CN115677533B - Preparation method of 4-heptyl benzonitrile - Google Patents
Preparation method of 4-heptyl benzonitrile Download PDFInfo
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- CN115677533B CN115677533B CN202110869059.4A CN202110869059A CN115677533B CN 115677533 B CN115677533 B CN 115677533B CN 202110869059 A CN202110869059 A CN 202110869059A CN 115677533 B CN115677533 B CN 115677533B
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- heptyl
- benzonitrile
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- sodium
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- XTIKBCXMOYZUMG-UHFFFAOYSA-N 4-heptylbenzonitrile Chemical compound CCCCCCCC1=CC=C(C#N)C=C1 XTIKBCXMOYZUMG-UHFFFAOYSA-N 0.000 title claims abstract description 19
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 claims abstract description 20
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims abstract description 20
- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- 239000003054 catalyst Substances 0.000 claims abstract description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
- LOQLDQJTSMKBJU-UHFFFAOYSA-N 4-(chloromethyl)benzonitrile Chemical compound ClCC1=CC=C(C#N)C=C1 LOQLDQJTSMKBJU-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 4
- 239000002994 raw material Substances 0.000 claims abstract description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 238000001914 filtration Methods 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000000706 filtrate Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- 238000002425 crystallisation Methods 0.000 claims description 5
- 230000008025 crystallization Effects 0.000 claims description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- 239000000047 product Substances 0.000 claims description 4
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 4
- DSVGQVZAZSZEEX-UHFFFAOYSA-N [C].[Pt] Chemical compound [C].[Pt] DSVGQVZAZSZEEX-UHFFFAOYSA-N 0.000 claims description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 3
- 239000007868 Raney catalyst Substances 0.000 claims description 2
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 claims description 2
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 claims description 2
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 230000003321 amplification Effects 0.000 abstract description 4
- 238000003199 nucleic acid amplification method Methods 0.000 abstract description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 230000009286 beneficial effect Effects 0.000 abstract description 2
- 238000009776 industrial production Methods 0.000 abstract description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 14
- 239000007788 liquid Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 239000012295 chemical reaction liquid Substances 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- LSXKDWGTSHCFPP-UHFFFAOYSA-N 1-bromoheptane Chemical compound CCCCCCCBr LSXKDWGTSHCFPP-UHFFFAOYSA-N 0.000 description 1
- HQSCPPCMBMFJJN-UHFFFAOYSA-N 4-bromobenzonitrile Chemical compound BrC1=CC=C(C#N)C=C1 HQSCPPCMBMFJJN-UHFFFAOYSA-N 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Abstract
The invention belongs to the field of organic chemical synthesis, and particularly relates to a preparation method of 4-heptyl benzonitrile. Condensing p-cyanobenzyl chloride serving as a raw material with triphenylphosphine to obtain a separable intermediate 1; reacting the intermediate 1 with n-hexanal under alkaline conditions to obtain an intermediate 2; and under the action of a catalyst, introducing hydrogen into the intermediate 2 at 20-100 ℃, wherein the hydrogen application pressure is 0.1-10 MPa, and carrying out hydrogenation reaction to obtain the 4-heptyl benzonitrile. Compared with the traditional synthetic route, the preparation method does not need anhydrous and anaerobic condition control, has low equipment requirement, is simple to operate, has high conversion rate, is beneficial to amplification, and is suitable for industrial production.
Description
Technical Field
The invention belongs to the field of organic chemical synthesis, and particularly relates to a preparation method of 4-heptyl benzonitrile.
Background
With the development of super twisted nematic liquid crystal (STN-LCD) and thin film transistor array driving liquid crystal display (TFT-LCD) technologies, the liquid crystal display technology is increasingly widely applied in the production and life of people, particularly the application of TFT-LCD products, and the revolutionary transformation of display technology is brought. Although many reports have been made on liquid crystal materials, they are not all suitable for use in display devices, because liquid crystal materials for display must meet the characteristics of a wide operating temperature range, a low operating voltage, low viscosity, rapid response, high resistivity, moderate dielectric anisotropy, and the like.
