diethyl 2-nitro-5-oxo-5-p-tolylpentan-2-ylphosphonate | 1360199-03-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: diethyl 2-nitro-5-oxo-5-p-tolylpentan-2-ylphosphonate
• 英文别名: 4-[Diethoxy(oxido)phosphaniumyl]-1-(4-methylphenyl)-4-nitropentan-1-one；4-[diethoxy(oxido)phosphaniumyl]-1-(4-methylphenyl)-4-nitropentan-1-one
• CAS: 1360199-03-6
• 化学式: C₁₆H₂₄NO₆P
• 分子量: 357.343
• InChiKey: FHPABNZHSQBYQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl 2-nitro-5-oxo-5-p-tolylpentan-2-ylphosphonate 在 间氯过氧苯甲酸 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 生成 p-tolyl (R)-4-(diethoxyphosphoryl)-4-nitropentanoate 、 4-(diethoxyphosphoryl)-4-nitropentanoic acid p-tolyl ester
  参考文献：
  名称：

  Enantioselective Synthesis of Quaternary α-Aminophosphonates via Conjugate Addition of α-Nitrophosphonates to Enones

  摘要：

  Enantioselective Michael addition of alpha-nitrophosphonates to enones for the synthesis of alpha-aminophosphonates is reported for the first time. The reaction proceeds in good to high yields and moderate to high selectivity in the presence of a new quinine thiourea catalyst. The quaternary nitrophosphonates were conveniently transformed to cyclic quaternary alpha-aminophosphonates via in situ reduction intramolecular cyclization or Baeyer-Villiger oxidation followed by in situ reduction intramolecular cyclization.

  DOI：

  10.1021/ol203132h
• 作为产物：
  描述：

  乙酰亚磷酸二乙酯 在 吡啶 、 9-amino(9-deoxy)epiquinine 、 盐酸羟胺 、 间氯过氧苯甲酸 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 99.0h， 生成 diethyl 2-nitro-5-oxo-5-p-tolylpentan-2-ylphosphonate
  参考文献：
  名称：

  Enantioselective Synthesis of Quaternary α-Aminophosphonates via Conjugate Addition of α-Nitrophosphonates to Enones

  摘要：

  Enantioselective Michael addition of alpha-nitrophosphonates to enones for the synthesis of alpha-aminophosphonates is reported for the first time. The reaction proceeds in good to high yields and moderate to high selectivity in the presence of a new quinine thiourea catalyst. The quaternary nitrophosphonates were conveniently transformed to cyclic quaternary alpha-aminophosphonates via in situ reduction intramolecular cyclization or Baeyer-Villiger oxidation followed by in situ reduction intramolecular cyclization.

  DOI：

  10.1021/ol203132h

文献信息

• Enantioselective Synthesis of Quaternary α-Aminophosphonates via Conjugate Addition of α-Nitrophosphonates to Enones
  作者：Kalisankar Bera、Irishi N. N. Namboothiri

  DOI：10.1021/ol203132h

  日期：2012.2.17

  Enantioselective Michael addition of alpha-nitrophosphonates to enones for the synthesis of alpha-aminophosphonates is reported for the first time. The reaction proceeds in good to high yields and moderate to high selectivity in the presence of a new quinine thiourea catalyst. The quaternary nitrophosphonates were conveniently transformed to cyclic quaternary alpha-aminophosphonates via in situ reduction intramolecular cyclization or Baeyer-Villiger oxidation followed by in situ reduction intramolecular cyclization.