204906-02-5

Basic information

• Product Name: Piperidine, 2,2,6,6-tetramethyl-1-[(3-phenyl-2-propenyl)oxy]-
• CAS NO: 204906-02-5
• Molecular Formula: C18H27NO
• Molecular Weight: 273.418
• Mol File: 204906-02-5.mol

Chemical Properties

• CAS DataBase Reference: Piperidine, 2,2,6,6-tetramethyl-1-[(3-phenyl-2-propenyl)oxy]-(CAS DataBase Reference)
• NIST Chemistry Reference: Piperidine, 2,2,6,6-tetramethyl-1-[(3-phenyl-2-propenyl)oxy]-(204906-02-5)
• EPA Substance Registry System: Piperidine, 2,2,6,6-tetramethyl-1-[(3-phenyl-2-propenyl)oxy]-(204906-02-5)

Safety Data

• Hazardous Substances Data: 204906-02-5(Hazardous Substances Data)

Upstream product

• 300-57-2 allylbenzene 
• 2564-83-2 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical 
• 4392-24-9 3-bromo-1-phenyl-1-propenyl bromide 
• 59625-54-6 1-phenyl-3-iodopropene 
• 2564-83-2 2,2,6,6-tetramethyl-piperidine-N-oxyl 

Relevant articles and documents

Bromine Radical Catalysis by Energy Transfer Photosensitization

We report here a mild, safe, and user-friendly bromine radical catalysis system that enables efficient [3 + 2] cycloaddition of diversely substituted vinyl- and ethynylcyclopropanes with a broad range of alkenes, including drug-like molecules and pharmaceuticals. Key to the success is the use of photosensitizing triplet-state β-fragmentation of a judiciously selected precatalyst, cinnamyl bromide, to generate bromine radicals in a controlled manner using parts per million-level photocatalyst (i.e., 4CzIPN) loading.

Enantioselective Reductive Homocoupling of Allylic Acetates Enabled by Dual Photoredox/Palladium Catalysis: Access to C2-Symmetrical 1,5-Dienes

Transition-metal-catalyzed reductive coupling reactions have emerged as powerful protocols to construct C-C bonds. However, the development of enantioselective C(sp3)-C(sp3) reductive coupling remains challenging. Herein, we report a highly regio-, diastereo-, and enantioselective reductive homocoupling of allylic acetates through cooperative palladium and photoredox catalysis using diisopropylethylamine or Hantzsch ester as a homogeneous organic reductant. This straightforward protocol enables the stereoselective construction of C(sp3)-C(sp3) bonds under mild reaction conditions. A series of C2-symmetrical chiral 1,5-dienes were easily prepared with excellent enantioselectivities (up to >99% ee), diastereoselectivities (up to >95:5 dr), and regioselectivities (up to >95:5 rr). The resultant chiral 1,5-dienes can be directly used as chiral ligands in asymmetric synthesis, and they can be also transformed into other valuable chiral ligands.

Photoinduced Palladium-Catalyzed Carbofunctionalization of Conjugated Dienes Proceeding via Radical-Polar Crossover Scenario: 1,2-Aminoalkylation and beyond

A photoinduced palladium-catalyzed 1,2-carbofunctionalization of conjugated dienes has been developed. This mild modular approach, which does not require employment of exogeneous photosensitizers and external oxidants, allows for efficient and highly regio- and stereoselective synthesis of a broad range of allylic amines from readily available 1,3-dienes, alkyl iodides, and amines. Employment of O- and C-nucleophiles toward oxyalkylation and dialkylation products was also demonstrated. A putative π-allyl palladium radical-polar crossover path is proposed as a key event in this three-component coupling process. The utility of this protocol is highlighted by its application for derivatization of several amine-containing drugs.

Metal-free, one-pot synthesis of allylic and benzylic esters via decarboxylation and C-H bond activation

A tetrabutylammonium iodide catalyzed method has been developed for the one-pot synthesis of allylic and benzylic esters from α-oxo carboxylic acids and alkenes/alkylbenzenes via decarboxylation and C-H bond activation. Various allylic and benzylic esters were obtained in good yield.

Redox-neutral α-allylation of amines by combining palladium catalysis and visible-light photoredox catalysis

An unprecedented α-allylation of amines was achieved by combining palladium catalysis and visible-light photoredox catalysis. In this dual catalysis process, the catalytic generation of allyl radical from the corresponding π-allylpalladium intermediate wa

Tetrabutylammonium iodide catalyzed synthesis of allylic ester with tert -butyl hydroperoxide as an oxidant

A metal-free C-H oxidation for the construction of allylic esters has been developed. The use of a commercially available and inexpensive catalyst and oxidant, and readily available starting materials, coupled with the operational simplicity of the reacti