1366421-67-1 Usage
Description
(S)-2-(2,3-bis(dicyclohexylamino)cyclopropenimine)-3-phenylpropan-1-ol hydrochloride is a chiral cyclopropenimine compound that belongs to a new class of enantioselective Br?nsted base catalysts, also known as "superbases." These catalysts are highly effective in enantioselective organocatalysis, playing a crucial role in organic synthetic chemistry by catalyzing proton transfer reactions enantioselectively, leading to the production of optically enriched products. The catalyst is stored as a co-salt for stability, and its conversion to the free catalyst requires a simple wash with an aqueous base.
Uses
Used in Enantioselective Organocatalysis:
(S)-2-(2,3-bis(dicyclohexylamino)cyclopropenimine)-3-phenylpropan-1-ol hydrochloride is used as an enantioselective Br?nsted base catalyst for promoting enantioselective proton transfer reactions in organic synthesis. Its application in this field is significant due to the prevalence of chemical reactions involving proton transfer as a key mechanistic event, making it an indispensable tool for the practice of organic synthetic chemistry.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (S)-2-(2,3-bis(dicyclohexylamino)cyclopropenimine)-3-phenylpropan-1-ol hydrochloride is used as a catalyst for the synthesis of optically active compounds, which are essential in the development of new drugs with improved efficacy and reduced side effects. The enantioselective nature of the catalyst allows for the production of specific enantiomers, which can have different biological activities and properties.
Used in Green Chemistry:
(S)-2-(2,3-bis(dicyclohexylamino)cyclopropenimine)-3-phenylpropan-1-ol hydrochloride is also used in the field of green chemistry, as it adheres to the 12 Principles of Greener Chemistry. The product has been enhanced for catalytic efficiency, making it a more environmentally friendly and sustainable option for chemical reactions and processes.
Check Digit Verification of cas no
The CAS Registry Mumber 1366421-67-1 includes 10 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 7 digits, 1,3,6,6,4,2 and 1 respectively; the second part has 2 digits, 6 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 1366421-67:
(9*1)+(8*3)+(7*6)+(6*6)+(5*4)+(4*2)+(3*1)+(2*6)+(1*7)=161
161 % 10 = 1
So 1366421-67-1 is a valid CAS Registry Number.
1366421-67-1Relevant articles and documents
Cyclopropenimine-catalyzed enantioselective mannich reactions of tert -butyl glycinates with N -Boc-imines
Bandar, Jeffrey S.,Lambert, Tristan H.
supporting information, p. 11799 - 11802 (2013/09/02)
Cyclopropenimine 1 is shown to catalyze Mannich reactions between glycine imines and N-Boc-aldimines with high levels of enantio- and diastereocontrol. The reactivity of 1 is shown to be substantially greater than that of a widely used thiourea cinchona alkaloid-derived catalyst. A variety of aryl and aliphatic N-Boc-aldimines are effective substrates for this transformation. A preparative-scale reaction to deliver >90 mmol of product is shown using 1 mol % catalyst. The products of this transformation can be converted into several useful derivatives.
Enantioselective Bronsted base catalysis with chiral cyclopropenimines
Bandar, Jeffrey S.,Lambert, Tristan H.
supporting information; experimental part, p. 5552 - 5555 (2012/05/20)
Cyclopropenimines are shown to be a highly effective new class of enantioselective Bronsted base catalysts. A chiral 2,3-bis(dialkylamino) cyclopropenimine catalyzes the rapid Michael reaction of a glycine imine substrate with high levels of enantioselectivity. A preparative scale reaction to deliver 25 g of product is demonstrated, and a trivial large scale synthesis of the optimal catalyst is shown. In addition, the basicity of a 2,3-bis(dialkylamino)cyclopropenimine is measured for the first time and shown to be approximately equivalent to the P1-tBu phosphazene base. An X-ray crystal structure of the protonated catalyst is shown along with a proposed mechanistic and stereochemical rationale.
