CN109942465A - A kind of cycloheptatriene -1- thio-ether type compounds and its synthetic method and application - Google Patents
A kind of cycloheptatriene -1- thio-ether type compounds and its synthetic method and application Download PDFInfo
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Abstract
The invention belongs to technical field of organic synthesis, a kind of cycloheptatriene -1- thio-ether type compounds and its synthetic method and application are disclosed.Cycloheptatriene -1- the thio-ether type compounds are that cycloheptatriene, phenyl-sulfhydrate compounds and oxidant are added in solvent to react at 20~30 DEG C, purified to be made；The oxidant is 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone；The structural formula of the phenyl-sulfhydrate compounds is R-SH, shown in the molecular structure such as formula (1) of the cycloheptatriene -1- thio-ether type compounds:Wherein, R is alkyl or aromatic radical.Cycloheptatriene -1- thio-ether type compounds prepared by the present invention, no side reaction occur, and yield is up to 60%~89%, high conversion rate；The chemical structure of cycloheptatriene -1- thio-ether type compounds has diversity, and has the various bioactivity such as antibacterial, antiviral and antitumor, desinsection, anti-inflammatory and enzyme inhibitor.
Description
Technical field
The invention belongs to technical field of organic synthesis, more particularly, to a kind of cycloheptatriene -1- thio-ether type compounds and
Its synthetic method and application.
Background technique
The chemical structure of cycloheptatriene and its phenolic ketone compound has diversity, and has mostly antibacterial, antiviral, anti-
The various bioactivity such as tumour, desinsection, anti-inflammatory and enzyme inhibitor.Currently, being closed in chemical synthesis and property, bioactivity, biology
At with metabolism etc. have been achieved for very big progress.But due to the complexity of cycloheptatriene class compound structure and more
They are applied to clinical diagnosis and also need more effort by sample.
Summary of the invention
In order to solve above-mentioned the deficiencies in the prior art and disadvantage, primary and foremost purpose of the present invention is to provide a kind of cycloheptyl
Triolefin -1- thio-ether type compounds.
Another object of the present invention is to provide a kind of conjunctions of the cycloheptatriene -1- thio-ether type compounds of above method preparation
At method.
Another object of the present invention is to provide a kind of answering for the cycloheptatriene -1- thio-ether type compounds of above method preparation
With.
The purpose of the present invention is realized by following technical proposals:
A kind of cycloheptatriene -1- thio-ether type compounds, the cycloheptatriene -1- thio-ether type compounds be by cycloheptatriene,
Phenyl-sulfhydrate compounds and oxidant are added in solvent to react at 20~30 DEG C, purified to be made；The oxidant is 2,3- bis-
Chloro- 5,6- dicyano-Isosorbide-5-Nitrae-benzoquinones；The structural formula of the phenyl-sulfhydrate compounds is R-SH, the cycloheptatriene -1- thioether class
Shown in the molecular structure such as formula (1) for closing object:
Wherein, R is alkyl or aromatic radical.
Preferably, the molecular structural formula of the cycloheptatriene -1- thio-ether type compounds are as follows:
Preferably, the alkyl is amyl or cyclohexyl；The aromatic radical is the derivative of mercaptobenzooxazole thiophene, pyridine or benzene
Object.
It is further preferable that the substituent group in the benzene derivate on phenyl ring is selected from methyl, benzyl, methoxyl group, hydroxyl, ammonia
Base, trifluoromethyl, chlorine, bromine or fluorine.
Preferably, the solvent is chloroform, toluene, methylene chloride, Isosorbide-5-Nitrae-dioxane, normal propyl alcohol, ethyl alcohol, second
One or more of nitrile, water.
Preferably, the molar ratio of the cycloheptatriene, phenyl-sulfhydrate compounds and oxidant is 2:(3~4): (8~2.2).
Preferably, the phenyl-sulfhydrate compounds mole is (0.3~0.4) mol:(2~3 with the volume ratio of solvent) L.
Preferably, the method for the purification is one or more of extraction, dry, vacuum distillation or silica gel column chromatography.
Preferably, the time of the reaction is 5~10min.
Application of the cycloheptatriene -1- thio-ether type compounds in organic synthesis, photoelectric material or pharmaceutical field.
Compared with prior art, the invention has the following advantages:
1. the chemical structure of cycloheptatriene -1- thio-ether type compounds of the invention has diversity, and has suppression mostly
The various bioactivity such as bacterium, antiviral and antitumor, desinsection, anti-inflammatory and enzyme inhibitor.
