CN105541569A - Synthesis method of 1-benzyloxy-2-[2-(3-methoxyphenyl)vinyl]benzene - Google Patents
Synthesis method of 1-benzyloxy-2-[2-(3-methoxyphenyl)vinyl]benzene Download PDFInfo
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- CN105541569A CN105541569A CN201511010491.9A CN201511010491A CN105541569A CN 105541569 A CN105541569 A CN 105541569A CN 201511010491 A CN201511010491 A CN 201511010491A CN 105541569 A CN105541569 A CN 105541569A
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- methoxy
- benzyloxy
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- benzene
- phenyl
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- YMHAQZODPXEMNF-UHFFFAOYSA-N 1-methoxy-3-[2-(2-phenylmethoxyphenyl)ethenyl]benzene Chemical compound COC1=CC=CC(C=CC=2C(=CC=CC=2)OCC=2C=CC=CC=2)=C1 YMHAQZODPXEMNF-UHFFFAOYSA-N 0.000 title abstract 3
- 238000001308 synthesis method Methods 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 claims abstract description 14
- 239000002904 solvent Substances 0.000 claims abstract description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 114
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 56
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 38
- 229920002554 vinyl polymer Polymers 0.000 claims description 38
- 238000010189 synthetic method Methods 0.000 claims description 20
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical group [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 16
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 9
- -1 methoxyl group Chemical group 0.000 claims description 9
- 229910052698 phosphorus Inorganic materials 0.000 claims description 9
- 239000011574 phosphorus Substances 0.000 claims description 9
- 235000010290 biphenyl Nutrition 0.000 claims description 8
- 238000013019 agitation Methods 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- 238000010792 warming Methods 0.000 claims description 5
- 238000011084 recovery Methods 0.000 claims description 4
- 230000006837 decompression Effects 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 abstract description 12
- 238000003786 synthesis reaction Methods 0.000 abstract description 12
- 238000002360 preparation method Methods 0.000 abstract description 10
- 238000000034 method Methods 0.000 abstract description 9
- PKUDHEUKHCKNAR-UHFFFAOYSA-N 1-(diphenylphosphorylmethyl)-3-methoxybenzene Chemical compound C(C1=CC(=CC=C1)OC)P(C1=CC=CC=C1)(C1=CC=CC=C1)=O PKUDHEUKHCKNAR-UHFFFAOYSA-N 0.000 abstract 2
- VGISFWWEOGVMED-UHFFFAOYSA-N 1-(chloromethyl)-3-methoxybenzene Chemical compound COC1=CC=CC(CCl)=C1 VGISFWWEOGVMED-UHFFFAOYSA-N 0.000 abstract 1
- OVSFXKCTADOYFM-UHFFFAOYSA-N benzhydryloxyphosphane Chemical compound C=1C=CC=CC=1C(OP)C1=CC=CC=C1 OVSFXKCTADOYFM-UHFFFAOYSA-N 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 239000002994 raw material Substances 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 238000001514 detection method Methods 0.000 description 3
- 238000009413 insulation Methods 0.000 description 3
- 238000012423 maintenance Methods 0.000 description 3
- 238000004064 recycling Methods 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 208000028867 ischemia Diseases 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
- C07F9/5333—Arylalkane phosphine oxides or thioxides
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a method for synthesizing 1-benzyloxy-2-[2-(3-methoxyphenyl)vinyl]benzene. The method comprises the following steps: making diphenylmethoxyphosphine react with m-methoxybenzyl chloride at 55-60 DEG C to obtain m-methoxybenzyldiphenylphosphine oxide; adding a solvent and a basifier into the m-methoxybenzyldiphenylphosphine oxide; and keeping reactions at room temperature to obtain 1-benzyloxy-2-[2-(3-methoxyphenyl)vinyl]benzene. The synthesis preparation method is simple, mild in reaction and easy to implement.
Description
Technical field
The invention belongs to organic compound synthesis technical field, particularly, relate to the synthetic method of a kind of 1-benzyloxy-2-[2-(3-p-methoxy-phenyl) vinyl] benzene.
