2-Benzyl-3-hydroxy-3-(1-hydroxy-propyl)-2,3-dihydro-isoindol-1-one | 270925-95-6

• 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: 2-Benzyl-3-hydroxy-3-(1-hydroxy-propyl)-2,3-dihydro-isoindol-1-one
• 英文别名: 2-Benzyl-3-hydroxy-3-(1-hydroxypropyl)isoindol-1-one
• CAS: 270925-95-6
• 化学式: C₁₈H₁₉NO₃
• 分子量: 297.354
• InChiKey: LQZVMOBPKDRDSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  60.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Benzyl-3-hydroxy-3-(1-hydroxy-propyl)-2,3-dihydro-isoindol-1-one 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 以99%的产率得到2-Benzyl-3-propionyl-2,3-dihydro-isoindol-1-one
  参考文献：
  名称：

  Novel and stereoselective methods for the preparation of aromatic lactams via reductive coupling reactions mediated by SmI2

  摘要：

  Samarium(II) diiodide-mediated reductive cross-coupling of N-alkylated phthalimides with carbonyl compounds is shown to afford hydroxylated alpha-hydroxylactams, Ketoamides obtained by dehydration of these compounds through keto-enol tautomer isomerization were reduced with NaBH4 in a completely stereoselective manner in the presence of CeCl3 to give three-aromatic lactams as the sole product. Direct reductive deoxygenation of these alpha-hydroxylactam intermediates with Et3SiH in the presence of Lewis acid also displayed high stereoselectivity to afford the same threo-lactams exclusively. The mechanistic origins of this stereoselectivity are briefly documented. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00014-9
• 作为产物：
  描述：

  N-苄基酞酰亚胺 、 丙醛 在 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 以79%的产率得到2-Benzyl-3-hydroxy-3-(1-hydroxy-propyl)-2,3-dihydro-isoindol-1-one
  参考文献：
  名称：

  Novel and stereoselective methods for the preparation of aromatic lactams via reductive coupling reactions mediated by SmI2

  摘要：

  Samarium(II) diiodide-mediated reductive cross-coupling of N-alkylated phthalimides with carbonyl compounds is shown to afford hydroxylated alpha-hydroxylactams, Ketoamides obtained by dehydration of these compounds through keto-enol tautomer isomerization were reduced with NaBH4 in a completely stereoselective manner in the presence of CeCl3 to give three-aromatic lactams as the sole product. Direct reductive deoxygenation of these alpha-hydroxylactam intermediates with Et3SiH in the presence of Lewis acid also displayed high stereoselectivity to afford the same threo-lactams exclusively. The mechanistic origins of this stereoselectivity are briefly documented. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00014-9

文献信息

• Novel and stereoselective methods for the preparation of aromatic lactams via reductive coupling reactions mediated by SmI2
  作者：Hidemi Yoda、Keigo Matsuda、Hiroaki Nomura、Kunihiko Takabe

  DOI：10.1016/s0040-4039(00)00014-9

  日期：2000.3

  Samarium(II) diiodide-mediated reductive cross-coupling of N-alkylated phthalimides with carbonyl compounds is shown to afford hydroxylated alpha-hydroxylactams, Ketoamides obtained by dehydration of these compounds through keto-enol tautomer isomerization were reduced with NaBH4 in a completely stereoselective manner in the presence of CeCl3 to give three-aromatic lactams as the sole product. Direct reductive deoxygenation of these alpha-hydroxylactam intermediates with Et3SiH in the presence of Lewis acid also displayed high stereoselectivity to afford the same threo-lactams exclusively. The mechanistic origins of this stereoselectivity are briefly documented. (C) 2000 Elsevier Science Ltd. All rights reserved.