CN109180446A - A kind of synthetic method of 2,3- diphenyl -1H- 1-Indanone derivative - Google Patents
A kind of synthetic method of 2,3- diphenyl -1H- 1-Indanone derivative Download PDFInfo
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- CN109180446A CN109180446A CN201810804043.3A CN201810804043A CN109180446A CN 109180446 A CN109180446 A CN 109180446A CN 201810804043 A CN201810804043 A CN 201810804043A CN 109180446 A CN109180446 A CN 109180446A
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- 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
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/48—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation involving decarboxylation
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- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
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- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
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Abstract
The invention discloses one kind 2, the synthetic method of 3- diphenyl -1H- 1-Indanone derivative, include the following steps: that benzoyl formic acid, (diphenyl) acetylene compounds, dichloride pentamethylcyclopentadiene are closed iridium, copper acetate, silver hexafluoroantimonate and Phosphine ligands and be added in organic solvent, heating is reacted under air conditions, after fully reacting, post-processing obtains 2, the 3- diphenyl -1H- 1-Indanone derivative.This method is by raw material one-step synthesis 2 simple and easy to get, 3- diphenyl -1H- 1-Indanone derivative, high conversion efficiency, and Atom economy is good；Simultaneously synthesizing method is easy to operate, and reaction yield is high, while substrate wide adaptability.
Description
Technical field
The invention belongs to organic synthesis fields, and in particular to the synthesis of one kind 2,3- diphenyl -1H- 1-Indanone derivative
Method.
Background technique
Indone is intermediate useful in organic synthesis, while being also used widely in biology and Material Field.It passes
Controlling for the method for indone is obtained by Fried-Crafts Cyclization method.This method is needed using Electron rich aromatic race
Reagent is as raw material, therefore that reacts is limited in scope.In addition, reaction condition is relatively harsh, and generally produce during reaction
Harmful by-product.Indone compound is prepared using transition metal-catalyzed ortho position Bifunctionalized aromatic hydrocarbons and alkynes cycloaddition later.
Raw material is not limited to electron rich aromatic compounds, and many electron-defect compounds have been successfully used in these reactions.However, adjacent double
Functionalization aromatic hydrocarbons is usually not readily available, it usually needs complicated pre- functionizing method obtains these aromatic hydrocarbons.
C h bond priming reaction transition metal-catalyzed in recent years has caused very big concern.Using functional group with
The kindred effect of metal center coordination realizes selective c h bond activation, then cyclization occurs to react to be construction annular point with alkynes molecule
The effective ways of son.This method does not need the Bifunctionalized aromatic hydrocarbons in ortho position as substrate, therefore is more efficient cyclization.Mesh
Before, some catalysis process have been developed, have prepared indone compound using orientation c h bond activation strategy.Kokubo seminar report
The reaction of road rhodium catalysis aryl chloride and alkynes prepares indone.Shi seminar, which reports, is catalyzed C-H activation process by ruthenium, makes benzene
Carboximide and alkynes cyclisation prepare indone.Then, have been reported that, about rhodium catalysis aldehyde, azomethine lactone and nitro replace successively
The cyclization of aromatic compound and alkynes prepares indone.Carboxylic acid compound is usually used in various organic reactions, and wherein decarboxylation intersects
Coupling reaction was rapidly developed in recent years.
Summary of the invention
In view of this, the present invention has studied the reaction of mandelic acid and alkynes, under iridium catalytic action, energy one-step synthesis is a variety of
Indenone derivative, benzoyl formic acid is similar with mandelic acid, and a kind of carboxylic acid compound simple and easy to get, further studies iridium
Catalysis benzoyl formic acid synthesizes indone compound with the c h bond of alkynes activation decarboxylation annulation.This method mild condition, reaction
Wide adaptability provides a kind of simple effective method for synthesis 2,3- diphenyl -1H- 1-Indanone derivative, overcomes existing skill
Severe reaction conditions in art, the defect for being also easy to produce harmful by-products.
The present invention provides the synthetic method of one kind 2,3- diphenyl -1H- 1-Indanone derivative, include the following steps: by
Benzoyl formic acid, (diphenyl) acetylene compounds, dichloride pentamethylcyclopentadiene close iridium, copper acetate, silver hexafluoroantimonate and phosphine and match
Body is added in organic solvent, and heating is reacted under air conditions, and after fully reacting, post-processing obtains 2, the 3- hexichol
Base -1H- 1-Indanone derivative.
