CN110256315A - A method of preparing Sulfide-containing Hindered formyl thioester conjugate - Google Patents
A method of preparing Sulfide-containing Hindered formyl thioester conjugate Download PDFInfo
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- CN110256315A CN110256315A CN201810199988.7A CN201810199988A CN110256315A CN 110256315 A CN110256315 A CN 110256315A CN 201810199988 A CN201810199988 A CN 201810199988A CN 110256315 A CN110256315 A CN 110256315A
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- formyl
- thioester
- containing hindered
- conjugate
- sulfide
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- -1 formyl thioester Chemical class 0.000 title claims abstract description 19
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 title claims abstract description 12
- 238000000034 method Methods 0.000 title claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 26
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 claims abstract description 24
- WQADWIOXOXRPLN-UHFFFAOYSA-N 1,3-dithiane Chemical compound C1CSCSC1 WQADWIOXOXRPLN-UHFFFAOYSA-N 0.000 claims abstract description 22
- 150000002561 ketenes Chemical class 0.000 claims abstract description 5
- 239000003054 catalyst Substances 0.000 claims abstract description 3
- 239000003960 organic solvent Substances 0.000 claims abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 8
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical class ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 3
- NHOWDZOIZKMVAI-UHFFFAOYSA-N (2-chlorophenyl)(4-chlorophenyl)pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(Cl)C=C1 NHOWDZOIZKMVAI-UHFFFAOYSA-N 0.000 claims description 2
- WQADWIOXOXRPLN-AZXPZELESA-N 1,3-dithiane Chemical group C1CS[13CH2]SC1 WQADWIOXOXRPLN-AZXPZELESA-N 0.000 claims description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims 2
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000003949 imides Chemical class 0.000 claims 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 4
- 239000003814 drug Substances 0.000 abstract description 3
- 239000000758 substrate Substances 0.000 abstract description 2
- 239000012190 activator Substances 0.000 abstract 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 24
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- 238000012512 characterization method Methods 0.000 description 6
- 238000001514 detection method Methods 0.000 description 6
- NQXWGWZJXJUMQB-UHFFFAOYSA-K iron trichloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].Cl[Fe+]Cl NQXWGWZJXJUMQB-UHFFFAOYSA-K 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 4
- 150000003568 thioethers Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000011017 operating method Methods 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000003124 biologic agent Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- OSVXSBDYLRYLIG-UHFFFAOYSA-N chlorine dioxide Inorganic materials O=Cl=O OSVXSBDYLRYLIG-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/20—Esters of monothiocarboxylic acids
- C07C327/22—Esters of monothiocarboxylic acids having carbon atoms of esterified thiocarboxyl groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to a kind of methods for preparing Sulfide-containing Hindered formyl thioester conjugate, and preparation method includes the following steps: in activator N- chlorosuccinimide and catalyst Fe Cl3·6H2In the presence of O, 1,3- dithiane and various unsaturated ketenes are dissolved in organic solvent, reacts at room temperature 2~8 hours, the formyl thioester compound of Sulfide-containing Hindered is obtained after isolating and purifying.Operation of the present invention mild condition, used substrate is cheap and easy to get, and reaction process is simple, can be advantageously applied in synthetic drug intermediate and biologically active conjugates.
Description
Technical field
The present invention relates to a kind of synthetic methods for preparing Sulfide-containing Hindered formyl thioester conjugate.
Background technique
Thioether, sulfolipins compound largely exist in nature, and structure is special to determine that it has preferable biology
Activity, in medicine, chemistry, the fields such as macromolecule are widely used.Thioether, sulfur ester are a kind of important in organic chemistry
Intermediate, can be used for the synthesis and conversion of various active materials, and for the building of complicated organic molecule skeleton and segment,
It can be applied to the synthesis of active pharmaceutical molecule and biological agent.Thioether and the research of thioester conjugate are less, and wherein C.G.Kruse is small
Group is studying 2- chlorine tetrahydrofuran and discovery can synthesize the sulfolipins compound of sulfur-bearing ehter bond when 2- chlorine thiophane, but this
Method low yield, reaction treatment are complicated；Philip C.Bulman Page group aoxidizes by 2- acyl group -1,3- dithiane 1-
Object is in ZnCl2, thioether sulfur ester has been obtained by rearrangement reaction under the conditions of THF, substrate spectrum is limited, while this method
Using the catalyst being more toxic, environmental pollution is larger.The preparation of conventional sulfide compound is needed using mercaptan compound, sulphur
The volatility and toxicity of alcohol increase operation and all have certain influence on environment.
