ethyl 3-(benzyl(3,4-dimethoxyphenyl)amino)-3-oxopropanoate | 1537188-64-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 3-(benzyl(3,4-dimethoxyphenyl)amino)-3-oxopropanoate
• CAS: 1537188-64-9
• 化学式: C₂₀H₂₃NO₅
• 分子量: 357.406
• InChiKey: BPCKUEAZRSEQFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.19
• 重原子数：
  26.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  65.07
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl 3-(benzyl(3,4-dimethoxyphenyl)amino)-3-oxopropanoate 在 甲烷磺酸 、 四磷十氧化物 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 生成 1-benzyl-4-hydroxy-6,7-dimethoxyquinolin-2(1H)-one
  参考文献：
  名称：

  Asymmetric synthesis of tetrahydropyran[3,2-c]quinolinones via an organocatalyzed formal [3 + 3] annulation of quinolinones and MBH 2-naphthoates of nitroolefin

  摘要：

  An efficient asymmetric and enantio-swithchable organocatalytic [3 + 3] annulation reaction using MBH-2-naphthoates of nitroalkenes and 4-hydroxyquinolin-2(1H)-ones has been developed. Densely substituted tetrahydropyrano[3,2-c]quinolinones scaffolds with two adjacent stereogenic centers are obtained with high yield (up to 95% yield) and good stereoselectivities (up to >20:1 dr and 96% ee) in an enantio-switchable manner. Furthermore, gram scale synthesis was achieved and the nitro group could easily transform into an amino group without any appreciable loss in the diastereo- and enantioselectivity. (C) 2019 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2019.08.040
• 作为产物：
  描述：

  N-benzyl-3,4-dimethoxyaniline 、 氯甲酰乙酸乙酯 在 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 生成 ethyl 3-(benzyl(3,4-dimethoxyphenyl)amino)-3-oxopropanoate
  参考文献：
  名称：

  Asymmetric synthesis of tetrahydropyran[3,2-c]quinolinones via an organocatalyzed formal [3 + 3] annulation of quinolinones and MBH 2-naphthoates of nitroolefin

  摘要：

  An efficient asymmetric and enantio-swithchable organocatalytic [3 + 3] annulation reaction using MBH-2-naphthoates of nitroalkenes and 4-hydroxyquinolin-2(1H)-ones has been developed. Densely substituted tetrahydropyrano[3,2-c]quinolinones scaffolds with two adjacent stereogenic centers are obtained with high yield (up to 95% yield) and good stereoselectivities (up to >20:1 dr and 96% ee) in an enantio-switchable manner. Furthermore, gram scale synthesis was achieved and the nitro group could easily transform into an amino group without any appreciable loss in the diastereo- and enantioselectivity. (C) 2019 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2019.08.040

文献信息

• Metal-Free Synthesis of 2-Oxindoles via PhI(OAc)₂-Mediated Oxidative C–C Bond Formation
  作者：Jinglei Lv、Daisy Zhang-Negrerie、Jun Deng、Yunfei Du、Kang Zhao

  DOI：10.1021/jo4025539

  日期：2014.2.7

  The series of 3-monofunctionalized 2-oxindoles 2 were conveniently synthesized from reactions between anilide 1 and phenyliodine(III) diacetate (PIDA) through hypervalent iodine mediated C(sp(2))-C(sp(2)) bond formation followed by a subsequent deacylation reaction. This metal-free method, shown to provide direct access to an important oxindole intermediate, could be applied to the total synthesis of naturally occurring horsfiline.