CN104557464B - A kind of tertiary alcohols compound and preparation method thereof - Google Patents
A kind of tertiary alcohols compound and preparation method thereof Download PDFInfo
- Publication number
- CN104557464B CN104557464B CN201310481955.9A CN201310481955A CN104557464B CN 104557464 B CN104557464 B CN 104557464B CN 201310481955 A CN201310481955 A CN 201310481955A CN 104557464 B CN104557464 B CN 104557464B
- Authority
- CN
- China
- Prior art keywords
- structural formula
- tertiary alcohols
- compound
- alkyl
- alcohols compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
- C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/333—Radicals substituted by oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/42—Singly bound oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The present invention provides a kind of tertiary alcohols compounds and preparation method thereof, as the tertiary alcohols compound salt medically acceptable for compound or its pesticide shown in structural formula (I), virtue (miscellaneous) the ring benzyl position Grignard Reagent as shown in structural formula (III) carries out nucleophilic addition with Propiophenone shown in structural formula (II) and is made:
Description
Technical field
The present invention relates to a kind of alcohol compounds more particularly to a kind of tertiary alcohols compound and preparation method thereof.
Background technique
The tertiary alcohol is that hydroxyl position does not have there are three substituent groupαThe alcohol of-H.Nucleophilic addition of the Grignard Reagent to ketone
Reaction equation prepare tertiary alcohols compound it is mostly important, with one of widest method.Not only raw material is easy to get, operates letter the method
It is single, the carbochain of reactant can also be increased, therefore can be used to prepare the various tertiary alcohols.But traditional Grignard Reagent is to ketone
Nucleophilic addition has the drawback that: during nucleophilic addition, usually along with the aldol condensation pair of substrate itself
The generation of product and reduzate causes the yield of principal product to substantially reduce.In order to prevent the generation of these side reactions, people make
It is reported with excessive additive, especially inorganic metal salt additive, such as Imamoto group and is used excessive anhydrous chlorination
Caesium promotes Grignard Reagent to reaction system (Imamoto, the T. of the efficient addition of ketone as additive; Sugiura, Y.;
Takiyama, N. Tetrahedron Lett. 1984,25,4233-4236), for another example Knochel group reports use
LnCl32LiCl promotes addition of the Grignard Reagent to ketone well, particularly with the addition of the LnCl of 30mol%32LiCl conduct
Additive is highly effective to this reaction.However, using anhydrous metal salt as additive, carrying out activated carbonyl or forming activity
Higher transition state intermediate, achieving the purpose that, which reduces side reaction, improves yield, and there is defect: 1, additive price is high
It is expensive, it is easier to the moisture absorption, to be weighed in glove box, be not suitable for industrialized production；2, use metal salt as additive, post-processing fiber crops
Tired complexity, and easy remaining metal ions in product after post-processing, it is unfriendly to environment or residual that final metal ion remains in pesticide
Staying in drug reduces drug effect and has a great impact to human health.
Tertiary alcohols compound is with a wide range of applications in the products such as methodology of organic synthesis and pesticide, medicine.
Such as CN102976891A discloses a kind of asymmetric tertiary alcohol, has monocycle or polycyclic non-aromatic ring or aromatic ring, it can
Raw material as the precision chemicals product such as the functional high-polymers such as photoresist or pharmaceuticals etc..Since tertiary alcohols compound has
There is very high application value, all there is positive effect to the exploitation of all kinds of related pesticides and medical product, therefore, it is necessary to further
More tertiary alcohols compounds are developed to meet research and production requirement.
Summary of the invention
The purpose of the present invention is to overcome the above shortcomings and to provide a kind of novel tertiary alcohols compound, and the tertiary alcohols
The preparation method of conjunction object is simple, reaction condition is mild, product purity is high, high income, and environmentally friendly.
The first aspect of the invention is to provide a kind of tertiary alcohols compound, which is characterized in that the tertiary alcohols compound
For compound shown in structural formula (I) or the medically acceptable salt of its pesticide:
(I)
Preferably, the tertiary alcohols compound includes optical isomer or its pesticide doctor of compound shown in structural formula (I)
The cis-trans-isomer of compound shown in acceptable salt or structural formula (I) or the medically acceptable salt of its pesticide on.
