N-[2-(3-cyclopentyloxy-4-methoxyphenyl)ethyl]-2-diazo-N-(2-phenylpropan-2-yl)acetamide | 854759-44-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-[2-(3-cyclopentyloxy-4-methoxyphenyl)ethyl]-2-diazo-N-(2-phenylpropan-2-yl)acetamide
• CAS: 854759-44-7
• 化学式: C₂₅H₃₁N₃O₃
• 分子量: 421.539
• InChiKey: SLKIVAROVXOWCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  40.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[2-(3-cyclopentyloxy-4-methoxyphenyl)ethyl]-2-diazo-N-(2-phenylpropan-2-yl)acetamide 在 dirhodium(II) tetrakis[methyl 4(R)-2-oxazolidinone-4-carboxylate] 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 (R)-(-)-咯利普兰 、 S- (+)-咯利普兰
  参考文献：
  名称：

  Dirhodium catalyzed intramolecular enantioselective C–H insertion reaction of N-cumyl-N-(2-p-anisylethyl)diazoacetamide: synthesis of (−)-Rolipram

  摘要：

  Cumyl(2,2-dimethyl-benzyl) was used as an N-protecting group for intramolecular C-H insertion reaction of a-diazoacetamide. Excellent chemoselectivity (>98:2) in C-H insertion over the aromatic addition of N-cumyl-N-(2-p-anisylethyl)-diazoacetamide was obtained with Rh-2[(4S)-MEOX)](4) catalyst in moderate enantioselectivity (53% ee). The reaction was successfully applied in the synthesis of (-)-Rolipram in 15% total yield. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.03.023
• 作为产物：
  描述：

  1-methyloxyl-2-(3-cyclopentyloxyl-4-methoxyphenyl)-ethylene 在 盐酸 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 18.5h， 生成 N-[2-(3-cyclopentyloxy-4-methoxyphenyl)ethyl]-2-diazo-N-(2-phenylpropan-2-yl)acetamide
  参考文献：
  名称：

  Dirhodium catalyzed intramolecular enantioselective C–H insertion reaction of N-cumyl-N-(2-p-anisylethyl)diazoacetamide: synthesis of (−)-Rolipram

  摘要：

  Cumyl(2,2-dimethyl-benzyl) was used as an N-protecting group for intramolecular C-H insertion reaction of a-diazoacetamide. Excellent chemoselectivity (>98:2) in C-H insertion over the aromatic addition of N-cumyl-N-(2-p-anisylethyl)-diazoacetamide was obtained with Rh-2[(4S)-MEOX)](4) catalyst in moderate enantioselectivity (53% ee). The reaction was successfully applied in the synthesis of (-)-Rolipram in 15% total yield. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.03.023