methyl 2-(3-methoxybenzoyl)-3-(2,4,6-trimethoxyphenyl)acrylate | 1416982-78-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: methyl 2-(3-methoxybenzoyl)-3-(2,4,6-trimethoxyphenyl)acrylate
• CAS: 1416982-78-9
• 化学式: C₂₁H₂₂O₇
• 分子量: 386.401
• InChiKey: HCKGXWPZWNBYAF-UHFFFAOYSA-N

物化性质

• 沸点：
  563.2±50.0 °C(predicted)
• 密度：
  1.199±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.16
• 重原子数：
  28.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl 2-(3-methoxybenzoyl)-3-(2,4,6-trimethoxyphenyl)acrylate 在 nickel(II) bis[bis((trifluoromethyl)sulfonyl)amide] 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 生成 methyl (1R,2R)-5-methoxy-3-oxo-1-(2,4,6-trimethoxyphenyl)-1,2-dihydroindene-2-carboxylate 、
  参考文献：
  名称：

  Catalytic Asymmetric Nazarov Cyclization of Heteroaryl Vinyl Ketones through a Crystallographically Defined Chiral Dinuclear Nickel Complex

  摘要：

  A Ni(NTf2)(2) and tetradentate bisimino-bisquinoline ligand complex catalyzed the enantioselective Nazarov cyclization of heteroaryl vinyl ketones. An X-ray-quality crystal was obtained from a mixture of the Ni complex and the substrate, which was the dinuclear chiral Ni complex. From information regarding the structure of the complex, the substrate was distorted to form a helical shape, and the carbon atoms involved in bond formation were close to each other. In addition, mechanistic studies revealed that the configuration of the olefin moiety was isomerized before bond formation.

  DOI：

  10.1021/acs.orglett.5b02497

文献信息

• Catalytic Nazarov Reaction of Aryl Vinyl Ketones via Binary Acid Strategy
  作者：Zhi-Guo Xi、Lihui Zhu、Sanzhong Luo、Jin-Pei Cheng

  DOI：10.1021/jo302451b

  日期：2013.1.18

  herein a viable binary acid strategy for the catalytic Nazarov reaction of aryl vinyl ketones. Simply combining a Lewis acid and a Brønsted acid led to a dramatic enhancement of the catalytic activity in the Nazarov reaction of aryl vinyl β-ketoesters. The obtained optimal binary acid catalyst In(OTf)3/diphenyl phosphoric acid (DPP) can be applied to a range of aryl vinyl ketones with good activity. A

  我们在本文中描述了用于芳基乙烯基酮的催化Nazarov反应的可行的二元酸策略。路易斯酸和布朗斯台德酸的简单组合导致芳基乙烯基β-酮酸酯的Nazarov反应中催化活性的显着提高。所获得的最佳二元酸催化剂In（OTf）3 /二苯基磷酸（DPP）可用于一系列具有良好活性的芳基乙烯基酮。还基于取代基的作图总结了反应性的趋势。