CN113185482A - Aldehyde cyclohexadienone and polyoxoalene compound and preparation method thereof - Google Patents

Aldehyde cyclohexadienone and polyoxoalene compound and preparation method thereof Download PDF

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CN113185482A
CN113185482A CN202110396123.1A CN202110396123A CN113185482A CN 113185482 A CN113185482 A CN 113185482A CN 202110396123 A CN202110396123 A CN 202110396123A CN 113185482 A CN113185482 A CN 113185482A
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cyclohexadienone
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彭士勇
张弘
朱雨琪
周婷
何洁银
汪舰
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Wuyi University
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Abstract

The invention provides an aldehyde cyclohexadienone and polyoxin compound and a preparation method thereof. The compound has a novel structure and comprises five stereocenters, wherein the five stereocenters comprise two all-carbon quaternary centers. The method is a high-efficiency construction of an oxygen-containing fused ring framework, and provides a set of general, high-efficiency, simple and rapid synthetic method for an important species rich in oxygen-containing fused four-membered ring; provides a reliable chemical tool for the synthesis of important chemical intermediates based on oxygen-containing fused ring structures and the discovery of lead drug molecules. The invention also provides a preparation method of the aldehyde cyclohexadienone and polyoxin compounds.

Description

Aldehyde cyclohexadienone and polyoxoalene compound and preparation method thereof
Technical Field
The invention belongs to the technical field of organic synthesis, and particularly relates to an aldehyde cyclohexadienone and polyoxirane compound and a preparation method thereof.
Background
The carbonyl ylide diazo compounds and carbon-oxygen double bonds formed by the transition metal catalyzed reaction of the diazo compounds with lewis bases are active intermediates and a variety of transformations can occur, of which the 1, 3-dipolar cycloaddition reaction of carbonyl ylides has been extensively studied and used for the synthesis of many biologically useful molecules and natural products.
The intermolecular carbonyl-ylide-chlorine addition reaction of three components relates to diazo compounds, aldehydes and amphipathic polarity, and is an effective method for constructing functional oxygen heterocycles. However, it is relatively limited in selectivity and substrate range. Intramolecular carbonyl ylide cycloadditions have received much attention in recent decades, including intramolecular ylide formation/intermolecular cycloaddition and intramolecular ylide formation/intramolecular cycloaddition. Despite considerable advances in the study of the above reactions, there is currently no general method available for a two-component intermolecular ylide formation/intramolecular cycloaddition reaction with a wide range of control of chemical and diastereoselectivity.
Disclosure of Invention
The present invention is directed to solving at least one of the above problems in the prior art. Therefore, the invention provides an aldehyde cyclohexadienone and poly-oxygen ring compound, which has five three-dimensional centers including two all-carbon four-membered centers, efficiently constructs an oxygen-containing ring-combining framework, and provides a set of general, efficient, simple and rapid synthetic method for enriching an important species of oxygen-containing four-membered rings; provides a reliable chemical tool for the synthesis of important chemical intermediates based on oxygen-containing fused ring structures.
The invention also provides a preparation method of the aldehyde cyclohexadienone and polyoxin compounds.
The invention provides a cyclohexadienone and poly-oxygen ring compound of aldehyde series in a first aspect, which comprises a compound with a structure shown in a formula I;
Figure BDA0003018625210000021
wherein:
r comprises one of an aliphatic group and an acetyl group;
R1including one of a hydrogen atom and a halogen;
R2comprises one of ester group, heterocyclic substituent, substituted and unsubstituted benzene ring;
R3comprises one of ester group, aliphatic group, benzyl, substituted and unsubstituted benzene ring;
R4including one of a hydrogen atom, a halogen, and an aliphatic group.
The aldehyde cyclohexadienone and poly-oxygen ring compound has at least the following beneficial effects:
the compound has a novel structure and comprises five stereocenters, wherein the five stereocenters comprise two all-carbon quaternary centers.
The compound provides a set of general, high-efficiency, simple and rapid synthetic method for an important species rich in oxygen-containing four-membered ring; provides a reliable chemical tool for the synthesis of important chemical intermediates based on oxygen-containing fused ring structures.
