4385-35-7Relevant academic research and scientific papers
Green Oxidation of Ketones to Lactones with Oxone in Water
Bertolini, Valentina,Appiani, Rebecca,Pallavicini, Marco,Bolchi, Cristiano
, p. 15712 - 15716 (2021/11/01)
Cyclic ketones were quickly and quantitatively converted to 5-, 6-, and 7-membered lactones, very important synthons, by treatment with Oxone, a cheap, stable, and nonpollutant oxidizing reagent, in 1 M NaH2PO4/Na2HPO4 water solution (pH 7). Under such simple and green conditions, no hydroxyacid was formed, thus making the adoption of more complex and non-eco-friendly procedures previously developed to avoid lactone hydrolysis unnecessary. With some changes, the method was successfully applied also to water-insoluble ketones such as adamantanone, acetophenone, 2-indanone, and the challenging cycloheptanone.
Visible Light-Promoted Magnesium, Iron, and Nickel Catalysis Enabling C(sp3)-H Lactonization of 2-Alkylbenzoic Acids
Li, Sasa,Su, Mincong,Sun, Jie,Hu, Kunjun,Jin, Jian
supporting information, p. 5842 - 5847 (2021/07/31)
A mild and practical C(sp3)-H lactonization protocol has been achieved by merging photocatalysis and magnesium (iron, nickel) catalysis. A diverse range of 2-alkylbenzoic acids with a variety of substitution patterns could be transformed into the corresponding phthalide products. Based on the mechanistic experimentation and reported prior studies, a possible mechanism for the benzylic oxidative lactonization reaction was proposed with the hypothetic photoactive ternary complex formed between the 2-alkylbenzoic acid substrate, magnesium ion, and bromate anion.
Nickel-Catalyzed Desymmetrizing Cyclization of 1,6-Dienes to Construct Quaternary Stereocenters
Zhao, Tian-Yuan,Li, Ke,Yang, Liang-Liang,Zhu, Shou-Fei,Zhou, Qi-Lin
supporting information, p. 3814 - 3817 (2021/05/26)
A highly enantioselective and diastereoselective nickel-catalyzed desymmetrizing cyclization of 1,6-dienes was developed by using chiral spiro phosphoramidite ligands. The reaction provides a new atom- and step-economical approach to chiral spiro lactones and analogues bearing a quaternary stereocenter.
Regioselective biocatalytic self-sufficient Tishchenko-type reactionviaformal intramolecular hydride transfer
Buljubasic, Isa,Hall, Mélanie,Laggner, Olivia,Merusic, Kemal,Reiter, Tamara,Tassano, Erika,Vogel, Andreas
supporting information, p. 6340 - 6343 (2020/06/21)
A self-sufficient nicotinamide-dependent intramolecular bio-Tishchenko-type reaction was developed. The reaction is catalyzed by alcohol dehydrogenases and proceeds through formal intramolecular hydride transfer on dialdehydes to deliver lactones. Regioselectivity on [1,1′-biphenyl]-2,2′-dicarbaldehyde substrates could be controlledviathe electronic properties of the substituents. Preparative scale synthesis provided access to substituted dibenzo[c,e]oxepin-5(7H)-ones.
(Cyclopentadienone)iron-Catalyzed Transfer Dehydrogenation of Symmetrical and Unsymmetrical Diols to Lactones
Tang, Yidan,Meador, Rowan I. L.,Malinchak, Casina T.,Harrison, Emily E.,McCaskey, Kimberly A.,Hempel, Melanie C.,Funk, Timothy W.
, p. 1823 - 1834 (2020/02/04)
Air-stable iron carbonyl compounds bearing cyclopentadienone ligands with varying substitution were explored as catalysts in dehydrogenative diol lactonization reactions using acetone as both the solvent and hydrogen acceptor. Two catalysts with trimethylsilyl groups in the 2- A nd 5-positions, [2,5-(SiMe3)2-3,4-(CH2)4(δ4-C4C= O)]Fe(CO)3 (1) and [2,5-(SiMe3)2-3,4-(CH2)3(δ4-C4C= O)]Fe(CO)3 (2), were found to be the most active, with 2 being the most selective in the lactonization of diols containing both primary and secondary alcohols. Lactones containing five-, six-, and seven-membered rings were successfully synthesized, and no over-oxidations to carboxylic acids were detected. The lactonization of unsymmetrical diols containing two primary alcohols occurred with catalyst 1, but selectivity was low based on alcohol electronics and modest based on alcohol sterics. Evidence for a transfer dehydrogenation mechanism was found, and insight into the origin of selectivity in the lactonization of 1°/2° diols was obtained. Additionally, spectroscopic evidence for a trimethylamine-ligated iron species formed in solution during the reaction was discovered.