In a kind of preferred embodiment of the tertiary alcohols compound described in first aspect of the present invention, Ar is aromatic radical, takes
For one of aromatic radical.
Wherein, aromatic radical can be for without hetero atom, can also be containing one or more hetero atoms, and the hetero atom can be with
For O, S, N, P, Si etc., preferably O, S, N.
It is further preferred that Ar is the phenyl without containing substituent group or containing one or more substituent groups, triazole
One of base, pyridyl group, naphthalene, thiazolyl, pyrimidine radicals, furyl, thienyl, oxazolyl, quinolyl.
It is further preferred that Ar be phenyl, triazol radical, pyridyl group, thiazolyl, pyrimidine radicals, tetrahydrofuran base or its
One of halides.
Preferably, the substituent group in the substituted aromatic base is 1-8, and more preferably 1-6, more preferably 1-4 is a, more
Preferably 1-3, such as 2.
Substituent group in the substituted aromatic base be selected from halogen, itrile group, nitro, hydroxyl, methylamino, dimethylamino, alkyl,
One of alkoxy or halogenated alkyl are a variety of.
Alkyl is preferably C1-20Alkyl, more preferably C1-10Alkyl, more preferably C1-8Alkyl, more preferably C1-6Alkyl, more
Preferably C1-4Alkyl, such as methyl, ethyl, propyl, isopropyl, butyl, tert-butyl etc..
Alkoxy is preferably C1-20Alkoxy, more preferably C1-10Alkoxy, more preferably C1-8Alkoxy is more preferably
C1-6Alkoxy, more preferably C1-4Alkoxy, such as methoxyl group, ethyoxyl, propoxyl group, isopropoxy, butoxy, tert-butoxy
Deng.
Halogenated alkyl is preferably C1-20Halogenated alkyl, more preferably C1-10Halogenated alkyl, more preferably C1-8Halogenated alkyl, more
Preferably C1-6Halogenated alkyl, more preferably C1-4Halogenated alkyl, such as halogenated methyl, halogenated ethyl, halopropyl, halogenated isopropyl
Base, halogenated butyl, halogenated tert-butyl etc..
Halogenated alkyl can be partially halogenated alkyl (such as unitary is halogenated, binary is halogenated or ternary is halogenated etc.) or perhalogeno
Alkyl.Halo groups can be I, Br, Cl, F etc..
In a kind of preferred embodiment of the tertiary alcohols compound described in first aspect of the present invention, R1For H, halogen (example
Such as I, Br, Cl, F), itrile group, nitro, hydroxyl, methylamino, dimethylamino, alkyl, alkoxy or halogenated alkyl, more preferably
Halogen, alkoxy, alkyl or nitro.
Alkyl is preferably C1-20Alkyl, more preferably C1-10Alkyl, more preferably C1-8Alkyl, more preferably C1-6Alkyl, more
Preferably C1-4Alkyl, such as methyl, ethyl, propyl, isopropyl, butyl, tert-butyl etc..
Alkoxy is preferably C1-20Alkoxy, more preferably C1-10Alkoxy, more preferably C1-8Alkoxy is more preferably
C1-6Alkoxy, more preferably C1-4Alkoxy, such as methoxyl group, ethyoxyl, propoxyl group, isopropoxy, butoxy, tert-butoxy
Deng.
Halogenated alkyl is preferably C1-20Halogenated alkyl, more preferably C1-10Halogenated alkyl, more preferably C1-8Halogenated alkyl, more
Preferably C1-6Halogenated alkyl, more preferably C1-4Halogenated alkyl, such as halogenated methyl, halogenated ethyl, halopropyl, halogenated isopropyl
Base, halogenated butyl, halogenated tert-butyl etc..
Halogenated alkyl can be partially halogenated alkyl (such as unitary is halogenated, binary is halogenated or ternary is halogenated etc.) or perhalogeno
Alkyl.Halo groups can be I, Br, Cl, F etc..