According to some embodiments of the present invention, the,
r is an aliphatic group or an acetyl group;
R1is a hydrogen atom or a halogen;
R2is an ester group, a substituted or unsubstituted benzene ring;
R3is an ester group;
R4is a hydrogen atom or an aliphatic group.
According to some embodiments of the invention, the compound of formula I is selected from any one of the following structures 1a to 1 f:
Figure BDA0003018625210000031
the second aspect of the present invention provides a method for preparing the above aldehyde-based cyclohexadienone and polyoxirane compound, comprising the following steps: reacting aldehyde cycloadienone compounds with structures shown in formula II and diazo compounds with structures shown in formula III in the presence of a catalyst and a solvent, wherein:
Figure BDA0003018625210000032
the preparation method of the aldehyde cyclohexadienone and polyoxin compounds has at least the following beneficial effects:
the aldehyde cyclohexadienone and poly-oxygen ring compound can be prepared from the aldehyde cyclohexadienone compound and the diazo compound by a one-pot method under the catalytic action of transition metal.
The preparation method of the aldehyde cyclohexadienone and poly-oxygen cyclics compound of the invention does not need separation and purification of intermediates in a series of conversion processes except final products, can reduce the investment of capital and labor force, and provides a simple and efficient preparation method for the aldehyde cyclohexadienone and poly-oxygen cyclics compound.
The preparation method of the aldehyde cyclohexadienone and polyoxin compounds is a novel copper-catalyzed intermolecular ylide formation/intramolecular cycloaddition reaction in series of diazo compounds and aldehyde cyclohexadienone, and can provide a polycyclic skeleton with chemical and diastereoselectivity under mild conditions with moderate or even excellent yield. Specifically, the reaction generates two C-C bonds and one C-O bond, wherein five stereocenters comprise two all-carbon quaternary centers, and a brand-new preparation idea and method are provided for the aldehyde cyclohexadienone and poly-oxygen ring compound.
According to some embodiments of the invention, the solvent comprises at least one of N, N-dimethylformamide, dichloromethane, methanol, toluene and trifluorotoluene.
According to some embodiments of the invention, the catalyst comprises a copper salt.
According to some embodiments of the invention, the catalyst comprises at least one of copper triflate, cuprous triflate and cuprous cyclooctadiene (hexafluoroacetylacetone).
According to some embodiments of the invention, the aldehyde-based cyclohexadienone compound, the diazonium compound and the catalyst are present in a molar ratio of 1: (1-5): (0.01-0.3).
According to some embodiments of the invention, the aldehyde-based cyclohexadienone compound, the diazonium compound and the catalyst are present in a molar ratio of 1: 2: 0.1.
according to some embodiments of the invention, the reaction temperature is 20 ℃ to 100 ℃ and the reaction time is 2h to 48 h.
According to some embodiments of the invention, the reaction temperature is 25 ℃ and the reaction time is 16 h.
According to some embodiments of the present invention, the method for preparing cyclohexadienone and polyoxirane compounds comprises the following steps:
dissolving a compound containing a catalyst, a 4A molecular sieve and aldehyde cyclohexadienone in a solvent, and stirring at room temperature;
and dissolving the diazo compound in a solvent, dropwise adding the mixture into the mixed solution, continuously stirring, removing the solvent after reaction, and separating the crude product by silica gel column chromatography to obtain the aldehyde cyclohexadienone and polyoxin compounds with the structure of the formula I.
In a third aspect, the invention provides a pharmaceutical composition comprising the aldehyde cyclohexadienone and polyoxin compounds or pharmaceutically acceptable salts thereof.
Pharmaceutically acceptable salts, including pharmaceutically acceptable salts, esters, hydrates, solvates, crystalline forms, enantiomers, stereoisomers, ethers, metabolites and prodrugs thereof.
