Metaphanine

Base Information

Chemical Name:Metaphanine
CAS No.:1805-86-3
Molecular Formula:C₁₉H₂₃NO₅
Molecular Weight:345.395
Hs Code.:
UNII:0GES8NR11A
ChEMBL ID:CHEMBL1187163
Nikkaji Number:J7.778J
Wikidata:Q27236754
Mol file:1805-86-3.mol

Synonyms:Metaphanine;Metaphanine [MI];1805-86-3;UNII-0GES8NR11A;0GES8NR11A;Hasubanan-7-one, 8,10-epoxy-8-hydroxy-3,4-dimethoxy-17-methyl-, (8beta,10beta)-;(1R,8S,10S,11R)-11-hydroxy-3,4-dimethoxy-17-methyl-18-oxa-17-azapentacyclo[8.4.3.18,11.01,10.02,7]octadeca-2(7),3,5-trien-12-one;CHEMBL1187163;Hasubanan-7-one, 8,10-epoxy-8-hydroxy-3,4-dimethoxy-17-methyl-, (8.beta.,10.beta.)-;Q27236754

Suppliers and Price of Metaphanine

Supply Marketing:

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

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 6 raw suppliers

Chemical Property of Metaphanine

Chemical Property:

Vapor Pressure:5.89E-13mmHg at 25°C
Melting Point:232°; mp 205-206° for the dl-form (Ibuka)
Boiling Point:550.6°C at 760 mmHg
PKA:6.03(at 25℃)
Flash Point:286.8°C
PSA：68.23000
Density:1.39g/cm³
LogP:1.48030
XLogP3:0.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:2
Exact Mass:345.15762283
Heavy Atom Count:25
Complexity:613

Purity/Quality:: 98%,99%, ^*data from raw suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:CN1CCC23C14CC(C5=C2C(=C(C=C5)OC)OC)OC4(C(=O)CC3)O
Isomeric SMILES:CN1CC[C@@]23[C@]14C[C@@H](C5=C2C(=C(C=C5)OC)OC)O[C@]4(C(=O)CC3)O
Description This alkaloid was first isolated by Kondo and Sanada from the stems of Stephania japonica Miers and has subsequently been discovered in S. abyssinica (Dill. and Rich.) Walp. The alkaloid was originally stated to be optically inactive but more recent determinations show [α]25D ~ 21° (c 1.0, CHC13). The original formula of ClsH2903N has also been altered to that given above. The ultraviolet spectrum in EtOH has two absorption maxima at 205 and 285 mil. The base yields a monoacetate, m.p. 150°C. The structure has been determined primarily from the mass spectrum.

Technology Process of Metaphanine

There total 26 articles about Metaphanine 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:

: 50-00-0,30525-89-4,61233-19-0
formaldehyd

: C₁₈H₂₁NO₅

: 1805-86-3
Metaphanin

Guidance literature:: With water; sodium cyanoborohydride; In acetonitrile; at 0 ℃; for 0.5h;
DOI:10.1021/jacs.1c00047

Reference yield:

: 2-(2-allyl-5-(methoxymethoxy)phenyl)-1-(2-bromo-4,5-dimethoxyphenyl)ethan-1-ol

: 1805-86-3
Metaphanin

Guidance literature:: Multi-step reaction with 18 steps

1.1: N-ethyl-N,N-diisopropylamine; (2S,3R)-3-isopropyl-2-phenyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine / toluene / 8 h / -60 °C

2.1: 1H-imidazole / N,N-dimethyl-formamide / 12 h / 0 - 65 °C

3.1: ozone / methanol / 0.08 h / -78 °C

4.1: sodium tetrahydroborate; methanol / 0.5 h / -78 - 0 °C

5.1: triethylamine / N,N-dimethyl-formamide / 0.17 h / 0 °C

6.1: sodium azide / N,N-dimethyl-formamide / 6 h / 0 - 65 °C

7.1: triphenylphosphine; water / tetrahydrofuran / 6 h / 65 °C

8.1: tetrahydrofuran; water / 1 h / 65 °C

9.1: carbon tetrabromide / isopropyl alcohol / 3 h / 65 °C

10.1: [bis(acetoxy)iodo]benzene; methanol / 0.08 h / 0 °C

11.1: sodium formate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 2 h / 100 °C

