methyl 1-oxo-2-(3-oxopropyl)-2,3-dihydro-1H-indene-2-carboxylate | 51686-56-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: methyl 1-oxo-2-(3-oxopropyl)-2,3-dihydro-1H-indene-2-carboxylate
• 英文别名: methyl 1-oxo-2-(3-oxo-propyl)-indan-2-carboxylate；Methyl-2-(2-formylaethyl)indan-1-on-2-carboxylat；methyl 3-oxo-2-(3-oxopropyl)-1H-indene-2-carboxylate
• CAS: 51686-56-7；58623-86-2；709037-20-7
• 化学式: C₁₄H₁₄O₄
• 分子量: 246.263
• InChiKey: YTDXVXWZZAWFRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1H-茚-2-甲酸,2,3-二氢-1-氧代-,甲酯 、 丙烯醛 在 NDEAP grafted on silica 作用下， 以 水 为溶剂， 反应 0.33h， 以75%的产率得到methyl 1-oxo-2-(3-oxopropyl)-2,3-dihydro-1H-indene-2-carboxylate
  参考文献：
  名称：

  Heterogeneous Amine Catalyst Grafted on Amorphous Silica: An Effective Organocatalyst for Microwave-promoted Michael Reaction of 1,3-Dicarbonyl Compounds in Water

  摘要：

  在微波加热下，于水中，N,N-二乙基氨基丙基化硅胶（NDEAP）有效地催化1,3-二羰基化合物与α,β-不饱和羰基化合物的迈克尔加成反应。反应条件温和、实用且环境友好。催化剂的可持续性通过重复使用多达5次得以体现。

  DOI：

  10.1246/cl.2006.926

文献信息

• Utilization of Nonionic Bases in Water as a Highly Efficient Organocatalytic System for Michael Addition of β‐Ketoesters
  作者：David Bensa、Jean Rodriguez

  DOI：10.1081/scc-120030703

  日期：2004.12.31

  Michael addition of various beta-ketoesters with several Michael acceptors in water containing 5 mol% of a nonionic base such as phosphazenes, guanidines, and more classical nitrogen containing derivatives or triphenyl phosphine results in high yield conversion to the corresponding adducts. The study also clearly establishes the benefical use of water as solvent compared to more conventional organic medium.
• 1,4-Michael additions of cyclic-β-ketoesters catalyzed by DNA in aqueous media
  作者：Cristina Izquierdo、Javier Luis-Barrera、Alberto Fraile、José Alemán

  DOI：10.1016/j.catcom.2013.08.015

  日期：2014.1

  In this work, we describe the 1,4-Michael addition of the 1,3-dicarbonyl compounds to activated ethylenes under st-DNA catalysis in water. The reaction of the beta-ketoester 4 with nitroolefins and conjugated carbonyls proceeds quite well, whereas other less activated ethylenes exhibit low or null reactivity. The catalyst can be recovered and reused for several catalytic cycles without significantly diminishing its efficiency. These reactions are similarly catalyzed by GMP, methyl-adenine and ethyl guanine, which suggests that the catalytic activity of st-DNA could be associated to the basic nature of their nucleotides' integrants. (C) 2013 Elsevier B.V. All rights reserved.