Page 228 - 《精细化工》2022年第4期

·864· 精细化工 FINE CHEMICALS 第 39 卷

氧基-3-苯基异色满-1-酮类衍生物。 学), 1992, 20(6): 674-676.
[8] CAI R X (蔡汝秀), WANG L S (王丽莎), CHENG L (程俐), et al.

Direct photometric determination of trace rare earth in human hair[J].
Physical Testing and Chemical Analysis Part B: Chemical Analysis
(理化检验: 化学分册), 1988, 24(1): 2-4.
[9] HOJO D, NOGUCHI K, HIRANO M, et al. Enantioselective
synthesis of spirocyclic benzopyranones by rhodium-catalyzed
intermolecular [4+2] annulation[J]. Angewandte ChemieInternational
Edition, 2008, 47(31): 5820-5822.
[10] ZARRABI S, MAHMOODI N O, TABATABAEIAN K, et al.
Baeyer-Villiger oxidation of cyclic ketones utilizing potassium
peroxydisulfate (K 2S 2O 8) or sodium perborate (NaBO 3) in acidic
media[J]. Chinese Chemical Letters, 2009, 20(12): 1400-1404.

[11] GE X M (葛晓敏). A new method and mechanism of synthesis of
图 2 反应机理 isochromanone[D]. Taiyuan: Shanxi University (山西大学), 2019.
Fig. 2 Reaction mechanism [12] EGAN B A, PARADOWSKI M, THOMAS L H, et al. Regiocontrolled

rearrangement of isobenzofurans[J]. Organic Letters, 2011, 13(8):
2086-2089.
3 结论
[13] RYU L, FUKUYAMA T, BANDO T. Electron-transfer-induced
intramolecular Heck carbonylation reactions leading to benzolactones
以异香豆素类衍生物作为底物，在室温下与卤 and benzolactams[J]. Synthesis, 2018, 50(15): 3015-3021.
化试剂（NBS/NCS）、醇类化合物发生 3,4-位的加成 [14] ZHANG G W (张广威), HU H H (胡海慧), LI S S (李双双), et al.
反应，其中醇类化合物既作为原料又作为溶剂，n(卤 Synthesis of 3-methyl-5-hydroxy-7-carboxyl heterochroman-1-ketone
by hydrothermal driven Claisen rearrangement-nucleophilic addition
代试剂)∶n(Ⅲa)= 2.0∶1，Ⅲa 0.09 mmol，室温（25 ℃）
series reaction[J]. Chinese Journal of Synthetic Chemistry (合成化
反应 7 h，即可得到 90%收率的异色满-1-酮类化合物。 学), 2021, 29(2): 100-104.
并在最佳反应条件下进一步探索反应可能的机理。 [15] SUN L Q, TAKAKI K, CHEN J, et al. N-{2-[2-(4-phenylbutyl)
该方法操作简单、条件温和、室温下反应收率 benzofuran-4-yl]cyclopropylmethyl}acetamide: An orally bioavailable
melatonin receptor agonist[J]. Bioorganic & Medcinal Chemisty
良好，且放大后收率依然稳定，极大地扩展了异色
Letters, 2004, 14(20): 5157-5160.
满-1-酮类化合物的合成途径并具有工业化潜力。 [16] SUN L Q, TAKAKI K, CHEN J, et al. (R)-2-(4-phenylbutyl)
dihydrobenzofuran derivatives as melatoninergic agents[J]. Bioorganic &
参考文献： Medcinal Chemisty Letters, 2005, 15(5): 1345-1349.
[1] LIU Y H (刘宇红), XIONG P W (熊培文), WANG Z C (王振川), et al. [17] SCHAETZER J, EDMUNDS A J F, GAUS K, et al. Efficient
Synthesis and progress of isochroman flavoring compounds[J]. Fine synthesis of fused bicyclic ethers and their application in herbicide
Chemicals (精细化工), 1994, 11(6): 24-27. chemistry[J]. Bioorganic & Medcinal Chemisty Letters, 2014, 24(19):
[2] LU P X (陆培溪). A novel tricyclic heterochromatic synthetic 4643-4649.
musk[J]. Fine Chemicals (精细化工), 1989, 6(5): 29-30. [18] ALEXEY Y D, DMITRY V D, MIKHAIL K, et al. Gold-catalyzed
[3] ZHAO Z F, KANG K W, YUE J X, et al. Research progress in oxidation of internal alkynes into benzils and its application for one-
biological activities of isochroman derivatives[J]. European Journal pot synthesis of five-, six-, and seven-membered azaheterocycles[J].
of Medicinal Chemistry, 2021, 210: 113073-113080. European Journal of Organic Chemistry, 2019, 2019(8): 1856-1864.
[4] FENG Z L, VIVIANE N, NENKEP L, et al. Biotransformation of [19] QIAO J, JIA X W, LI P Y, et al. Gold-catalyzed rapid construction of
bioactive (–)-mellein by a marine isolate of bacterium Stappia sp.[J]. nitrogen-containing heterocyclic compound library with scaffold
Journal of Microbiology and Biotechnology, 2010, 20(6): 985-987. diversity and molecular complexity[J]. Advanced Synthesis & Catalysis,
[5] HIGGINS C A, DELBEDERI Z, MCGAREL K, et al. Synthesis and 2019, 361(6): 1419-1440.
in vitro and in vivo evaluation of a series of dihydroisocoumarin [20] UCHIYAMA M, OZAWA H, TAKUMA K, et al. Regiocontrolled
derivatives conjugated with fatty acids, alcohols, and amines as intramolecular cyclizations of carboxylic acids to carbon-carbon
potential anticancer agents[J]. Bioconjugate Chemistry, 2009, 20(9): triple bonds promoted by acid or base catalyst[J]. Organic Letters,
1737-1751. 2006, 8(24): 5517-5520.
[6] KOUJI K, KAZUNORI T, ISOKO K, et al. Synthesis, structure, and [21] CHOI H Y, SRISOOK E, JANG K S, et al. Electrophilic aromatic
cytotoxicity studies of some fungal isochromanes[J]. Journal of addition reaction: Electrophilic attack at an aromatic H substituent
Natural Products, 2013, 76(9): 1737-1745. position[J]. The Journal of Organic Chemistry, 2005, 70(4): 1222-1226.
[7] PAN F Y (潘富友), ZHANG S W (张孙玮). A new chromogenic [22] VAN DER LINDE J, HAVINGA E. The addition of bromine to
agent 1-(2-imidazolazo)-2-naphthol-4-sulfonic acid as a complexometric phenanthrene in methanol as a solvent[J]. Recueil des Travaux
titration indicator[J]. Chinese Journal of Analysis Chemistry (分析化 Chimiques des Pays-Bas, 1965, 84(8): 1047-1058.