74612-20-7

Basic information

• Product Name: (13aR,13bR)-4,4-dimethyl-4,5,8,10,12,13,13a,13b-octahydro-2H-[1,6]dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione
• CAS NO: 74612-20-7
• Molecular Formula: C₁₅H₂₁NO₄
• Molecular Weight: 279.3315
• Mol File: 74612-20-7.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 504.6°C at 760 mmHg
• Flash Point: 259°C
• Density: 1.22g/cm³
• Vapor Pressure: 2.62E-10mmHg at 25°C
• Refractive Index: 1.551
• CAS DataBase Reference: (13aR,13bR)-4,4-dimethyl-4,5,8,10,12,13,13a,13b-octahydro-2H-[1,6]dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (13aR,13bR)-4,4-dimethyl-4,5,8,10,12,13,13a,13b-octahydro-2H-[1,6]dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione(74612-20-7)
• EPA Substance Registry System: (13aR,13bR)-4,4-dimethyl-4,5,8,10,12,13,13a,13b-octahydro-2H-[1,6]dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione(74612-20-7)

Safety Data

• Hazardous Substances Data: 74612-20-7(Hazardous Substances Data)

Upstream product

• 4160-82-1 3,3-dimethylglutaric anhydride 
• 68-12-2 N,N-dimethyl-formamide 
• 480-85-3 retronecine 

Relevant articles and documents

Pyrrolizidine Alkaloids. Synthesis of 13,13-Dimethyl-1,2-didehydrocrotalanine

The first synthesis of an 11-membered macrocyclic pyrrolizidine diester has been achieved from (+)-retronicine and 3,3-dimethylglutaric anhydride.

Pyrrolizidine Alkaloid Analoques. Synthesis of Eleven-membered Macrocyclic Diesters of Retronecine

Treatment of (+)-retronecine (1) with 3,3-disubstituted glutaric anhydride derivatives (2) yielded mixtures of the retronecine 7- and 9-monoesters, which were assayed by 1H n.m.r. spectrometry.Lactonisation of these mixtureswas achieved by the Corey-Nicolaou method to give a range of eleven-membered macrocyclic pyrrolizidine diesters (5) with different substituents at C-13.The macrocyclic nature of these pyrrolizidine alkaloid analogues was established by comparison of their 1H n.m.r. and mass spectra with those of natural pyrrolizidine alkaloids.