2. the preparation method of cycloheptatriene -1- thio-ether type compounds of the present invention, reaction condition is mild, and side reaction is few, yield
Up to 60%~89%, high conversion rate is tested easy to operate.
3. cycloheptatriene -1- thio-ether type compounds of the invention have high value in organic synthesis and pharmaceutical field
Precursor is synthesized, various potential enantiomer specificity cycloaddition is can be used as and the starting of conjugate addition or alkylated reaction is former
Material, in addition, application of the cycloheptatriene -1- thio-ether type compounds in photoelectric material also has very big prospect.
Detailed description of the invention
Fig. 1 is cycloheptatriene -1- made from embodiment 1 to methyl diphenyl sulfide1H-NMR map；
Fig. 2 is cycloheptatriene -1- made from embodiment 1 to methyl diphenyl sulfide13C-NMR map；
Fig. 3 is cycloheptatriene -1- o-methyl-benzene thioether made from embodiment 21H-NMR map；
Fig. 4 is cycloheptatriene -1- o-methyl-benzene thioether made from embodiment 213C-NMR map；
Bromobenzene thioether between Fig. 5 is cycloheptatriene -1- made from embodiment 31H-NMR map；
Bromobenzene thioether between Fig. 6 is cycloheptatriene -1- made from embodiment 313C-NMR map；
Fig. 7 is cycloheptatriene -1- made from embodiment 4 to fluorobenzene thioether1H-NMR map；
Fig. 8 is cycloheptatriene -1- made from embodiment 4 to fluorobenzene thioether13C-NMR map；
Fig. 9 is cycloheptatriene -1- m-chloro diphenyl sulfide made from embodiment 51H-NMR map；
Figure 10 is cycloheptatriene -1- m-chloro diphenyl sulfide made from embodiment 513C-NMR map；
Figure 11 is cycloheptatriene -1- made from embodiment 6 to chlorobenzene thioether1H-NMR map；
Figure 12 is cycloheptatriene -1- made from embodiment 6 to chlorobenzene thioether13C-NMR map；
Figure 13 is cycloheptatriene -1- (3,4- dimethyl) diphenyl sulfide made from embodiment 71H-NMR map；
Figure 14 is cycloheptatriene -1- (3,4- dimethyl) diphenyl sulfide made from embodiment 713C-NMR map；
Figure 15 is cycloheptatriene -1- (2- mercaptopyridine) diphenyl sulfide made from embodiment 81H-NMR map；
Figure 16 is cycloheptatriene -1- (2- mercaptopyridine) diphenyl sulfide made from embodiment 813C-NMR map.
Specific embodiment
The contents of the present invention are further illustrated combined with specific embodiments below, but should not be construed as limiting the invention.
Unless otherwise specified, the conventional means that technological means used in embodiment is well known to those skilled in the art.Except non-specifically
Illustrate, reagent that the present invention uses, method and apparatus is the art conventional reagents, method and apparatus.
Oxidant described in embodiment is that 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) is purchased from Adamas in the present invention
Company.
Synthesis of the 1 cycloheptatriene -1- of embodiment to methyl diphenyl sulfide
Weigh 0.2mmol cycloheptatriene, 0.4mmol adds methylbenzene phenyl-sulfhydrate, 0.22mmol DDQ and 2mL chloroform
Enter in 15mL pressure resistance reaction tube, magnetic stir bar is added, 5min, chemical equation such as formula (1) institute are stirred to react at 25 DEG C
Show.
Vacuum distillation is carried out at -0.090MPa, 40 DEG C after reaction and removes chloroform, then with 50mL methylene chloride
Carry out decompression suction filtration, gained filtrate carries out vacuum distillation at -0.085MPa, 35 DEG C and removes methylene chloride, then with 200-300 mesh
Silica white carries out silica gel column chromatography purification, and eluent is petroleum ether, obtains cycloheptatriene -1- to methyl diphenyl sulfide, yield is
78%.
Fig. 1 and Fig. 2 is that gained cycloheptatriene -1- characterizes map to the nuclear-magnetism of methyl diphenyl sulfide, wherein Fig. 1 is cycloheptyl three
Alkene -1- is to methyl diphenyl sulfide1H-NMR map, Fig. 2 are cycloheptatriene -1- to methyl diphenyl sulfide13C-NMR map.Cycloheptyl three
Alkene -1- is characterized methyl diphenyl sulfide by nuclear-magnetism and is confirmed with existing chromatogram characteristic structure.
