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180-44-9 Usage


3-Azaspiro[5.5]undecane is a heterocyclic compound that features a spiro-connected azaspiro ring structure. It is a unique and versatile building block in organic synthesis, particularly for the development of pharmaceuticals and agrochemicals.


Used in Pharmaceutical Industry:
3-Azaspiro[5.5]undecane is used as a key intermediate in the synthesis of various drug molecules. Its unique ring structure and functional groups make it a valuable component in the development of new medications with improved efficacy and selectivity.
Used in Agrochemical Industry:
3-Azaspiro[5.5]undecane is utilized as a structural element in the design of novel agrochemicals, such as insecticides and herbicides. Its incorporation into these compounds can enhance their target specificity, reducing the environmental impact and improving their overall performance.
Used in Organic Synthesis:
3-Azaspiro[5.5]undecane serves as a versatile building block in organic synthesis, allowing for the creation of a wide range of complex molecules with diverse applications. Its unique spiro-connected azaspiro ring system provides opportunities for the development of innovative synthetic routes and methodologies.
As an M2 Proton Channel Blocker:
3-Azaspiro[5.5]undecane is used as a salt-free form of 4,4-Pentamethylenepiperidine Hydrochloride (P271760), which is an M2 proton channel blocker. This application is particularly relevant in the development of treatments for neurological disorders and conditions where modulation of proton channels is beneficial.

Biological Activity

M2 proton channel blocker (IC 50 = 0.92 μ M). Inhibits influenza virus M2 protein (AM2).

Check Digit Verification of cas no

The CAS Registry Mumber 180-44-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,8 and 0 respectively; the second part has 2 digits, 4 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 180-44:
49 % 10 = 9
So 180-44-9 is a valid CAS Registry Number.



According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017


1.1 GHS Product identifier

Product name 3-AZASPIRO[5.5]UNDECANE

1.2 Other means of identification

Product number -
Other names EINECS 214-404-1

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:180-44-9 SDS

180-44-9Relevant articles and documents

C-H/C-C Functionalization Approach to N-Fused Heterocycles from Saturated Azacycles

Ham, Jin Su,Park, Bohyun,Son, Mina,Roque, Jose B.,Jurczyk, Justin,Yeung, Charles S.,Baik, Mu-Hyun,Sarpong, Richmond

supporting information, p. 13041 - 13050 (2020/09/01)

Herein we report the synthesis of substituted indolizidines and related N-fused bicycles from simple saturated cyclic amines through sequential C-H and C-C bond functionalizations. Inspired by the Norrish-Yang Type II reaction, C-H functionalization of azacycles is achieved by forming α-hydroxy-β-lactams from precursor α-ketoamide derivatives under mild, visible light conditions. Selective cleavage of the distal C(sp2)-C(sp3) bond in α-hydroxy-β-lactams using a Rh-complex leads to α-acyl intermediates which undergo sequential Rh-catalyzed decarbonylation, 1,4-addition to an electrophile, and aldol cyclization, to afford N-fused bicycles including indolizidines. Computational studies provide mechanistic insight into the observed positional selectivity of C-C cleavage, which depends strongly on the groups bound to Rh trans to the phosphine ligand.

Discovery of spiro-piperidine inhibitors and their modulation of the dynamics of the M2 proton channel from influenza A virus

Wang, Jun,Cady, Sarah D.,Balannik, Victoria,Pinto, Lawrence H.,DeGrado, William F.,Hong, Mei

experimental part, p. 8066 - 8076 (2009/12/03)

Amantadine has been used for decades as an inhibitor of the influenza A virus M2 protein (AM2) in the prophylaxis and treatment of influenza A infections, but its clinical use has been limited by its central nervous system (CNS) side effects as well as emerging drug-resistant strains of the virus. With the goal of searching for new classes of M2 inhibitors, a structure-activity relation study based on 2-[3-azaspiro(5,5)undecanol]-2-midazoline (BL-1743) was initiated. The first generation BL-1743 series of compounds has been synthesized and tested by two-electrode voltage-clamp (TEV) assays. The most active compound from this library, 3-azaspiro[5,5]undecane hydrochloride (9), showed an IC50 as low as0.92 ± 0.11 μM against AM2, more than an order of magnitude m ore potent than amantadine (IC50 = 16 μM). 15N and 13C solid-state NMR was employed to determine the effect of compound 9 on the structure and dynamics of the transmembrane domain of AM2 (AM2-TM) in phospholipid bilayers. Compared to amantadine, spiro-piperidine 9 (1) induces a more homogeneous conformation of the peptide,(2) reduces the dynamic disorder of the G34-I35 backbone near the water -filled central cavity of the helical bundle, and (3) influences the dynamics and magnetic environment of more residues within the transmembranehelices. These data suggest that spiro-piperidine 9 binds more extensiv ely with the AM2 channel, thus leading to stronger inhibitory potency.

Substituted benzothiazole amide derivatives


, (2008/06/13)

A compound of formula I and a method of treatment of diseases, related to modulation of the adenosine A2 receptor system comprising administering a compound of formula 1to a person in need of such treatment.

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