(4S,5R)-3-(ethoxycarbonyl)-5-formyl-4-(4-methoxyphenyl)-5-propyl-4,5-dihydroisoxazole 2-oxide | 1255517-10-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (4S,5R)-3-(ethoxycarbonyl)-5-formyl-4-(4-methoxyphenyl)-5-propyl-4,5-dihydroisoxazole 2-oxide
• 英文别名: ethyl (4S,5R)-5-formyl-4-(4-methoxyphenyl)-2-oxido-5-propyl-4H-1,2-oxazol-2-ium-3-carboxylate
• CAS: 1255517-10-2
• 化学式: C₁₇H₂₁NO₆
• 分子量: 335.357
• InChiKey: ZSEBWZVCIAKPDJ-YOEHRIQHSA-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：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  90.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  ethyl 3-(4'-methoxyphenyl)-2-nitroacrylate 、 iodopentanaldehyde 在 (S)-2-(azidodiphenylmethyl)pyrrolidine 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 (4S,5R)-3-(ethoxycarbonyl)-5-formyl-4-(4-methoxyphenyl)-5-propyl-4,5-dihydroisoxazole 2-oxide 、 (4RS,5RS)-3-(ethoxycarbonyl)-5-formyl-4-(4-methoxyphenyl)-5-propyl-4,5-dihydroisoxazole 2-oxide
  参考文献：
  名称：

  Catalytic Asymmetric Formal [4 + 1] Annulation Leading to Optically Active cis-Isoxazoline N-Oxides

  摘要：

  The catalytic asymmetric synthesis of densely functionalized cis-isoxazoline N-oxides was realized with novel use of an organocatalyst, (S)-2-(azidodiphenylmethyl)pyrrolidine (4e) (Tan, B.; Zhu, D.; Zhang, L.; Chua, P. J.; Zeng, X.; Zhong, G. Chem.-Eur. J. 2010, 16, 3842; Olivares-Romero, J. L.; Juaristi, E. Tetrahedron 2008, 64, 9992), via an elegant formal [4 + 1] annulation strategy using readily available 2-nitroacrylates and alpha-iodoaldehydes.

  DOI：

  10.1021/ol102181r

文献信息

• Catalytic Asymmetric Formal [4 + 1] Annulation Leading to Optically Active <i>cis</i>-Isoxazoline <i>N</i>-Oxides
  作者：Zugui Shi、Bin Tan、Wendy Wen Yi Leong、Xiaofei Zeng、Min Lu、Guofu Zhong

  DOI：10.1021/ol102181r

  日期：2010.12.3

  The catalytic asymmetric synthesis of densely functionalized cis-isoxazoline N-oxides was realized with novel use of an organocatalyst, (S)-2-(azidodiphenylmethyl)pyrrolidine (4e) (Tan, B.; Zhu, D.; Zhang, L.; Chua, P. J.; Zeng, X.; Zhong, G. Chem.-Eur. J. 2010, 16, 3842; Olivares-Romero, J. L.; Juaristi, E. Tetrahedron 2008, 64, 9992), via an elegant formal [4 + 1] annulation strategy using readily available 2-nitroacrylates and alpha-iodoaldehydes.