173948-30-6

Usage

Uses

Used in Organic Synthesis:
(E)-N,N-diisopropyl-3-phenylprop-2-en-1-amine is used as a ligand or catalyst in organic synthesis, facilitating various chemical reactions and improving their efficiency. Its unique structural features allow it to interact with a wide range of substrates, making it a valuable tool in the development of new chemical processes.
Used in Pharmaceutical and Agrochemical Compounds:
(E)-N,N-diisopropyl-3-phenylprop-2-en-1-amine serves as a building block in the preparation of various pharmaceutical and agrochemical compounds. Its structural diversity and reactivity enable the creation of novel molecules with potential therapeutic or pesticidal properties.
Used in Medicinal Chemistry and Drug Discovery:
(E)-N,N-diisopropyl-3-phenylprop-2-en-1-amine has potential applications in medicinal chemistry and drug discovery due to its structural features and versatile reactivity. Researchers can leverage these properties to design and synthesize new drug candidates with improved pharmacological profiles.
Used in Research and Industrial Applications:
(E)-N,N-diisopropyl-3-phenylprop-2-en-1-amine plays a significant role in both research and industrial applications within the field of chemistry. Its unique properties and reactivity make it an essential component in the development of new chemical processes, materials, and products.

Upstream product

• 108-18-9 diisopropylamine 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 2687-12-9 cinnamyl chloride 
• 4392-24-9 3-bromo-1-phenyl-1-propenyl bromide 
• 104-54-1 3-Phenylpropenol 
• 300-57-2 allylbenzene 
• 1586-98-7 (2,3-dibromopropyl)benzene 

Downstream Products

• 124936-74-9 N,N-diiso-propyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropanamine 
• 837376-36-0 3-(2-hydroxy-5-methylphenyl)-N,N-diisopropyl-3-phenylpropan-1-aminium bromide 
• 194482-44-5 Tolterodine acid 
• 124937-51-5 (R)-(+)-tolterodine 
• 1000377-72-9 C₃₁H₄₈N₂OSi 
• 1000377-73-0 (R)-N,N-diisopropyl-3-phenyl-3-(5-formyl-2-triisopropylsilyloxyphenyl)propyl-1-amine 
• 214601-12-4 (R)-N,N-diisopropyl-3-phenyl-3-(5-formyl-2-hydroxyphenyl)propyl-1-amine 
• 1587713-27-6 (Z)-N,N-diisopropyl-3-phenylprop-2-en-1-amine 
• 1333234-71-1 2-(3-(diisopropylamino)-1-phenylpropyl)-4-formylphenyl isobutyrate 
• 156755-20-3 PNU 200577 l-mandelate salt 
• 286930-03-8 fesoterodine fumarate 

Relevant academic research and scientific papers

Palladium-Catalyzed Allylic Amination of Allylic Alcohols with Tin(II) Chloride and Triethylamine

Allylic alcohols caused allylic amination with primary or secondary amines in the presence of a catalytic amount of Pd(PPh3)4 and stoichiometric amount of tin(II) chloride in THF at 50 deg C to produce the corresponding allylic amines regioselectively.

Practical regio- and stereoselective azidation and amination of terminal alkenes

There is significant interest in developing more rapid and efficient production of nitrogen-containing allylic compounds, as widely used in various syntheses. This work reports a variety of allylic azides and allylic amines synthesized by an efficient, new one-pot protocol that employs readily available terminal alkenes as starting materials. This method is highly regio- and stereoselective, affording the linear (E)-isomer, under metal-free conditions. This process tolerates several functional groups including halogen-containing molecules; it is general for azides and amine nucleophiles; and, adducts were obtained in good yields.

C-N Bond Formation from Allylic Alcohols via Cooperative Nickel and Titanium Catalysis

Amination of allylic alcohols is facilitated via cooperative catalysis. Catalytic Ti(O-i-Pr)4 is shown to dramatically increase the rate of nickel-catalyzed allylic amination, and mechanistic experiments confirm activation of the allylic alcohol by titanium. Aminations of primary and secondary allylic alcohols are demonstrated with a variety of amine nucleophiles. Diene-containing substrates also cyclize onto the nickel allyl intermediate prior to amination, generating carbocyclic amine products. This tandem process is only achieved under our cooperative catalytic system.

Direct Allylic Amination of Allylic Alcohol Catalyzed by Palladium Complex Bearing Phosphine-Borane Ligand

The direct electrophilic, nucleophilic, and amphiphilic allylations of allylic alcohol by use of a palladium catalyst and organometallic reagents such as organoborane and organozinc has been developed. The phosphine-borane compound works as the effective ligand for palladium-catalyzed direct allylic amination of allylic alcohol. Thus, with secondary amines, the reaction was completed in only 1 h, even at room temperature.

Anti-Markovnikov rearrangement in sulfur mediated allylic C-H amination of olefins

Cationic rearrangement reactions usually follow Markovnikov's rule to give more substituted carbocations as stable intermediates. During our study on sulfur mediated allylic C-H amination of olefins, very rare cases of anti-Markovnikov rearrangement from secondary carbocations toward primary carbocations or primary triflates were observed.

Stereoselective synthesis of (E)-3,3-diaryl and (E)-3-aryl-3-aryloxy allylamines and allylalcohols from trans-cinnamyl chloride and alcohol

In this work we describe the regio and stereoselective synthesis of (E)-3,3-diaryl and (E)-3-aryl-3-aryloxy allylamines and allylalcohols. The starting materials are the non-expensive commercially available cinnamyl alcohol and chloride. The bromination/dehydrobromination sequence furnished the (E)-3-bromo-3-phenylallyl amines and alcohol as single regioisomers and with high stereoselectivity (>98%). These vinyl bromides were used as substrates in cross-coupling reactions furnishing the arylated products with good to excellent yields and total E-configuration retention. With this protocol, we were able to produce regio and stereospecifically trisubstituted olefins and vinyl ethers by Suzuki cross-coupling and Ullmann vinylation.

SHORT SYNTHESIS OF TOLTERODINE, INTERMEDIATES AND METABOLITES

A process is described for the preparation of intermediates which can be used for preparation of agents for urinary incontinence therapy, specifically to 2-(3-(diisopropylamino)- 1-phenylpropyl)-4-(hydroxymethyl)phenol and its prodrugs.

METHOD OF OBTAINING 3,3-DIPHENYLPROPYLAMINES

The invention relates to a method of obtaining 3,3-diphenylpropylamines (I), wherein R1 is H, alkyl, haloalkyl or alkoxyalkyl, R2 is alkyl, alkoxy, halogen, NO2, CN, CHO, which may be free or protected, CH2OH or COOR6, and R3 and R4 are selected independently from H and alkyl or together with the nitrogen to which they are bound form a ring having 3 to 7 members. The inventive method consists in reacting a propylenephenylamine and a disubstituted aromatic hydrocarbon and, if necessary, separating the desired enantiomer or the mixture of enantiomers, and/or converting the compound (I) into a salt. Compounds (I) are muscarinic receptor antagonists which can be used in the treatment of urinary incontinence and other symptoms of urinary bladder hyperactivity. Said compounds include tolterodine.

PROCESS FOR PREPARATION OF 3-(2-HYDROXY-5-SUBSTITUTED PHENYL)-N-ALKYL-3-PHENYLPROPYLAMINES

A new process for preparation of 3-(2-hydroxy-5-substituted phenyl)-N,alkyl-3- phenylpropylamiηes from cinamoyl chloride via N-alky-3-phenylprop-2-en-1 -amine has been developed.