4830-93-7Relevant academic research and scientific papers
Nucleophilic substitution reactions of unbranched alkyl amines using triazine reagents
Kitamura, Masanori,Kitaoka, Yuki,Fujita, Hikaru,Kunishima, Munetaka
, (2022/03/02)
Since amines are present in many organic, biological, and drug molecules, a strategy of synthesizing desired compounds by nucleophilic substitution reactions of these amines is very attractive. By using triazine reagents, we have found that nucleophilic substitution reactions of unbranched alkyl amines via morpholine derivatives are feasible. This method can be performed under milder reaction conditions than those in previously reported methods.
Chemoselective Homologation-Deoxygenation Strategy Enabling the Direct Conversion of Carbonyls into (n+1)-Halomethyl-Alkanes
Citarella, Andrea,Holzer, Wolfgang,Ielo, Laura,Langer, Thierry,Miele, Margherita,Pace, Vittorio,Urban, Ernst,Zehl, Martin
supporting information, p. 7629 - 7634 (2020/10/12)
The sequential installation of a carbenoid and a hydride into a carbonyl, furnishing halomethyl alkyl derivatives, is reported. Despite the employment of carbenoids as nucleophiles in reactions with carbon-centered electrophiles, sp3-type alkyl halides remain elusive materials for selective one-carbon homologations. Our tactic levers on using carbonyls as starting materials and enables uniformly high yields and chemocontrol. The tactic is flexible and is not limited to carbenoids. Also, diverse carbanion-like species can act as nucleophiles, thus making it of general applicability.
Preparation method of p-phenylbutoxybenzoic acid
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Paragraph 0049-0050, (2020/07/24)
The invention discloses a preparation method of p-phenylbutoxybenzoic acid. The preparation method comprises the following steps: using tetrahydrofuran as an initial raw material; carrying out a catalytic reaction with benzoyl chloride to prepare 4-chlorobutanol benzoate; carrying out a Friedel-Crafts alkylation reaction and hydrolysis on 4-chlorobutanol benzoate and benzene to obtain 4-phenylbutanol, carrying out a reaction on the 4-phenylbutanol and thionyl chloride to obtain 4-phenylchlorobutane, carrying out an alkylation reaction on the 4-phenylchlorobutane and methyl p-hydroxybenzoate under the action of potassium carbonate to obtain methyl p-phenylbutoxybenzoate. The raw materials used in the invention are cheap and easily available, the process is easy to realize industrialization,and the obtained final product has the advantages of high purity, novel route, short synthesis route, no dangerous process and simple equipment.
Preparation method for p-phenylbutoxybenzoic acid
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, (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.
Organocatalytic Chlorination of Alcohols by P(III)/P(V) Redox Cycling
Longwitz, Lars,Jopp, Stefan,Werner, Thomas
supporting information, p. 7863 - 7870 (2019/06/27)
A catalytic system for the chlorination of alcohols under Appel conditions was developed. Benzotrichloride is used as a cheap and readily available chlorinating agent in combination with trioctylphosphane as the catalyst and phenylsilane as the terminal reductant. The reaction has several advantages over other variants of the Appel reaction, e.g., no additional solvent is required and the phosphane reagent is used only in catalytic amounts. In total, 27 different primary, secondary, and tertiary alkyl chlorides were synthesized in yields up to 95%. Under optimized conditions, it was also possible to convert epoxides and an oxetane to the dichlorinated products.
Halogenation through Deoxygenation of Alcohols and Aldehydes
Chen, Jia,Lin, Jin-Hong,Xiao, Ji-Chang
supporting information, p. 3061 - 3064 (2018/05/28)
An efficient reagent system, Ph3P/XCH2CH2X (X = Cl, Br, or I), was very effective for the deoxygenative halogenation (including fluorination) of alcohols (including tertiary alcohols) and aldehydes. The easily available 1,2-dihaloethanes were used as key reagents and halogen sources. The use of (EtO)3P instead of Ph3P could also realize deoxy-halogenation, allowing for a convenient purification process, as the byproduct (EtO)3Pa?O could be removed by aqueous washing. The mild reaction conditions, wide substrate scope, and wide availability of 1,2-dihaloethanes make this protocol attractive for the synthesis of halogenated compounds.
Synthesis of N-ω-phenylalkyl-4-(p-chlorophenyl)-piperidin-4-ol analogues with potent antiproliferative activity against HCT-116 cells
Hatae, Noriyuki,Kujime, Eiko,Yano, Keigo,Kizuka, Mami,Ashida, Rina,Choshi, Tominari,Nishiyama, Takashi,Okada, Chiaki,Iwamura, Tatsunori,Yoshimura, Teruki
, p. 560 - 568 (2019/07/31)
Some opioid analogues, such as morphine and loperamide, were reported to exhibit weak antiproliferative activity against tumor cells. In a study of loperamide analogues, we found that adding an N-ω-phenylalkyl group onto the 4-arylpiperidin-4-ol unit can have important effects on the antiproliferative activity of such compounds against HCT-116 cells. We optimized the distance between the phenyl group and 4-arylpiperidin unit to promote such activity.
To a synthesis process of benzene butoxy benzoic acid (by machine translation)
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Paragraph 0052; 0079-0081; 0083-0085, (2018/10/19)
The invention discloses a synthesis process of benzene butoxy benzoic acid, comprises the following synthetic steps: chlorobenzene with magnesium format obtained by reaction of Grignard reagent, Grignard reagent with 1 - bromo - 4 - chlorobutane coupling reaction to obtain the 1 - chloro - 4 - phenyl butane, 1 - chloro - 4 - phenyl butane with the hydroxy benzoic acid condensation reaction to get the butoxy benzoic acid, its reaction equation as follows: This synthetic route step is simple, easy to operate, in the course of synthesizing highly toxic intermediate [...] and avoids the generation of a large amount of waste water, thus not only environment friendly, thereby saving the production cost, the process is obtained by the synthesis of high-purity para-butoxy benzoic acid, suitable for large-scale industrial production. (by machine translation)
Catalytic Access to Alkyl Bromides, Chlorides and Iodides via Visible Light-Promoted Decarboxylative Halogenation
Candish, Lisa,Standley, Eric A.,Gómez-Suárez, Adrián,Mukherjee, Satobhisha,Glorius, Frank
supporting information, p. 9971 - 9974 (2016/07/19)
Herein is reported the catalytic, visible light-promoted, decarboxylative halogenation (bromination, chlorination, and iodination) of aliphatic carboxylic acids. This operationally-simple reaction tolerates a range of functional groups, proceeds at room temperature, and is redox neutral. By employing an iridium photocatalyst in concert with a halogen atom source, the use of stoichiometric metals such as silver, mercury, thallium, and lead can be circumvented. This reaction grants access to valuable synthetic building blocks from the large pool of cheap, readily available carboxylic acids.
Visible light promoted hydrochlorination of olefin over Pt, Au and Pd supported on zirconia
Yang, Xuzhuang,Zhu, Huaiyong,Gao, Guanjun,Han, Chenhui,Wang, Jie,Liu, Jie,Lu, Huailiang,Tong, Min,Liang, Xiaoyuan
, p. 81 - 86 (2014/03/21)
The Pt, Au and Pd catalysts supported on zirconia were prepared by the colloid deposition method. The catalytic activities of the catalysts for the hydrochlorination of 4-phenyl-1-butene were investigated under the irradiation of visible light, taking hyd