Background technology
1-benzyloxy-2-[2-(3-p-methoxy-phenyl) vinyl] benzene is the important intermediate improving ischemia all symptom medicines Sarpogrelatehydrochlorides such as ulcer, pain and creeping chill caused by chronic arteria occlusion disease.Traditional synthetic method, as shown in Figure 1, synthesize meta-methoxy benzyl diethyl phosphoric acid (Wittig reagent) with triethyl-phosphite and meta-methoxy benzyl chloride, need to use a large amount of or excessive triethyl-phosphite in its synthesis, because of through pyroreaction, and it is not bery stable, second-rate after reclaiming, can not reuse, intractability is very big, and processing costs is expensive.Sodium hydride is made in addition in the process of synthesis 1-benzyloxy-2-[2-(3-p-methoxy-phenyl) vinyl] benzene, dangerous high, harsh to equipment requirements, control difficulty large, and mass yield is unstable.This name adopts phenylbenzene methoxyl group phosphorus and methoxyl group benzyl chloride Reactive Synthesis meta-methoxy benzyldiphenyl oxygen phosphorus (Wittig reagent), again at methanol as solvent, sodium methylate makes basifier synthesis 1-benzyloxy-2-[2-(3-p-methoxy-phenyl) vinyl] benzene, the a small amount of phosphorus-containing wastewater of methyl alcohol recyclable recycling by-product, through conventional processing, can effectively be disposed.
Summary of the invention
Goal of the invention: for the deficiencies in the prior art, the invention provides the synthetic method of the simple 1-benzyloxy of a kind of preparation process-2-[2-(3-p-methoxy-phenyl) vinyl] benzene.
Technical scheme: the synthetic method that the invention provides a kind of meta-methoxy benzyldiphenyl oxygen phosphorus, phenylbenzene methoxyl group phosphorus and meta-methoxy benzyl chloride react to obtain meta-methoxy benzyldiphenyl oxygen phosphorus in 55 ~ 60 DEG C; In meta-methoxy benzyldiphenyl oxygen phosphorus, add solvent and basifier at room temperature react to obtain 1-benzyloxy-2-[2-(3-p-methoxy-phenyl) vinyl] benzene.The synthetic method of 1-benzyloxy-2-of the present invention [2-(3-p-methoxy-phenyl) vinyl] benzene, wherein Wittig reagent (meta-methoxy benzyldiphenyl oxygen phosphorus) preparation employs different raw materials, make preparation process simple, and Wittig reagent preparation feedback is gentle.Two kinds of raw materials all drop into theoretical amount, effectively prevent the excessive and problem that recovery is difficult, process is difficult that causes of phosphorous raw material.In addition, the present invention's (Wittig reagent) meta-methoxy benzyldiphenyl oxygen phosphorus activity is active higher than former (Wittig reagent) meta-methoxy benzyl diethyl phosphoric acid far away, therefore follow-up reaction makes the basifier of work simple and easy to get, and reaction temperature and, effective solve former technique and use expensive and dangerous basifier greatly.In addition the recyclable recycling of by-product carbinol, and product yield, purity are high.
Concrete, the synthetic method of above-mentioned 1-benzyloxy-2-[2-(3-p-methoxy-phenyl) vinyl] benzene, phenylbenzene methoxyl group phosphorus and meta-methoxy benzyl chloride are joined reaction unit, 55 ~ 60 DEG C are warming up under agitation condition, and react 8 ~ 12h at this temperature, reaction terminates rear cool to room temperature, obtains meta-methoxy benzyldiphenyl oxygen phosphorus; In meta-methoxy benzyldiphenyl oxygen phosphorus, add solvent and basifier, control temperature, at 10 ~ 20 DEG C, continues to drip solvent; 6 ~ 10h is incubated at 10 ~ 20 DEG C; Decompression and solvent recovery, to dry, add after water stirs and filters; Material water is washed till neutrality, in 55 ~ 60 DEG C of dry 1-benzyloxy-2-[2-(3-p-methoxy-phenyl) vinyl] benzene.Method is reasonable, reaction temperature and, be easy to realize.