And the present invention using the unsaturated ketenes for being commercialized and being easy to get by may be implemented with 1,3- dithiane one kettle way, bottom
Object strong applicability, mild condition have efficiently, pollute the features such as small, the efficient preparation suitable for thioether thioesters conjugate.
Summary of the invention
Thioether, sulfolipins compound are in chemical industry, and medicine, pesticide, the fields such as material are widely used.The present invention relates to a kind of new
The synthesis of type Sulfide-containing Hindered formyl sulfolipins conjugate, method is easy to operate, and reaction condition is mild, and agents useful for same is cheap and easy to get, and
And yield is higher, can be easily separated purifying.
The method for preparing Sulfide-containing Hindered formyl thioester conjugate, preparation process is in reacting movable agent N- chlorosuccinimide
(NCS) and the FeCl of catalytic amount3·6H2In the presence of O, 1,3- dithiane and the unsaturated ketenes of various substitutions are dissolved in organic solvent
In, it is placed in air and reaction is stirred at room temperature 2~8 hours, isolate and purify to obtain Sulfide-containing Hindered formyl thioester after complete reaction
Conjugate, structure are as follows:
Solvent is methylene chloride or 1,2- dichloroethanes in the operating procedure.
The molar ratio of reactant is 1,3- dithiane: N- chlorosuccinimide: ethylenic unsaturation in the operating procedure
Ketone: FeCl3·6H2O=1.2:1.44:1:0.1.
R in the structure1,R2Respectively one of fatty alkyl, substituted aryl or a variety of, wherein fatty alkyl is
Methyl, ethyl, amyl, tert-butyl, naphthenic base；Substituted aryl is phenyl, o-tolyl, Chloro-O-Phenyl, tolyl, bromobenzene
Base, p-methylphenyl, p-methoxyphenyl, rubigan, p-bromophenyl, naphthalene.
Specific embodiment
The raw materials used present invention is known compound, it is available on the market or can be used means known in the art and synthesize
It arrives.
Embodiment 1:
It in 10 milliliters of round-bottomed flasks, is added 1,3- dithiane 2 (30mg, 0.25mmol), adds after being dissolved with 2 milliliters of methylene chloride
Enter N- chlorosuccinimide (40mg, 0.3mmol), adds FeCl3.6H2O (7mg, 0.025mmol), 1a (30mg,
0.21mmol), it is placed in air and reaction 3h is stirred at room temperature.TLC detection stops reaction after complete reaction, after solvent is evaporated off
Column chromatographs to obtain product 3a.Products obtained therefrom data characterization is as follows: yellow oily；Yield 89%；Rf=0.18 (EA/PE=1:10)；1H
NMR(300MHz,CDCl3) δ 10.08 (s, 1H), 7.42-7.15 (m, 5H), 4.31 (t, J=7.2Hz, 1H), 3.14-2.81
(m,4H),2.51–2.25(m,2H),2.09(s,3H),1.81–1.72(m,2H)；13C NMR(75MHz,CDCl3)δ205.2,
187.4,141.6,128.6,127.7,127.4,77.4,77.0,76.6,49.9,43.9,30.7,29.9,28.7,25.4；
HRMS(ESI):m/z:calcd for C14H19O2S2[M+H]+:283.0826,found:283.0816.
Embodiment 2:
It in 10 milliliters of round-bottomed flasks, is added 1,3- dithiane 2 (30mg, 0.25mmol), is dissolved with 2 milliliters of 1,2- dichloroethanes
N- chlorosuccinimide (40mg, 0.3mmol) is added afterwards, adds FeCl3.6H2O (7mg, 0.025mmol), 1b (34mg,
0.21mmol), it is placed in air and reaction 5h is stirred at room temperature.TLC detection stops reaction after complete reaction, after solvent is evaporated off
Column chromatographs to obtain product 3b.Products obtained therefrom data characterization is as follows: yellow oily；Yield 80%；Rf=0.2 (EA/PE=1:10)；1H
NMR(300MHz,CDCl3) δ 10.08 (s, 1H), 7.24-7.09 (m, 3H), 7.06 (s, 1H), 4.28 (t, J=7.2Hz, 1H),
2.99–2.89(m,4H),2.42–2.29(m,5H),2.10(s,3H),1.82–1.73(m,2H)；13C NMR(75MHz,
CDCl3)δ205.4,187.5,141.3,138.2,128.4,128.2,128.1,124.6,77.4,77.0,76.6,49.8,
43.7,30.7,29.8,28.6,25.3,21.4；HRMS(ESI):m/z:calcd for C15H21O2S2[M+H]+:
297.0983,found:297.0980.
