57032-14-1

Basic information

• Product Name: 2,3-QUINOLINEDIMETHANOL
• Synonyms: 2,3-QUINOLINEDIMETHANOL
• CAS NO: 57032-14-1
• Molecular Formula: C₁₁H₁₁NO₂
• Molecular Weight: 189.21
• Mol File: 57032-14-1.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 388.4°C at 760 mmHg
• Flash Point: 188.7°C
• Appearance: /
• Density: 1.31g/cm³
• Vapor Pressure: 9.96E-07mmHg at 25°C
• Refractive Index: 1.688
• CAS DataBase Reference: 2,3-QUINOLINEDIMETHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-QUINOLINEDIMETHANOL(57032-14-1)
• EPA Substance Registry System: 2,3-QUINOLINEDIMETHANOL(57032-14-1)

Safety Data

• Hazardous Substances Data: 57032-14-1(Hazardous Substances Data)

Usage

Description

2,3-Quinolinedimethanol is an organic compound with the chemical formula C11H13NO2. It is a white crystalline solid that serves as an important intermediate in the synthesis of various pharmaceutical compounds.

Uses

Used in Pharmaceutical Industry:
2,3-Quinolinedimethanol is used as a reactant in the synthesis of camptothecin (C175150), a potent cytotoxic antitumor agent. Camptothecin binds irreversibly to the DNA-topoisomerase I complex, inhibiting the reassociation of DNA after cleavage by topoisomerase I and trapping the enzyme in a covalent linkage with DNA. This mechanism of action makes camptothecin a valuable compound in the development of anticancer drugs.

InChI:InChI=1/C11H11NO2/c13-6-9-5-8-3-1-2-4-10(8)12-11(9)7-14/h1-5,13-14H,6-7H2

Upstream product

• 1088402-56-5 (3-formylquinolin-2-yl)methyl acetate 
• 529-23-7 o-aminobenzaldehyde 
• 778593-73-0 2-methyl-3-(hydroxymethyl)quinoline 1-oxide 
• 30160-03-3 methyl 2-methylquinoline-3-carboxylate 
• 53936-95-1 3-(hydroxymethyl)-2-methylquinoline 
• 778593-74-1 acetic acid {2-(acetoxymethyl)quinolin-3-yl}methyl ester 
• 17507-03-8 dimethyl quinoline-2,3-dicarboxylate 

Downstream Products

• 7689-03-4 camptothecin 
• 156969-69-6 Benzoic acid 5-(1,3-dihydro-pyrrolo[3,4-b]quinoline-2-carbonyl)-3-ethyl-4-formyl-2-oxo-3,6-dihydro-2H-pyran-3-yl ester 
• 156969-70-9 Benzoic acid 4-ethyl-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-4-yl ester 
• 31456-25-4 camptothecin 

Relevant articles and documents

Letter: A total synthesis of natural 20(S)-camptothecin.

-

Short protecting group-free syntheses of camptothecin and 10-hydroxycamptothecin using cascade methodologies

A convergent protecting group-free total synthesis route of camptothecin and 10-hydroxycamptothecin has been developed in this work. Cascade oxidation of 3-(hydroxymethyl)furan-2(5 H)-one and in situ intermolecular oxa Diels-Alder reaction with vinyl ether was developed and applied to construct the E-ring, and TMSCl-promoted cascade closure of the D-ring delivered the whole skeleton of the alkaloids in the total synthesis. The new short syntheses were advantageous with regard to step economy, low cost, easily available starting materials and reagents, and convenient operations.

Regioselective Synthesis of Camptothecin

A convergent synthesis of (+/-)camtothecin is described.