Further, the synthetic method of above-mentioned 1-benzyloxy-2-[2-(3-p-methoxy-phenyl) vinyl] benzene, described solvent is methyl alcohol.Raw material sources are wide, and application cost is low.
Further, the synthetic method of above-mentioned 1-benzyloxy-2-[2-(3-p-methoxy-phenyl) vinyl] benzene, described basifier is sodium methylate.Raw material sources are wide, and application cost is low.
Further, the synthetic method of above-mentioned 1-benzyloxy-2-[2-(3-p-methoxy-phenyl) vinyl] benzene, described room temperature is 10 ~ 20 DEG C.Mild condition, is easy to realize.
Further, the synthetic method of above-mentioned 1-benzyloxy-2-[2-(3-p-methoxy-phenyl) vinyl] benzene, described methyl alcohol is analytical pure methyl alcohol.The purity of solvent is high, the 1-benzyloxy-2-of preparation [2-(3-p-methoxy-phenyl) vinyl] benzene purity is high, and steady quality.
Further, the synthetic method of above-mentioned 1-benzyloxy-2-[2-(3-p-methoxy-phenyl) vinyl] benzene, described sodium methylate purity >=99.5%.Basifier purity is high, the 1-benzyloxy-2-of preparation [2-(3-p-methoxy-phenyl) vinyl] benzene purity is high, and steady quality.
Beneficial effect: compared with prior art, the synthetic method of meta-methoxy benzyldiphenyl oxygen phosphorus of the present invention, and utilize this meta-methoxy benzyldiphenyl oxygen phosphorus to synthesize the method for 1-benzyloxy-2-[2-(3-p-methoxy-phenyl) vinyl] benzene, have the following advantages:
(1) employ different raw materials in the preparation of Wittig reagent, make preparation process simple, and Wittig preparation feedback is gentle.Two kinds of raw materials all drop into theoretical amount, effectively prevent the excessive and problem that recovery is difficult, process is difficult that causes of phosphorous raw material.
(2) Wittig reagent meta-methoxy benzyldiphenyl oxygen phosphorus activity of the present invention is active higher than former Wittig reagent meta-methoxy benzyl diethyl phosphoric acid far away, therefore follow-up reaction makes the basifier of work simple and easy to get, and reaction temperature and, effective solve former technique and use expensive and dangerous basifier greatly.
(3) the recyclable recycling of methyl alcohol, and product yield, purity are high.
Accompanying drawing explanation
Fig. 1 is the synthetic route chart of traditional technology 1-benzyloxy-2-of the present invention [2-(3-p-methoxy-phenyl) vinyl] benzene;
Fig. 2 is the synthetic route chart of 1-benzyloxy-2-of the present invention [2-(3-p-methoxy-phenyl) vinyl] benzene.
Embodiment
By several specific embodiment, will illustrate the present invention further below, these embodiments, just in order to describe the problem, are not a kind of restriction.
Embodiment 1
Synthetic route as shown in Figure 2,
1) Wittig reagent meta-methoxy benzyldiphenyl oxygen phosphorus synthesis
99.5g(0.46mol is added in 1000ml reaction flask) phenylbenzene methoxyl group phosphorus and 72g(0.42mol) meta-methoxy benzyl chloride, be warming up to 55 DEG C under agitation condition, and be incubated 10 hours at this temperature, protect end and be cooled to 10 DEG C, directly enter the next step.
