetric Michael reaction of β-aryl-α-ketophosphonates and nitroalkenes

  摘要：

  The first enantioselective Michael reaction of beta-aryl-alpha-ketophosphonates and nitroalkenes has been realized by using a new bifunctional Takemoto-type thiourea catalyst. The primary Michael adducts obtained were converted in situ to the corresponding amides through the aminolysis. High yields, excellent diaste-reoselectivities (>95:5 dr), and good enantioselectivities (up to 81% ee) have been achieved for the corresponding oc,13-disubstituted gamma-nitroamides. This reaction again demonstrated that alpha-ketophosphonates are interesting pronucleophiles that can be used as amide surrogates in organocatalyzed reactions. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.08.015

文献信息

• Organocatalyzed asymmetric Michael reaction of β-aryl-α-ketophosphonates and nitroalkenes
  作者：Jie Guang、John Cong-Gui Zhao

  DOI：10.1016/j.tetlet.2013.08.015

  日期：2013.10

  The first enantioselective Michael reaction of beta-aryl-alpha-ketophosphonates and nitroalkenes has been realized by using a new bifunctional Takemoto-type thiourea catalyst. The primary Michael adducts obtained were converted in situ to the corresponding amides through the aminolysis. High yields, excellent diaste-reoselectivities (>95:5 dr), and good enantioselectivities (up to 81% ee) have been achieved for the corresponding oc,13-disubstituted gamma-nitroamides. This reaction again demonstrated that alpha-ketophosphonates are interesting pronucleophiles that can be used as amide surrogates in organocatalyzed reactions. (C) 2013 Elsevier Ltd. All rights reserved.