Pharmaceutically acceptable salts include, but are not limited to, at least one of inorganic acid salts, organic acid salts, alkylsulfonic acid salts, and arylsulfonic acid salts. Wherein, the inorganic acid salt includes but not limited to at least one of hydrochloride, hydrobromide, nitrate, sulfate and phosphate. The organic acid salt includes, but is not limited to, at least one of formate, acetate, propionate, benzoate, maleate, fumarate, succinate, tartrate, and citrate. The alkyl sulfonate includes, but is not limited to, at least one of a methyl sulfonate and an ethyl sulfonate. The aryl sulfonate includes, but is not limited to, at least one of benzene sulfonate and p-toluene sulfonate.
Drawings
FIG. 1 shows the product 1a obtained in example 1 of the present invention1H NMR spectrum.
FIG. 2 shows the product 1a obtained in example 1 of the present invention13C NMR spectrum.
FIG. 3 shows the product 1b obtained in example 2 according to the invention1H NMR spectrum.
FIG. 4 shows the product 1b obtained in example 2 according to the invention13C NMR spectrum.
FIG. 5 shows the product 1c obtained in example 3 according to the invention1H NMR spectrum.
FIG. 6 shows the product 1c obtained in example 3 according to the invention13C NMR spectrum.
FIG. 7 shows the product 1d obtained in example 4 of the present invention1H NMR spectrum.
FIG. 8 shows the product 1d obtained in example 4 of the present invention13C NMR spectrum.
FIG. 9 shows the product 1e obtained in example 5 of the present invention1H NMR spectrum.
FIG. 10 shows the product 1e obtained in example 5 of the present invention13C NMR spectrum.
FIG. 11 shows the product 1f obtained in example 6 of the present invention1H NMR spectrum.
FIG. 12 shows the product 1f obtained in example 6 of the present invention13C NMR spectrum.
Detailed Description
The following are specific examples of the present invention, and the technical solutions of the present invention will be further described with reference to the examples, but the present invention is not limited to the examples.
In the present invention, the position of the term "substituted" may be arbitrary, if not specifically stated; for example, each independently at the "site of attachment of the aryl group to another group", or at the "site of attachment of the heteroaryl group to another group", and phenyl, for example, means that the substituent is at the ortho, meta, or para position relative to the central bond.
The term "halogen" includes F, Cl, Br or I.
The term "heterocyclic substituent" denotes an aryl or heteroalkyl group containing one or more heteroatoms selected from S or O, heteroaryl groups within the scope of this definition including, but not limited to: acridinyl, carbazolyl, cinnolinyl, quinoxalinyl, pyrazolyl, indolyl, benzotriazolyl, furanyl, thienyl, benzothienyl, benzofuranyl, quinolinyl, isoquinolinyl, oxazolyl, isoxazolyl, indolyl, pyrazinyl, pyridazinyl, pyridyl, pyrimidinyl, pyrrolyl, tetrahydroquinoline.
Additional aspects and advantages of the invention will be set forth in part in the description which follows and, in part, will be obvious from the description, or may be learned by practice of the invention.
The aldehyde-based cyclohexadienone starting material used in the following examples 1 to 6 can be prepared by the following method:
Figure BDA0003018625210000061
example 1
This example prepares an aldehyde cyclohexadienone and polyoxin compounds shown in formula 1a, and the reaction process is as follows:
Figure BDA0003018625210000062
the preparation process comprises the following steps:
a25 mL reaction flask was charged with a solution of the catalyst (93mg, 0.1mmol), 4A molecular sieve (300mg) and aldehyde cyclohexadienone compound 2a (228mg,1.0mmol) in dichloromethane (5.0mL), and stirred at room temperature for 2 h.
Then, the diazo compound 3a (352mg, 2.0mmol) was dissolved in dichloromethane (5.0mL), and slowly injected into the above mixed solution by means of a syringe pump with continuous stirring, the reaction system was stirred at room temperature for 16 hours, and the crude product was separated by means of silica gel column chromatography after removal of the solvent to give the product 1a as a white solid (534mg, yield: 71%).