Embodiment 3:
It in 10 milliliters of round-bottomed flasks, is added 1,3- dithiane 2 (30mg, 0.25mmol), adds after being dissolved with 2 milliliters of methylene chloride
Enter N- chlorosuccinimide (40mg, 0.3mmol), adds FeCl3.6H2O (7mg, 0.025mmol), 1c (38mg,
0.21mmol), it is placed in air and reaction 8h is stirred at room temperature.TLC detection stops reaction after complete reaction, after solvent is evaporated off
Column chromatographs to obtain product 3c.Products obtained therefrom data characterization is as follows: yellow oily；Yield 83%；Rf=0.11 (EA/PE=1:10)；1H
NMR(300MHz,CDCl3) δ 10.09 (s, 1H), 7.29 (d, J=0.9Hz, 4H), 4.30 (t, J=7.2Hz, 1H), 3.05-
2.89(m,4H),2.41–2.30(m,2H),2.09(s,3H),1.83–1.73(m,2H)；13C NMR(75MHz,CDCl3))δ
204.7,187.2,140.2,133.0,129.0,128.7,77.4,77.0,76.6,49.8,43.2,30.6,29.9,28.7,
25.3；HRMS(ESI):m/z:calcd for C14H18ClO2S2[M+H]+:317.0437,found:317.0436.
Embodiment 4:
It in 10 milliliters of round-bottomed flasks, is added 1,3- dithiane 2 (30mg, 0.25mmol), adds after being dissolved with 2 milliliters of methylene chloride
Enter N- chlorosuccinimide (40mg, 0.3mmol), adds FeCl3.6H2O (7mg, 0.025mmol), 1d (20mg,
0.21mmol), it is placed in air and reaction 2h is stirred at room temperature.TLC detection stops reaction after complete reaction, after solvent is evaporated off
Column chromatographs to obtain product 3d.Products obtained therefrom data characterization is as follows: yellow oily；Yield 92%；Rf=0.13 (EA/PE=1:10)；1H
NMR(300MHz,CDCl3) δ 10.14 (s, 1H), 3.09 (t, J=6.6Hz, 2H), 2.69-2.57 (m, 3H), 2.44-2.30
(m,3H),2.21–2.08(m,3H),1.97–1.85(m,2H),1.77–1.69(m,2H)；13C NMR(75MHz,CDCl3))δ
208.5,187.2,77.4,77.0,76.6,48.0,42.7,40.8,31.5,29.3,29.1,25.4,24.1；HRMS(ESI):
m/z:calcd for C10H17O2S2[M+H]+:233.0670,found:233.0663.
Embodiment 5:
It in 10 milliliters of round-bottomed flasks, is added 1,3- dithiane 2 (30mg, 0.25mmol), adds after being dissolved with 2 milliliters of methylene chloride
Enter N- chlorosuccinimide (40mg, 0.3mmol), adds FeCl3.6H2O (7mg, 0.025mmol), 1e (17mg,
0.21mmol), it is placed in air and reaction 2h is stirred at room temperature.TLC detection stops reaction after complete reaction, after solvent is evaporated off
Column chromatographs to obtain product 3e.Products obtained therefrom data characterization is as follows: yellow liquid；Yield 81%；Rf=0.1 (EA/PE=1:10)；1H
NMR(300MHz,CDCl3) δ 10.15 (s, 1H), 3.48 (m, 1H), 3.10 (t, J=7.8Hz, 2H), 2.68-2.58 (m, 3H),
2.50–2.32(m,2H),2.31–2.15(m,2H),2.04–1.85(m,3H)；13C NMR(75MHz,CDCl3)δ216.3,
187.2,77.4,77.0,76.6,45.6,40.3,37.0,30.0,29.9,29.3,25.4；HRMS(ESI):m/z:calcd
for C9H15O2S2[M+H]+:219.0513,found:219.0509.