Synthesis method of 3-isochromanone
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, (2021/01/04)
The invention belongs to the technical field of synthesis of organic intermediates, and particularly relates to a synthesis method of 3-isochromanone, which comprises the following steps of: (1) synthesizing o-methyl benzyl chloride by using o-xylene as a raw material; (2) synthesizing o-methyl benzyl cyanide by taking o-methyl benzyl chloride as a raw material; (3) synthesizing sodium o-methyl phenylacetate by taking o-methyl benzyl cyanide as a raw material; (4) synthesizing o-methyl phenylacetic acid by taking sodium o-methyl phenylacetate as a raw material; (5) synthesizing 2-chloromethylphenylacetic acid by taking o-methyl phenylacetic acid as a raw material; and (6) synthesizing 3-isochromanone by taking 2-chloromethyl phenylacetic acid as a raw material. The synthesis method of 3-isochromanone has the advantages of simple reaction process, easily available raw materials, mild reaction conditions, high product yield, low production cost, high yield, high product purity, good quality, low production waste discharge amount and the like, the product purity is greater than or equal to 99.5%, the production yield is greater than or equal to 92%, and the product meets the use requirements of foreign high-end users.
Platinum-on-Carbon-Catalyzed Aqueous Oxidative Lactonization of Diols by Using Molecular Oxygen
Ban, Kazuho,Sajiki, Hironao,Sawama, Yoshinari,Takakura, Ryoya
supporting information, p. 1919 - 1923 (2019/09/30)
A lactonization of various diols catalyzed by platinum on carbon (Pt/C) in water under an atmosphere of molecular oxygen was developed. Derivatives of 1,4- 1,5- and 1,6-diols were transformed into the corresponding five-, six-, and seven-membered lactones by the present oxidative lactonization method.
3 - Isochromanone micro-channel synthesis method (by machine translation)
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Paragraph 0026-0035, (2019/03/28)
The invention discloses a 3 - isochromanone micro-channel synthesis method, the reaction steps are as follows: 1) to O-methyl acetic acid as the raw material, under an appropriate temperature and in a suitable solvent, using microchannel reaction technology, in order to chloride is a chlorination reagent to prepare the O-methyl acetic acid; 2) synthesis of O-methyl acetic acid without purification, in the appropriate alkali and temperature, cyclization reaction to obtain 3 - isochromanone. Through the above-mentioned way, the invention can be high-yield, high-purity, controllable production of O-methyl acetic acid, while the latter can be smoothly under alkaline conditions to produce the target product 3 - isochromanone. (by machine translation)
A General, Activator-Free Palladium-Catalyzed Synthesis of Arylacetic and Benzoic Acids from Formic Acid
Wang, Lin,Neumann, Helfried,Beller, Matthias
supporting information, p. 6910 - 6914 (2018/06/04)
A new catalyst for the carboxylative synthesis of arylacetic and benzoic acids using formic acid (HCOOH) as the CO surrogate was developed. In an improvement over previous work, CO is generated in situ without the need for any additional activators. Key to success was the use of a specific system consisting of palladium acetate and 1,2-bis((tert-butyl(2-pyridinyl)phosphinyl)methyl)benzene. The generality of this method is demonstrated by the synthesis of more than 30 carboxylic acids, including non-steroidal anti-inflammatory drugs (NSAIDs), under mild conditions in good yields.
A 3 - different chromone preparation method
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Paragraph 0019-0033, (2017/08/17)
The invention discloses a method for preparing 3-isochromanone. The method includes the steps that organic solvent is added into o-tolylacetic acid to be heated to 50-60 DEG C, phosphorus oxychloride is added while stirring is conducted, reacting continues till the o-tolylacetic acid disappears, and reacting is stopped; then the organic solvent is cooled, washed and dried, and accordingly the 3-isochromanone is obtained. According to the method, the technology is relatively simple, the raw materials can be obtained easily, and cost is low. Moreover, the quantity of three wastes is small, the content and yield of target products are high, and the method is suitable for industrial production.
