7515-41-5Relevant academic research and scientific papers
Enantioselective Copper(I)/Chiral Phosphoric Acid Catalyzed Intramolecular Amination of Allylic and Benzylic C?H Bonds
Ye, Liu,Tian, Yu,Meng, Xiang,Gu, Qiang-Shuai,Liu, Xin-Yuan
, p. 1129 - 1133 (2019/12/12)
Radical-involved enantioselective oxidative C?H bond functionalization by a hydrogen-atom transfer (HAT) process has emerged as a promising method for accessing functionally diverse enantioenriched products, while asymmetric C(sp3)?H bond amination remains a formidable challenge. To address this problem, described herein is a dual CuI/chiral phosphoric acid (CPA) catalytic system for radical-involved enantioselective intramolecular C(sp3)?H amination of not only allylic positions but also benzylic positions with broad substrate scope. The use of 4-methoxy-NHPI (NHPI=N-hydroxyphthalimide) as a stable and chemoselective HAT mediator precursor is crucial for the fulfillment of this transformation. Preliminary mechanistic studies indicate that a crucial allylic or benzylic radical intermediate resulting from a HAT process is involved.
Ring opening of methylenecyclopropanes with halides in liquid sulfur dioxide
Le?kovskis, Kristaps,Gulbe, Krista,Mishnev, Anatoly,Turks, Māris
supporting information, (2020/10/19)
Methylenecyclopropanes (MCP) undergo ring opening reactions with group I and II metal halides and ammonium halides in liquid SO2 to afford homoallylic halides, which are versatile reagents in organic synthesis. The developed reaction conditions are compatible with acid-labile substrates such as N-Boc-protected compounds. Liquid SO2 is a polar reaction medium with Lewis acid properties that solubilizes inorganic salts. The unique properties of SO2 were demonstrated by control experiments: 1) upon performing the reactions with the aforementioned salts in conventional solvents, the MCP ring opening was not observed either in the presence of catalytic amounts of H3PO4 (similar pKa to that of H2SO3), or in the absence of H3PO4; 2) a solution of SO2 in THF exhibited similar properties to that of liquid SO2.
Arene Trifunctionalization with Highly Fused Ring Systems through a Domino Aryne Nucleophilic and Diels–Alder Cascade
He, Jia,Jia, Zizi,Tan, Hongcheng,Luo, Xiaohua,Qiu, Dachuan,Shi, Jiarong,Xu, Hai,Li, Yang
supporting information, p. 18513 - 18518 (2019/11/19)
A convenient and efficient domino aryne process was developed under transition-metal-free conditions to generate a range of tetra- and pentacyclic ring systems. This transformation was realized via a 1,2-benzdiyne through a nucleophilic and Diels–Alder reaction cascade using styrene as the diene moiety. Three new chemical bonds, namely one C?N and two C?C bonds, and two benzofused rings could be constructed concomitantly, which was made possible by distinct chemoselective control at both the 1,2-aryne and 2,3-aryne stages. Moreover, in-depth studies were carried out on the domino aryne precursors and controlling the diastereoselectivity.
Spiro[3.5]nonenyl Meroterpenoid Lactones, Cryptolaevilactones G-L, an Ionone Derivative, and Total Synthesis of Cryptolaevilactone M from Cryptocarya laevigata
Tsurumi, Fumika,Miura, Yuta,Nakano, Misaki,Saito, Yohei,Fukuyoshi, Shuichi,Miyake, Katsunori,Newman, David J.,O'Keefe, Barry R.,Lee, Kuo-Hsiung,Nakagawa-Goto, Kyoko
, p. 2368 - 2378 (2019/10/02)
A CH3OH-CH2Cl2 (1:1) extract (N025439) of the leaves and twigs of Cryptocarya laevigata furnished eight new compounds, 1-8. Based on extensive 1D and 2D NMR spectroscopic data examination, the new δ-lactone derivatives 1-6 are monoterpene-polyketide hybrids containing a unique spiro[3.5]nonenyl moiety. Their trivial names, cryptolaevilactones G-L, follow those of the related known meroterpenoids cryptolaevilactones A-F. Cryptolaevilactone L (6) contains 11,12-cis-oriented substituents, while the other cryptolaevilactones contain trans-oriented groups. The structure of the linear δ-lactone 7, cryptolaevilactone M, was characterized from various spectroscopic data analysis, and the absolute configuration was determined by total synthesis through stereoselective allylation and Grubbs olefin metathesis. Compound 8 was elucidated to be an ionone derivative with a 3,4-syn-diol functionality.
