2221-44-5

Basic information

• Product Name: 1,3-Dioxolo[4,5-g]isoquinoline, 5-[(3,4-dimethoxyphenyl)methyl]-7,8-dihydro-
• CAS NO: 2221-44-5
• Molecular Formula: C19H19NO4
• Molecular Weight: 325.35800
• Mol File: 2221-44-5.mol
• Article Data: 4

Chemical Properties

• Melting Point: 68-70 °C
• Boiling Point: 476.9±45.0 °C(Predicted)
• Density: 1.28±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 1,3-Dioxolo[4,5-g]isoquinoline, 5-[(3,4-dimethoxyphenyl)methyl]-7,8-dihydro-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Dioxolo[4,5-g]isoquinoline, 5-[(3,4-dimethoxyphenyl)methyl]-7,8-dihydro-(2221-44-5)
• EPA Substance Registry System: 1,3-Dioxolo[4,5-g]isoquinoline, 5-[(3,4-dimethoxyphenyl)methyl]-7,8-dihydro-(2221-44-5)

Safety Data

• Hazardous Substances Data: 2221-44-5(Hazardous Substances Data)

Usage

Description

1,3-Dioxolo[4,5-g]isoquinoline, 5-[(3,4-dimethoxyphenyl)methyl]-7,8-dihydrois a complex chemical compound that belongs to the class of isoquinolines. It features a dioxolo ring system and a phenylmethyl group with dimethoxy substituents. This unique structure and potential biological activities make it a promising candidate for pharmaceutical and medicinal chemistry applications.
Used in Pharmaceutical Industry:
1,3-Dioxolo[4,5-g]isoquinoline, 5-[(3,4-dimethoxyphenyl)methyl]-7,8-dihydrois used as a chemical compound for its potential applications in the development of new drugs and therapies. Its unique structure and potential biological activities make it a valuable candidate for further research and exploration in the field of medicinal chemistry.
Used in Medicinal Chemistry Research:
1,3-Dioxolo[4,5-g]isoquinoline, 5-[(3,4-dimethoxyphenyl)methyl]-7,8-dihydrois used as a research compound for studying its properties and potential uses in medicinal chemistry. Further research is required to fully understand its biological activities and explore its potential applications in the development of new pharmaceuticals and treatments.

Upstream product

• 20341-16-6 N-(2-benzo[1,3]dioxol-5-yl-ethyl)-2-(3,4-dimethoxy-phenyl)-acetamide 
• 108-88-3 toluene 
• 10025-87-3 trichlorophosphate 
• 56-23-5 tetrachloromethane 
• 1484-85-1 3,4-methylenedioxyphenylethylamine 
• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 

Downstream Products

• 20341-48-4 (7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-(3,4-dimethoxy-phenyl)-methanone 
• 112970-23-7 1-(3,4-dimethoxyphenyl)-5,6-dihydro-3H-[1,3]dioxolo[4,5-g]oxazolo[4,3-a]isoquinolin-3-one 
• 81165-49-3 3-[5-(3,4-Dimethoxy-benzyl)-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-6-yl]-propionic acid 2-{3-[5-(3,4-dimethoxy-benzyl)-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-6-yl]-propionyloxy}-ethyl ester; compound with oxalic acid 
• 64229-27-2 C₅₁H₆₄N₂O₁₂⁽²⁺⁾*2I^(1-) 
• 64229-26-1 C₄₈H₅₈N₂O₁₂⁽²⁺⁾*2I^(1-) 
• 81165-50-6 3-[5-(3,4-Dimethoxy-benzyl)-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-6-yl]-propionic acid 5-{3-[5-(3,4-dimethoxy-benzyl)-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-6-yl]-propionyloxy}-pentyl ester; compound with oxalic acid 
• 112970-22-6 ethyl 1-(3,4-dimethoxybenzylidene)-3,4-dihydro-6,7-(methylenedioxy)-2(1H)-isoquinolinecarboxylate 
• 19918-74-2 5-[(3,4-dimethoxyphenyl)methyl]-5,6,7,8-tetrahydro-1,3-dioxolo[4,5-g]isoquinoline 

Relevant articles and documents

Copper(ii)-catalyzed and acid-promoted highly regioselective oxidation of tautomerizable C(sp3)-H bonds adjacent to 3,4-dihydroisoquinolines using air (O2) as a clean oxidant

A mild, efficient and eco-friendly method for the oxidation of 1-Bn-DHIQs to 1-Bz-DHIQs without concomitant excessive oxidation of 1-Bz-DHIQs to 1-Bz-IQs is very important for the syntheses of 1-Bz-DHIQ alkaloids and analogues. In this article, we developed a novel Cu(ii)-catalyzed and acid-promoted highly regioselective oxidation of tautomerizable C(sp3)-H bonds adjacent to the C-1 positions of various 1-Bn-DHIQs. It was observed that when 0.2 equiv. of Cu(OAc)2·2H2O was used as the catalyst, 3.0 equiv. of AcOH was used as the additive and air (O2) was used as a clean oxidant, various 1-Bn-DHIQs could be efficiently oxidized to corresponding 1-Bz-DHIQs at 25 °C in DMSO. Especially, almost no concomitant excessive oxidation of 1-Bz-DHIQs to 1-Bz-IQs was observed during the above reaction. In addition, this method was successfully applied in the first total synthesis of the alkaloid canelillinoxine.

Synthesis of (±)-Glaucine and (±)-Neospirodienone via an One-Pot Bischler-Napieralski Reaction and Oxidative Coupling by a Hypervalent Iodine Reagent

Condensation of 3,4-dimethoxybenzeneethanamine (3d) and various benzeneacetic acids, i.e., 4a-e, via a practical and efficient one-pot Bischler-Napieralski reaction, followed by NaBH4 reduction, produced a series of 1-benzyl-1,2,3,4-tetrahydroisoquinolines, i.e., 5a-e, in satisfactory yields (Scheme 3). Oxidative coupling of the N-acyl and N-methyl derivatives 6a-e of the latter with hypervalent iodine ([IPh(CF 3COO)2]) yielded products with two different skeletons (Scheme 4). The major products from N-acyl derivatives 6a-c were (±)-N-acylneospirodienones 2a-c, while the minor was the 3,4-dihydroisoquinoline 7. (±)-Glaucine (1), however, was the major product starting from N-methyl derivative 6e. Possible reaction mechanisms for the formation of these two types of skeleton are proposed (Scheme 5).