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2020 , Vol. 40 >Issue 2: 501 - 510

DOI: https://doi.org/10.6023/cjoc201907033

研究论文

新型螺[色烯并(2,3-c)吡唑-4,1'-异苯并呋喃]-3'-酮类化合物的合成及光学性能研究

  • 岳永双 ,
  • 解正峰 ,
  • 褚义成 ,
  • 薛松松
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  • 西南石油大学化学化工学院 油气田应用化学四川省重点实验室 成都 615000

收稿日期: 2019-07-24

  修回日期: 2019-09-09

  网络出版日期: 2019-10-09

基金资助

西南石油大学精细化学品青年科技创新团队（No.2017CXTD05）资助项目.

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Synthesis and Optical Properties of Novel Spiro[chromo(2,3-c)-pyrazole-4,1'-isobenzofuran]-3'-one Compounds

  • Yue Yongshuang ,
  • Xie Zhengfeng ,
  • Chu Yicheng ,
  • Xue Songsong
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  • Oil&Gas Field Applied Chemistry Key Laboratory of Sichuan Province, College of Chemistry and Chemical Engineering, Southwest Petroleum University, Chengdu 610500

Received date: 2019-07-24

  Revised date: 2019-09-09

  Online published: 2019-10-09

Supported by

Project supported by the Youth Science and Technology Innovation Team of Southwest Petroleum University (No. 2017CXTD05).

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摘要

在酸催化及脱水作用下，以2-（4-二丁基氨基-2-羟基苯甲酰基）苯甲酸或2-（4-二乙基氨基-2-羟基苯甲酰基）苯甲酸和吡唑啉酮为原料，通过Knoevenagel缩合和脱水反应，合成了一系列新型螺[色烯并（2，3-c）吡唑-4，1'-异苯并呋喃]-3'-酮类化合物.考察了反应物配比、催化剂、温度和时间等因素对反应的影响，初步探究了所合成化合物在不同pH、溶剂中的光学性能，其中1-（4-氯苯基）-7-（二乙基氨基）-3-甲基-1H，3'H-螺[色烯并[2，3-c]吡唑-4，1'-异苯并呋喃]-3'-酮（1e）和1-（4-氯苯基）-7-（二丁基氨基）-3-甲基-1H，3'H-螺[色烯并[2，3-c]吡唑-4，1'-异苯并呋喃]-3'-酮（1j）有潜力作为强酸强碱的pH指示剂.

关键词： 螺[色烯并(2,3-c)吡唑-4,1'-异苯并呋喃]-3'-酮; 吡唑啉酮; Knoevenagel反应; pH

本文引用格式

岳永双 , 解正峰 , 褚义成 , 薛松松 . 新型螺[色烯并(2,3-c)吡唑-4,1'-异苯并呋喃]-3'-酮类化合物的合成及光学性能研究[J]. 有机化学, 2020 , 40(2) : 501 -510 . DOI: 10.6023/cjoc201907033

Abstract

A series of novel spiro[chromo(2,3-c)pyrazole-4,1'-isobenzofuran]-3'-one compounds were synthesized via Knoevenagel condensation and dehydration reaction of 2-(4-dibutylamino-2-hydroxybenzoyl)benzoic acid or 2-[4-(diethylamino)-2-hydroxybenzoyl]benzoic acid with pyrazolones using acid as catalysts and dehydrants. The effects of the ratio of the substrates, catalyst, temperature and reaction time were examined. Their optical properties in different pH and solvent were investigated. It shows that 1-(4-chlorophenyl)-7-(diethylamino)-3-methyl-1H,3'H-spiro[chromene[2,3-c]pyrazole-4,1'-isobenzofuran]-3'-one (1e) and 1-(4-chlorophenyl)-7-(dibutylamino)-3-methyl-1H,3'H-spiro[chromene[2,3-c]pyrazole-4,1'-isobenzofuran]-3'-one (1j) have potential as pH indicators for strong acids and bases.

Key words： spiro[chromo(2,3-c)pyrazole-4,1'-isobenzofuran]-3'-one; pyrazolone; Knoevenagel reaction; pH

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