352304-41-7

Basic information

• Product Name: Butylcycloheptylprodigiosin
• Synonyms: Butylcycloheptylprodigiosin;)-Butylcycloheptylprodiginine;4-Butyl-1,4,5,6,7,8,9,10-octahydro-2-[[3-methoxy-5-(1H-pyrrol-2-yl)-2H-pyrrol-2-ylidene]methyl]-cyclonona[b]pyrrole
• CAS NO: 352304-41-7
• Molecular Formula: C25H33N3O
• Molecular Weight: 391.54902
• Mol File: 352304-41-7.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 619.3±55.0 °C(Predicted)
• Appearance: /
• Density: 1.15±0.1 g/cm3(Predicted)
• PKA: 15.35±0.50(Predicted)
• CAS DataBase Reference: Butylcycloheptylprodigiosin(CAS DataBase Reference)
• NIST Chemistry Reference: Butylcycloheptylprodigiosin(352304-41-7)
• EPA Substance Registry System: Butylcycloheptylprodigiosin(352304-41-7)

Safety Data

• Hazardous Substances Data: 352304-41-7(Hazardous Substances Data)

Usage

Uses

Butylcycloheptylprodigiosin is a pigment like prodigiosin with antimalerial, antiulcer, and apoptotic activity.

Upstream product

• 1213263-03-6 tert-butyl 5′-formyl-4′-methoxy-1H,1′H-[2,2′-bipyrrole]-1-carboxylate 
• 135884-31-0 N-boc-2-pyrroleboronic acid 
• 42052-30-2 (Z)-cyclonon-2-enone 
• 857256-88-3 (Z,Z)-cyclonona-2,8-dienol 
• 33525-29-0 (Z,Z)-cyclonona-2,8-dienone 
• 857256-81-6 2-methyl-7,8,9,10-tetrahydro-6H-cyclonona[b]pyrrole-1-carboxylic acid tert-butyl ester 
• 857256-78-1 2-((2Z,8Z)-Cyclonona-2,8-dienyl)-3-oxo-butyric acid methyl ester 
• 857256-75-8 2-methyl-1,6,7,8,9,10-hexahydro-cyclonona[b]pyrrole 
• 857256-89-4 ((2Z,8Z)-1-Cyclonona-2,8-dienyl)-propan-2-one oxime 
• 857256-80-5 (4Z,9Z)-2-Methyl-3,3a,6,7,8,10a-hexahydro-cyclonona[b]pyrrole 
• 857256-76-9 cyclonona-(Z,Z)-2,8-dienylacetone 
• 857256-77-0 (Z,Z)-cyclonona-2,8-dienyl acetate 
• 69778-83-2 4-methoxy-3-pyrrolin-2-one 
• 940288-03-9 C₁₇H₂₅NO₂ 

Relevant articles and documents

A concise synthesis of butylcycloheptylprodigiosin

A short and efficient total synthesis of the tripyrrole alkaloid butylcycloheptylprodigiosin is described. Key to the brevity of the approach is a two-step synthesis of macrocyclic formylpyrrole 4 from cyclononenone 6.

Total synthesis, molecular editing and evaluation of a tripyrrolic natural product: The case of "butylcycloheptylprodigiosin"

Conflicting reports are found in the literature on whether the ortho-pyrrolophane derivative 6, which has been named " butylcycloheptylprodigiosin" even though it is a cyclononane derivative, is a natural product or merely a mis-assigned structure. This dispute has now been resolved by an unambiguous total synthesis of this complex alkaloid which confirms the initial structure assignment. The chosen approach is largely catalysis-based, featuring the first application of a "Narasaka-Heck" reaction in natural product chemistry. This palladium-catalyzed transformation allows the unsaturated oxime ester 26 to be converted into the bicyclic dihydropyrrole 27. Other notable reactions of the reported approach to 6 are a regioselective Tsuji-Trost reaction of the doubly allylic acetate 21 with methyl acetoacetate. a base-induced aromatization of 27 to the corresponding pyrrole 28. a chemoselective oxidation of the benzylic methyl group in 33 with cerium ammonium nitrate in a biphasic reaction medium that does not affect the labile pyrrole nucleus, and a Suzuki cross-coupling for the completion of the heterocyclic domain. Diversification in the latter step leads to a set of analogues that differ from the natural product in the terminal (hetero)arene ring. This structural modification results in complete loss of the very pronounced ability of the parent compound 6 to induce oxidative cleavage in double stranded DNA in the presence of Cu11. Several cyclononane-, cyclononene- and cyclononadiene derivatives prepared en route to 6 have been characterized by crystal structure analysis, allowing the conformational behavior of nine-membered carbocycles to be studied.