2) 1-benzyloxy-2-[2-(3-p-methoxy-phenyl) vinyl] benzene synthesis
25.4g(0.47mol is added in above-mentioned Wittig reagent meta-methoxy benzyldiphenyl oxygen phosphorus) sodium methylate and 300ml methyl alcohol, control temperature 10 DEG C, drip 95.5g(0.45mol) 200ml methanol solution, drip at terminating maintenance 10 DEG C and be incubated 8 hours, insulation terminates, and reclaim under reduced pressure methyl alcohol, to dry, add after 500ml water stirs and filters, material water is washed till neutrality, 55 DEG C of dry 1-benzyloxy-2-[2-(3-p-methoxy-phenyl) vinyl] benzene 132.9g(0.42mol).HPLC detection 1-benzyloxy-2-[2-(3-p-methoxy-phenyl) vinyl] benzene purity 99.63%.
HPLC condition: moving phase: 800ml water; Acetonitrile 200ml.Determined wavelength: 254nm, flow velocity 1.0ml/min, sample 0.01g, is diluted to 25ml by moving phase, sample size 5 μ l.
Embodiment 2
Synthetic route as shown in Figure 2,
2) Wittig reagent meta-methoxy benzyldiphenyl oxygen phosphorus synthesis
95.2g(0.44mol is added in 1000ml reaction flask) phenylbenzene methoxyl group phosphorus and 77g(0.45mol) meta-methoxy benzyl chloride, be warming up to 60 DEG C under agitation condition, and be incubated 12 hours at this temperature, protect end and be cooled to 20 DEG C, directly enter the next step.
2) 1-benzyloxy-2-[2-(3-p-methoxy-phenyl) vinyl] benzene synthesis
25.4g(0.47mol is added in above-mentioned Wittig reagent meta-methoxy benzyldiphenyl oxygen phosphorus) sodium methylate and 300ml methyl alcohol, control temperature 20 DEG C, drip 95.5g(0.45mol) 200ml methanol solution, drip at terminating maintenance 20 DEG C and be incubated 10 hours, insulation terminates, and reclaim under reduced pressure methyl alcohol, to dry, add after 500ml water stirs and filters, material water is washed till neutrality, 60 DEG C of dry 1-benzyloxy-2-[2-(3-p-methoxy-phenyl) vinyl] benzene 134.5g(0.43mol).HPLC detection 1-benzyloxy-2-[2-(3-p-methoxy-phenyl) vinyl] benzene purity 99.71%.
HPLC condition: moving phase: 800ml water; Acetonitrile 200ml.Determined wavelength: 254nm, flow velocity 1.0ml/min, sample 0.01g, is diluted to 25ml by moving phase, sample size 5 μ l.
Embodiment 3
Synthetic route as shown in Figure 2,
3) Wittig reagent meta-methoxy benzyldiphenyl oxygen phosphorus synthesis
99.5g(0.46mol is added in 1000ml reaction flask) phenylbenzene methoxyl group phosphorus and 72g(0.42mol) meta-methoxy benzyl chloride, be warming up to 58 DEG C under agitation condition, and be incubated 8 hours at this temperature, protect end and be cooled to 15 DEG C, directly enter the next step.
2) 1-benzyloxy-2-[2-(3-p-methoxy-phenyl) vinyl] benzene synthesis
25.4g(0.47mol is added in above-mentioned Wittig reagent meta-methoxy benzyldiphenyl oxygen phosphorus) sodium methylate and 300ml methyl alcohol, control temperature 15 DEG C, drip 95.5g(0.45mol) 200ml methanol solution, drip at terminating maintenance 15 DEG C and be incubated 6 hours, insulation terminates, and reclaim under reduced pressure methyl alcohol, to dry, add after 500ml water stirs and filters, material water is washed till neutrality, 58 DEG C of dry 1-benzyloxy-2-[2-(3-p-methoxy-phenyl) vinyl] benzene 135.8g(0.43mol).HPLC detection 1-benzyloxy-2-[2-(3-p-methoxy-phenyl) vinyl] benzene purity 99.66%.
HPLC condition: moving phase: 800ml water; Acetonitrile 200ml.Determined wavelength: 254nm, flow velocity 1.0ml/min, sample 0.01g, is diluted to 25ml by moving phase, sample size 5 μ l.
The above is only several embodiments of invention, and it should be pointed out that for those skilled in the art, under the prerequisite not departing from inventive principle, can also make some improvement, these improvement also should be considered as protection scope of the present invention.
