6704-31-0Relevant articles and documents
Synthesis method of 3-oxetanone
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Paragraph 0040; 0046-0048; 0054-0056; 0062-0062, (2020/11/25)
The invention discloses a synthesis method of 3-oxetanone. Specifically, 1, 3-dichloroacetone and ethylene glycol are taken as raw materials, 3-oxetanone is synthesized at high yield through three steps of carbonyl protection reaction, ring closing reaction and deprotection reaction. The preparation method of 3-oxetanone is a synthesis method which is high in yield, low in cost, environment-friendly, easy to operate and suitable for industrialization.
A method for synthesis of oxetane butanone (by machine translation)
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Paragraph 0021; 0022, (2019/03/26)
The present invention provides a method for synthesis of oxetane butanone, the method is used in the organic solvent, diluent, organic alkali exist under the conditions, by dehydrating the oxidizing agent will be 3 - oxygen heterocyclic butanol oxidation, further separation and purification to obtain 3 - oxetanone; the organic solvent as chain alkanes, halogenated hydrocarbon, alcohol, ethers in a; the thinner is dimethyl sulfoxide, N, N - dimethyl formamide in a; the organic base is triethylamine, ethylenediamine, diisopropyl ethylamine in a; the dehydration of the oxidizing agent is P2 O5 , P2 O3 In a. The present invention uses a phosphorus pentoxide system to oxidation to produce 3 - oxetanone, materials used in the cheap, is relatively simple in operation, avoids the use of hazardous chemicals, friendly to the environment, there are higher reaction yield, conducive to 3 - oxetanone in organic chemical and biological medicinal further application and development. (by machine translation)
3-oxetanone synthesis method
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Paragraph 0019; 0021, (2019/05/04)
The invention provides a 3-oxetanone synthesis method, which comprises: removing the protection group from an intermediate in an organic solvent I by using an organic strong acid, neutralizing with aweak alkali to achieve an alkaline pH value, carrying out concentration distillation on the solvent to obtain a oxetan-3-ol crude product, oxidizing the oxetan-3-ol with an oxidizing agent in the presence of a catalyst I, a halide and an alkali, and carrying out separating purification to obtain the 3-oxetanone product, wherein the intermediate preparation method comprises: carrying out a ring opening reaction by using epichlorohydrin and glacial acetic acid as raw materials under the catalysis of a catalyst II, adding ethyl vinyl ether under an organic strong acid condition, carrying out a protection group forming reaction, and carrying out a ring formation reaction under a strong alkali condition so as to obtain the key intermediate solution. According to the present invention, the oxetan-3-ol preparation process is combined without the purifying of oxetan-3-ol so as to eliminate the oxetan-3-ol purifying step; and the method has characteristics of inexpensive raw materials, short route, no use of dangerous reagents and the like.
Preparation method for 3-oxetanone
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Paragraph 0050; 0051; 0052; 0053; 0054; 0055; 0056-0064, (2019/01/08)
The invention discloses a preparation method for 3-oxetanone and belongs to the technical field of medicinal chemical synthesis. The method includes: with a compound (I), o-bromobenzoic acid, being aninitial raw material, performing a nucleophilic substitution reaction under effect of a phase-transfer catalyst with epoxy chloropropane to obtain a compound (II); oxidizing the compound (II) under effect of an oxidant to prepare a compound (III); under alkaline condition, performing a hydrolysis reaction and an intramolecular nucleophilic substitution reaction on the compound (III) to obtain thetarget compound (IV), 3-oxetanone. The method can be used for preparing the target compound within three steps, employs controllable conditions and simple post-treatment, is less in side reactions and high in yield, can satisfy industrial production demands. Synthesis route is represented as the equations.
A β-Carbon elimination strategy for convenient: In situ access to cyclopentadienyl metal complexes
Smits,Audic,Wodrich,Corminboeuf,Cramer
, p. 7174 - 7179 (2017/10/05)
The electronic and steric properties of tailored cyclopentadienyl (Cp) ligands are powerful handles to modulate the catalytic properties of their metal complexes. This requires the individual preparation, purification and storage of each ligand/metal combination. Alternative, ideally in situ, complexation protocols would be of high utility. We disclose a new approach to access Cp metal complexes. Common metal precursors rapidly react with cyclopentadienyl carbinols via β-carbon eliminations to directly give the Cp-metal complexes. An advantage of this is the direct and flexible use of storable pre-ligands. No auxiliary base is required and the Cp complexes can be prepared in situ in the reaction vessel for subsequent catalytic transformations.
