methyl 3-((3-methoxyphenyl)amino)-3-phenylacrylate | 1363379-11-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: methyl 3-((3-methoxyphenyl)amino)-3-phenylacrylate
• CAS: 1363379-11-6
• 化学式: C₁₇H₁₇NO₃
• 分子量: 283.327
• InChiKey: UTEHCGLMSWDYOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.32
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  47.56
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 3-((3-methoxyphenyl)amino)-3-phenylacrylate 、 丙酮 在 silver carbonate 作用下， 反应 24.0h， 以56%的产率得到methyl 1-(3-methoxyphenyl)-5-methyl-2-phenyl-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  Cross-Dehydrogenative Coupling between Enamino Esters and Ketones: Synthesis of Tetrasubstituted Pyrroles

  摘要：

  Tetrasubstituted pyrroles have been synthesized via the cross-dehydrogenative coupling between enamino esters and acetone. Silver carbonate proved to be an effective oxidant, and no transition metal catalyst is necessary.

  DOI：

  10.1021/ol300147t
• 作为产物：
  描述：

  苯乙酮 在 sodium hydride 、 对甲苯磺酸 作用下， 以 甲醇 、 甲苯 为溶剂， 生成 methyl 3-((3-methoxyphenyl)amino)-3-phenylacrylate
  参考文献：
  名称：

  Cross-Dehydrogenative Coupling between Enamino Esters and Ketones: Synthesis of Tetrasubstituted Pyrroles

  摘要：

  Tetrasubstituted pyrroles have been synthesized via the cross-dehydrogenative coupling between enamino esters and acetone. Silver carbonate proved to be an effective oxidant, and no transition metal catalyst is necessary.

  DOI：

  10.1021/ol300147t

文献信息

• An Oxidant-Free Strategy for Indole Synthesis via Intramolecular C–C Bond Construction under Visible Light Irradiation: Cross-Coupling Hydrogen Evolution Reaction
  作者：Cheng-Juan Wu、Qing-Yuan Meng、Tao Lei、Jian-Ji Zhong、Wen-Qiang Liu、Lei-Min Zhao、Zhi-Jun Li、Bin Chen、Chen-Ho Tung、Li-Zhu Wu

  DOI：10.1021/acscatal.6b00917

  日期：2016.7.1

  We describe here an oxidant-free strategy to synthesize indoles, i.e., under visible-light irradiation (λ = 450 nm), catalytic amounts of an iridium(III) photosensitizer and cobaloxime catalyst transform various N-aryl enamines exclusively into indoles. Our methodology affords indoles in good to excellent yields under mild reaction conditions and produces H2 as the only byproduct. Spectroscopic and

  我们在这里描述了一种无氧化剂的合成吲哚的策略，即在可见光辐射（λ= 450 nm）下，催化量的铱（III）光敏剂和钴肟催化剂将各种N-芳基烯胺专门转化为吲哚。我们的方法在温和的反应条件下，吲哚类化合物的收率高至优，并产生H 2作为唯一的副产物。光谱和电化学研究证实，所设计的系统是通过可见光催化的N-芳基烯胺的氧化，然后进行分子内自由基加成，在环境条件下平稳生成吲哚而进行的。
• A facile synthesis of 3-hydroxy-3-(trifluoromethyl)-1H-pyrrol-2(3H)-ones with Brønsted acid-catalyzed condensation–cyclization reactions of β-enamino esters and ethyl trifluoropyruvate
  作者：Qing-Lan Pei、Bao-Dong Cui、Wen-Yong Han、Zhi-Jun Wu、Xiao-Mei Zhang、Wei-Cheng Yuan

  DOI：10.1016/j.tet.2014.05.052

  日期：2014.8

  A facile synthesis of 3-hydroxy-3-(trifluoromethyl)-1H-pyrrol-2(3H)-ones based on trifluoroacetic acid-catalyzed condensation-cyclization reactions of beta-enamino esters and ethyl trifluoropyruvate is described. These reactions afford a series of alpha-trifluoromethylated gamma-lactam compounds in good to excellent yields under mild conditions. A preliminary trial of an asymmetric catalytic version with chiral BINOL-derived phosphoric acid as enantioselective catalyst was conducted and showed promising enantioselectivity of the desired product. (C) 2014 Elsevier Ltd. All rights reserved.