In a kind of preferred embodiment of the tertiary alcohols compound described in first aspect of the present invention, R2For C1-6Alkyl is (more
Preferably C1-4Alkyl, such as methyl, ethyl, propyl, isopropyl, butyl, tert-butyl etc.), allyl, benzyl, C1-4Alkoxy-
C1-4Alkyl (such as first alkoxy methyl, ethane oxygroup propyl, methane oxygroup tert-butyl etc.) or Ar, more preferably C1-6Alkyl
(more preferably C1-4Alkyl, such as methyl, ethyl, propyl, isopropyl, butyl, tert-butyl etc.) or C1-4Alkoxy -C1-4Alkyl
(such as first alkoxy methyl, ethane oxygroup propyl, methane oxygroup tert-butyl etc.).
In a particularly preferred embodiment, in tertiary alcohols compound shown in structural formula (I), Ar is triazol radical,
R1For halogen (such as I, Br, Cl, F etc.) or methoxyl group, R2For tert-butyl or methyl.
The second aspect of the invention is to provide a kind of preparation method of above-mentioned tertiary alcohols compound, by structural formula (II) institute
Show that carbonyls is reacted with Grignard Reagent shown in structural formula (III) and tertiary alcohols compound shown in structural formula (I), reaction equation is made
It is as follows:
(II) (III) (I)
Wherein, the X in structural formula (III) is Cl or Br.
Wherein, Grignard Reagent shown in carbonyls shown in structural formula (II) and structural formula (III) after the reaction was completed, hydrolysis,
Extraction, concentrated extract is up to tertiary alcohols compound shown in structural formula (I).
Wherein, the halide as shown in structural formula (IV) of Grignard Reagent shown in structural formula (III) is reacted with magnesium is made:
(IV).
Halide shown in structural formula (IV), which reacts the solvent used with magnesium, to be one in tetrahydrofuran, ether, toluene
Kind is a variety of.
Preferably, the concentration of the Grignard Reagent be 0.1-10 mol/L, more preferably 0.2-8 mol/L, more preferably
0.5-6 mol/L, more preferably 1-4 mol/L, more preferably 1.5-3 mol/L.
Preferably, carbonyls shown in structural formula (II) and Grignard Reagent reaction temperature shown in structural formula (III) are 0-70
DEG C, more preferably 10-60 DEG C, more preferably 15-50 DEG C, more preferably 20-40 DEG C, more preferably 25-35 DEG C.
Preferably, carbonyls shown in structural formula (II) and Grignard Reagent reaction time shown in structural formula (III) are 1-
4h, more preferably 1.5-3.5h, more preferably 2-3h.
Above-mentioned various aspects of the invention and each preferred embodiment can be with unrestricted any combination.
The present invention is using fragrant (miscellaneous) ring benzyl position Grignard Reagent (shown in structural formula (III)) and Propiophenone (structural formula (II)
It is shown) nucleophilic addition is carried out, reactivity is good, can be reacted at room temperature, and deadline, short aldol condensation are reacted
By-product and reduction by-product greatly reduce, and promote nucleophilic addition it is not necessary that additive is added, reaction yield is high, Er Qieyi
Purifying only need to can be obtained the tertiary alcohols compound that purity is 95% or so, gained tertiary alcohols chemical combination by simple extraction concentration
Object is with a wide range of applications in the products such as methodology of organic synthesis and pesticide, medicine.
Through biological activity test, tertiary alcohol class formation provided by the present invention is to wheat sharp eyespot and alternaria leaf spot of apple
Inhibitory activity it is more significant.
Specific embodiment
The present invention is further described referring to specific embodiment, to better understand the invention.
1 2- methyl-1 of embodiment, the synthesis of 4- diphenyl -2- butanol
4- Phenyl 2 butanone (2 mmol) is added in 25ml tetrahydrofuran, adds benzyl bromine Grignard Reagent (2 mmol/
Ml, 1 ml), the completion of reaction in 2 hours is stirred, aqueous acetic acid is added, continues stirring 1 hour, methylene chloride and water extraction is added,
Merge organic phase, drying is concentrated to get product, yield 82%, and purity 97% is accredited as 2- methyl-1,4- hexichol through infrared and nuclear-magnetism
Base -2- butanol.