The detection data for the product 1a obtained are as follows:1H NMR(500MHz,CDCl3):δ7.65(d,J＝7.4Hz,1H),7.56-7.44(m,3H),7.23(s,5H),6.56(dd,J＝10.4,1.1Hz,1H),5.82(d,J＝10.3Hz,1H),5.57(d,J＝7.0Hz,1H),4.43(d,J＝10.2Hz,1H),3.86(s,3H),3.76-3.73(m,1H),3.20(s,3H)；13C NMR(125MHz,CDCl3):δ196.3,172.8,146.6,145.5,138.2,135.0,132.0,131.0,130.2,128.6,128.3,126.8,125.7,124.3,96.2,86.4,82.3,55.2,53.8,52.4,51.7；HRMS(ESI):calcd.for C23H21O5[M+H]+:377.1384,found 377.1376。
example 2
This example prepares an aldehyde cyclohexadienone and polyoxin compounds of formula 1b by the following reaction sequence:
Figure BDA0003018625210000071
the preparation process comprises the following steps:
a25 mL reaction flask was charged with a solution of the catalyst (93mg, 0.1mmol), 4A molecular sieve (300mg) and aldehyde cyclohexadienone compound 2a (228mg,1.0mmol) in dichloromethane (5.0mL), and stirred at room temperature for 2 h.
Then, the diazo compound 3b (316mg, 2.0mmol) was dissolved in dichloromethane (5.0mL), slowly injected into the above mixed solution by means of a syringe pump with continuous stirring, the reaction system was stirred at room temperature for 16 hours, and the crude product was separated by means of silica gel column chromatography after removal of the solvent to give the product 1b as a white solid (338mg, yield: 47%).
The detection data of the obtained product 1b were as follows:1H NMR(500MHz,CDCl3):δ7.57-7.54(m,1H),7.45-7.41(m,2H),7.34-7.31(m,1H),7.08(d,J＝10.4Hz,1H),6.25(d,J＝10.4Hz,1H),5.95-5.88(m,1H),3.88(s,3H),3.81-3.75(m,2H),3.38(s,3H),3.15(s,3H)；13C NMR(125MHz,CDCl3):δ193.0,168.4,167.3,147.4,143.6,139.4,130.7,130.5,130.3,127.0,124.5,91.0,87.9,82.3,53.9,52.7,52.1,51.5,49.4；HRMS(ESI):calcd.for C19H19O7[M+H]+:359.1125,found 359.1121。
example 3
This example prepares an aldehyde cyclohexadienone and polyoxin compounds of formula 1c by the following reaction sequence:
Figure BDA0003018625210000081
the preparation process comprises the following steps:
a25 mL reaction flask was charged with a solution of the catalyst (93mg, 0.1mmol), 4A molecular sieve (300mg) and aldehyde cyclohexadienone compound 2a (228mg,1.0mmol) in dichloromethane (5.0mL), and stirred at room temperature for 2 h.
Then, the diazo compound 3c (388mg, 2.0mmol) was dissolved in dichloromethane (5.0mL), slowly injected into the above mixed solution by means of a syringe pump, continuously stirred, the reaction system was stirred at room temperature for 16 hours, and the crude product was separated by means of silica gel column chromatography after removal of the solvent to give the product 1c (521mg, yield: 66%) as a white solid.
The detection data for the product 1c obtained are as follows:1H NMR(500MHz,CDCl3):δ7.64(d,J＝7.3Hz,1H),7.57–7.43(m,3H),7.28–7.20(m,2H),6.91(t,J＝8.7Hz,2H),6.58(d,J＝10.4Hz,1H),5.82(d,J＝10.3Hz,1H),5.58(d,J＝7.0Hz,1H),4.39(d,J＝10.2Hz,1H),3.86(s,3H),3.78–3.71(m,1H),3.19(s,3H)；13C NMR(125MHz,CDCl3):δ196.2,172.6,163.7,161.7,147.0,145.4,138.1,131.9,130.8(d,J＝2.9Hz),130.8,130.2,127.7(d,J＝8.3Hz),126.8,124.3,115.3,115.2,95.6,86.4,82.3,55.2,53.8,52.2,51.6；HRMS(ESI):calcd.for C23H20FO5[M+H]+:395.1289,found 395.1288。
example 4
This example prepares an aldehyde cyclohexadienone and polyoxin compounds of formula 1d by the following reaction sequence:
Figure BDA0003018625210000091
the preparation process comprises the following steps:
a25 mL reaction flask was charged with a solution of the catalyst (93mg, 0.1mmol), 4A molecular sieve (300mg) and aldehyde cyclohexadienone compound 2b (256mg, 1.0mmol) in dichloromethane (5.0mL), and stirred at room temperature for 2 h.
