Ungeremine

Base Information

• Chemical Name: Ungeremine
• CAS No.: 2121-12-2
• Deprecated CAS: 6883-38-1,72510-04-4
• Molecular Formula: C₁₆H₁₁NO₃
• Molecular Weight: 265.268
• UNII: 9EVC5B2RPS
• DSSTox Substance ID: DTXSID50175439
• Wikipedia: Ungeremine
• Wikidata: Q15633984
• Metabolomics Workbench ID: 68241
• ChEMBL ID: CHEMBL253553
• Mol file: 2121-12-2.mol

Synonyms:AT 1840;lycobetaine;lycobetaine acetate;ungeremine;ungeremine chloride;ungeremine, acetate salt

Chemical Property of Ungeremine

Chemical Property:

• Melting Point: 270-272℃ (dec.)
• Refractive Index: 1.5300 (estimate)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 42.57000
• Density: g/cm³
• LogP: 2.27090
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 266.08171824
• Heavy Atom Count: 20
• Complexity: 403

Purity/Quality:

99%, ^*data from raw suppliers

Lycobetaine（Ungeremine） >98%,StandardReferencesGrade ^*data from reagent suppliers

Safty Information:

• Safety Statements: Poison by ingestion and intraperitoneal routes. Experimental reproductive effects. When heated to decomposit"> x." target="_blank">Poison by ingestion and intraperitoneal routes. Experimental reproductive effects. When heated to decomposit

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C[N+]2=CC3=CC4=C(C=C3C5=CC(=CC1=C52)O)OCO4

Technology Process of Ungeremine

There total 18 articles about Ungeremine 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: 54.0%

Methanesulfonic acid 7-oxo-4,5-dihydro-7H-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridin-2-yl ester (128810-30-0) → ungeremine (97438-92-1,2121-12-2)

Guidance literature:

With sodium bis(2-methoxyethoxy)aluminium dihydride; In toluene; Heating;

DOI:10.1016/0040-4039(90)80006-8

Reference yield:

→ ungeremine (97438-92-1,2121-12-2)

Guidance literature:

With selenium(IV) oxide; ethanol;

DOI:10.1021/ja01627a032

Reference yield:

3,4-(methylenedioxy)benzoyl chloride (25054-53-9) → ungeremine (97438-92-1,2121-12-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 66 percent / pyridine / 13 h / 100 °C

2: 27 percent / K₂CO₃, benzyl triethylammonium chloride (BTAC) / dimethylsulfoxide / 155 °C

3: 93 percent / H₂ / Pd/C / trifluoroacetic acid / 0.5 h / 25 °C / 760 Torr

4: 76 percent / ONOSO₃H, NaBF₄, H₂SO₄ / 1 h / 0 °C

5: 40 percent / trifluoroacetic acid / 40 h / Heating

6: 51 percent / NaH / dimethylformamide / 0.75 h / 70 °C

7: 95 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / Heating

8: 1) H₂,MnO₂*nH₂O, 2) H₂O₂ / 1) Pd/C / 1) EtOH, 70 deg C, 2h, ambient pressure, 2) AcOH, 25 deg C, 2h

With pyridine; manganese(IV) oxide; lithium aluminium tetrahydride; sodium tetrafluoroborate; nitrosylsulfuric acid; sulfuric acid; N-benzyl-N,N,N-triethylammonium chloride; hydrogen; dihydrogen peroxide; sodium hydride; potassium carbonate; palladium on activated charcoal; In tetrahydrofuran; dimethyl sulfoxide; N,N-dimethyl-formamide; trifluoroacetic acid;

DOI:10.1016/S0040-4039(00)71219-6

upstream raw materials:

pyridine

tert-butylhypochlorite

N,N-dimethyl-formamide

lycorine

Downstream raw materials:

ungeremine hydrochloride

Refernces

• 1、 Schrader, Kevin K.,Avolio, Fabiana,Andolfi, Anna,Cimmino, Alessio,Evidente, Antonio. "Ungeremine and its hemisynthesized analogues as bactericides against flavobacterium columnare". . p. 1179 - 1183. Retrieved 2013.
• 2、 Siddiqui,Snieckus. "Concise syntheses of the amaryllidaceae alkaloids ungerimine and hippadine via the suzuki aryl-aryl cross coupling reaction". . p. 1523 - 1526. Retrieved 2007/10/02.