FeCl3/pyridine: Dual-activation in opening of epoxide with carboxylic acid under solvent free condition
Zhao, Yichao,Wang, Wen,Li, Jian,Wang, Feng,Zheng, Xiufang,Yun, Hongying,Zhao, Weili,Dong, Xiaochun
, p. 5849 - 5852 (2013/10/21)
Inexpensive, non-toxic, and readily available catalyst system FeCl 3/pyridine was found to be highly efficient for the opening of a wide variety of epoxides with carboxylic acid under solvent free conditions.
Efficient aerobic oxidation of secondary alcohols at ambient temperature with an ABNO/NOx catalyst system
Lauber, Markus B.,Stahl, Shannon S.
, p. 2612 - 2616 (2013/11/19)
New highly practical methods are presented for aerobic oxidation of secondary alcohols with a nitroxyl radical in combination with HNO3, NaNO2, or both as cocatalysts. Diverse nitroxyls are compared, including several novel bicyclic derivatives. Catalyst systems with the readily available nitroxyls, 9-azabicyclo[3.3.1]nonane-N-oxyl (ABNO) and 9-azabicyclo[3.3.1]nonan-3-one-N-oxyl (keto-ABNO), are optimized in acetic acid or acetonitrile as the solvent. The reactions are compatible with substrates bearing diverse functional groups and proceed efficiently under mild conditions at ambient pressure and temperature.
HETEROARYL BTK INHIBITORS
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Page/Page column 120, (2011/04/14)
The present invention provides compounds useful as inhibitors of Btk, compositions thereof, and methods of using the same.
Gold-catalyzed one-step practical synthesis of oxetan-3-ones from readily available propargylic alcohols
Ye, Longwu,He, Weimin,Zhang, Liming
supporting information; experimental part, p. 8550 - 8551 (2010/08/06)
A general solution for the synthesis of various oxetan-3-ones is developed. This reaction uses readily available propargylic alcohols as substrates and proceeds without the exclusion of moisture or air ("open flask"). Notably, oxetan-3-one, a highly valuable substrate for drug discovery, can be prepared in one step from propargyl alcohol in a fairly good yield. The facile formation of the strained oxetane ring provides strong support for the intermediacy of α-oxo gold carbenes. This safe and efficient generation of gold carbenes via intermolecular alkyne oxidation offers a potentially general entry into α-oxo metal carbene chemistry without using hazardous diazo ketones.
Oxetanes in drug discovery: Structural and synthetic insights
Wuitschik, Georg,Carreira, Erick M.,Wagner, Bj?rn,Fischer, Holger,Parrilla, Isabelle,Schuler, Franz,Rogers-Evans, Mark,Müller, Klaus
supporting information; experimental part, p. 3227 - 3246 (2010/08/19)
An oxetane can trigger profound changes in aqueous solubility, lipophilicity, metabolic stability, and conformational preference when replacing commonly employed functionalities such as gem-dimethyl or carbonyl groups. The magnitude of these changes depends on the structural context. Thus, by substitution of a gem-dimethyl group with an oxetane, aqueous solubility may increase by a factor of 4 to more than 4000 while reducing the rate of metabolic degradation in most cases. The incorporation of an oxetane into an aliphatic chain can cause conformational changes favoring synclinal rather than antiplanar arrangements of the chain. Additionally spirocyclic oxetanes (e.g., 2-oxa-6-aza-spiro[3.3]heptane) bear remarkable analogies to commonly used fragments in drug discovery, such as morpholine, and are even able to supplant the latter in its solubilizing ability. A rich chemistry of oxetan-3-one and derived Michael acceptors provide venues for the preparation of a broad variety of novel oxetanes not previously documented, thus providing the foundation for their broad use in chemistry and drug discovery.
