1215-59-4 Usage
Description
5-Benzyloxyindole is an organic compound with the chemical formula C16H13NO. It is an off-white to beige powder and is widely used as a reagent or reactant in various chemical reactions and synthesis processes.
Uses
1. Used in Chemical Synthesis:
5-Benzyloxyindole is used as a reactant in regioand stereoselective morpholine-catalyzed direct C-3 alkenylation with α,β-unsaturated aldehydes. This application allows for the selective formation of specific alkenylated products, which are important in the synthesis of complex organic molecules.
2. Used in Protective Group Debenzylation:
5-Benzyloxyindole is used as a reactant in selective debenzylation of protective groups using SiliaCat-palladium under mild reaction conditions. This process is crucial in the synthesis of various organic compounds, as it allows for the controlled removal of protective groups without affecting other functional groups in the molecule.
3. Used in Metal-Free Friedel-Crafts Alkylation:
5-Benzyloxyindole is used as a reactant in metal-free Friedel-Crafts alkylation reactions. This environmentally friendly method allows for the formation of carbon-carbon bonds without the need for metal catalysts, which can be toxic and difficult to remove from the final product.
4. Used in Preparation of Protein Kinase (PKC) Inhibitors:
5-Benzyloxyindole is used as a reactant in the preparation of protein kinase (PKC) inhibitors. PKC inhibitors have potential applications in the treatment of various diseases, including cancer, by modulating the activity of specific protein kinases involved in cell signaling pathways.
5. Used in Preparation of Indole/Quinoline Carbothioic Acid Amide Derivatives:
5-Benzyloxyindole is used as a reactant in the preparation of indole/quinoline carbothioic acid amide derivatives. These compounds have potential applications in the development of new pharmaceuticals, as they may exhibit various biological activities, such as anti-inflammatory, anti-cancer, or anti-microbial properties.
6. Used in Regioselective Preparation of CF3-β-Tryptamine Derivatives:
5-Benzyloxyindole is used as a reagent/reactant in the regioselective preparation of CF3-β-tryptamine derivatives via base-free thermal ring-opening reaction of N-nosyl-2-CF3-aziridine with indoles. This process is important for the synthesis of novel tryptamine-based compounds with potential applications in the pharmaceutical industry.
Purification Methods
It is recrystallised from *C6H6/pet ether or pet ether. The picrate forms red crystals from *C6H6 and has m 142-143o. [Burton & Leong Chem Ind (London) 1035 1953, Ek & Witkop J Am Chem Soc 76 5579 1954, fluorescence: Bridges & Williams Biochem J 107 225 1968, Beilstein 27 III/IV 1758.]
Check Digit Verification of cas no
The CAS Registry Mumber 1215-59-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,2,1 and 5 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 1215-59:
(6*1)+(5*2)+(4*1)+(3*5)+(2*5)+(1*9)=54
54 % 10 = 4
So 1215-59-4 is a valid CAS Registry Number.
InChI:InChI=1/C15H13NO/c1-2-4-12(5-3-1)11-17-14-6-7-15-13(10-14)8-9-16-15/h1-10,16H,11H2
1215-59-4Relevant articles and documents
The synthesis of 1-[2-(dimethylamino)ethyl]-7,12-dihydro-3H-[2]-benzoxepino[4,3-e]indole . A potential antidepressant agent
Dunsdon,Martin
, p. 2919 - 2922 (1985)
The structures of doxepin and serotonin were overlayed using molecular graphics and 1-[2-(dimethylamino)ethyl]-7,12-dihydro-3H-[2]-benzoxepino[4,3-e]indole was proposed as a potential antidepressant agent. This paper deals with the synthesis of the title compound. Key steps in the synthesis include a regioselective electrophilic substitution at C-4 of ethyl 5-hydroxy-1-indolecarboxylate and subsequent modification to 7,12-dihydro-3H-[2]-benzoxepino[4,3-e]indole. Standard procedures were then used to construct the dimethylaminoethyl side chain to yield the title compound.
Synthesis of a deuterium-labelled standard of bufotenine (5-HO-DMT)
Wang, Yu-Yun,Chen, Chinpiao
, p. 1262 - 1265 (2007)
The Batcho-Leimgruber strategy was employed to synthesize 3-(2-dimethylamino-[2H4]-ethyl)-1H-indol-5-ol (bufotenine, 5-HO-DMT) (8) from commercial 3-methyl-4-nitro-phenol (1), benzyl bromide and N,N-dimethylformamide-dimethylacetal. Compound 4 was synthesized from compound 3 using the Batcho-Leimgruber strategy in the presence of Raney nickel and hydrazine hydrate. Compound 4 was treated with oxalyl chloride, dimethylamine and lithium aluminum [2H4]-hydride to yield [2-(5-benzyloxy-1H-indol-3-yl)-[2H4]-ethyl] -dimethyl-amine (7). The benzyl ether in compound 7 was cleaved by hydrogenolysis to give bufotenine 8. Copyright
mTORC1 MODULATORS
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Paragraph 0602-0604, (2019/04/30)
Provided herein, inter alia, are methods and compounds for inhibiting mTORC1 and for treating diseases associated with mTORC1 activity.
HYDROXYINDALPINE DERIVATIVES AND THEIR MEDICAL USE
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Page/Page column 28; 29, (2014/09/03)
The present invention relates to hydroxyindalpine derivatives of formula (I) as defined herein and pharmaceutical compositions comprising these compounds, as well as their medical use, particularly in the treatment or prevention of gastrointestinal diseases/disorders, such as constipation and functional dyspepsia.