Reaction process is shown below:
The synthetic method of present invention one kind 2,3- diphenyl -1H- 1-Indanone derivative as described above, it is further, described
Shown in benzoyl formic acid structure such as formula (II):
Shown in the diphenyl acetylene derivatire class compound structure such as formula (Ш):
Shown in the 2,3- diphenyl -1H- 1-Indanone derivant structure such as formula (Ι):
In formula (Ι), R1Selected from H, methyl, methoxyl group, phenyl, 1- naphthalene, halogen；
R2, R3Selected from methyl, alkoxy, tert-butyl, halogen, trifluoromethyl, trifluoromethoxy, ester group, phenyl.
In formula (II), R2, R3Selected from methyl, alkoxy, tert-butyl, halogen, trifluoromethyl, trifluoromethoxy, ester group, benzene
Base.
Preferably, 2, the 3- diphenyl -1H- 1-Indanone derivative is chemical combination shown in formula (I-1)-formula (I-16)
One of object:
Preferably, the organic solvent is toluene.
Preferably, 120 DEG C~130 DEG C, the reaction time is 15~25 hours.
Compared with the existing technology, the beneficial effects of the present invention are embodied in:
(1) present invention passes through raw material one-step synthesis 2 simple and easy to get, 3- diphenyl -1H- 1-Indanone derivative, conversion effect
Rate is high, and Atom economy is good；
(2) synthetic method of the invention is easy to operate, and reaction yield is high, while substrate wide adaptability.
Specific embodiment
The present invention will be further described combined with specific embodiments below, following specific embodiments be all it is of the invention most
Excellent embodiment.
Embodiment 1~16
Benzoyl formic acid (0.2mmol), alkynes compound are added in test tube according to the raw material proportioning of table 1
(0.2mmol), dichloride pentamethylcyclopentadiene close iridium (0.02mmol), copper acetate (0.04mmol), silver hexafluoroantimonate
(0.02mmol), three (3- methoxyphenyl) phosphines (0.02mmol) and organic solvent 1ml, are mixed evenly, according to the anti-of table 2
It is cooling after the completion of answering conditioned response, it filters, silica gel mixed sample obtains corresponding 2,3- diphenyl -1H- indenes-by column chromatographic purifying
1- ketone derivatives (I).
The raw material proportioning of 1 embodiment 1~16 of table
The reaction condition and reaction result of 2 embodiment 1~16 of table
In Tables 1 and 2, T is reaction temperature, and t is the reaction time, and n-Bu is normal-butyl, and 1-naphthyl is that 1- replaces naphthalene
Base.In addition to Ι -2, the R of Ι -122Other than ortho position substitution, R2All replace for contraposition.
The structure confirmation data of part of compounds is prepared in embodiment 1~16:
The structural formula of 2,3- diphenyl -1H- 1-Indanone derivative prepared by the embodiment of the present invention 1 are as follows:
Yield: 24.0mg, yield: 85%, red solid, fusing point are as follows: 149 DEG C of -150 DEG C of
The hydrogen of product is composed are as follows: δ 7.61 (d, J=6.96Hz, 1H), 7.46-7.37 (m, 6H), 7.33-7.27 (m, 6H),
7.17 (d, J=7.20Hz, 1H)；
Carbon spectrum are as follows:13C NMR(CDCl3,100MHz):δ196.37,155.23,145.11,133.36,132.61,
132.27,131.51,130.65,129.90,129.22,128.87,128.71,128.42,127.99,127.66,122.87,
121.18；
Infrared spectrum are as follows: IR (KBr): ν 3739,3446,3062,2921,2360,1708,1609,1450,1349,
1183,1075,919,840,734,695cm-1；
Mass spectrogram are as follows: HRMS (ESI) m/zcalcd for C21H14O([M+H]+)283.1125,found 283.1131.
