294-42-8

Basic information

• Product Name: 1-Azacycloundecane
• Synonyms: 1-Azacycloundecane
• CAS NO: 294-42-8
• Molecular Formula: C10H21 N
• Molecular Weight: 155.28
• Mol File: 294-42-8.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-Azacycloundecane(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Azacycloundecane(294-42-8)
• EPA Substance Registry System: 1-Azacycloundecane(294-42-8)

Safety Data

• Hazardous Substances Data: 294-42-8(Hazardous Substances Data)

Upstream product

• 79130-42-0 1-(Toluene-4-sulfonyl)-azacycloundecane 
• 2972-01-2 cyclodecanone oxime 
• 1502-06-3 cyclodecanone 
• 1009-89-8 azacycloundecan-2-one 

Downstream Products

• 78252-72-9 ethyl 4-(2-(5-chloro-2-decamethyleneimino-benzoylamino)-ethyl)-benzoate 
• 78243-86-4 5-amino-2-(azacycloundec-1-yl)-benzoic acid 
• 78251-87-3 5-chloro-2-decamethyleneimino-benzoic acid 

Relevant articles and documents

Motuporamines, anti-invasion and anti-angiogenic alkaloids from the marine sponge Xestospongia exigua (Kirkpatrick): Isolation, structure elucidation, analogue synthesis, and conformational analysis

Extracts of the sponge Xestospongia exigua collected in Papua New Guinea were positive in a new assay for anti-invasion activity. Bioassay-guided fractionation led to the identification of the three known motuporamines A (1), B (2), and C (3) along with the new motuporamines D (4), E (5), and F (6) and a mixture of G, H, and I (15). Motuporamines A (1), B (2), and C (3) and the mixture of G, H, and I (15) were responsible for the anti-invasion activity of the crude extract. Motuporamine C (3) has also been found to be anti-angiogenic. A series of analogues of the motuporamines have been synthesized and evaluated for anti-invasive activity. These SAR results revealed that a saturated 15-membered cyclic amine fused to the natural motuporamine diamine side chain (13) represented the optimal structure for anti-invasive activity in this family. Single-crystal X-ray diffraction analysis of one of the analogues 20 showed that in the solid state its 16-membered macrocyclic amine fragment adopted the [4444] quadrangular conformation predicted by calculations to be the lowest energy conformation for the corresponding cycloalkane, cyclohexadecane. These data along with literature X-ray data and conformational analysis for derivatives of azacyclotridecane have been used as precedents for predicting the lowest energy ring conformations of other motuporamines. The SAR data from the natural and synthetic motuporamines have been combined with the conformational analyses to provide an outline of the functionality and shape required for activity in this family of alkaloids and to design a new analogue 49 that showed good anti-invasion activity.

Structural and Mechanistic Effects on the Rates of Ring-Opening Reactions in the 5-16-Membered-Ring Region

Partial rate coefficients have been determined for the reaction of cyclic dimethylammonium ions with sodium methoxide in the 7-16-membered-ring region.Three second-order parallel reactions take place and lead to exocyclic demethylation (A), ring-opening substitution (B), and ring-opening olefin-forming elimination (C).The results were compared with the behavior of the five- and six-membered rings.Reaction A shows negligible dependence on ring size.In contrast, reactions B and C are affected by ring size through ring strain and geometry of the transition state: the latter factor is held responsible for major differences in the reactivity profiles between such reactions.