The synthesis of 2 4- of embodiment (4- chlorphenyl) -1- (furans -2- base) -2- methyl 2- butanol
4- rubigan -2- butanone (2 mmol) is added in 25ml tetrahydrofuran, adds the grignard of bromomethyl furans
Reagent (2 mmol/ml, 1 ml) stirs the completion of reaction in 3 hours, aqueous acetic acid is added, continue stirring 1 hour, dichloro is added
Methane and water extraction merge organic phase, and drying is concentrated to get product, yield 75%, and purity 96% is accredited as 4- through infrared and nuclear-magnetism
(4- chlorphenyl) -1- (furans -2- base) -2- methyl 2- butanol.
The synthesis of 3 3- of embodiment (2- methoxyphenyl) -1- phenyl -1- (1H- pyrroles -2- base) -1- propyl alcohol:
3- (2- methoxyphenyl) -1- phenyl -1- acetone (2 mmol) is added in 25ml tetrahydrofuran, adds bromine first
The Grignard Reagent (2 mmol/ml, 1 ml) of base pyrroles stirs the completion of reaction in 2 hours, aqueous acetic acid is added, it is small to continue stirring 1
When, methylene chloride and water extraction is added, merges organic phase, dry to be concentrated to get product, yield 71%, purity 94%, through infrared and
Nuclear-magnetism is accredited as 3- (2- methoxyphenyl) -1- phenyl -1- (1H- pyrroles -2- base) -1- propyl alcohol.
The conjunction of embodiment 4 4,4- dimethyl -1- (p-methylphenyl) -3- (1H-1,2,3- triazol-1-yl) -3- amylalcohol
At:
4,4- dimethyl -1- (p-methylphenyl)-propione (2.0 mmol) is added in 25ml tetrahydrofuran, adds
The Grignard Reagent (2.0 mmol/ml, 1.0 ml) of bromomethyl triazole stirs the completion of reaction in 2 hours, aqueous acetic acid is added, after
Methylene chloride and water extraction is added in continuous stirring 1 hour, merges organic phase, dry to be concentrated to get product, yield 74%, purity 95%,
4,4- dimethyl -1- (p-methylphenyl) -3- (1 is accredited as through infrared and nuclear-magnetismH- 1,2,3- triazol-1-yl) -3- amylalcohol.
The synthetic method of the above-mentioned Grignard Reagent of embodiment 5 and reactive ketone, synthesis tertiary alcohols structural compounds is equally applicable to
The synthesis (3- ((1H-1,2,4- triazole -1- base) methyl) -1- (4- chlorphenyl) -4,4- dimethyl -3- amylalcohol) of Tebuconazole
1- (4- chlorphenyl) -4,4- dimethyl-propione (2.0 mmol) is added in 25ml tetrahydrofuran, addsN-
The Grignard Reagent (2.0 mmol/ml, 1.0 ml) of bromomethyl triazole stirs the completion of reaction in 2 hours, aqueous acetic acid is added,
Continue stirring 1 hour, methylene chloride and water extraction is added, merge organic phase, drying is concentrated to get product, yield 78%, purity
96%, 3- ((1H-1,2,4- triazole -1- bases) methyl) -1- (4- chlorphenyl) -4,4- dimethyl-is accredited as through infrared and nuclear-magnetism
3- amylalcohol.
Compound as described in Table 1 is prepared according to the method similar with embodiment 1-5, and by the identification confirmation of infrared and nuclear-magnetism
Structure.
(II) (III) (I)
Table 1, compound structure and bioactivity list
R in table 11Number before group in is corresponding with the location label in structural formula (I), such as R1For 2-Cl,
Corresponding tertiary alcohols compound are as follows:
。
Specific embodiments of the present invention are described in detail above, but it is merely an example, the present invention is simultaneously unlimited
It is formed on particular embodiments described above.To those skilled in the art, any couple of present invention carries out equivalent modifications and
Substitution is also all among scope of the invention.Therefore, without departing from the spirit and scope of the invention made by equal transformation and
Modification, all should be contained within the scope of the invention.
Claims (6)
1. a kind of tertiary alcohols compound, which is characterized in that the tertiary alcohols compound is compound or its agriculture shown in structural formula (I)
The medically acceptable salt of medicine:
Wherein, Ar group is one of furyl without containing substituent group, pyrrole radicals；
R1For H, halogen, C1-2Alkyl, methoxyl group；
R2For C1-4Alkyl, phenyl.