The structural formula of 2,3- diphenyl -1H- 1-Indanone derivative prepared by the embodiment of the present invention 2 are as follows:
Yield: 19.2mg, yield: 62%；Red solid；Fusing point are as follows: 150 DEG C of -151 DEG C of
The hydrogen of product is composed are as follows:1H NMR(CDCl3, 400MHz): δ 7.60 (d, J=7.76Hz, 1H), 7.39-7.35 (m,
1H), 7.32-7.27 (m, 2H), 7.23-7.06 (m, 6H), 6.96 (d, J=7.56Hz, 1H), 6.90 (d, J=7.12Hz,
1H),2.17(s,3H),2.11(s,3H)；
Carbon spectrum are as follows:13C NMR(CDCl3,100MHz):δ196.20,157.57,157.51,145.87,137.06,
135.91,135.78,133.47,132.27,130.97,130.69,130.53,130.22,128.84,128.10,125.77,
125.35,122.84,121.44,20.62,20.13；
Infrared spectrum are as follows: IR (KBr): ν 3563,2920,1711,1606,1457,1341,1261,1176,1070,
1033,925,849,752cm-1；
Mass spectrogram are as follows: HRMS (ESI) m/zcalcd for C23H18O([M+H]+)311.1438,found 311.1442.
The structural formula of 2,3- diphenyl -1H- 1-Indanone derivative prepared by the embodiment of the present invention 3 are as follows:
Yield: 27.0mg, yield: 87%；Red solid；Fusing point are as follows: 147 DEG C of -148 DEG C of
The hydrogen of product is composed are as follows:1H NMR(CDCl3, 400MHz): δ 7.59 (d, J=7.00Hz, 1H), 7.39-7.30 (m,
4H), 7.25-7.18 (m, 5H), 7.12 (d, J=7.80Hz, 2H), 2.43 (s, 3H), 2.35 (s, 3H)；
Carbon spectrum are as follows:13C NMR(CDCl3,100MHz):δ196.67,154.71,145.38,139.26,137.44,
133.23,131.96,130.86,129.83,129.78,129.74,129.39,129.34,128.76,128.65,128.42,
127.91,123.83,122.70,121.06,120.94,21.45,21.28；
Infrared spectrum are as follows: IR (KBr): ν 3620,2925,1709,1604,1507,1460,1346,1186,1071,
1018,818,736cm-1；
Mass spectrogram are as follows: HRMS (ESI) m/zcalcd for C23H18O([M+H]+)311.1438,found 311.1439.
The structural formula of 2,3- diphenyl -1H- 1-Indanone derivative prepared by the embodiment of the present invention 4 are as follows:
Yield: 27.7mg, yield: 81%；Red solid；Fusing point are as follows: 141 DEG C of -142 DEG C of
The hydrogen of product is composed are as follows:1H NMR(CDCl3, 400MHz): δ 7.57 (d, J=6.92Hz, 1H), 7.48-7.37 (m,
3H), 7.30-7.25 (m, 3H), 7.19 (d, J=7.24Hz, 1H), 6.96 (d, J=8.76Hz, 2H), 6.84 (d, J=
8.76Hz,2H),3.88(s,3H),3.82(s,3H)；
Carbon spectrum are as follows:13C NMR(CDCl3,100MHz):δ196.91,160.29,159.09,153.75,145.49,
133.22,131.25,131.03,130.15,128.58,127.11,125.13,123.43,122.68,120.92,114.20,
113.66,55.29,55.17；
Infrared spectrum are as follows: IR (KBr): ν 3450,2925,2360,1703,1606,1507,1459,1403,1294,
1249,1175,1029,788cm-1；
Mass spectrogram are as follows: HRMS (ESI) m/zcalcd for C23H18O3([M+H]+)343.1336,found 343.1339.
The structural formula of 2,3- diphenyl -1H- 1-Indanone derivative prepared by the embodiment of the present invention 5 are as follows:
Yield: 29.6mg, yield: 80%；Red solid；Fusing point are as follows: 145 DEG C of -146 DEG C of
The hydrogen of product is composed are as follows:1H NMR(CDCl3, 400MHz): δ 7.57 (d, J=7.48Hz, 1H), 7.36 (d, J=
8.64Hz, 3H), 7.29-7.24 (m, 3H), 7.19 (d, J=7.20Hz, 1H), 6.94 (d, J=8.76Hz, 2H), 6.82 (d, J
=8.84Hz, 2H), 4.12-4.02 (m, 4H), 1.49-1.41 (m, 6H)；
Carbon spectrum are as follows:13C NMR(CDCl3,100MHz):δ196.97,159.70,158.47,153.73,153.73,
145.52,133.18,131.24,131.06,130.15,128.53,124.98,123.29,122.64,120.92,114.65,
114.17,63.52,63.33,14.82,14.79；
Infrared spectrum are as follows: IR (KBr): ν 3579,2977,2925,2360,1701,1604,1468,1346,1289,
1178,1075,1042,919,823,764,667cm-1；
Mass spectrogram are as follows: HRMS (ESI) m/zcalcd for C25H22O3([M+H]+)371.1649,found 371.1643.