The characterize data of the compound is as follows:1H NMR(400MHz,CDCl3) δ 7.30 (d, J=8.1Hz, 2H), 7.08
(d, J=7.9Hz, 2H), 6.63-6.61 (m, 2H), 6.28-6.24 (m, 2H), 5.55 (dd, J=9.4,6.9Hz, 2H), 3.86
(t, J=6.9Hz, 1H), 2.32 (s, 3H)；13C NMR(100MHz,CDCl3)δ137.06(s),132.05(s),131.42
(s),129.60(s),126.82(s),124.78(s),46.37(s),21.11(s)。
The synthesis of 2 cycloheptatriene -1- o-methyl-benzene thioether of embodiment
Weigh 0.2mmol cycloheptatriene, 0.4mmol o-methyl-benzene thiophenol, 0.22mmol DDQ and 2.5mL chloroform
It is added in 15mL pressure resistance reaction tube, magnetic stir bar is added, 5min, chemical equation such as formula (2) are stirred to react at 25 DEG C
It is shown.
Vacuum distillation is carried out at -0.090MPa, 40 DEG C after reaction and removes chloroform, then with 50mL methylene chloride
Carry out decompression suction filtration, gained filtrate carries out vacuum distillation at -0.085MPa, 35 DEG C and removes methylene chloride, then with 200-300 mesh
Silica white carries out silica gel column chromatography purification, and eluent is petroleum ether, obtains cycloheptatriene -1- o-methyl-benzene thioether, and yield is
70%.
Fig. 3 and Fig. 4 is that the nuclear-magnetism of cycloheptatriene -1- o-methyl-benzene thioether characterizes map.Wherein, Fig. 3 is cycloheptatriene -1-
O-methyl-benzene thioether1H-NMR map, Fig. 4 are cycloheptatriene -1- o-methyl-benzene thioether13C-NMR map.Cycloheptatriene -1-
O-methyl-benzene thioether is characterized by nuclear-magnetism and is confirmed with existing chromatogram characteristic structure.
The characterize data of the compound is as follows:1H NMR(400MHz,CDCl3)δ7.33–7.31(m,1H),7.17–7.15
(m, 1H), 7.12-7.10 (m, 1H), 6.68-6.66 (m, 2H), 6.30-6.26 (m, 2H), 5.54 (dd, J=9.3,6.7Hz,
2H), 3.84 (t, J=6.7Hz, 1H), 2.37 (s, 3H)；13C NMR(100MHz,CDCl3)δ138.55(s),134.84(s),
131.54(s),130.15(s),130.08(s),126.75(s),126.36(s),126.31(s),124.61(s),44.85
(s),20.55(s)。
The synthesis of bromobenzene thioether between 3 cycloheptatriene -1- of embodiment
Weigh bromo thiophenol between 0.2mmol cycloheptatriene, 0.4mmol, 0.22mmol DDQ and 2.5mL chloroform adds
Enter in 15mL pressure resistance reaction tube, magnetic stir bar is added, 5min, chemical equation such as formula (3) institute are stirred to react at 25 DEG C
Show.
Vacuum distillation is carried out at -0.090MPa, 40 DEG C after reaction and removes chloroform, then with 50mL methylene chloride
Carry out decompression suction filtration, gained filtrate carries out vacuum distillation at -0.085MPa, 35 DEG C and removes methylene chloride, then with 200-300 mesh
Silica white carries out silica gel column chromatography purification, and eluent is petroleum ether, obtains bromobenzene thioether between cycloheptatriene -1-, yield 72%.
The nuclear-magnetism of Fig. 5 and Fig. 6 bromobenzene thioether between cycloheptatriene -1- characterizes map, wherein Fig. 5 is between cycloheptatriene -1-
Bromobenzene thioether1H-NMR map, Fig. 6 bromobenzene thioether between cycloheptatriene -1-13C-NMR map.Bromobenzene between cycloheptatriene -1-
Thioether is characterized by nuclear-magnetism and is confirmed with existing chromatogram characteristic structure.
