Synthesis of Polysubstituted Benzenes from 2-Pyrone-4,6-dicarboxylic Acid

被引：16

作者：

Okura, Keisho ^{[1
,2
]}

Tamura, Ryuichi ^{[1
]}

Shigehara, Kiyotaka ^{[3
]}

Masai, Eiji ^{[4
]}

Nakamura, Masaya ^{[5
]}

Otsuka, Yuichiro ^{[5
]}

Katayama, Yoshihiro ^{[6
]}

Nakao, Yoshiaki ^{[1
,7
]}

机构：

[1] Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Nishikyo Ku, Kyoto 6158510, Japan

[2] Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan

[3] Tokyo Univ Agr & Technol, Grad Sch Engn, Koganei, Tokyo 1848588, Japan

[4] Nagaoka Univ Technol, Dept Bioengn, Nagaoka, Niigata 9402188, Japan

[5] Forestry & Forest Prod Res Inst, Tsukuba, Ibaraki 3058687, Japan

[6] Nihon Univ, Coll Bioresource Sci, Fujisawa, Kanagawa 2520880, Japan

[7] Japan Sci & Technol Agcy, PRESTO, Kawaguchi, Saitama 3320012, Japan

来源：

CHEMISTRY LETTERS | 2014年 / 43卷 / 08期

关键词：

INTERMOLECULAR ORBITAL THEORY; METABOLIC INTERMEDIATE; CONJUGATED SYSTEMS; CYCLOADDITION; LIGNIN;

D O I：

10.1246/cl.140427

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Cycloaddition reactions of a lignin-derived pyrone derivative, 2-pyrone-4,6-dicarboxylic acid, and its dimethyl ester with alkenyl acetates and alkynes under thermal conditions proceed with decarboxylation to give isophthalic acids and various mono- and disubstituted isophthalates. A ruthenium complex catalyzes the reaction with alkynes under milder conditions and affords products with different regioselectivity from that observed under thermal conditions.

引用

页码：1349 / 1351

页数：3

共 50 条

[21] Development of the production of 2-pyrone-4,6-dicarboxylic acid from lignin extracts, which are industrially formed as by-products, as raw materials
Suzuki, Yuzo
Okamura-Abe, Yuriko
Nakamura, Masaya
Otsuka, Yuichiro
Araki, Takuma
Otsuka, Hiroyuki
Navarro, Ronald Ragudo
Kamimura, Naofumi
Masai, Eiji
Katayama, Yoshihiro
JOURNAL OF BIOSCIENCE AND BIOENGINEERING, 2020, 130 (01) : 71 - 75
[22] Unique Complexation Behavior of Alkali Metal Ions and 2-Pyrone-4,6-Dicarboxylic Acid (PDC) Obtained from a Metabolic Intermediate of Lignin
Masami Bito
Yuichiro Otsuka
Masaya Nakamura
Eiji Masai
Yoshihiro Katayama
Kiyotaka Shigehara
Kazuhiro Shikinaka
Waste and Biomass Valorization, 2019, 10 : 1261 - 1265
[23] Microbial production of 2-pyrone-4,6-dicarboxylic acid from lignin derivatives in an engineered Pseudomonas putida and its application for the synthesis of bio-based polyester
Lee, Siseon
Jung, Ye Jean
Park, Si Jae
Ryu, Mi-Hee
Kim, Joo Eon
Song, Hye Min
Kang, Kyoung Hee
Song, Bong Keun
Sung, Bong Hyun
Kim, Yong Hwan
Kim, Hee Taek
Joo, Jeong Chan
BIORESOURCE TECHNOLOGY, 2022, 352
[24] Preferential cesium ion trapping by 2-pyrone-4,6-dicarboxylic acid (PDC) obtained from a metabolic intermediate of lignin, a woody biomass resource
Shikinaka, Kazuhiro
Otsuka, Yuichiro
Iguchi, Yuri
Nakamura, Masaya
Itoh, Yuko
Masai, Eiji
Katayama, Yoshihiro
Shigehara, Kiyotaka
JOURNAL OF NUCLEAR SCIENCE AND TECHNOLOGY, 2016, 53 (09) : 1256 - 1259
[25] Metabolic engineering of Escherichia coli for high-level production of the biodegradable polyester monomer 2-pyrone-4,6-dicarboxylic acid
Wu, Fengli
Wang, Shucai
Zhou, Dan
Gao, Shukai
Song, Guotian
Liang, Yanxia
Wang, Qinhong
METABOLIC ENGINEERING, 2024, 83 : 52 - 60
[26] Application of microalgae hydrolysate as a fermentation medium for microbial production of 2-pyrone 4,6-dicarboxylic acid
Htet, April N.
Noguchi, Mana
Ninomiya, Kazuaki
Tsuge, Yota
Kuroda, Kosuke
Kajita, Shinya
Masai, Eiji
Katayama, Yoshihiro
Shikinaka, Kazuhiro
Otsuka, Yuichiro
Nakamura, Masaya
Honda, Ryo
Takahashi, Kenji
JOURNAL OF BIOSCIENCE AND BIOENGINEERING, 2018, 125 (06) : 717 - 722
[27] High-level production of 2-pyrone-4,6-dicarboxylic acid from vanillic acid as a lignin-related aromatic compound by metabolically engineered fermentation to realize industrial valorization processes of lignin
Otsuka, Yuichiro
Araki, Takuma
Suzuki, Yuzo
Nakamura, Masaya
Kamimura, Naofumi
Masai, Eiji
BIORESOURCE TECHNOLOGY, 2023, 377
[28] Mechanical Properties of Poly(L-Lactide) Films Controlled by Blending with Polyesters of Lignin-Derived Stable Metabolic Intermediate, 2-Pyrone-4,6-Dicarboxylic Acid (PDC)
Michinobu, Tsuyoshi
Bito, Masami
Tanimura, Miki
Katayama, Yoshihiro
Masai, Eiji
Nakamura, Masaya
Otsuka, Yuichiro
Ohara, Seiji
Shigehara, Kiyotaka
POLYMER JOURNAL, 2009, 41 (10) : 843 - 848
[29] Efficient production of 2-pyrone 4,6-dicarboxylic acid as a novel polymer-based material from protocatechuate by microbial function
Yuichiro Otsuka
Masaya Nakamura
Kiyotaka Shigehara
Kosuke Sugimura
Eiji Masai
Seiji Ohara
Yoshihiro Katayama
Applied Microbiology and Biotechnology, 2006, 71 : 608 - 614
[30] Theoretical study of the hydrolysis mechanism of 2-pyrone-4,6-dicarboxylate (PDC) catalyzed by LigI
Zhang, Shujun
Ma, Guangcai
Liu, Yongjun
Ling, Baoping
JOURNAL OF MOLECULAR GRAPHICS & MODELLING, 2015, 61 : 21 - 29

← 1 2 3 4 5 →