The structural formula of 2,3- diphenyl -1H- 1-Indanone derivative prepared by the embodiment of the present invention 6 are as follows:
Yield: 33.9mg, yield: 86%；Red solid；Fusing point are as follows: 151 DEG C of -152 DEG C of
The hydrogen of product is composed are as follows:1H NMR(CDCl3, 400MHz): δ 7.60 (d, J=7.20Hz, 1H), 7.47 (d, J=
8.52Hz, 2H), 7.40-7.33 (m, 4H), 7.32-7.28 (m, 4H), 7.19 (d, J=7.24Hz, 1H), 1.41 (s, 9H),
1.35(s,9H)；
Carbon spectrum are as follows:13C NMR(CDCl3,100MHz):δ196.86,154.63,152.37,150.47,145.55,
133.21,131.74,130.87,129.85,129.53,128.60,128.24,127.87,125.54,124.93,122.67,
121.21,34.81,34.55,31.23,31.17；
Infrared spectrum are as follows: IR (KBr): ν 3456,2525,1634,1415,1390,1167,1106,1054,1026,945,
891,750cm-1；
Mass spectrogram are as follows: HRMS (ESI) m/zcalcd for C29H30O([M+H]+)395.2377,found 395.2376.
The structural formula of 2,3- diphenyl -1H- 1-Indanone derivative prepared by the embodiment of the present invention 7 are as follows:
Yield: 26.6mg, yield: 76%；Red solid；Fusing point are as follows: 142 DEG C of -143 DEG C of
The hydrogen of product is composed are as follows:1H NMR(CDCl3, 400MHz): δ 7.61 (d, J=7.00Hz, 1H), 7.45-7.40 (m,
3H), 7.34 (d, J=8.28Hz, 3H), 7.29-7.27 (m, 2H), 7.22 (d, J=7.56Hz, 2H), 7.14 (d, J=
8.64Hz,1H)；
Carbon spectrum are as follows:13C NMR(CDCl3,100MHz):δ195.77,154.28,144.63,135.52,134.03,
133.67,133.65,131.52,131.18,130.85,130.48,129.83,129.34,129.32,128.53,123.27,
121.16；
Infrared spectrum are as follows: IR (KBr): ν 3535,2962,2871,2354,1723,1607,1457,1389,1283,
1120,1082,1013,960,866,721,661cm-1；
Mass spectrogram are as follows: HRMS (ESI) m/zcalcd for C21H12Cl2O([M+H]+)351.0345,found
351.0349.
The structural formula of 2,3- diphenyl -1H- 1-Indanone derivative prepared by the embodiment of the present invention 8 are as follows:
Yield: 31.9mg, yield: 73%；Red solid；Fusing point are as follows: 145 DEG C of -146 DEG C of
The hydrogen of product is composed are as follows:1H NMR(CDCl3,400MHz):δ7.62-7.56(m,2H),7.46-7.39(m,4H),
7.35-7.27(m,4H),7.16-7.12(m,2H)；
Carbon spectrum are as follows:13C NMR(CDCl3,100MHz):δ195.61,154.28,144.52,133.63,132.27,
132.09,131.46,131.43,130.43,130.01,129.88,129.80,129.32,123.78,123.25,122.35,
121.15；
Infrared spectrum are as follows: IR (KBr): ν 3059,2925,2851,1709,1602,1456,1342,1263,1179,
1069,1010,921,827,760,673cm-1；
Mass spectrogram are as follows: HRMS (ESI) m/zcalcd for C21H12Br2O([M+H]+)438.9335,found
438.9337.