2. tertiary alcohols compound according to claim 1, which is characterized in that the tertiary alcohols compound includes structural formula
(I) optical isomer of compound shown in or the medically acceptable salt of its pesticide.
3. tertiary alcohols compound according to claim 1 or 2, which is characterized in that the tertiary alcohols compound includes structure
The medically acceptable salt of the cis-trans-isomer or its pesticide of compound shown in formula (I).
4. a kind of preparation method of tertiary alcohols compound described in claim 1, which is characterized in that the carbonyl as shown in structural formula (II)
Based compound is reacted with Grignard Reagent shown in structural formula (III), is hydrolyzed, extracting, tertiary alcohols shown in obtained structural formula (I) are concentrated
Object is closed, reaction equation is as follows:
Wherein, the X in structural formula (III) is Cl or Br.
5. the preparation method according to claim 4, which is characterized in that the concentration of the Grignard Reagent is 0.1-10mol/L.
6. the preparation method according to claim 4, which is characterized in that carbonyls and structural formula shown in structural formula (II)
(III) Grignard Reagent reaction temperature shown in is 0-70 DEG C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310481955.9A CN104557464B (en) | 2013-10-15 | 2013-10-15 | A kind of tertiary alcohols compound and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310481955.9A CN104557464B (en) | 2013-10-15 | 2013-10-15 | A kind of tertiary alcohols compound and preparation method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104557464A CN104557464A (en) | 2015-04-29 |
| CN104557464B true CN104557464B (en) | 2019-05-07 |
Family
ID=53074649
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201310481955.9A Active CN104557464B (en) | 2013-10-15 | 2013-10-15 | A kind of tertiary alcohols compound and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104557464B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106117009A (en) * | 2016-06-13 | 2016-11-16 | 湖北华世通生物医药科技有限公司 | The preparation method of tertiary alcohols compound |
| CN106588791A (en) * | 2016-11-01 | 2017-04-26 | 盐城辉煌化工有限公司 | Novel technology for synthesizing bactericide tebuconazole without solvent |
| CN114409600A (en) * | 2022-01-19 | 2022-04-29 | 武汉回盛生物科技股份有限公司 | Synthetic method of enilconazole |
| CN117924197B (en) * | 2024-03-21 | 2024-06-07 | 山东百农思达生物科技有限公司 | High-purity synthesis method of tebuconazole |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4870093A (en) * | 1980-05-16 | 1989-09-26 | Bayer Aktiengesellschaft | Antimicrobial agents and their use |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4174405A (en) * | 1974-02-25 | 1979-11-13 | Uniroyal, Inc. | Thiophenes useful in control of acarids |
| KR20130082100A (en) * | 2010-05-27 | 2013-07-18 | 바이엘 인텔렉쳐 프로퍼티 게엠베하 | Heterocyclic alkanol derivatives as fungicides |
-
2013
- 2013-10-15 CN CN201310481955.9A patent/CN104557464B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4870093A (en) * | 1980-05-16 | 1989-09-26 | Bayer Aktiengesellschaft | Antimicrobial agents and their use |
Non-Patent Citations (1)
| Title |
|---|
| Oxygen Versus Carbon Acidity in the Side-Chain Fragmentation of 2-, 3-, and 4-Arylalkanol Radical Cations in Aqueous Solution: TheInfluence of the Distance between the OH Group and the Aromatic Ring;Enrico Baciocchi等;《Journal of the American Chemical Society》;19990207;第121卷(第28期);参见6629页左栏倒数第2段 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN104557464A (en) | 2015-04-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN104557464B (en) | A kind of tertiary alcohols compound and preparation method thereof | |
| Wan et al. | Synthesis, antiviral bioactivity of novel 4-thioquinazoline derivatives containing chalcone moiety | |
| Nicolaou et al. | A Novel Regio‐and Stereoselective Synthesis of Sulfamidates from 1, 2‐Diols Using Burgess and Related Reagents: A Facile Entry into β‐Amino Alcohols | |
