Eburnamenine-14-carboxylic acid, 14,15-dihydro-17,21-epoxy-14-hydroxy-12-methoxy-, methyl ester, (3-alpha,14-alpha,16-alpha,17-alpha)-

Base Information

Chemical Name:Eburnamenine-14-carboxylic acid, 14,15-dihydro-17,21-epoxy-14-hydroxy-12-methoxy-, methyl ester, (3-alpha,14-alpha,16-alpha,17-alpha)-
CAS No.:53492-09-4
Molecular Formula:C22H26N2O5
Molecular Weight:398.4522
Hs Code.:
DSSTox Substance ID:DTXSID50968222
Mol file:53492-09-4.mol

Eburnamenine-14-carboxylic acid, 14,15-dihydro-17,21-epoxy-14-hydroxy-12-methoxy-, methyl ester, (3-alpha,14-alpha,16-alpha,17-alpha)-

Synonyms:Cuanzine;BRN 3598691;53492-09-4;Eburnamenine-14-carboxylic acid, 14,15-dihydro-17,21-epoxy-14-hydroxy-12-methoxy-, methyl ester, (3-alpha,14-alpha,16-alpha,17-alpha)-;DTXSID50968222;Methyl 14-hydroxy-12-methoxy-14,15-dihydro-17,21-epoxyeburnamenine-14-carboxylate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of Eburnamenine-14-carboxylic acid, 14,15-dihydro-17,21-epoxy-14-hydroxy-12-methoxy-, methyl ester, (3-alpha,14-alpha,16-alpha,17-alpha)-

Chemical Property:

Vapor Pressure:1.08E-14mmHg at 25°C
Melting Point:196°C
Boiling Point:588.4°Cat760mmHg
Flash Point:309.7°C
Density:1.53g/cm³
XLogP3:1.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:3
Exact Mass:398.18417193
Heavy Atom Count:29
Complexity:705

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:COC1=CC=CC2=C1N3C4=C2CCN5C4C6(CCOC6CC5)CC3(C(=O)OC)O
Isomeric SMILES:COC1=CC=CC2=C1N3C4=C2CCN5[C@H]4C6(CCO[C@H]6CC5)C[C@@]3(C(=O)OC)O
Description The root bark of Voacanga chalotiana furnishes this alkaloid which forms colourless needles when recrystallized from C6H6 . It has the following specific rotations: [α]22D + 30° (c 2.0, pyridine) and α]22D - 11 ° (c 1.0, CHCI3). The ultraviolet spectrum in MeOH has absorption maxima at 226, 270 and 292 nm.

Technology Process of Eburnamenine-14-carboxylic acid, 14,15-dihydro-17,21-epoxy-14-hydroxy-12-methoxy-, methyl ester, (3-alpha,14-alpha,16-alpha,17-alpha)-

There total 22 articles about Eburnamenine-14-carboxylic acid, 14,15-dihydro-17,21-epoxy-14-hydroxy-12-methoxy-, methyl ester, (3-alpha,14-alpha,16-alpha,17-alpha)- 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:

: 109021-64-9
8-methoxy-1-oxo-1,2,3,4-tetrahydro-β-carboline

: 53492-09-4,55955-24-3,125132-61-8,132015-34-0,137492-14-9
cuanzine

Guidance literature:: Multi-step reaction with 16 steps

1: 94 percent / CH₂Cl₂ / Ambient temperature

2: 67 percent / TsOH / methanol

3: 99 percent / H₂ / PtO₂ / methanol

4: 65 percent / Ac₂O, KOAc / 10 h / 100 °C

5: 1) LDA, HMPA / 1) THF, -70 deg C, 2) -40 deg C

6: 98 percent / LiAlH₄ / tetrahydrofuran / 0 °C

7: 89 percent / pyridine

8: 68 percent / TsOH / methanol

9: 46 percent / I₂, IO₃K, HOAc / dioxane; H₂O

10: 1) H₂, 2) K₂CO₃ / 1) PtO₂ / 1) MeOH, 2) MeOH, H₂O

11: 1) (COCl)2, DMSO, 2) NEt₃ / 1) -70 deg C, 2) CH₂Cl₂, 20 deg C

12: 78 percent / LiHMDS / tetrahydrofuran / -15 °C / also with Cu₂O in CH₂Cl₂

13: 91 percent / HCl / H₂O; ethanol

14: 82 percent / pyridine, DMAP

15: DBU / tetrahydrofuran / 45 h / 80 °C

16: 1) HCl, 2) Na₂CO₃ / 1) MeOH, 4h, reflux, 2) MeOH, RT

With pyridine; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; potassium iodate; lithium aluminium tetrahydride; oxalyl dichloride; hydrogen; iodine; potassium acetate; acetic anhydride; sodium carbonate; potassium carbonate; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium hexamethyldisilazane; lithium diisopropyl amide; platinum(IV) oxide; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water;
DOI:10.1016/0040-4039(91)80020-7

Reference yield:

: 37734-05-7
Methyl 3-oxo-4-pentenoate

: 53492-09-4,55955-24-3,125132-61-8,132015-34-0,137492-14-9
cuanzine

Guidance literature:: Multi-step reaction with 15 steps

1: 67 percent / TsOH / methanol

2: 99 percent / H₂ / PtO₂ / methanol

3: 65 percent / Ac₂O, KOAc / 10 h / 100 °C

4: 1) LDA, HMPA / 1) THF, -70 deg C, 2) -40 deg C

5: 98 percent / LiAlH₄ / tetrahydrofuran / 0 °C

6: 89 percent / pyridine

7: 68 percent / TsOH / methanol

8: 46 percent / I₂, IO₃K, HOAc / dioxane; H₂O

9: 1) H₂, 2) K₂CO₃ / 1) PtO₂ / 1) MeOH, 2) MeOH, H₂O

10: 1) (COCl)2, DMSO, 2) NEt₃ / 1) -70 deg C, 2) CH₂Cl₂, 20 deg C

11: 78 percent / LiHMDS / tetrahydrofuran / -15 °C / also with Cu₂O in CH₂Cl₂

12: 91 percent / HCl / H₂O; ethanol

13: 82 percent / pyridine, DMAP

14: DBU / tetrahydrofuran / 45 h / 80 °C

15: 1) HCl, 2) Na₂CO₃ / 1) MeOH, 4h, reflux, 2) MeOH, RT

With pyridine; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; potassium iodate; lithium aluminium tetrahydride; oxalyl dichloride; hydrogen; iodine; potassium acetate; acetic anhydride; sodium carbonate; potassium carbonate; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium hexamethyldisilazane; lithium diisopropyl amide; platinum(IV) oxide; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; water;
DOI:10.1016/0040-4039(91)80020-7

Reference yield:

: 122835-08-9
8-Methoxy-β-carboline

: 53492-09-4,55955-24-3,125132-61-8,132015-34-0,137492-14-9
cuanzine

Guidance literature:: Multi-step reaction with 13 steps

1: 36 percent / chlorobenzene / 6 h / 130 °C

2: 1) LDA, HMPA / 1) THF, -70 deg C, 2) -40 deg C

3: 98 percent / LiAlH₄ / tetrahydrofuran / 0 °C

4: 89 percent / pyridine

5: 68 percent / TsOH / methanol

6: 46 percent / I₂, IO₃K, HOAc / dioxane; H₂O

7: 1) H₂, 2) K₂CO₃ / 1) PtO₂ / 1) MeOH, 2) MeOH, H₂O

8: 1) (COCl)2, DMSO, 2) NEt₃ / 1) -70 deg C, 2) CH₂Cl₂, 20 deg C

9: 78 percent / LiHMDS / tetrahydrofuran / -15 °C / also with Cu₂O in CH₂Cl₂

10: 91 percent / HCl / H₂O; ethanol

11: 82 percent / pyridine, DMAP

12: DBU / tetrahydrofuran / 45 h / 80 °C

13: 1) HCl, 2) Na₂CO₃ / 1) MeOH, 4h, reflux, 2) MeOH, RT

With pyridine; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; potassium iodate; lithium aluminium tetrahydride; oxalyl dichloride; hydrogen; iodine; sodium carbonate; potassium carbonate; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium hexamethyldisilazane; lithium diisopropyl amide; platinum(IV) oxide; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; water; chlorobenzene;
DOI:10.1016/0040-4039(91)80020-7