The structural formula of 2,3- diphenyl -1H- 1-Indanone derivative prepared by the embodiment of the present invention 9 are as follows:
Yield: 31.4mg, yield: 75%；Red solid；Fusing point are as follows: 148 DEG C of -149 DEG C of
The hydrogen of product is composed are as follows:
1H NMR(CDCl3, 400MHz): δ 7.75 (d, J=8.08Hz, 2H), 7.66 (d, J=6.92Hz, 1H), 7.55
(dd, J=7.44,6.68Hz, 4H), 7.45 (t, J=7.68Hz, 1H), 7.40-7.37 (m, 3H), 7.14 (d, J=7.52Hz,
1H)；
Carbon spectrum are as follows:13C NMR(CDCl3,100MHz):δ195.28,155.01,144.30,135.92,133.89,
133.80,131.55 (q, J=32Hz), 130.20,129.76,128.81,126.09 (q, J=3.72Hz), 125.21 (q, J
=3.72Hz), 123.97 (q, J=271Hz), 123.73 (q, J=272Hz), 123.61,121.43；
Fluorine spectrum are as follows:19F NMR(376MHz,CDCl3): δ -62.77 (s, 3F), -62.86 (s, 3F)；
Infrared spectrum are as follows: IR (KBr): ν 3626,2921,2363,1712,1603,1459,1343,1272,1183,
1072,1026,915,849,757,694cm-1；
Mass spectrogram are as follows: HRMS (ESI) m/zcalcd for C23H12F6O([M+H]+)419.0872,found
419.0865.
The structural formula of 2,3- diphenyl -1H- 1-Indanone derivative prepared by the embodiment of the present invention 10 are as follows:
Yield: 31.9mg, yield: 71%；Red solid；Fusing point are as follows: 154 DEG C of -156 DEG C of
The hydrogen of product is composed are as follows:1H NMR(CDCl3, 400MHz): δ 7.63 (d, J=6.92Hz, 1H), 7.46-7.41 (m,
3H),7.37-7.30(m,5H),7.17-7.14(m,3H)；
Carbon spectrum are as follows:13C NMR(CDCl3, 100MHz): δ 195.76,154.26,149.34 (q, J=102Hz), 144.59,
133.73,131.45,131.37,130.85,130.35,130.13,129.44,128.93,123.36,121.66,120.59,
120.38 (q, J=258Hz)；
Fluorine spectrum are as follows:19F NMR(376MHz,CDCl3):δ–57.73(s,6F)；
Infrared spectrum are as follows: IR (KBr): ν 3567,2922,2361,1715,1611,1408,1346,1267,1173,
1021,926,837,744,692cm-1；
Mass spectrogram are as follows: HRMS (ESI) m/zcalcd for C23H12F6O3([M+H]+)451.0771,found
450.0765.
The structural formula of 2,3- diphenyl -1H- 1-Indanone derivative prepared by the embodiment of the present invention 11 are as follows:
Yield: 25.6mg, yield: 60%；Red solid；Fusing point are as follows: 160 DEG C of -161 DEG C of
The hydrogen of product is composed are as follows:1H NMR(CDCl3, 400MHz): δ 8.12 (d, J=8.44Hz, 2H), 7.96 (d, J=
8.52Hz, 2H), 7.65 (d, J=7.0Hz, 1H), 7.47-7.42 (m, 3H), 7.38-7.33 (m, 3H), 7.15 (d, J=
8.28Hz,1H),4.46-4.35(m,4H),1.46-1.38(m,6H)；
Carbon spectrum are as follows:13C NMR(CDCl3,100MHz):δ194.35,165.87,155.49,151.20,144.54,
140.78,136.91,134.94,133.78,131.43,130.15,129.83,129.58,129.34,128.44,123.45,
121.43,61.29,60.98,14.31；
Infrared spectrum are as follows: IR (KBr): ν 3578,2928,2367,1718,1606,1459,1368,1277,1180,
1070,1021,927,836,771,711cm-1；
Mass spectrogram are as follows: HRMS (ESI) m/zcalcd for C27H22O5([M+H]+)427.1547,found 427.1544.