The characterize data of the compound is as follows:1H NMR(400MHz,CDCl3)δ7.44-7.43(m,1H),7.27–7.24
(m,1H),7.21–7.18(m,1H),7.06–7.03(m,1H),6.57–6.55(m,2H),6.24–6.20(m,2H),5.49
(dd, J=9.4,7.0Hz, 2H), 3.92 (t, J=6.9Hz, 1H)；13C NMR(100MHz,CDCl3)δ137.93(s),
133.27(s),131.64(s),130.10(s),129.66(s),129.31(s),127.36(s),123.88(s),122.58
(s),45.81(s)。
Synthesis of the 4 cycloheptatriene -1- of embodiment to fluorobenzene thioether
Weigh 0.2mmol cycloheptatriene, 0.4mmol adds fluoro thiophenol, 0.22mmol DDQ and 2.5mL chloroform
Enter in 15mL pressure resistance reaction tube, magnetic stir bar is added, 5min, chemical equation such as formula (4) institute are stirred to react at 25 DEG C
Show.
Vacuum distillation is carried out at -0.090MPa, 40 DEG C after reaction and removes chloroform, then with 50mL methylene chloride
Carry out decompression suction filtration, gained filtrate carries out vacuum distillation at -0.085MPa, 35 DEG C and removes methylene chloride, then with 200-300 mesh
Silica white carries out silica gel column chromatography purification, and eluent is petroleum ether, and products therefrom yield is 65%.
Fig. 7 and Fig. 8 is that cycloheptatriene -1- characterizes map to the nuclear-magnetism of fluorobenzene thioether.Wherein, Fig. 7 is -1- pairs of cycloheptatriene
Fluorobenzene thioether1H-NMR map, Fig. 8 are cycloheptatriene -1- to fluorobenzene thioether13C-NMR map.Cycloheptatriene -1- is to fluorobenzene
Thioether is characterized by nuclear-magnetism and is confirmed with existing chromatogram characteristic structure.
The characterize data of the compound is as follows:1H NMR(400MHz,CDCl3)δ7.33–7.29(m,2H),6.92–6.87
(m, 2H), 6.51-6.46 (m, 2H), 6.21-6.17 (m, 2H), 5.46 (dd, J=9.3,7.4Hz, 2H), 3.84 (t, J=
7.0Hz,1H)；13C NMR(100MHz,CDCl3) δ 163.69 (s), 161.23 (s), 134.63 (d, J=8.1Hz), 131.48
(s), 129.90 (d, J=3.5Hz), 127.21 (s), 124.38 (s), 115.97 (s), 115.75 (s), 47.09 (s).
The synthesis of 5 cycloheptatriene -1- m-chloro diphenyl sulfide of embodiment
0.2mmol cycloheptatriene, 0.4mmol 3-Chlorothiophenol, 0.22mmol DDQ and 2.5mL chloroform is weighed to add
Enter in 15mL pressure resistance reaction tube, magnetic stir bar is added, 5min, chemical equation such as formula (5) institute are stirred to react at 25 DEG C
Show.
Vacuum distillation is carried out at -0.090MPa, 40 DEG C after reaction and removes chloroform, then with 50mL methylene chloride
Carry out decompression suction filtration, gained filtrate carries out vacuum distillation at -0.085MPa, 35 DEG C and removes methylene chloride, then with 200-300 mesh
Silica white carries out silica gel column chromatography purification, and eluent is petroleum ether, obtains cycloheptatriene -1- m-chloro diphenyl sulfide, yield 68%.
Fig. 9 and Figure 10 is that the nuclear-magnetism of cycloheptatriene -1- m-chloro diphenyl sulfide characterizes map.Wherein, Fig. 9 is cycloheptatriene -1-
M-chloro diphenyl sulfide1H-NMR map, Figure 10 are cycloheptatriene -1- m-chloro diphenyl sulfide13C-NMR map.Between cycloheptatriene -1-
Chlorobenzene thioether is characterized by nuclear-magnetism and is confirmed with existing chromatogram characteristic structure.
The characterize data of the compound is as follows:1H NMR(400MHz,CDCl3)δ7.28–7.27(m,1H),7.17–7.13
(m, 1H), 7.11-7.10 (m, 2H), 6.58-6.56 (m, 2H), 6.24-6.20 (m, 2H), 5.49 (dd, J=9.4,7.0Hz,
2H), 3.91 (t, J=6.9Hz, 1H)；13C NMR(100MHz,CDCl3)δ137.65(s),134.45(s),131.65(s),
130.33(s),129.81(s),128.75(s),127.32(s),126.73(s),123.90(s),45.71(s)。
Synthesis of the 6 cycloheptatriene -1- of embodiment to chlorobenzene thioether
Weigh 0.2mmol cycloheptatriene, 0.4mmol adds chlorothio-phenol, 0.22mmol DDQ and 2.5mL chloroform
Enter in 15mL pressure resistance reaction tube, magnetic stir bar is added, 5min, chemical equation such as formula (6) institute are stirred to react at 25 DEG C
Show.