Preparation method for p-phenylbutoxybenzoic acid
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Paragraph 0084-0085, (2019/11/04)
The invention provides a preparation method for p-phenylbutoxybenzoic acid, belonging to the field of organic synthesis. According to the invention, palladium-based catalytic coupling is adopted, andthe Grignard reaction and the Friedel-Craft reaction are avoided, thereby avoiding the production of blue-green copper ion wastewater and generation of a large amount of acidic wastewater due to usageof aluminum trichloride; the preparation method of the invention is friendly to environment, simple in synthesis route and high in the yield of each step; and halogeno-benzene is used for replacing more expensive phenylmagnesium bromide and used as a starting material, so the preparation cost of p-phenylbutoxybenzoic acid is lowered. The p-phenylbutoxybenzoic acid obtained in the invention has good crystal form, high purity and good solubility. The data of embodiments of the invention show that the total yield of p-phenylbutoxybenzoic acid prepared in the invention is 60% or above, and the HPLC purity of p-phenylbutoxybenzoic acid is 99.9% or above.
MANUFACTURING METHOD OF BROMINATED CYCLOPROPANES
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Paragraph 0035, (2017/04/28)
PROBLEM TO BE SOLVED: To provide a manufacturing method capable of simply providing bromoalkyl cyclopropanes in an industrial scale. SOLUTION: There is provided a manufacturing method of bromoalkyl cyclopropanes represented by the formula (3) or the formula (4) by reacting corresponding alcohols and HBr dissolved in an aprotic solvent such as 1,4-dioxanes and substituting a hydroxyl group by Br. (3) (4), where R1 is H, a C1 to 10 substituted/unsubstituted linear/branched alkyl group, a C3 to 10 substituted/unsubstituted cyclic alkyl group, R2 is a substituted/unsubstituted phenyl group and n is an integer of 1 to 10. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT
Discovery of Potent Benzofuran-Derived Diapophytoene Desaturase (CrtN) Inhibitors with Enhanced Oral Bioavailability for the Treatment of Methicillin-Resistant Staphylococcus aureus (MRSA) Infections
Wang, Youxin,Chen, Feifei,Di, Hongxia,Xu, Yong,Xiao, Qiang,Wang, Xuehai,Wei, Hanwen,Lu, Yanli,Zhang, Lingling,Zhu, Jin,Sheng, Chunquan,Lan, Lefu,Li, Jian
, p. 3215 - 3230 (2016/05/19)
Blocking the staphyloxanthin biosynthesis process has emerged as a new promising antivirulence strategy. Previously, we first revealed that CrtN is a druggable target against infections caused by pigmented Staphylococcus aureus (S. aureus) and that naftifine was an effective CrtN inhibitor. Here, we identify a new type of benzofuran-derived CrtN inhibitor with submicromolar IC50 values that is based on the naftifine scaffold. The most potent analog, 5m, inhibits the pigment production of S. aureus Newman and three MRSA strains, with IC50 values of 0.38-5.45 nM, without any impact on the survival of four strains (up to 200 μM). Notably, compound 5m (1 μM) could significantly sensitize four strains to immune clearance and could effectively attenuate the virulence of three strains in vivo. Moreover, 5m was determined to be a weak antifungal reagent (MIC > 16 μg/mL). Combined with good oral bioavailability (F = 42.2%) and excellent safety profiles, these data demonstrate that 5m may be a good candidate for the treatment of MRSA infections.
A mild and efficient method for bromination of alcohols using α,α-dibromo-β-dicarbonyl compounds as halogen sources
Cui, Xiao-Meng,Guan, Yong-Hong,Li, Na,Lv, Hao,Fu, Lin-An,Guo, Kun,Fan, Xiaohui
supporting information, p. 90 - 93 (2014/01/06)
Exploration of α,α-dibromo-β-dicarbonyl compounds as novel bromine agents for the conversion of alcohols to alkyl bromides under neutral conditions has been achieved. This method can be used for acid-sensitive substrates and allows the bromination of various primary and secondary alcohols to proceed at room temperature within a very short period of time.
A method for synthesis of homoallylic bromide
Qi, Wenke,Wang, Peipei,Fan, Liyuan,Zhang, Songlin
, p. 5918 - 5924 (2013/07/26)
Cyclopropyl Grignard reagents react with carbonyl compounds in the presence of diethyl phosphite to give homoallylic bromides. The reaction is effectively carried out under mild conditions in a one-pot fashion with moderate to good yields.
One-pot synthesis of benzo[f]quinolin-3-ones and benzo[a]phenanthridein-5- ones by the photoanuulation of 6-chloropyridin-2-ones and 3-chloroisoquinolin-1- ones to phenylacetylene
Wang, Ren,Lu, Shen-Ci,Zhang, Yi-Ming,Shi, Zong-Jun,Zhang, Wei
, p. 5802 - 5808 (2011/10/02)
The one-pot synthesis of benzo[f]quinolin-3-ones and benzo[a] phenanthridein-5-ones was achieved by the inter- and intramolecular photoannulation of 6-chloropyridin-2-ones and 3-chloroisoquinolin-1-ones with phenylacetylene or tethered phenylacetylene. The reactions were proceeded by photoaddition of 6-chloropyridin-2-ones and 3-chloroisoquinolin-1-ones to phenylacetylene to give the chlorine-substituted stilbenoids, and then 6π electrocyclization of the stilbenoids and oxidation aromatization to afford the polycyclic products.
