methyl (2Z)-3-{[(4-methoxyphenyl)methyl]amino}but-2-enoate | 847974-60-1

• 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: methyl (2Z)-3-{[(4-methoxyphenyl)methyl]amino}but-2-enoate
• 英文别名: (Z)-methyl 3-(4-methoxybenzylamino)but-2-enoate；methyl (Z)-3-[(4-methoxyphenyl)methylamino]but-2-enoate
• CAS: 847974-60-1
• 化学式: C₁₃H₁₇NO₃
• 分子量: 235.283
• InChiKey: UOIYHGZTVYIABN-NTMALXAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (2Z)-3-{[(4-methoxyphenyl)methyl]amino}but-2-enoate 、 2-bromo-6-methoxybenzoquinone 在 copper(II) acetate monohydrate 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 4.5h， 以89%的产率得到methyl 6-methoxy-1-(4-methoxybenzyl)-2-methyl-4,7-dioxo-4,7-dihydro-1H-indole-3-carboxylate
  参考文献：
  名称：

  Synthesis of Indolequinones from Bromoquinones and Enamines Mediated by Cu(OAc)₂·H₂O

  摘要：

  A Cu(II)-mediated synthesis of indolequinones from the corresponding bromoquinones and enamines is reported. The key oxidative cyclization proceeds in good yield for a broad range of substrates and can be performed on a multigram scale, allowing access to biologically interesting structures.

  DOI：

  10.1021/jo101071c
• 作为产物：
  描述：

  乙酰乙酸甲酯 、 4-甲氧基苄胺 在 silica gel 作用下， 反应 13.0h， 以100%的产率得到methyl (2Z)-3-{[(4-methoxyphenyl)methyl]amino}but-2-enoate
  参考文献：
  名称：

  Synthesis of Indolequinones from Bromoquinones and Enamines Mediated by Cu(OAc)₂·H₂O

  摘要：

  A Cu(II)-mediated synthesis of indolequinones from the corresponding bromoquinones and enamines is reported. The key oxidative cyclization proceeds in good yield for a broad range of substrates and can be performed on a multigram scale, allowing access to biologically interesting structures.

  DOI：

  10.1021/jo101071c

文献信息

• Trifluoromethanesulfonyl Hypervalent Iodonium Ylide for Copper-Catalyzed Trifluoromethylthiolation of Enamines, Indoles, and β-Keto Esters
  作者：Yu-Dong Yang、Ayaka Azuma、Etsuko Tokunaga、Mikio Yamasaki、Motoo Shiro、Norio Shibata

  DOI：10.1021/ja402455f

  日期：2013.6.19

  A novel electrophilic-type trifluoromethylthiolation reagent, a trifluoromethanesulfonyl hypervalent iodonium ylide, was designed and reacted well with various nucleophiles to afford the desired CF3S-substituted products. In situ reduction of the trifluoromethanesulfonyl group to give the trifluoromethylthio group, which is the key step in this process, was realized in the presence of copper(I) chloride

  设计了一种新型的亲电型三氟甲硫基化试剂，一种三氟甲磺酰基高价碘鎓叶立德，并与各种亲核试剂反应良好，得到所需的 CF3S 取代产物。三氟甲磺酰基的原位还原得到三氟甲硫基，这是该过程中的关键步骤，是在氯化铜 (I) 存在下实现的。
• Synthesis of Indolequinones from Bromoquinones and Enamines Mediated by Cu(OAc)₂·H₂O
  作者：Martyn Inman、Christopher J. Moody

  DOI：10.1021/jo101071c

  日期：2010.9.3

  A Cu(II)-mediated synthesis of indolequinones from the corresponding bromoquinones and enamines is reported. The key oxidative cyclization proceeds in good yield for a broad range of substrates and can be performed on a multigram scale, allowing access to biologically interesting structures.