(R)-diphenyl 1-(4-cyanophenyl)-2-nitroethylphosphonate | 1334553-58-0

• 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)-diphenyl 1-(4-cyanophenyl)-2-nitroethylphosphonate
• 英文别名: 4-[(1R)-2-nitro-1-[oxido(diphenoxy)phosphaniumyl]ethyl]benzonitrile
• CAS: 1334553-58-0
• 化学式: C₂₁H₁₇N₂O₅P
• 分子量: 408.35
• InChiKey: VGMJYPDLDYCJRO-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  反-4-(2-硝基乙烯基)苯甲腈 、 亚磷酸二苯酯 在 C₂₉H₂₈F₆N₄OS 作用下， 以 二氯甲烷 为溶剂， 反应 1.33h， 生成 (S)-diphenyl 1-(4-cyanophenyl)-2-nitroethylphosphonate 、 (R)-diphenyl 1-(4-cyanophenyl)-2-nitroethylphosphonate
  参考文献：
  名称：

  Quinidine thiourea-catalyzed enantioselective synthesis of β-nitrophosphonates: beneficial effects of molecular sieves

  摘要：

  An efficient method for enantioselective synthesis of beta-nitrophosphonates via the Michael addition of diphenyl phosphite to nitroalkenes using the readily available quinidine thiourea organocatalyst has been developed. The desired beta-nitrophosphonates were obtained in good ee values. Molecular sieves were found to be crucial for achieving high reproducible yields in this reaction. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.07.059

文献信息

• Quinidine thiourea-catalyzed enantioselective synthesis of β-nitrophosphonates: beneficial effects of molecular sieves
  作者：Santhi Abbaraju、Mayur Bhanushali、Cong-Gui Zhao

  DOI：10.1016/j.tet.2011.07.059

  日期：2011.9

  An efficient method for enantioselective synthesis of beta-nitrophosphonates via the Michael addition of diphenyl phosphite to nitroalkenes using the readily available quinidine thiourea organocatalyst has been developed. The desired beta-nitrophosphonates were obtained in good ee values. Molecular sieves were found to be crucial for achieving high reproducible yields in this reaction. (C) 2011 Elsevier Ltd. All rights reserved.