(3R)-3-dimethoxyphosphoryl-2-[(1S)-1-phenylethyl]-3H-isoindol-1-one | 1338474-40-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (3R)-3-dimethoxyphosphoryl-2-[(1S)-1-phenylethyl]-3H-isoindol-1-one
• CAS: 1338474-40-0
• 化学式: C₁₈H₂₀NO₄P
• 分子量: 345.335
• InChiKey: WMLBSIVCVAKORO-SCLBCKFNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (1'S)-2,3-dihydro-3-hydroxy-1-(1'-phenylethyl)-1H-isoindol-1-one 在 三氟化硼乙醚 、 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 为溶剂， 生成 (3R)-3-dimethoxyphosphoryl-2-[(1S)-1-phenylethyl]-3H-isoindol-1-one 、
  参考文献：
  名称：

  One-pot three-component highly diastereoselective synthesis of isoindolin-1-one-3-phosphonates under solvent and catalyst free-conditions

  摘要：

  The one-pot three-component reaction of 2-formylbenzoic acid with (S)- and (R)-methylbenzylamine and dimethyl phosphite (Kabachnik-Fields reaction) proceeded in short reaction times under solvent and catalyst free-conditions to afford the corresponding (3R,1'S)- and (3S,1'R)-isoindolin-1-one-3-phosphonates 3, respectively, in good yield and with high diastereoselectivity (95:5 dr). The use of a solvent decreases the diastereoselectivity and slows the reaction rate. The reaction rate was also influenced by CO2H functionality through protonation of the imine intermediate. The absolute configuration at the new stereogenic center was determined by X-ray crystal analysis, and a mechanism was proposed to explain the high diastereoselectivity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.08.003

文献信息

• One-pot three-component highly diastereoselective synthesis of isoindolin-1-one-3-phosphonates under solvent and catalyst free-conditions
  作者：José Luis Viveros-Ceballos、Carlos Cativiela、Mario Ordóñez

  DOI：10.1016/j.tetasy.2011.08.003

  日期：2011.7

  The one-pot three-component reaction of 2-formylbenzoic acid with (S)- and (R)-methylbenzylamine and dimethyl phosphite (Kabachnik-Fields reaction) proceeded in short reaction times under solvent and catalyst free-conditions to afford the corresponding (3R,1'S)- and (3S,1'R)-isoindolin-1-one-3-phosphonates 3, respectively, in good yield and with high diastereoselectivity (95:5 dr). The use of a solvent decreases the diastereoselectivity and slows the reaction rate. The reaction rate was also influenced by CO2H functionality through protonation of the imine intermediate. The absolute configuration at the new stereogenic center was determined by X-ray crystal analysis, and a mechanism was proposed to explain the high diastereoselectivity. (C) 2011 Elsevier Ltd. All rights reserved.