| Yan et al. | Pictet–Spengler reaction-based biosynthetic machinery in fungi | |
| Fang et al. | Synthesis, antifungal activity, and sar study of some new 6‐perfluoropropanyl quinoline derivatives | |
| Malm et al. | Palladium-catalyzed coupling of heteroaryl alkylstannanes with heteroaryl halides in the presence of silver (I) oxide | |
| CN106336383B (en) | A kind of trinitrogenazole alcohol analog derivative and its preparation method and application | |
| CN103819413A (en) | Pentadienone compound containing quinazolinone aryloxy as well as preparation method and application thereof | |
| CN105669503A (en) | Trifluoromethylthiolation reagent and its preparation method and use in asymmetric trifluoromethylthiolation reaction | |
| Umamatheswari et al. | Synthesis, stereochemistry, antimicrobial evaluation and QSAR studies of 2, 6-diaryltetrahydropyran-4-one thiosemicarbazones | |
| Jarrahpour et al. | Design, synthesis, activity evaluation and QSAR studies of novel antimalarial 1, 2, 3-triazolo-β-lactam derivatives | |
| Shaik et al. | Synthesis, antimicrobial, and computational evaluation of novel isobutylchalcones as antimicrobial agents | |
| Fu et al. | Azo-incorporating increases inhibitory activity of succinate dehydrogenase | |
| Mallikanti et al. | Synthesis, antimicrobial activity and molecular docking of novel benzimidazole conjugated 1, 2, 3-triazole analogues | |
| CN103201266A (en) | Aryloxy dihalopropenyl ether compound and use thereof | |
| Senge et al. | The dithianyl group as a synthon in porphyrin chemistry: condensation reactions and preparation of formylporphyrins under basic conditions | |
| Krompiec et al. | Nitrile Oxide, Alkenes, Dipolar Cycloaddition, Isomerization and Metathesis Involved in the Syntheses of 2-Isoxazolines | |
| Komatsuda et al. | Ring‐Opening Fluorination of Carbo/Heterocycles and Aromatics: Construction of Complex and Diverse Fluorine‐Containing Molecules | |
| CN106188011B (en) | The ultrasound synthesis and application of quaternary ring-type beta-lactam derivatives based on arylpyrazole skeleton | |
| Mlostoń et al. | Synthesis and selected transformations of 2-unsubstituted imidazole N-oxides using a ball-milling mechanochemical approach | |
| Rasheed et al. | Palladium (0) catalyzed Suzuki cross-coupling reactions of 2, 4-dibromothiophene: Selectivity, characterization and biological applications | |
| JP2012214405A (en) | N,n'-methylenebis(1,2-benzisothiazolin-3-one) compound and method for producing the same | |
| Liu et al. | Pyrido [1, 2-a] pyrimidinone mesoionic compounds containing vanillin moiety: design, synthesis, antibacterial activity, and mechanism | |
| Pedada et al. | An improved kilogram-scale synthesis of 2-Bromo-4-nitro-1 H-imidazole: a key building block of nitroimidazole drugs | |
| CN109824610A (en) | A kind of chalcone derivative, preparation method and application containing quinoxaline |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| CP01 | Change in the name or title of a patent holder | ||
| CP01 | Change in the name or title of a patent holder |
Address after: Songjiang District Jing Dong Zhen Dong Zhou road 201619 Shanghai City No. 51 Co-patentee after: As Dong Zhongyi Chemical Co., Ltd. Patentee after: Shanghai biochemical products Limited by Share Ltd Address before: Songjiang District Jing Dong Zhen Dong Zhou road 201619 Shanghai City No. 51 Co-patentee before: As Dong Zhongyi Chemical Co., Ltd. Patentee before: Shengnong Biological-Chemical Products Co., Ltd., Shanghai |
|
| TR01 | Transfer of patent right | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20200103 Address after: Yimatu town yimatu village, Fumeng County, Fuxin City, Liaoning Province (Fluorine Industry Development Zone) Patentee after: Liaoning Zhonghui Biotechnology Co., Ltd Address before: Songjiang District Jing Dong Zhen Dong Zhou road 201619 Shanghai City No. 51 Co-patentee before: As Dong Zhongyi Chemical Co., Ltd. Patentee before: Shanghai biochemical products Limited by Share Ltd |