methyl 3-(ethylamino)pent-2-enoate | 1048645-06-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 3-(ethylamino)pent-2-enoate
• CAS: 1048645-06-2
• 化学式: C₈H₁₅NO₂
• 分子量: 157.213
• InChiKey: MPSWCDMEHLWASV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 3-(ethylamino)pent-2-enoate 、 1,4-二羟基-2-萘甲酸甲酯 在 manganese(IV) oxide 、 magnesium sulfate 、 溶剂黄146 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 3.5h， 以69%的产率得到methyl 2-3-diethyl-1,2,5,10-tetrahydro-1,5,10-trioxobenzo[g]isoquinoline-4-carboxylate
  参考文献：
  名称：

  Investigation towards an efficient synthesis of benzo[g]isoquinoline-1,5,10(2H)-triones

  摘要：

  As part of our research on 2-aza analogues of pentalongin, the active principle of Pentas longiflora Oliv., the first synthesis of 2,3-disubstituted benzo[g]isoquinoline-1,5,10(2H)-triones via 3,4-disubstituted 6-hydroxybenzo[g]furo[4,3,2-de]isoquinoline-2,5(4H)-diones as the key intermediates is reported. The latter compounds have been prepared by treating 2-methoxycarbonyl-1,4-naphthoquinone with N-substituted enaminoesters under acidic conditions. These reagents are easily accessible from readily available 1,4-dihydroxy-2-naphthoic acid, beta-ketoesters and primary amines. Finally, a short synthesis of substituted benzo[g]isoquinoline-1,5,10(2H)-triones is achieved by an oxidative addition of N-substituted enaminoesters onto methyl 1,4-dihydroxynaphthalene-2-carboxylate. (C) 2011 Elsevier Ad. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.021

文献信息

• Regioselective Iodine-Catalyzed Construction of Polysubstituted Pyrroles from Allenes and Enamines
  作者：Yu Wang、Chen-Min Jiang、Hong-Liang Li、Fu-Sheng He、Xiaoyan Luo、Wei-Ping Deng

  DOI：10.1021/acs.joc.6b01737

  日期：2016.9.16

  A novel I2-catalyzed tandem Michael addition/oxidative annulation of allenes and enamines for the construction of polysubstituted pyrroles has been developed. This protocol represents an efficient and highly regioselective way to access functionalized pyrroles in moderate to excellent yields under mild conditions.

  已经开发了用于构建多取代的吡咯的新颖的I 2催化的Allen和烯胺的串联Michael加成/氧化环化反应。该方案代表在温和条件下以中等至极高收率获得官能化吡咯的有效且高度区域选择性的方式。