244056-96-0 Usage
Description
5-ALLYLOXY-3,6-DIHYDRO-2H-PYRIDINE-1-CARBOXYLIC ACID BENZYL ESTER, also known as 3,6-Dihydro-5-(2-propenyloxy)-1(2H)-pyridinecarboxylic Acid Phenylmethyl Ester (CAS# 244056-96-0), is a colorless oil compound with significant utility in organic synthesis. Its unique chemical structure, featuring a pyridine ring and allyl ester group, makes it a versatile building block for the development of various chemical products and pharmaceuticals.
Uses
Used in Organic Synthesis:
5-ALLYLOXY-3,6-DIHYDRO-2H-PYRIDINE-1-CARBOXYLIC ACID BENZYL ESTER is used as a synthetic intermediate for the creation of various organic compounds. Its chemical properties, including the reactivity of the allyl and ester groups, make it a valuable precursor in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 5-ALLYLOXY-3,6-DIHYDRO-2H-PYRIDINE-1-CARBOXYLIC ACID BENZYL ESTER is used as a key component in the development of novel drug candidates. Its unique structure can be further modified to target specific biological pathways, potentially leading to the discovery of new therapeutic agents for various diseases.
Used in Agrochemical Industry:
5-ALLYLOXY-3,6-DIHYDRO-2H-PYRIDINE-1-CARBOXYLIC ACID BENZYL ESTER is also utilized in the agrochemical industry as a starting material for the synthesis of new pesticides and other crop protection agents. Its chemical versatility allows for the development of innovative products with improved efficacy and reduced environmental impact.
Used in Chemical Research:
In the field of chemical research, 5-ALLYLOXY-3,6-DIHYDRO-2H-PYRIDINE-1-CARBOXYLIC ACID BENZYL ESTER serves as a model compound for studying various reaction mechanisms and exploring new synthetic methodologies. Its unique structure provides researchers with opportunities to investigate novel chemical transformations and develop innovative synthetic strategies.
Overall, 5-ALLYLOXY-3,6-DIHYDRO-2H-PYRIDINE-1-CARBOXYLIC ACID BENZYL ESTER is a versatile and valuable compound with a wide range of applications across different industries, including organic synthesis, pharmaceuticals, agrochemicals, and chemical research. Its unique chemical properties and potential for further modification make it an essential tool in the development of new products and technologies.
Check Digit Verification of cas no
The CAS Registry Mumber 244056-96-0 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,4,4,0,5 and 6 respectively; the second part has 2 digits, 9 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 244056-96:
(8*2)+(7*4)+(6*4)+(5*0)+(4*5)+(3*6)+(2*9)+(1*6)=130
130 % 10 = 0
So 244056-96-0 is a valid CAS Registry Number.
InChI:InChI=1/C16H19NO3/c1-2-11-19-15-9-6-10-17(12-15)16(18)20-13-14-7-4-3-5-8-14/h2-5,7-9H,1,6,10-13H2
244056-96-0Relevant articles and documents
Metabolites of febrifugine and its synthetic analogue by mouse liver S9 and their antimalarial activity against Plasmodium malaria parasite
Hirai, Shingo,Kikuchi, Haruhisa,Kim, Hye-Sook,Begum, Khurshida,Wataya, Yusuke,Tasaka, Hidehisa,Miyazawa, Yuriko,Yamamoto, Keisuke,Oshima, Yoshiteru
, p. 4351 - 4359 (2007/10/03)
Quinazolinone type alkaloids, febrifugine (1) and isofebrifugine (2), isolated from Dichroa febrifuga roots, show powerful antimalarial activity against Plasmodium falciparum. Unfortunately, their emetic effect and other undesirable side effects have precluded their clinical use for malaria. Because of their antimalarial potency, analogues were searched for, with the goal of preserving the strong antimalarial activity, while dramatically reducing side effects. We expected that compounds useful in drug development would exist in metabolites derived from 1 and Df-1 (3), the condensation product of 1 with acetone, by mouse liver S9. Feb-A and -B (4 and 5) were isolated as the major metabolites of 1. In addition to 4 and 5, feb-C and -D (6 and 7) were also purified from the metabolic mixture of 3. Compounds 4 and 5 were compounds oxidized at C-6 and C-2 of the quinazolinone ring of 1, respectively. Compounds 6 and 7, derived from 3, also bear febrifugine type structures in which the 4″- and 6″-positions of the piperidine ring of 1 were oxidized. In vitro antimalarial and cytotoxic tests using synthetically obtained racemic 4-6 and enantiomerically pure 7 demonstrated that 4 and 6 had antimalarial activity against P. falciparum, of similar potency to that of 1, with high selectivity. The antimalarial activity of 5 and 7, however, was dramatically decreased in the test. The in vitro antimalarial activity of analogues 22 and 43, which are stereoisomers of 4 and 6, was also evaluated, showing that 22 is active. The results suggest that basicity of both the 1- and the 1″-nitrogen atoms of 1 is crucial in conferring powerful antimalarial activity. Racemic 4 and 6 exhibited powerful in vivo antimalarial activity against mouse malaria P. berghei, and especially, no serious side effects were observed with 4. Thus, the metabolite 4 appears to be a promising lead compound for the development of new types of antimalarial drugs.
Total synthesis of dl-febrifugine and dl-isofebrifugine
Takeuchi, Yasuo,Abe, Hitoshi,Harayama, Takashi
, p. 905 - 906 (2007/10/03)
Racemic compounds (1 and 2) of the antimalarial agents febrifugine (d- l) and isofebrifugine (d-2) were synthesized using an unusual Claisen rearrangement of allyl enol ether (7) and the stereoselective reduction of 2- allyl-3-piperidone (8). This method is widely applicable to the synthesis of derivatives needed to study the structure-activity relationship of febrifugine.