Then, the diazo compound 3a (352mg, 2.0mmol) was dissolved in dichloromethane (5.0mL), and slowly injected into the above mixed solution by means of a syringe pump with continuous stirring, the reaction system was stirred at room temperature for 16 hours, and after removing the solvent, the crude product was isolated by means of silica gel column chromatography to give the product 1d as a white solid (324mg, yield: 40%).
The detection data of the obtained product 1d were as follows:1H NMR(500MHz,CDCl3):δ7.70-7.66(m,1H),7.59-7.49(m,3H),7.29-7.19(m,5H),6.51(dd,J＝10.3,1.1Hz,1H),5.74(d,J＝10.2Hz,1H),5.54(d,J＝7.0Hz,1H),4.53(d,J＝10.0Hz,1H),3.99-3.96(m,1H),3.85(s,3H),2.04(s,3H)；13C NMR(125MHz,CDCl3):δ195.2,172.6,170.5,144.3,142.5,138.2,135.1,131.4,131.0,130.6,128.5,128.3,126.9,125.7,124.3,95.7,85.6,83.5,55.7,55.2,53.7,21.8；HRMS(ESI):calcd.for C24H21O6[M+H]+:405.1333,found 405.1329。
example 5
This example prepares an aldehyde cyclohexadienone and polyoxin compounds of formula 1e by the following reaction sequence:
Figure BDA0003018625210000101
the preparation process comprises the following steps:
a25 mL reaction flask was charged with a solution of the catalyst (93mg, 0.1mmol), 4A molecular sieve (300mg) and aldehyde cyclohexadienone-based compound 2c (263mg, 1.0mmol) in dichloromethane (5.0mL), and stirred at room temperature for 2 h.
Then, diazo compound 3a (352mg, 2.0mmol) was dissolved in dichloromethane (5.0mL), and slowly injected into the above mixed solution by means of a syringe pump with continuous stirring, the reaction system was stirred at room temperature for 16 hours, and the crude product was separated by means of silica gel column chromatography after removal of the solvent to give product 1e (403mg, yield: 49%) as a white solid.
The detection data for the product 1e obtained are as follows:1H NMR(500MHz,CDCl3):δ7.65(d,J＝7.5Hz,1H),7.58-7.48(m,2H),7.45(d,J＝7.5Hz,1H),7.28-7.18(m,5H),6.88-6.52(m,1H),5.56(d,J＝6.7Hz,1H),4.67(d,J＝10.1Hz,1H),3.87(s,3H),3.7989.3,172.4,144.9,143.68(m,1H),3.19(s,3H)；13C NMR(125MHz,CDCl3):δ189.3,172.4,144.9,142.9,137.9,135.3,134.4,131.2,130.4,128.8,128.6,126.8,125.6,124.2,96.1,86.4,84.0,56.7,53.9,52.7,51.7；HRMS(ESI):calcd.for C23H20ClO5[M+H]+:411.0994,found 411.0991。
example 6
This example prepares an aldehyde cyclohexadienone and polyoxin compounds of formula 1f, the reaction is as follows:
Figure BDA0003018625210000111
the preparation process comprises the following steps:
a25 mL reaction flask containing the catalyst (93mg, 0.1mmol), 4A molecular sieve (300mg) and aldehyde cyclohexadienone compound 2d (258mg, 1.0mmol) was dissolved in a dichloromethane (5.0mL) solution and stirred at room temperature for 2 h.
