CN105601597B - A kind of method of the synthesizing tricyclic class compound of anion driving - Google Patents
A kind of method of the synthesizing tricyclic class compound of anion driving Download PDFInfo
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- CN105601597B CN105601597B CN201610086850.7A CN201610086850A CN105601597B CN 105601597 B CN105601597 B CN 105601597B CN 201610086850 A CN201610086850 A CN 201610086850A CN 105601597 B CN105601597 B CN 105601597B
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- 150000001450 anions Chemical class 0.000 title claims abstract description 16
- 150000001875 compounds Chemical class 0.000 title claims abstract description 14
- 238000000034 method Methods 0.000 title claims abstract description 10
- 230000002194 synthesizing effect Effects 0.000 title claims abstract description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 14
- 150000002148 esters Chemical class 0.000 claims abstract description 14
- 239000002904 solvent Substances 0.000 claims abstract description 11
- 239000002253 acid Substances 0.000 claims abstract description 10
- 150000001336 alkenes Chemical class 0.000 claims abstract description 10
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 9
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 7
- 238000003756 stirring Methods 0.000 claims abstract description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 125000004185 ester group Chemical group 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical class CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 150000001335 aliphatic alkanes Chemical group 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 abstract description 5
- 238000001228 spectrum Methods 0.000 abstract description 3
- 239000000758 substrate Substances 0.000 abstract description 3
- 239000003863 metallic catalyst Substances 0.000 abstract description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 7
- HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 description 7
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- PZKNYJWHOZUWDF-MYZSUADSSA-N (1R,4S,8S,12R)-1,3,3,8-tetramethyl-2-oxatricyclo[6.3.1.04,12]dodecane Chemical compound CC1(C)O[C@@]2(C)[C@H]3[C@](C)(CCC2)CCC[C@H]13 PZKNYJWHOZUWDF-MYZSUADSSA-N 0.000 description 2
- -1 aryl phenol sodium Chemical compound 0.000 description 2
- 150000002240 furans Chemical class 0.000 description 2
- 229930014626 natural product Natural products 0.000 description 2
- 150000003233 pyrroles Chemical class 0.000 description 2
- BMLWUWFRRLHVAJ-UHFFFAOYSA-N 2-oxatricyclo[6.3.1.04,12]dodeca-1(11),4,6,8(12),9-pentaene Chemical group C1=CC(CO2)=C3C2=CC=CC3=C1 BMLWUWFRRLHVAJ-UHFFFAOYSA-N 0.000 description 1
- 239000005878 Azadirachtin Substances 0.000 description 1
- VEHPJKVTJQSSKL-UHFFFAOYSA-N azadirachtin Natural products O1C2(C)C(C3(C=COC3O3)O)CC3C21C1(C)C(O)C(OCC2(OC(C)=O)C(CC3OC(=O)C(C)=CC)OC(C)=O)C2C32COC(C(=O)OC)(O)C12 VEHPJKVTJQSSKL-UHFFFAOYSA-N 0.000 description 1
- FTNJWQUOZFUQQJ-IRYYUVNJSA-N azadirachtin A Natural products C([C@@H]([C@]1(C=CO[C@H]1O1)O)[C@]2(C)O3)[C@H]1[C@]23[C@]1(C)[C@H](O)[C@H](OC[C@@]2([C@@H](C[C@@H]3OC(=O)C(\C)=C/C)OC(C)=O)C(=O)OC)[C@@H]2[C@]32CO[C@@](C(=O)OC)(O)[C@@H]12 FTNJWQUOZFUQQJ-IRYYUVNJSA-N 0.000 description 1
- FTNJWQUOZFUQQJ-NDAWSKJSSA-N azadirachtin A Chemical compound C([C@@H]([C@]1(C=CO[C@H]1O1)O)[C@]2(C)O3)[C@H]1[C@]23[C@]1(C)[C@H](O)[C@H](OC[C@@]2([C@@H](C[C@@H]3OC(=O)C(\C)=C\C)OC(C)=O)C(=O)OC)[C@@H]2[C@]32CO[C@@](C(=O)OC)(O)[C@@H]12 FTNJWQUOZFUQQJ-NDAWSKJSSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
Classifications
-
- 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
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/92—Naphthofurans; Hydrogenated naphthofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/54—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of compounds containing doubly bound oxygen atoms, e.g. esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/64—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/90—Benzo [c, d] indoles; Hydrogenated benzo [c, d] indoles
Abstract
The invention discloses a kind of methods of the synthesizing tricyclic class compound of anion driving, belong to organic synthesis field.It specifically carries out as steps described below: sequentially adding connection olefin(e) acid ester, solvent and reagents for anion under nitrogen protection into reaction flask, tricyclic compounds can be prepared in 40 degrees Celsius of stirrings.The present invention has the advantages that without metallic catalyst, reagents for anion are cheap and easy to get, simple and effective, yield is high and substrate spectrum is wide.
