(2E)-3-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]prop-2-enal
(E)-3-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-2-propenal
CAS: 148901-68-2
Molecular Formula: C21H16FNO
(2E)-3-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]prop-2-enal - Names and Identifiers
(2E)-3-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]prop-2-enal - Physico-chemical Properties
| Molecular Formula | C21H16FNO |
| Molar Mass | 317.36 |
| Density | 1.256±0.06 g/cm3(Predicted) |
| Melting Point | 136-142 °C |
| Boling Point | 491.8±45.0 °C(Predicted) |
| Flash Point | 251.228°C |
| Vapor Presure | 0mmHg at 25°C |
| pKa | 3.82±0.50(Predicted) |
| Storage Condition | 2-8℃ |
| Refractive Index | 1.675 |
(2E)-3-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]prop-2-enal - Reference Information
| Introduction | (E)-3-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinoline-2-acrolein is pitavastatin calcium synthesis intermediate, pitavastatin calcium (PitavastatinCalcium) trade name is Livalo, it is the third-generation statin lipid-lowering drug jointly developed and produced by Japan's Nissan Chemical Industry Co., Ltd. Hexinghe Co., Ltd. This product has been listed in Japan in October 2003. It is used to treat primary hypercholesterolemia and familial hypercholesterolemia. It has good safety and effectiveness. |
| Preparation | (E)-3-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolin-2-acrolein is prepared as follows: 1) Add 26g 2-cyclopropyl -4-(4-fluorophenyl) quinoline -3-formaldehyde, 37.3g (triphenyl n-phosphorus) methyl acetate and 300mLDMF into a 500mL reaction bottle respectively, stir, raise the temperature to 80 ℃ for reaction, and TLC monitors the reaction; After the reaction is completed, cool to room temperature, add 800mL of water, stir to separate the liquid, the water layer is extracted with ethyl acetate (300mL × 3), and the organic phase is combined, the organic phase was washed with 500mL of water and 500mL of saturated sodium chloride solution, anhydrous sodium sulfate was dried, the solvent was evaporated under reduced pressure to obtain 63.2g of brown-yellow solid residue, 300mL of methanol was added, heated and dissolved, cooled, stirred, crystallized, filtered, rinsed, dried, and other 26.9g of light yellow solid product intermediate 1. Yield: 83%. 2) At room temperature, 25g of intermediate 1 and 5.9g of lithium bromide are placed in 230mL tetrahydrofuran, stirred for 30 minutes, 2.6g of sodium borohydride is added, then the reaction is carried out at room temperature, and TLC monitors the reaction; After the reaction of the raw materials is complete, the solvent is evaporated under reduced pressure, 100mL of water is added, and then extracted with ethyl acetate (100mL × 3); The organic layer is dried with anhydrous sodium sulfate, leached, evaporated to dry the solvent under reduced pressure, 60mL of ether, 20.5g white solid product intermediate 2. Yield: 93%. 3) In 150mL of dichloromethane, 20g of intermediate 2 is added, stirred and dissolved, then 1g of catalyst TEMPO is added, then 10mL of potassium bromide aqueous solution is added dropwise, the temperature is reduced to 0 ℃, and then 50g of 10% sodium hypochlorite solution is added dropwise. After dropping, the temperature is raised to room temperature for reaction, and TLC is used to detect the reaction. After the reaction is completed, 50mL of water is added into the reaction solution, stirred, left to layer, and the water layer is extracted; the organic phase was combined, washed with 50mL of saturated sodium sulfite solution and 50mL of saturated salt water, dried with anhydrous sodium sulfate, and concentrated to dry under reduced pressure to obtain 16.9g of product (E)-3-[2-cyclopropyl -4-(4-fluorophenyl)-3-quinoline -2-acrolein. The yield was 85%. |
Last Update：2024-04-09 21:04:16
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Product Name: (E)-3-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl-2-propenal Visit Supplier Webpage Request for quotationCAS: 148901-68-2
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Product Name: (E) -3- [2-cyclopropyl-4- (4-fluorophenyl) -3-quinolinyl] -2-acrolein Request for quotation
CAS: 148901-68-2
Tel: +86-21-56795779
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CAS: 148901-68-2
Tel: +86-21-56795779
Email: charles7788@worldyachem.com
Mobile: +86-13651600618
QQ: 2850607228
Wechat: 13651600618
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