In order to improve the performance of liquid crystal materials, research and development of novel cyano-containing liquid crystal compounds are carried out. The cyano-containing liquid crystal material has the unique properties of high clearing point, wide liquid crystal working range and the like. The use of the liquid crystal is becoming wider, and the liquid crystal is one of main components of mixed liquid crystals for liquid crystal displays such as STN, TFT and the like, so the synthesis of the liquid crystal is one of the important research subjects at present.
4-heptyl benzonitrile is an important compound of the cyano-containing liquid crystal material monomer. The traditional synthetic route is that 4-bromobenzonitrile is coupled with 1-bromoheptane, the method has high requirement on preparation conditions, anhydrous and anaerobic condition control is needed, precious metal and ligand catalysts thereof are difficult to recycle and reuse, production amplification is not facilitated, and reaction yield is low.
Disclosure of Invention
Aiming at the problems of harsh reaction conditions, difficult recovery and application of noble metal and ligand catalyst thereof, difficult production and amplification, high production cost and the like in the prior art, the invention provides a method for synthesizing 4-heptyl benzonitrile.
In order to achieve the above purpose, the invention is realized by the following technical scheme:
a preparation method of 4-heptyl benzonitrile comprises the following synthetic routes:
s1: condensing p-cyanobenzyl chloride serving as a raw material with triphenylphosphine to obtain a separable intermediate 1;
s2: reacting the intermediate 1 with n-hexanal under alkaline conditions to obtain an intermediate 2;
s3: under the action of a catalyst, hydrogen is introduced into the intermediate 2 at 20 ℃ -100 ℃ (preferably at 25 ℃ -50 ℃), the hydrogen using pressure is 0.1-10 MPa (preferably the hydrogen using pressure is 0.2-1 MPa), and 4-heptyl benzonitrile is obtained through hydrogenation reaction.
The step S1: the p-cyanoborobenzyl and triphenylphosphine are heated to 55-140 ℃ in a proper solvent for reflux reaction, and the target intermediate 1 is obtained by crystallization and filtration at room temperature; the molar ratio of the p-cyanoborobenzyl to the triphenylphosphine is 1:0.8-1.2;
suitable solvents are selected from toluene, xylene, tetrahydrofuran, dioxane, ethyl acetate, methyl tertiary butyl ether.
The step S2: reacting the intermediate 1 with n-hexanal in a proper solvent under alkaline condition, filtering, collecting filtrate, and distilling under reduced pressure to obtain an intermediate 2; wherein, the molar ratio of the intermediate 1 to the n-hexanal is 1:0.8-1.5.
The alkali is one or more of potassium tert-butoxide, sodium ethoxide, sodium methoxide, sodium hydrogen, potassium hydroxide, sodium hydroxide, potassium carbonate and sodium carbonate; more preferably, the base is potassium tert-butoxide, sodium ethoxide or sodium methoxide.
Suitable solvents are tetrahydrofuran, dioxane and methyl tert-butyl ether.
The step S3: the intermediate 2 is hydrogenated in a proper solvent under the action of a catalyst to obtain a product 4-heptyl benzonitrile; the addition amount of the catalyst is 0.5% -10% of the mass of the intermediate 2.
The solvent is one or more selected from methanol, ethanol, isopropanol and tetrahydrofuran.
The catalyst is one or more of palladium carbon, platinum carbon, raney nickel, palladium chloride and palladium hydroxide.
Compared with the prior art, the invention has the following advantages:
1. compared with the traditional synthetic route, the preparation method does not need anhydrous and anaerobic condition control, has low equipment requirement, is simple to operate, has high conversion rate, is beneficial to amplification, and is suitable for industrial production.
2. The catalyst of the preparation method can be recycled, the reaction condition is mild, and the cost for producing 4-heptyl benzonitrile is low.
The specific embodiment is as follows:
the following description of the embodiments of the present invention is further provided in connection with the accompanying examples, and it should be noted that the embodiments described herein are for the purpose of illustration and explanation only, and are not limiting of the invention.
Example 1:
100g of p-cyanobenzyl chloride, 182g of triphenylphosphine and 600ml of toluene are added into a 2L single-port bottle, the temperature is raised to 110 ℃ for reaction for 16 hours, the mixture is cooled to room temperature, stirred for crystallization, 253g of white solid of intermediate 1 is obtained through filtration and drying, and the yield is 93.0%.