12.1: potassium tert-butylate / tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide / 0.08 h / 0 °C

13.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / -78 °C

13.2: 6 h / -78 - 20 °C

14.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 1 h / 20 °C

15.1: triethylamine tris(hydrogen fluoride) / acetonitrile / 6 h / 20 °C

16.1: hydrogen; palladium on activated charcoal / tetrahydrofuran / 0.5 h / 20 °C

17.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 0.5 h / 0 - 20 °C

18.1: sodium cyanoborohydride; water / acetonitrile / 0.5 h / 0 °C

With 1H-imidazole; hydrogenchloride; methanol; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium azide; carbon tetrabromide; [bis(acetoxy)iodo]benzene; (2S,3R)-3-isopropyl-2-phenyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine; palladium on activated charcoal; potassium tert-butylate; water; hydrogen; sodium formate; potassium hexamethylsilazane; sodium cyanoborohydride; sodium hydrogencarbonate; Dess-Martin periodane; ozone; triethylamine tris(hydrogen fluoride); triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; toluene; acetonitrile; 7.1: |Staudinger Azide Reduction / 12.1: |Michael Addition;
DOI:10.1021/jacs.1c00047

Reference yield:

: 2-(2-allyl-5-(methoxymethoxy)phenyl)-1-(2-bromo-4,5-dimethoxyphenyl)ethyl isobutyrate

: 1805-86-3
Metaphanin

Guidance literature:: Multi-step reaction with 19 steps

1.1: sodium hydroxide; water / methanol / 20 °C

2.1: N-ethyl-N,N-diisopropylamine; (2S,3R)-3-isopropyl-2-phenyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine / toluene / 8 h / -60 °C

3.1: 1H-imidazole / N,N-dimethyl-formamide / 12 h / 0 - 65 °C

4.1: ozone / methanol / 0.08 h / -78 °C

5.1: sodium tetrahydroborate; methanol / 0.5 h / -78 - 0 °C

6.1: triethylamine / N,N-dimethyl-formamide / 0.17 h / 0 °C

7.1: sodium azide / N,N-dimethyl-formamide / 6 h / 0 - 65 °C

8.1: triphenylphosphine; water / tetrahydrofuran / 6 h / 65 °C

9.1: tetrahydrofuran; water / 1 h / 65 °C

10.1: carbon tetrabromide / isopropyl alcohol / 3 h / 65 °C

11.1: [bis(acetoxy)iodo]benzene; methanol / 0.08 h / 0 °C

12.1: sodium formate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 2 h / 100 °C

13.1: potassium tert-butylate / tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide / 0.08 h / 0 °C

14.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / -78 °C

14.2: 6 h / -78 - 20 °C

15.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 1 h / 20 °C

16.1: triethylamine tris(hydrogen fluoride) / acetonitrile / 6 h / 20 °C

17.1: hydrogen; palladium on activated charcoal / tetrahydrofuran / 0.5 h / 20 °C

18.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 0.5 h / 0 - 20 °C

19.1: sodium cyanoborohydride; water / acetonitrile / 0.5 h / 0 °C

With 1H-imidazole; hydrogenchloride; methanol; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium azide; carbon tetrabromide; [bis(acetoxy)iodo]benzene; (2S,3R)-3-isopropyl-2-phenyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine; palladium on activated charcoal; potassium tert-butylate; water; hydrogen; sodium formate; potassium hexamethylsilazane; sodium cyanoborohydride; sodium hydrogencarbonate; Dess-Martin periodane; ozone; triethylamine tris(hydrogen fluoride); triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; toluene; acetonitrile; 8.1: |Staudinger Azide Reduction / 13.1: |Michael Addition;
DOI:10.1021/jacs.1c00047