155989-69-8

Basic information

• Product Name: 3-Iodo-azetidine-1-carboxylic acid tert-butyl ester
• Synonyms: 3-Iodo-azetidine-1-carboxylic acid tert-butyl ester;4-Phenoxy-piperidine-1-carboxylic acid tert-butyl ester;tert-Butyl 4-phenoxypiperidine-1-carboxylate
• CAS NO: 155989-69-8
• Molecular Formula: C₁₆H₂₃NO₃
• Molecular Weight: 277.36
• EINECS: 604-604-1
• Mol File: 155989-69-8.mol
• Article Data: 11

Chemical Properties

• Melting Point: 65-68 °C
• Boiling Point: 374.5±35.0 °C(Predicted)
• Appearance: /
• Density: 1.091±0.06 g/cm3(Predicted)
• PKA: -2.54±0.40(Predicted)
• CAS DataBase Reference: 3-Iodo-azetidine-1-carboxylic acid tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Iodo-azetidine-1-carboxylic acid tert-butyl ester(155989-69-8)
• EPA Substance Registry System: 3-Iodo-azetidine-1-carboxylic acid tert-butyl ester(155989-69-8)

Safety Data

• Hazardous Substances Data: 155989-69-8(Hazardous Substances Data)

Usage

Description

3-Iodo-azetidine-1-carboxylic acid tert-butyl ester is a chemical compound derived from azetidine-1-carboxylic acid, featuring an iodine atom and a tert-butyl ester group. This versatile molecule is recognized for its potential biological activities and is valued in the fields of organic synthesis and drug discovery for its stability, ease of handling, and applicability in radio-labeling.

Uses

Used in Pharmaceutical Synthesis:
3-Iodo-azetidine-1-carboxylic acid tert-butyl ester serves as a crucial building block in the synthesis of various pharmaceuticals and organic compounds. Its unique structure allows for the creation of new molecules with potential therapeutic properties.
Used in Anti-Cancer Research:
In the field of oncology, 3-Iodo-azetidine-1-carboxylic acid tert-butyl ester is utilized as a potential anti-cancer agent. Its biological activities are being studied for effectiveness against different types of cancer, offering a promising avenue for developing novel cancer treatments.
Used in Anti-Infective Agents:
3-Iodo-azetidine-1-carboxylic acid tert-butyl ester also shows promise as an anti-infective agent, being investigated for its potential to combat various infectious diseases. Its ability to be radio-labeled could enhance diagnostic and therapeutic approaches in infectious disease management.
Used in Organic Synthesis:
3-Iodo-azetidine-1-carboxylic acid tert-butyl ester is a key component in organic synthesis, where its iodine atom and tert-butyl ester group provide opportunities for a wide range of chemical reactions, leading to the development of new organic compounds with diverse applications.
Used in Radio-Labeling Applications:
The presence of an iodine atom in 3-Iodo-azetidine-1-carboxylic acid tert-butyl ester makes it suitable for radio-labeling purposes. This feature is particularly useful in medical imaging and tracing the behavior of molecules within biological systems, aiding in both diagnostic and research applications.

Upstream product

• 5382-16-1 4-HYDROXYPIPERIDINE 
• 24424-99-5 di-tert-butyl dicarbonate 
• 109384-19-2 t-butyl 4-hydroxy piperidine-1-carboxylate 
• 108-95-2 phenol 
• 1972-28-7 diethylazodicarboxylate 

Downstream Products

• 3413-27-2 4-phenoxypiperidine hydrochloride 
• 442198-48-3 (2E)-3-(4-Chlorophenyl)-N-[(1S)-2-oxo-2-{[2-oxo-2-(4-phenoxy-1-piperidinyl)ethyl]amino}-1-(2-pyridylmethyl)ethyl]-acrylamide 
• 855267-34-4 3-(4-phenoxypiperidin-1-yl)propan-1-ol 
• 944808-49-5 N'-hydroxy-6-(4-phenoxypiperidin-1-yl)pyridazine-3-carboxamide 
• 944808-43-9 6-(4-phenoxypiperidin-1-yl)pyridazine-3-carbonitrile 
• 3413-27-2 4-(phenoxy)-piperidine hydrochloride 
• 3202-33-3 4-phenoxypiperidine 

Relevant articles and documents

Removable phosphine reagents for the Mitsunobu reaction

We have developed a novel triphenylphosphine replacement for the Mitsunobu reaction. We have demonstrated that 4-diphenylphosphanyl-benzoic acid 2-trimethylsilanyl-ethyl ester (DPPBE) is an efficient reagent and greatly facilitates the isolation of the desired product.

COMPOUNDS AND USES THEREOF

The present invention features compounds useful in the treatment of neurological disorders and primary brain cancer. The compounds of the invention, alone or in combination with other pharmaceutically active agents, can be used for treating or preventing neurological disorders and primary brain cancer.

Synthesis of 11C-labelled ureas by palladium(II)-mediated oxidative carbonylation

Positron emission tomography is an imaging technique with applications in clinical settings as well as in basic research for the study of biological processes. A PET tracer, a biologically active molecule where a positron-emitting radioisotope such as carbon-11 has been incorporated, is used for the studies. Development of robust methods for incorporation of the radioisotope is therefore of the utmost importance. The urea functional group is present in many biologically active compounds and is thus an attractive target for incorporation of carbon-11 in the form of [11C]carbon monoxide. Starting with amines and [11C]carbon monoxide, both symmetrical and unsymmetrical 11C-labelled ureas were synthesised via a palladium(II)-mediated oxidative carbonylation and obtained in decay-corrected radiochemical yields up to 65%. The added advantage of using [11C]carbon monoxide was shown by the molar activity obtained for an inhibitor of soluble epoxide hydrolase (247 GBq/μmol-319 GBq/μ mol). DFT calculations were found to support a reaction mechanism proceeding through an 11C-labelled isocyanate intermediate.