500g of intermediate 1 is added into a 2L single-mouth bottle, 1.25L of THF is added, 133g of sodium tert-butoxide is added under the temperature of 20 ℃ and reacts for 0.5 hour at 20 ℃, 111g of hexanal is added dropwise, filtration is carried out after 0.5 hour of reaction, filtrate is collected and concentrated, reduced pressure distillation (2 mm Hg) is carried out, and fractions at 100-110 ℃ are collected.
205g of intermediate 2 is obtained as colorless liquid, and the yield is 85.1%.
30g of intermediate 2 and 300ml of methanol are taken in a 1L autoclave, 3g of palladium carbon (0.5%) is added as a catalyst, after hydrogen replacement, the pressure of a hydrogen reaction system is 0.3MPa, the reaction is carried out for 4 hours at 25 ℃, the reaction liquid is filtered, the precipitated catalyst is collected, the filtrate is decompressed and concentrated to obtain 30g of colorless liquid, and the yield is 99.3%.
Example 2:
100g of p-cyanobenzyl chloride, 182g of triphenylphosphine and 600ml of dimethylbenzene are added into a 2L single-port bottle, the temperature is raised to 140 ℃ for reaction for 10 hours, the mixture is cooled to room temperature, stirred for crystallization, 257.4g of white solid of intermediate 1 is obtained through filtration and drying, and the yield is 94.3%.
500g of intermediate 1 is added into a 2L single-port bottle, THF 1.25L is added, the temperature is controlled below 0 ℃, 133g of sodium tert-butoxide is added, the mixture is reacted for 1 hour at the temperature of 0 ℃, hexanal 130g is added dropwise, the mixture is filtered after the reaction for 4 hours, filtrate is collected and concentrated, colorless liquid 210g of intermediate 2 is obtained through reduced pressure distillation, and the yield is 87.2%.
30g of intermediate 2 and 300ml of ethanol are taken in a 1L autoclave, 0.3g of palladium carbon (5%) is added as a catalyst, after hydrogen replacement, the pressure of a hydrogen reaction system is 0.2MPa, the reaction is carried out for 4 hours at 40 ℃, the reaction liquid is filtered, the precipitated catalyst is collected, the filtrate is concentrated under reduced pressure to obtain 29.5g of colorless liquid, and the yield is 97.4%.
Example 3:
100g of p-cyanobenzyl chloride, 180g of triphenylphosphine and 600ml of toluene are added into a 2L single-port bottle, the temperature is raised to 110 ℃ for reaction for 16 hours, the mixture is cooled to room temperature, stirred for crystallization, and filtered and dried to obtain 249.9g of white solid of the intermediate 1, and the yield is 91.5%.
500g of intermediate 1 is added into a 2L single-port bottle, THF 1.25L is added, 94.2g of sodium ethoxide is added below the temperature of 40 ℃ to react for 1 hour at the temperature of 40 ℃, hexanal 130g is added dropwise to react for 4 hours, filtration is carried out, filtrate concentration is collected, and the intermediate 2 colorless liquid 198g is obtained through reduced pressure distillation, so that the yield is 82.2%.
30g of intermediate 2 and 300ml of methanol are taken in a 1L autoclave, 3g of platinum carbon (0.5%) is added, after hydrogen replacement, the reaction system pressure of hydrogen is 0.1MPa, the reaction is carried out for 2 hours at 50 ℃, the reaction liquid is filtered, the precipitated catalyst is collected, the filtrate is concentrated under reduced pressure to obtain 29.9g of colorless liquid, and the yield is 98.7%.
Example 4:
intermediate 1 and intermediate 2 preparation the final hydrogenation reaction investigation example 1 filtration recovery palladium on carbon (0.5%) batch test was carried out by operating with example 1 with the following specific reaction results:
| batch number of catalyst sets | Product quality g | Yield% |
| 1 | 30 | 99.3 |
| 2 | 29.9 | 98.7 |
| 3 | 29.5 | 97.4 |
| 4 | 29.8 | 98.3 |
| 5 | 29.5 | 97.4 |
Claims (6)
1. A preparation method of 4-heptyl benzonitrile is characterized in that:
the synthetic route is as follows:
s1: condensing p-cyanobenzyl chloride serving as a raw material with triphenylphosphine to obtain a separable intermediate 1;
s2: reacting the intermediate 1 with n-hexanal under alkaline conditions to obtain an intermediate 2;
s3: and under the action of a catalyst, introducing hydrogen into the intermediate 2 at 20-100 ℃, wherein the hydrogen application pressure is 0.1-10 MPa, and carrying out hydrogenation reaction to obtain the 4-heptyl benzonitrile.