The structural formula of 2,3- diphenyl -1H- 1-Indanone derivative prepared by the embodiment of the present invention 12 are as follows:
Yield: 21.9mg, yield: 55%；Red solid；Fusing point are as follows: 180 DEG C of -182 DEG C of
The hydrogen of product is composed are as follows:1H NMR(CDCl3,400MHz):δ8.09-8.06(m,1H),8.00-7.97(m,1H),
7.57 (d, J=8.48Hz, 1H), 7.45-7.42 (m, 2H), 7.33-7.28 (m, 3H), 7.25-7.23 (m, 2H), 7.06-
7.04 (m, 1H), 6.72 (d, J=7.16Hz, 1H), 3.84 (s, 3H), 3.72 (s, 3H)；
Carbon spectrum are as follows:13C NMR(CDCl3,100MHz):δ195.14,167.60,167.15,155.02,146.26,
134.80,134.13,133.44,132.71,132.26,131.70,131.42,131.15,130.39,130.24,130.00,
128.83,128.34,127.81,123.04,119.95,52.26,52.14；
Infrared spectrum are as follows: IR (KBr): ν 3667,2951,2363,1721,1668,1437,1344,1269,1187,
1074,1042,927,853,761,681cm-1；
Mass spectrogram are as follows: HRMS (ESI) m/zcalcd for C25H18O5([M+H]+)399.1234,found 399.1236.
The structural formula of 2,3- diphenyl -1H- 1-Indanone derivative prepared by the embodiment of the present invention 13 are as follows:
Yield: 21.6mg, yield: 73%；Red solid；Fusing point are as follows: 174 DEG C of -176 DEG C of
The hydrogen of product is composed are as follows:1H NMR(CDCl3, 400MHz): δ 7.51 (d, J=7.24Hz, 1H), 7.45-7.44 (m,
3H), 7.41-7.38 (m, 2H), 7.29-7.27 (m, 5H), 7.10 (d, J=7.28Hz, 1H), 6.96 (s, 1H), 2.38 (s,
3H)；
Carbon spectrum are as follows:13C NMR(CDCl3,100MHz):δ196.16,154.93,145.72,144.38,132.90,
132.81,130.88,129.97,129.14,128.91,128.77,128.51,128.38,128.01,127.65,123.05,
122.51,22.08；
Infrared spectrum are as follows: IR (KBr): ν 3572,2920,2361,1704,1603,1469,1357,1275,1188,
1070,1031,922,839,732,695cm-1；
Mass spectrogram are as follows: HRMS calcd.for C27H18O:358.1358,found:358.1365；
The structural formula of 2,3- diphenyl -1H- 1-Indanone derivative prepared by the embodiment of the present invention 14 are as follows:
Yield: 25.1mg, yield: 70%；Red solid；Fusing point are as follows: 181 DEG C of -183 DEG C of
The hydrogen of product is composed are as follows:1H NMR(CDCl3, 400MHz): δ 7.89 (d, J=1.72Hz, 1H), 7.67-7.63 (m,
3H),7.52-7.41(m,7H),7.36-7.29(m,7H)；
Carbon spectrum are as follows:13C NMR(CDCl3,100MHz):δ196.29,155.39,144.00,142.26,139.92,
132.81,131.67,131.57,130.79,129.97,129.35,128.94,128.82,128.51,128.10,127.90,
127.78,126.78,121.95,121.61；
Infrared spectrum are as follows: IR (KBr): ν 3362,2925,1707,1605,1466,1346,1260,1077,969,846,
768,730,696cm-1；
Mass spectrogram are as follows: HRMS calcd.for C27H18O:358.1358,found:358.1365；
The structural formula of 2,3- diphenyl -1H- 1-Indanone derivative prepared by the embodiment of the present invention 15 are as follows:
Yield: 26.9mg, yield: 66%；Red solid；Fusing point are as follows: 193 DEG C of -195 DEG C of
The hydrogen of product is composed are as follows:1H NMR(CDCl3, 400MHz): δ 7.94-7.88 (m, 3H), 7.77 (d, J=1.12Hz,
1H),7.56-7.53(m,3H),7.51-7.44(m,7H),7.34-7.28(m,6H)；
Carbon spectrum are as follows:13C NMR(CDCl3,100MHz):δ196.35,155.34,144.12,141.86,138.94,
134.74,133.84,132.77,132.68,131.28,130.98,130.76,129.97,129.44,129.36,128.84,
128.61,128.51,128.43,128.21,128.10,127.78,126.74,126.35,125.97,125.56,125.37,
124.87,121.23；
Infrared spectrum are as follows: IR (KBr): ν 2926,2847,1728,1602,1460,1378,1260,1162,1033,808,
781,749cm-1；
Mass spectrogram are as follows: HRMS calcd.for C31H20O:409.1594,found:409.1591；
The structural formula of 2,3- diphenyl -1H- 1-Indanone derivative prepared by the embodiment of the present invention 16 are as follows:
Yield: 22.7mg, yield: 63%；Red solid；Fusing point are as follows: 167 DEG C of -168 DEG C of
