Caffeine, 8-morpholino-

Base Information

• Chemical Name: Caffeine, 8-morpholino-
• CAS No.: 5436-38-4
• Molecular Formula: C₁₂H₁₇N₅O₃
• Molecular Weight: 279.299
• NSC Number: 21709
• DSSTox Substance ID: DTXSID20184937
• Nikkaji Number: J55.505C
• Wikidata: Q83055880
• ChEMBL ID: CHEMBL1446123
• Mol file: 5436-38-4.mol

Synonyms:CAFFEINE, 8-MORPHOLINO-;8-Morpholino-caffeine;30958-52-2;MLS000737994;SMR000104554;NSC21709;8-Morpholinocaffeine;Guarana Seed P.E.;Cambridge id 5849104;Oprea1_085265;Oprea1_306848;MLS000108600;F1070-0203;CHEMBL1446123;DTXSID20184937;LZQBJEYAJKIENE-UHFFFAOYSA-N;1,3,7-trimethyl-8-morpholino-1H-purine-2,6(3H,7H)-dione;HMS2167J16;HMS3316B01;1,3,7-Trimethyl-8-morpholin-4-yl-3,7-dihydro-purine-2,6-dione;NSC-21709;STK089110;AKOS000677931;LS-48599;VU0229545-4;AB00099201-01;SR-01000469703;SR-01000469703-1;1,3,7-trimethyl-8-morpholino-3,7-dihydro-1 h -purine-2,6-dione;1,3,7-trimethyl-8-(morpholin-4-yl)-3,7-dihydro-1H-purine-2,6-dione

Chemical Property of Caffeine, 8-morpholino-

Chemical Property:

• Vapor Pressure: 5.74E-10mmHg at 25°C
• Boiling Point: 495.8°Cat760mmHg
• Flash Point: 253.6°C
• Density: 1.49g/cm³
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 279.13313942
• Heavy Atom Count: 20
• Complexity: 425

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C2=C(N=C1N3CCOCC3)N(C(=O)N(C2=O)C)C

Technology Process of Caffeine, 8-morpholino-

There total 5 articles about Caffeine, 8-morpholino- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

morpholine (110-91-8,99108-56-2) + 8-((1,1,1,3,3,3-hexafluoropropan-2-yl)oxy)caffeine → 8-morpholinocaffeine (5436-38-4)

Guidance literature:

With palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In N,N-dimethyl acetamide; at 100 ℃; for 14h; Reagent/catalyst;

DOI:10.1002/chem.202001171

Reference yield: 86.0%

morpholine (110-91-8,99108-56-2) + 8-chlorocaffeine (4921-49-7) → 8-morpholinocaffeine (5436-38-4)

Guidance literature:

In 2-methoxy-ethanol; at 120 ℃; for 3h; Microwave irradiation;

DOI:10.1007/s10600-020-03169-x

Reference yield:

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione (58-08-2,138455-22-8,95789-13-2) → 8-morpholinocaffeine (5436-38-4)

Guidance literature:

Multi-step reaction with 2 steps

1: lithium tert-butoxide; iodine / N,N-dimethyl-formamide / 2 h / 140 °C / Microwave irradiation

2: N,N-dimethyl-formamide / 2 h / 140 °C / Microwave irradiation

With iodine; lithium tert-butoxide; In N,N-dimethyl-formamide;

DOI:10.1055/s-0032-1316868

upstream raw materials:

morpholine

8-chlorocaffeine

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

8-iodo-1,3,7-trimethyl-3,7-dihydro-1 H-purine-2,6-dione

Refernces

• 1、 Reshetnikov,Patrushev,Shults. "Synthetic Transformations of Sesquiterpene Lactones. 11.* Conjugates Based on Caffeine and Eudesmanolides with N-Containing Linkers". . p. 855 - 860. Retrieved 2020/09/21.
• 2、 Yotphan, Sirilata,Beukeaw, Danupat,Reutrakul, Vichai. "A convenient one-pot synthesis of N-substituted 2-aminoazole derivatives". . p. 936 - 942. Retrieved 2013/05/09.