Description
Technical field
The invention belongs to organic synthesis field, specifically a kind of side of the synthesizing tricyclic class compound of anion driving
Method.
Background technique
Tricyclic skeleton structure is widely present in the structure of natural molecule.Naphtho- [1,8-bc] furan structure unit is very much
The mother nucleus structure of natural products, such as its structure of (-)-Maalioxide and Azadirachtin are as follows:
Such natural products has important bioactivity.
Summary of the invention
Anion (ArX is used the present invention provides a kind of-) drive the side for joining olefin(e) acid ester (I) synthesizing tricyclic class compound (II)
Method, specific reaction equation are as follows:
Reaction equation 1 (ArXNa, aryl phenol sodium or aryl vulcanized sodium)
A kind of method of the synthesizing tricyclic class compound of anion driving, specifically carries out: nitrogen protection as steps described below
It is lower that connection olefin(e) acid ester (I), solvent and reagents for anion (ArXNa) are sequentially added into reaction flask, it can be made in 40 degrees Celsius of stirrings
Standby tricyclic compounds (II).
Wherein the solvent is methylene chloride, dichloroethanes, chloroform, toluene, tetrahydrofuran, N, N- methyl
Formamide and acetonitrile；Best solvent is acetonitrile；
The wherein structural formula of the connection olefin(e) acid ester (I) are as follows:
The wherein structural formula of the tricyclic compounds (II) are as follows:
The substituent group in structure described in wherein: R1=hydrogen atom or alkyl；R2=hydrogen atom or alkyl；R3=alkyl, alkane
Oxygroup, ester group or aryl；R4=alkyl or aryl；X '=O, NBoc or CH2；X=O or S.
The wherein structural formula of the reagents for anion (ArXNa) are as follows:(R is any substitution
Base), preferred aryl groups phenol sodium or aryl vulcanized sodium.
Advantages of the present invention
The invention has the advantages that reaction is without using metallic catalyst, reagents for anion are cheap and easy to get, and operation is simply high
Effect, high income and substrate spectrum are wide.
Specific embodiment
Below will by specific embodiment, the present invention will be further described, the invention is not limited to implementations below
Example:
6- hydroxyl 1. -4- (p-methoxyphenyl) -8a- methyl -3- phenoxy group -2,2a- dihydro -3H- naphtho- [1,8-bc]
The synthesis of furans -5 (8aH) -one (II-a):
Connection olefin(e) acid ester (I-a) (170mg), acetonitrile (3mL) and benzene are sequentially added under nitrogen protection into dry reaction tube
Phenol sodium (70mg)；It is stirred 5 hours at 40 degrees Celsius later.Reaction solution evaporating solvent under reduced pressure, residual solution are obtained by column chromatographic purifying
To 6- hydroxyl -4- (p-methoxyphenyl) -8a- methyl -3- phenoxy group -2,2a- dihydro -3H- naphtho- [1,8-bc] furans -5
(8aH) -one (II-a) (183mg, Yield:91%) be yellow solid, Mp:135-137 DEG C.1H NMR(300MHz,CDCl3)δ
14.86 (s, 1H), 7.42-7.24 (m, 4H), 7.19 (t, J=7.4Hz, 1H), 6.97 (d, J=7.6Hz, 2H), 6.90 (d, J
=7.6Hz, 2H), 6.31 (d, J=9.9Hz, 1H), 6.17 (d, J=9.9Hz, 1H), 3.91-3.82 (m, 1H), 3.79 (s,
3H),3.78–3.69(m,1H),3.47–3.33(m,2H),1.30(s,3H)；13C NMR(75MHz,CDCl3)δ187.35,
168.60,163.64,158.99,154.01,141.60,131.44,130.01,125.91,125.23,123.34,123.29,
120.01,113.50,97.46,78.49,71.42,55.23,44.02,42.18,27.30.