Claims (7)
1. a synthetic method for 1-benzyloxy-2-[2-(3-p-methoxy-phenyl) vinyl] benzene, is characterized in that: phenylbenzene methoxyl group phosphorus and meta-methoxy benzyl chloride react to obtain meta-methoxy benzyldiphenyl oxygen phosphorus in 55 ~ 60 DEG C; In meta-methoxy benzyldiphenyl oxygen phosphorus, add solvent and basifier at room temperature react to obtain 1-benzyloxy-2-[2-(3-p-methoxy-phenyl) vinyl] benzene.
2. the synthetic method of a 1-benzyloxy-2-[2-(3-p-methoxy-phenyl) vinyl] benzene, it is characterized in that: phenylbenzene methoxyl group phosphorus and meta-methoxy benzyl chloride are joined reaction unit, 55 ~ 60 DEG C are warming up under agitation condition, and react 8 ~ 12h at this temperature, reaction terminates rear cool to room temperature, obtains meta-methoxy benzyldiphenyl oxygen phosphorus; In meta-methoxy benzyldiphenyl oxygen phosphorus, add solvent and basifier, control temperature, at 10 ~ 20 DEG C, continues to drip solvent; 6 ~ 10h is incubated at 10 ~ 20 DEG C; Decompression and solvent recovery, to dry, add after water stirs and filters; Material water is washed till neutrality, in 55 ~ 60 DEG C of dry 1-benzyloxy-2-[2-(3-p-methoxy-phenyl) vinyl] benzene.
3. the synthetic method of 1-benzyloxy-2-according to claim 1 and 2 [2-(3-p-methoxy-phenyl) vinyl] benzene, is characterized in that: described solvent is methyl alcohol.
4. the synthetic method of 1-benzyloxy-2-according to claim 1 and 2 [2-(3-p-methoxy-phenyl) vinyl] benzene, is characterized in that: described basifier is sodium methylate.
5. the synthetic method of 1-benzyloxy-2-according to claim 1 and 2 [2-(3-p-methoxy-phenyl) vinyl] benzene, is characterized in that: described room temperature is 10 ~ 20 DEG C.
6. the synthetic method of 1-benzyloxy-2-according to claim 3 [2-(3-p-methoxy-phenyl) vinyl] benzene, is characterized in that: described methyl alcohol is analytical pure methyl alcohol.
7. the synthetic method of 1-benzyloxy-2-according to claim 4 [2-(3-p-methoxy-phenyl) vinyl] benzene, is characterized in that: described sodium methylate purity >=99.5%.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101723827A (en) * | 2009-12-15 | 2010-06-09 | 上虞新和成生物化工有限公司 | Preparation method of 4-acetoxyl-2-methyl-2-butylenoic aldehyde |
| CN103539812A (en) * | 2013-09-25 | 2014-01-29 | 广州智特奇生物科技股份有限公司 | Synthetic method for intermediate of vitamin D3 metabolite |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101723827A (en) * | 2009-12-15 | 2010-06-09 | 上虞新和成生物化工有限公司 | Preparation method of 4-acetoxyl-2-methyl-2-butylenoic aldehyde |
| CN103539812A (en) * | 2013-09-25 | 2014-01-29 | 广州智特奇生物科技股份有限公司 | Synthetic method for intermediate of vitamin D3 metabolite |
Non-Patent Citations (3)
| Title |
|---|
| GUO HUA CHEN ET AL.: ""A practical synthesis of sarpogrelate hydrochloride and in vitro platelet aggregation inhibitory activities of its analogues"", 《CHINESE CHEMICAL LETTERS》 * |
| HANI EL MOLL ET AL.: ""Resorcin[4]arene-Derived Mono- and Diphosphines in Suzuki Cross-Coupling"", 《ADV. SYNTH. CATAL.》 * |
| 尹志刚等: "《有机磷化合物》", 31 March 2011, 化学工业出版社 * |
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