Vacuum distillation is carried out at -0.090MPa, 40 DEG C after reaction and removes chloroform, then with 50mL methylene chloride
Carry out decompression suction filtration, gained filtrate carries out vacuum distillation at -0.085MPa, 35 DEG C and removes methylene chloride, then with 200-300 mesh
Silica white carries out silica gel column chromatography purification, and eluent is petroleum ether, obtains cycloheptatriene -1- to chlorobenzene thioether, yield 45%.
Figure 11 and Figure 12 is that cycloheptatriene -1- characterizes map to the nuclear-magnetism of chlorobenzene thioether.Wherein, Figure 11 is cycloheptatriene-
1- is to chlorobenzene thioether1H-NMR map, Figure 12 are cycloheptatriene -1- to chlorobenzene thioether13C-NMR map.Cycloheptatriene -1-
Chlorobenzene thioether is characterized by nuclear-magnetism and is confirmed with existing chromatogram characteristic structure.
The characterize data of the compound is as follows:1H NMR(400MHz,CDCl3)δ7.25–7.21(m,2H),7.19–7.15
(m, 2H), 6.56-6.54 (m, 2H), 6.23-6.19 (m, 2H), 5.47 (dd, J=9.4,6.9Hz, 2H), 3.86 (t, J=
6.9Hz,1H)；13C NMR(100MHz,CDCl3)δ133.79(s),132.96(s),132.70(s),131.60(s),128.94
(s),127.23(s),124.12(s),46.22(s)。
The synthesis of embodiment 7 cycloheptatriene -1- (3,4- dimethyl) diphenyl sulfide
Weigh 0.2mmol cycloheptatriene, 0.4mmol 3,4- thiophenol dimethyl benzene, 0.22mmol DDQ and 2.5mL tri-
Chloromethanes is added in 15mL pressure resistance reaction tube, and magnetic stir bar is added, 5min, the chemistry of the present embodiment are stirred to react at 25 DEG C
Equation please refers to formula 7.
Vacuum distillation is carried out at -0.090MPa, 40 DEG C after reaction and removes chloroform, then with 50mL methylene chloride
Carry out decompression suction filtration, gained filtrate carries out vacuum distillation at -0.085MPa, 35 DEG C and removes methylene chloride, then with 200-300 mesh
Silica white carries out silica gel column chromatography purification, and eluent is petroleum ether: ethyl acetate=100:1, obtains cycloheptatriene -1- (3,4- bis-
Methyl) diphenyl sulfide, yield 45%.
Figure 13 and Figure 14 is that the nuclear-magnetism of cycloheptatriene -1- (3,4- dimethyl) diphenyl sulfide characterizes map.Wherein, Figure 13 is ring
Heptantriene -1- (3,4- dimethyl) diphenyl sulfide1H-NMR map, Figure 14 are cycloheptatriene -1- (3,4- dimethyl) diphenyl sulfide
's13C-NMR map.Cycloheptatriene -1- (3,4- dimethyl) diphenyl sulfide is characterized by nuclear-magnetism and is obtained with existing chromatogram characteristic structure
Confirmation.
The characterize data of the compound is as follows:1H NMR(400MHz,CDCl3) δ 7.19 (d, J=1.5Hz, 1H), 7.14
(dd, J=7.8,1.9Hz, 1H), 7.03 (d, J=7.8Hz, 1H), 6.63-6.62 (m, 2H), 6.27-6.23 (m, 2H), 5.55
(dd, J=9.9,6.9Hz, 2H), 3.84 (t, J=6.8Hz, 1H), 2.22 (s, 6H)；13C NMR(101MHz,CDCl3)δ
137.21(s),135.78(s),133.23(s),131.63(s),131.51(s),130.11(s),129.46(s),126.73
(s),124.91(s),46.30(s),19.72(s),19.43(s)。
The synthesis of embodiment 8 cycloheptatriene -1- (2- mercaptopyridine) diphenyl sulfide
Weigh 0.2mmol cycloheptatriene, 0.4mmol 2- mercaptopyridine, 0.22mmol DDQ and 2.5mL chloroform
It is added in 15mL pressure resistance reaction tube, magnetic stir bar is added, 5min, chemical equation such as formula (8) are stirred to react at 25 DEG C
It is shown.