2. 6- hydroxyl -8a- methoxyl group -4- (4- methoxyphenyl) -3- (to toloxyl) -1,2,2a, 8a- tetrahydro acenaphthene -
5 (3H) -one (synthesis of (II-b):
Connection olefin(e) acid ester (I-b) (177mg), acetonitrile (3mL) and right are sequentially added under nitrogen protection into dry reaction tube
Cresols sodium (78mg)；It is stirred 5 hours at 40 degrees Celsius later.Reaction solution evaporating solvent under reduced pressure, residual solution are chromatographed pure by column
Change obtains 6- hydroxyl -8a- methoxyl group -4- (4- methoxyphenyl) -3- (to toloxyl) -1,2,2a, 8a- tetrahydro acenaphthene -5
(3H) -one ((II-b) (157mg, Yield:73%) be yellow solid, Mp:156-158 DEG C.1H NMR(400MHz,CDCl3)δ
15.22 (s, 1H), 7.33-7.28 (m, 2H), 7.11 (d, J=8.2Hz, 2H), 6.90 (t, J=8.8Hz, 4H), 6.55 (d, J
=10.1Hz, 1H), 6.07 (d, J=10.1Hz, 1H), 3.79 (s, 3H), 3.59 (d, J=7.5Hz, 1H), 3.19 (s, 3H),
3.13–3.04(m,1H),2.33(s,3H),2.02–1.84(m,3H),1.78–1.66(m,1H)；13C NMR(75MHz,
CDCl3)δ187.16,169.59,169.33,158.73,151.75,144.50,134.74,131.56,130.22,129.37,
126.10,123.99,120.55,113.44,98.50,88.09,55.21,52.26,40.42,39.21,38.23,29.86,
20.82.
3.N- tertbutyloxycarbonyl -6- hydroxyl -4- propyl -8a- butyl -3- phenoxy group -2,2a- dihydro -3H- naphtho- [1,8-
Bc] pyrroles -5 (8aH) -one (II-c)
Connection olefin(e) acid ester (I-c) (208mg), acetonitrile (3mL) and benzene are sequentially added under nitrogen protection into dry reaction tube
Phenol sodium (70mg)；It is stirred 5 hours at 40 degrees Celsius later.Reaction solution evaporating solvent under reduced pressure, residual solution are obtained by column chromatographic purifying
To N- tertbutyloxycarbonyl -6- hydroxyl -4- (p-methoxyphenyl) -8a- butyl -3- phenoxy group -2,2a- dihydro -3H- naphtho- [1,
8-bc] pyrroles -5 (8aH) -one (II-c) (196mg, Yield:82%) be yellow viscous liquid.1H NMR(300MHz,CDCl3)
δ15.29(s,1H),15.27(s,0.8H),7.44–7.34(m,3H),7.24–7.16(m,2H),7.06–6.94(m,4H),
6.80 (d, J=10.1Hz, 1H), 6.48 (d, J=10.1Hz, 0.8H), 6.15-6.05 (m, 1.8H), 3.53-2.99 (m,
7.2H),2.53–2.31(m,3.6H),2.20–2.07(m,1H),1.98–1.86(m,0.8H),1.55–1.45(m,3.6H),
1.42 (s, 7.2H), 1.37 (s, 9H), 1.30-1.19 (m, 6H), 1.14-1.02 (m, 3H), 0.94 (t, J=7.4Hz,
5.4H),0.89–0.82(m,5.4H)；13C NMR(75MHz,CDCl3)δ187.72,187.30,170.69,169.70,
164.33,163.72,154.65,154.20,152.75,152.47,143.13,142.54,130.11,130.00,124.95,
124.63,124.60,124.57,124.53,123.69,119.57,119.06,96.95,96.72,80.44,79.84,
63.20,62.46,51.68,51.44,41.99,40.71,37.56,36.96,36.85,35.94,29.73,29.08,
28.56,28.46,24.48,24.44,23.08,23.02,22.08,22.05,14.23,14.17,14.04,13.93.
