methyl 1-oxo-2-(4-oxobutan-2-yl)-2,3-dihydro-1H-indene-2-carboxylate

• 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-(4-oxobutan-2-yl)-2,3-dihydro-1H-indene-2-carboxylate
• 英文别名: methyl 1-oxo-2-(1-methyl-3-oxo-propyl)-indan-2-carboxylate；methyl 1-oxo-2-(1-methyl-3-oxopropyl)indan-2-carboxylate；methyl 3-oxo-2-(4-oxobutan-2-yl)-1H-indene-2-carboxylate
• 化学式: C₁₅H₁₆O₄
• 分子量: 260.29
• InChiKey: OSAGSMBYCGFSPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  巴豆醛 、 1H-茚-2-甲酸,2,3-二氢-1-氧代-,甲酯 在 polystyrene supported P₁ iminophosphorane P-BEMP 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以78%的产率得到methyl 1-oxo-2-(4-oxobutan-2-yl)-2,3-dihydro-1H-indene-2-carboxylate
  参考文献：
  名称：

  P-BEMP：一种新型高效且可商购的、用户友好且可回收的多相有机催化剂，用于迈克尔加成 1,3-二羰基化合物

  摘要：

  已发现 1,3-二羰基与各种迈克尔受体的迈克尔加成可通过固定在聚苯乙烯树脂 (P-BEMP) 上的市售、用户友好和可回收的 N-苯基-三(二甲氨基)亚氨基正膦催化。该反应不需要无水溶剂或惰性气氛，在室温下顺利进行，得到相应的加合物，通过简单的过滤即可方便地以高收率和高化学纯度进行分离。

  DOI：

  10.1055/s-2004-815996

文献信息

• Highly Efficient Phosphazene Base-Catalyzed Michael Addition of <i>β</i>-Ketoesters in Water
  作者：David Bensa、Jean-Michel Brunel、Gérard Buono、Jean Rodriguez

  DOI：10.1055/s-2001-13369

  日期：——

  Michael addition of various β-ketoesters with several Michael acceptors in water containing 10 mol% of N-phenyltris(dimethylamino)iminophosphorane results in high yield conversion to the corresponding adducts.

  含有10摩尔% N-苯基三(二甲基氨基)亚胺膦的水中，各种β-酮酯与多个Michael受体发生Michael加成反应，结果是相应加合产物的高产率转化。
• 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.