2. The method for producing 4-heptyl benzonitrile according to claim 1, wherein:
the step S1: the p-cyanoborobenzyl and triphenylphosphine are heated to 55-140 ℃ in a proper solvent for reflux reaction, and the target intermediate 1 is obtained by crystallization and filtration at room temperature; the molar ratio of the p-cyanoborobenzyl to the triphenylphosphine is 1:0.8-1.2; suitable solvents are selected from toluene, xylene, tetrahydrofuran, dioxane, ethyl acetate, methyl tertiary butyl ether.
3. The method for producing 4-heptyl benzonitrile according to claim 1, wherein: the step S2: reacting the intermediate 1 with n-hexanal in a proper solvent under alkaline condition, filtering, collecting filtrate, and distilling under reduced pressure to obtain an intermediate 2; wherein, the molar ratio of the intermediate 1 to the n-hexanal is 1:0.8-1.5.
4. A process for the preparation of 4-heptyl benzonitrile according to claim 3, wherein: the alkali is one or more of potassium tert-butoxide, sodium ethoxide, sodium methoxide, sodium hydrogen, potassium hydroxide, sodium hydroxide, potassium carbonate and sodium carbonate;
suitable solvents are tetrahydrofuran, dioxane and methyl tert-butyl ether.
5. A process for the preparation of 4-heptyl benzonitrile according to claim 3, wherein:
the step S3: the intermediate 2 is hydrogenated in a proper solvent under the action of a catalyst to obtain a product 4-heptyl benzonitrile; the addition amount of the catalyst is 0.5% -10% of the mass of the intermediate 2.
6. The method for producing 4-heptyl benzonitrile according to claim 5, wherein:
the solvent is one or more selected from methanol, ethanol, isopropanol and tetrahydrofuran;
the catalyst is one or more of palladium carbon, platinum carbon, raney nickel, palladium chloride and palladium hydroxide.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3977768A (en) * | 1974-07-31 | 1976-08-31 | Dai Nippon Toryo Kaubshiki Kaisha | Nematic liquid crystal compositions |
| US4043634A (en) * | 1974-07-25 | 1977-08-23 | Dai Nippon Toryo Co., Ltd. | Liquid crystal electro optical element |
| CN103443119A (en) * | 2010-12-15 | 2013-12-11 | 伊索技术制药公司 | Cyclosporine analogue molecules modified at amino acid 1 and 3 |
-
2021
- 2021-07-30 CN CN202110869059.4A patent/CN115677533B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4043634A (en) * | 1974-07-25 | 1977-08-23 | Dai Nippon Toryo Co., Ltd. | Liquid crystal electro optical element |
| US3977768A (en) * | 1974-07-31 | 1976-08-31 | Dai Nippon Toryo Kaubshiki Kaisha | Nematic liquid crystal compositions |
| CN103443119A (en) * | 2010-12-15 | 2013-12-11 | 伊索技术制药公司 | Cyclosporine analogue molecules modified at amino acid 1 and 3 |
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| Title |
|---|
| 2-(4-Alkylphenyl)-5- (alkenyloxy)pyrimidines: Synthesis, liquid crystal transition temperatures and some physical properties;S. M. Kelly 等;《Liquid Crystals》;第16卷(第5期);第813-829页 * |
| Negishi Alkyl-Aryl Cross-Coupling Catalyzed by Rh: Efficiency of Novel Tripodal 3-Diphenylphosphino-2- (diphenylphosphino)methyl-2-methylpropyl Acetate Ligand;Syogo Ejiri 等;《ORGANIC LETTERS》;第12卷(第8期);第1692-1695页 * |
| Weinreb Amide Based Building Blocks for Convenient Access to Analogues of Phenstatin;Balasubramaniam Sivaraman 等;《Eur. J. Org. Chem.》;第2010卷(第26期);第4991-5003页 * |
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