Vacuum distillation is carried out at -0.090MPa, 40 DEG C after reaction and removes chloroform, then with 50mL methylene chloride
Carry out decompression suction filtration, gained filtrate carries out vacuum distillation at -0.085MPa, 35 DEG C and removes methylene chloride, then with 200-300 mesh
Silica white carries out silica gel column chromatography purification, and eluent is petroleum ether: ethyl acetate=100:1, obtains cycloheptatriene -1- (2- sulfydryl
Pyridine) benzene sulfane, yield 67%.
Figure 15 and Figure 16 is that the nuclear-magnetism of cycloheptatriene -1- (2- mercaptopyridine) diphenyl sulfide characterizes map, wherein Figure 13 is ring
Heptantriene -1- (2- mercaptopyridine) benzene sulfane1H-NMR map, Figure 14 are cycloheptatriene -1- (2- mercaptopyridine) benzene sulfane
's13C-NMR map.Cycloheptatriene -1- (2- mercaptopyridine) benzene sulfane is characterized by nuclear-magnetism and is obtained with existing chromatogram characteristic structure
Confirmation.
The characterize data of the compound is as follows:1H NMR(400MHz,CDCl3)δ8.42–8.41(m,1H),7.45–7.41
(m, 1H), 7.04 (dt, J=8.1,1.0Hz, 1H), 6.97-6.94 (m, 1H), 6.65-6.63 (m, 2H), 6.32-6.28 (m,
2H),5.83-5.78(m,2H),5.02–4.97(m,1H)；13C NMR(101MHz,CDCl3)δ158.81(s),149.44(s),
136.04(s),131.69(s),127.82(s),124.73(s),122.13(s),119.54(s),41.46(s)。
The above embodiment is a preferred embodiment of the present invention, but embodiments of the present invention are not by above-described embodiment
Limitation, it is other it is any without departing from the spirit and principles of the present invention made by change, modification, substitution, combination and simplify,
It should be equivalent substitute mode, be included within the scope of the present invention.
Claims (10)
1. a kind of cycloheptatriene -1- thio-ether type compounds, which is characterized in that the cycloheptatriene -1- thio-ether type compounds be by
Cycloheptatriene, phenyl-sulfhydrate compounds and oxidant are added in solvent to react at 20~30 DEG C, purified to be made；The oxidant
For 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone；The structural formula of the phenyl-sulfhydrate compounds is R-SH, the cycloheptatriene -1-
Shown in the molecular structure of thio-ether type compounds such as formula (1):
Wherein, R is alkyl or aromatic radical.
2. cycloheptatriene -1- thio-ether type compounds according to claim 1, which is characterized in that the cycloheptatriene -1- sulphur
The molecular structural formula of ether compound are as follows:
3. cycloheptatriene -1- thio-ether type compounds according to claim 1, which is characterized in that the alkyl be amyl or
Cyclohexyl；The aromatic radical is mercaptobenzooxazole thiophene, pyridine or benzene derivate.
4. cycloheptatriene -1- thio-ether type compounds according to claim 3, which is characterized in that in the benzene derivate
Substituent group on phenyl ring is methyl, benzyl, methoxyl group, hydroxyl, amino, trifluoromethyl, chlorine, bromine or fluorine.
5. cycloheptatriene -1- thio-ether type compounds according to claim 1, which is characterized in that the solvent is three chloromethanes
One or more of alkane, toluene, methylene chloride, 1,4- dioxane, normal propyl alcohol, ethyl alcohol, acetonitrile or water.
6. cycloheptatriene -1- thio-ether type compounds according to claim 1, which is characterized in that the cycloheptatriene, thiophenol
The molar ratio of class compound and oxidant is 2:(3~4): (8~2.2).
7. cycloheptatriene -1- thio-ether type compounds according to claim 1, which is characterized in that the phenyl-sulfhydrate compounds
Mole and solvent volume ratio be (0.3~0.4) mol:(2~3) L.
8. cycloheptatriene -1- thio-ether type compounds according to claim 1, which is characterized in that the time of the reaction is 5
~10min.
9. cycloheptatriene -1- thio-ether type compounds according to claim 1, which is characterized in that the method for the purification is
One or more of extraction, dry, vacuum distillation or silica gel column chromatography.
10. the described in any item cycloheptatriene -1- thio-ether type compounds of claim 1-9 are in organic synthesis, photoelectric material or system
Application in medicine field.
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