6- hydroxyl 4. -4- (p-methoxyphenyl) -8a- methoxyl group -3- thiophenyl -2,2a- dihydro -3H- naphtho- [1,8-
Bc] furans -5 (8aH) -one (II-d) synthesis:
Connection olefin(e) acid ester (I-d) (170mg), acetonitrile (3mL) and benzene are sequentially added under nitrogen protection into dry reaction tube
Phenol sodium (70mg)；It is stirred 5 hours at 40 degrees Celsius later.Reaction solution evaporating solvent under reduced pressure, residual solution are obtained by column chromatographic purifying
To 6- hydroxyl -4- (p-methoxyphenyl) -8a- methoxyl group -3- thiophenyl -2,2a- dihydro -3H- naphtho- [1,8-bc] furans -5
(8aH) -one (II-d) (184mg, Yield:85%) is brown solid, Mp:58-60 DEG C of1H NMR(300MHz,CDCl3)δ
13.30 (s, 1H), 7.36-7.18 (m, 7H), 6.87 (d, J=8.7Hz, 2H), 6.64 (d, J=10.3Hz, 1H), 6.22 (d, J
=10.3Hz, 1H), 4.70 (dd, J=12.6,1.7Hz, 1H), 4.50 (dd, J=12.6,1.7Hz, 1H), 4.14 (s, 1H),
3.78(s,3H),3.52(s,1H),3.41(s,3H)；13C NMR(75MHz,CDCl3)δ195.68,166.68,159.14,
146.76,133.08,132.34,131.00,129.44,128.54,127.77,126.32,125.64,124.71,114.45,
102.81,102.33,66.87,55.45,55.32,48.99,47.37.
By the example of above-mentioned offer show the step driven the present invention provides a kind of no metal catalytic, anion it is easy,
Efficiently synthesize tricyclic compounds (6- hydroxyl -4- (4- aryl) -8a-3- aryloxy group/aromatic thiohydroxy -2,2a, 2a1,8a- tetrahydro -
5H- naphthalene [1,8-bc] furans -5- ketone) method, have the advantages that high income and substrate spectrum are wide.
Claims (2)
1. a kind of method of the synthesizing tricyclic class compound of anion driving, it is characterised in that carry out as steps described below: nitrogen
Connection olefin(e) acid ester (I), solvent and reagents for anion are sequentially added under protection into reaction flask, can be prepared in 40 degrees Celsius of stirrings
Tricyclic compounds (II)；Wherein the solvent is methylene chloride, dichloroethanes, chloroform, toluene, tetrahydrofuran, N, N- first
Base formamide or acetonitrile；
The wherein structural formula of the connection olefin(e) acid ester (I) are as follows:；Described
Substituent group in structure: R1=hydrogen atom or alkyl；R2=hydrogen atom or alkyl；R3=alkyl, alkoxy, ester group or aryl；R4
=alkyl or aryl；X '=O, NBoc or CH2；
The wherein structural formula of the tricyclic compounds (II) are as follows:；The structure
On substituent group: R1=hydrogen atom or alkyl；R2=hydrogen atom or alkyl；R3=alkyl, alkoxy, ester group or aryl；R4=alkane
Base or aryl；X '=O, NBoc or CH2；X=O or S；
The reagents for anion are ArXNa and structural formula are as follows:Or, R is any substitution
Base.
2. a kind of method of the synthesizing tricyclic class compound of anion driving described in claim 1, it is characterised in that wherein institute
The solvent stated is acetonitrile.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102786466A (en) * | 2012-07-13 | 2012-11-21 | 常州大学 | Synthetic method of chiral Salan ligand |
| CN102924278A (en) * | 2012-11-14 | 2013-02-13 | 常州大学 | Synthesis method of (S)-5-chloro-2- methoxycarbonyl-2- hydroxyl-1-indanone |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102786466A (en) * | 2012-07-13 | 2012-11-21 | 常州大学 | Synthetic method of chiral Salan ligand |
| CN102924278A (en) * | 2012-11-14 | 2013-02-13 | 常州大学 | Synthesis method of (S)-5-chloro-2- methoxycarbonyl-2- hydroxyl-1-indanone |
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Application publication date: 20160525 Assignee: Senbiao Technology Services (Shandong) Co.,Ltd. Assignor: CHANGZHOU University Contract record no.: X2023980051006 Denomination of invention: A method for synthesizing tricyclic compounds driven by anions Granted publication date: 20190125 License type: Common License Record date: 20231209 |
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