130144-33-1

Basic information

• Product Name: [1,4'-Bipiperidine]-1'-carboxylic acid, 4,11-diethyl-3,4,12,14-tetrahydro-4-hydroxy-3,14-dioxo-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl ester, (+-)-
• Synonyms: [1,4'-Bipiperidine]-1'-carboxylic acid, 4,11-diethyl-3,4,12,14-tetrahydro-4-hydroxy-3,14-dioxo-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl ester (9CI);[1,4'-Bipiperidine]-1'-carboxylic acid, 4,11-diethyl-3,4,12,14-tetrahydro-4-hydroxy-3,14-dioxo-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl ester, (+-)-
• CAS NO: 130144-33-1
• Molecular Formula: C₃₃H₃₈N₄O₆
• Molecular Weight: 586.68
• Mol File: 130144-33-1.mol
• Article Data: 32

Chemical Properties

• Boiling Point: 873.4°Cat760mmHg
• Flash Point: 482°C
• Appearance: /
• Density: 1.4g/cm³
• CAS DataBase Reference: [1,4'-Bipiperidine]-1'-carboxylic acid, 4,11-diethyl-3,4,12,14-tetrahydro-4-hydroxy-3,14-dioxo-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl ester, (+-)-(CAS DataBase Reference)
• NIST Chemistry Reference: [1,4'-Bipiperidine]-1'-carboxylic acid, 4,11-diethyl-3,4,12,14-tetrahydro-4-hydroxy-3,14-dioxo-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl ester, (+-)-(130144-33-1)
• EPA Substance Registry System: [1,4'-Bipiperidine]-1'-carboxylic acid, 4,11-diethyl-3,4,12,14-tetrahydro-4-hydroxy-3,14-dioxo-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl ester, (+-)-(130144-33-1)

Safety Data

• Hazardous Substances Data: 130144-33-1(Hazardous Substances Data)

Upstream product

• 174092-83-2 (S)-4-ethyl-4-hydroxy-6-iodo-7-(pent-2-yn-1-yl)-1,7-dihydro-3H-pyrano[3,4-c]pyridino-3,8(4H)-dione 
• 202744-81-8 4-isocyanophenyl [1,4'-bipiperidine]-1'-carboxylate 
• 4897-50-1 4-piperidinopiperidin 
• 110351-94-5 (4S)-4-ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 86639-52-3 7-ethyl-10-hydroxycamptothecin 
• 530-62-1 1,1'-carbonyldiimidazole 
• 100286-90-6 irinotecan hydrochloirde 
• 86639-53-4 (S)-4,11-diethyl-4-hydroxy-9-methoxy-1H-pyrano[3',4':6,7]-indolizino[1,2-b]quinoline-3,14(4H,12H)-dione 
• 103816-16-6 10-[4-(1-piperidino)-1-piperidino]carbonyloxycamptothecin 
• 123-38-6 propionaldehyde 
• 455-67-4 1-(3-fluorophenyl)propan-1-one 
• 403-54-3 m-Fluorobenzonitrile 
• 458-02-6 3-fluorobenzaldehyde oxime 

Downstream Products

• 86639-52-3 7-ethyl-10-hydroxycamptothecin 
• 4897-50-1 4-piperidinopiperidin 
• 181467-56-1 7-ethyl-10-[4-N-(5-aminopentanoic acid)-1-piperidino]carbonyloxycamptothecin 
• 130144-34-2 4,11-diethyl-4,9-dihydroxy-1H-pyrano[3′,4′:6,7]indolizino[1,2-b]quinoline-3,14 (4H,12H)-dione 
• 100286-90-6 irinotecan hydrochloirde 

Relevant articles and documents

Preparation method of irinotecan hydrochloride

The invention relates to a preparation method of irinotecan hydrochloride. The preparation method comprises the following steps: a) enabling 4-piperidylpiperidine and N, N'-carbonyldiimidazole to react with 7-ethyl-10-hydroxycamptothecine in an aprotic solvent containing a hemp and cotton resin compound to generate an irinotecan monomer, and b) adding water to dissolve the irinotecan monomer, adding a hydrochloric acid solution to adjust the pH value to 2-3, adding acetone of which the volume is 3-5 times that of the water, carrying out crystallizing, filtering and recrystallizing with a mixedsolvent of acetone and water, and carrying out vacuum drying to obtain the irinotecan hydrochloride finished product. Compared with the prior art, according to the invention, in preparatuion of irinotecan hydrochloride, no high-toxicity dangerous reagent is used, the N, N-dimethylformamide with relatively stable commercial easy-to-obtain property is used, a carbonyl group is introduced into N, N'-carbonyldiimidazole, an irinotecan monomer is obtained through a one-step reaction, the harsh condition that N, N'-carbonyldiimidazole needs to be anhydrous is avoided through cooperation with a hempand cotton resin compound, the reaction process is greatly simplified, the production period is shortened, and the preparation method has obvious industrial production advantages.

Visible-Light-Induced Radical Cascade Cyclization: Synthesis of (20S)-Camptothecin, SN-38 and Irinotecan

(20S)-Camptothecin, irinotecan and SN-38 were successfully synthesized by a photocatalyzed radical cascade cyclization from an N-propargyl iodopyridinone and an arylisonitrile under visible light with a ruthenium catalyst. This synthetic method provided a useful entry into composing camptothecin family of antitumor agents in good yields under mild reaction conditions without the use of heavy metal reagents.

Method for producing irinotecan

PROBLEM TO BE SOLVED: To provide a novel method for producing irinotecan using amines.SOLUTION: A method of producing irinotecan represented by the chemical formula (1) includes reacting 7-ethyl-10-hydroxycamptothecin with 1-chlorocarbonyl-4-piperidinopiperidine or hydrochloride thereof in the presence of a nonaromatic tertiary amine having 5 or less carbon atoms.