Embodiment 6:
It in 10 milliliters of round-bottomed flasks, is added 1,3- dithiane 2 (30mg, 0.25mmol), adds after being dissolved with 2 milliliters of methylene chloride
Enter N- chlorosuccinimide (40mg, 0.3mmol), adds FeCl3.6H2O (7mg, 0.025mmol), 1f (20mg,
0.21mmol), it is placed in air and reaction 4h is stirred at room temperature.TLC detection stops reaction after complete reaction, after solvent is evaporated off
Column chromatographs to obtain product 3f.Products obtained therefrom data characterization is as follows: colourless liquid；Yield 85%；Rf=0.36 (EA/PE=1:10)；1H
NMR(300MHz,CDCl3) δ 10.15 (s, 1H), 3.32-3.20 (m, 1H), 3.08 (t, J=7.2Hz, 2H), 2.78-2.39
(m, 6H), 1.97-1.84 (m, 2H), 1.28 (d, J=6.9Hz, 3H), 1.06 (t, J=7.2Hz, 3H)；13C NMR(75MHz,
CDCl3))δ209.2,187.5,77.4,77.0,76.6,49.4,36.7,34.9,29.3,29.1,25.4,21.6,7.5；
HRMS(ESI):m/z:calcd forC10H19O2S2[M+H]+:235.0826,found:235.0822。
Claims (4)
1. a kind of method for preparing Sulfide-containing Hindered formyl thioester conjugate, which is characterized in that comprise the steps of: in N- chloro fourth two
Acid imide (NCS) and catalyst Fe Cl3·6H2In the presence of O, 1,3- dithiane and various unsaturated ketenes are dissolved in organic solvent
In, it is placed in air and reaction is stirred at room temperature 2~8 hours, isolate and purify to obtain thioether formyl thioester after complete reaction and sew
Close object.
2. according to the method described in claim 1 for preparing Sulfide-containing Hindered formyl thioester conjugate, it is characterised in that: used solvent
For methylene chloride or 1,2- dichloroethanes.
3. according to the method described in claim 1 for preparing Sulfide-containing Hindered formyl thioester conjugate, it is characterised in that: the operation step
The molar ratio of reactant is 1,3- dithiane: N- chlorosuccinimide: unsaturated ketenes: FeCl in rapid3·6H2O=1.2:
1.44:1:0.1。
4. according to the method described in claim 1 for preparing Sulfide-containing Hindered formyl thioester conjugate, it is characterised in that: the structure R1,
R2Respectively one of fatty alkyl, substituted aryl or a variety of, wherein fatty alkyl be methyl, ethyl, amyl, tert-butyl,
Naphthenic base；Substituted aryl be phenyl, o-tolyl, Chloro-O-Phenyl, tolyl, m-bromophenyl, p-methylphenyl, to methoxy benzene
Base, rubigan, p-bromophenyl, naphthalene.
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|---|---|---|---|---|
| CN115304465A (en) * | 2021-05-06 | 2022-11-08 | 北京中医药大学 | Green method for converting 1, 3-dithiane derivative into carbonyl compound |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN107151239A (en) * | 2017-05-19 | 2017-09-12 | 兰州大学 | A kind of synthesis α 1,3 dithiane replaces the method for aldehyde compound |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107151239A (en) * | 2017-05-19 | 2017-09-12 | 兰州大学 | A kind of synthesis α 1,3 dithiane replaces the method for aldehyde compound |
Non-Patent Citations (2)
| Title |
|---|
| DENG MIN，等: "Fe-catalyzed dithiane radical induced C-S bond activation addition to a,b-unsaturated ketones", 《ADV. SYNTH. CATAL.》 * |
| TENG LIU,等: "Regiodivergent radical oxidative coupling of vinyl ethers with dithiane by copper or iron catalysis", 《ORG. CHEM. FRONT.》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115304465A (en) * | 2021-05-06 | 2022-11-08 | 北京中医药大学 | Green method for converting 1, 3-dithiane derivative into carbonyl compound |
| CN115304465B (en) * | 2021-05-06 | 2023-12-08 | 北京中医药大学 | Green method for converting 1, 3-dithiane derivative into carbonyl compound |
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