The hydrogen of product is composed are as follows:1H NMR(CDCl3,400MHz):δ7.46-7.42(m,5H),7.37-7.34(m,2H),
7.27-7.26(m,6H)；
Carbon spectrum are as follows:13C NMR(CDCl3,100MHz):δ195.18,154.15,147.28,133.40,132.19,
131.62,130.27,129.98,129.56,129.35,129.00,128.36,128.14,128.08,124.69,124.07；
Infrared spectrum are as follows: IR (KBr): ν 3561,3059,2957,2926,2852,1713,1601,1485,1445,
1350,1262,1063,1029,786cm-1；
Mass spectrogram are as follows: HRMS calcd.for C21H13BrO:361.0230,found:361.0237。
Claims (7)
1. one kind 2, the synthetic method of 3- diphenyl -1H- 1-Indanone derivative, which comprises the steps of: by benzene
Formic acid, (diphenyl) acetylene compounds, dichloride pentamethylcyclopentadiene close iridium, copper acetate, silver hexafluoroantimonate and Phosphine ligands
It being added in organic solvent, heating is reacted under air conditions, and it is cooling after fully reacting, it filters, silica gel mixed sample, by column
Chromatographic purifying obtains 2, the 3- diphenyl -1H- 1-Indanone derivative, as shown in following formula (Ι):
R1Selected from H, methyl, methoxyl group, phenyl, 1- naphthalene, any one in halogen；
R2, R3It is respectively selected from methyl, alkoxy, tert-butyl, halogen, trifluoromethyl, trifluoromethoxy, ester group is any in phenyl
It is a kind of.
2. the synthetic method of 2,3- diphenyl -1H- 1-Indanone derivative according to claim 1, which is characterized in that institute
It states benzoyl formic acid, (diphenyl) acetylene compounds, dichloride pentamethylcyclopentadiene and closes iridium, copper acetate, silver hexafluoroantimonate and phosphine
The molar ratio of ligand is followed successively by 0.2:(0.2-0.3): (0.01-0.03): (0.03-0.05): (0.01-0.03): (0.01-
0.03)。
3. the synthetic method of 2,3- diphenyl -1H- 1-Indanone derivative according to claim 1, which is characterized in that institute
2,3- diphenyl -1H- 1-Indanone the derivative stated is one of compound shown in formula (I-1)-formula (I-16):
4. the synthetic method of 2,3- diphenyl -1H- 1-Indanone derivative according to claim 1, which is characterized in that institute
Shown in the benzoyl formic acid structure such as formula (II) stated:
R1Selected from H, methyl, methoxyl group, phenyl, 1- naphthalene, any one in halogen.
5. the synthetic method of 2,3- diphenyl -1H- 1-Indanone derivative according to claim 1, which is characterized in that institute
Shown in the (diphenyl) acetylene compounds structure such as formula (Ш) stated:
R2, R3It is respectively selected from methyl, alkoxy, tert-butyl, halogen, trifluoromethyl, trifluoromethoxy, ester group is any in phenyl
It is a kind of.
6. the synthetic method of 2,3- diphenyl -1H- 1-Indanone derivative according to claim 1-5, feature
It is, the organic solvent is toluene.
7. the synthetic method of 2,3- diphenyl -1H- 1-Indanone derivative according to claim 1-5, feature
It is, reaction temperature is 120 DEG C~130 DEG C, and the reaction time is 15~25 hours.
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| CN114560761A (en) * | 2022-01-29 | 2022-05-31 | 南京林业大学 | Method for synthesizing 2, 3-disubstituted indanone derivative in aqueous phase at one time |
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| CN114560761A (en) * | 2022-01-29 | 2022-05-31 | 南京林业大学 | Method for synthesizing 2, 3-disubstituted indanone derivative in aqueous phase at one time |
| CN114560761B (en) * | 2022-01-29 | 2023-02-24 | 南京林业大学 | Method for one-time synthesis of 2,3-disubstituted indanone derivative in aqueous phase |
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