Then, diazo compound 3a (352mg, 2.0mmol) was dissolved in dichloromethane (5.0mL), and slowly injected into the above mixed solution by means of a syringe pump with continuous stirring, the reaction system was stirred at room temperature for 16 hours, and the crude product was separated by means of silica gel column chromatography after removal of the solvent to give product 1f (512mg, yield: 63%) as a white solid.
The detection data of the obtained product 1f were as follows:1H NMR(500MHz,CDCl3):δ7.33(d,J＝8.5Hz,1H),7.25-7.22(m,5H),7.15(d,J＝2.3Hz,1H),7.07(dd,J＝8.5,2.4Hz,1H),6.55(d,J＝10.4Hz,1H),5.78(d,J＝10.3Hz,1H),5.54(d,J＝7.1Hz,1H),4.39(d,J＝10.3Hz,1H),3.86(d,J＝2.6Hz,6H),3.75(dd,J＝10.2,7.2Hz,1H),3.18(s,3H)；13C NMR(125MHz,CDCl3):δ196.1,172.7,161.5,146.9,139.8,137.2,135.0,131.3,128.6,128.3,125.7,125.2,118.6,110.2,96.1,86.2,81.9,55.7,55.0,53.7,52.6,51.6；HRMS(ESI):calcd.for C24H23O6[M+H]+:407.1489,found 407.1488。
the present invention has been described in detail with reference to the embodiments, but the present invention is not limited to the embodiments described above, and various changes can be made within the knowledge of those skilled in the art without departing from the gist of the present invention.

Claims (9)

1. An aldehyde cyclohexadienone and poly-oxygen ring compound is characterized by comprising a compound with a structure shown in a formula I;
Figure FDA0003018625200000011
wherein:
r comprises one of an aliphatic group and an acetyl group;
R1including one of a hydrogen atom and a halogen;
R2comprises one of ester group, heterocyclic substituent, substituted and unsubstituted benzene ring;
R3comprises one of ester group, aliphatic group, benzyl, substituted and unsubstituted benzene ring;
R4including one of a hydrogen atom, a halogen, and an aliphatic group.
2. The compound of claim 1, wherein the aldehyde is cyclohexadieno-polyoxirane compound:
R2is an ester group, a substituted or unsubstituted benzene ring;
R3is an ester group;
R4is a hydrogen atom or an aliphatic group.
3. The aldehyde cyclohexadienone and polyoxin ring compound according to claim 1, wherein the compound having the structure represented by formula I is selected from any one of the following structures 1a to 1 f:
Figure FDA0003018625200000021
4. the process for producing the cyclohexadienone and polyoxomethoxylate compound according to any one of claims 1 to 3, comprising the steps of: reacting aldehyde cycloadienone compounds with structures shown in formula II and diazo compounds with structures shown in formula III in the presence of a catalyst and a solvent, wherein:
Figure FDA0003018625200000022
5. the method according to claim 4, wherein the solvent comprises at least one of N, N-dimethylformamide, dichloromethane, methanol, toluene, and trifluorotoluene.
6. The method of claim 4, wherein the catalyst comprises a copper salt.
7. The method according to claim 4, wherein the aldehyde-based cyclohexadienone compound, the diazo compound and the catalyst are present in a molar ratio of 1: (1-5): (0.01-0.3).
8. The preparation method according to claim 4, wherein the reaction temperature is 20 ℃ to 100 ℃ and the reaction time is 2h to 48 h.
9. A pharmaceutical composition comprising the aldehydic cyclohexadienone and polyoxirane compound or a pharmaceutically acceptable salt thereof according to any one of claims 1 to 3.
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Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110204554A (en) * 2019-06-21 2019-09-06 五邑大学 Polysubstituted 1,4- oxaza heptane class compound and synthetic method

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Publication number Priority date Publication date Assignee Title
CN110204554A (en) * 2019-06-21 2019-09-06 五邑大学 Polysubstituted 1,4- oxaza heptane class compound and synthetic method

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Title
SVETLANA YU. KURBAKOVA ET AL.: "The short way to chiral compounds with hexahydrofluoreno[9,1-bc] furan framework: Synthesis and cytotoxic activity", 《BIOORGANIC & MEDICINAL CHEMISTRY》 *

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