(15aR)-4-(4-Aminobutyl)icosahydropyrido[1,2-e][1,5]diazacycloheptadecin-5-one

Base Information

Chemical Name:(15aR)-4-(4-Aminobutyl)icosahydropyrido[1,2-e][1,5]diazacycloheptadecin-5-one
CAS No.:21008-79-7
Molecular Formula:C₂₃H₄₅N₃O
Molecular Weight:379.63
Hs Code.:
Mol file:21008-79-7.mol

Synonyms:Oncinotin;(-)-oncinotine;(R)-8-(4-Amino-butyl)-octadecahydro-4a,8-diaza-benzocycloheptadecen-9-one;

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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 (15aR)-4-(4-Aminobutyl)icosahydropyrido[1,2-e][1,5]diazacycloheptadecin-5-one

Chemical Property:

Vapor Pressure:8.7E-12mmHg at 25°C
Boiling Point:541.4°Cat760mmHg
Flash Point:281.2°C
PSA：49.57000
Density:0.99g/cm³
LogP:5.28920

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Description A macrocycIic alkaloid, the base has been isolated from Oncinotis nitida. The structure has been determined by degradation to methyl 11-(N-methyl-2-pyridyl)-undecanoate. It may be converted into isooncinotine by an amide exchange reaction.

Technology Process of (15aR)-4-(4-Aminobutyl)icosahydropyrido[1,2-e][1,5]diazacycloheptadecin-5-one

There total 16 articles about (15aR)-4-(4-Aminobutyl)icosahydropyrido[1,2-e][1,5]diazacycloheptadecin-5-one 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: 71.0%

: 164365-96-2
17(R)-5-<4-<(tert-butoxycarbonyl)amino>butyl>-1,5-diazabicyclo<15.4.0>henicosan-6-one

: 21008-79-7
Oncinotin

Guidance literature:: With hydrogenchloride; In methanol; Ambient temperature;
DOI:10.1039/c39950001015

Reference yield:

: 34418-91-2
2,3,4,5-tetrahydropyridine N-oxide

: 21008-79-7
Oncinotin

Guidance literature:: Multi-step reaction with 12 steps

1: 69 percent / toluene / 14 h / Heating

2: 86 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1.5 h / 45 °C

3: 91 percent / H₂, PdCl₂ / methanol / 37 h / 4940 Torr

4: 85 percent / Na₂CO₃ / CH₂Cl₂; H₂O / 14 h / Ambient temperature

5: 84 percent / HIO₄ / tetrahydrofuran; H₂O / 2 h / 0 °C

6: 56 percent / potassium tert-butoxide / tetrahydrofuran / 0.33 h / 0 °C

7: 96 percent / aq. KOH / methanol / 5 h / Ambient temperature

8: 95 percent / (EtO)2P(O)CN, Et₃N / dimethylformamide / 14 h / Ambient temperature

9: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

10: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1) CH₂Cl₂, -78 deg C, 2 h; 2) CH₂Cl₂, -78 deg C - rt

11: 66 percent / Pd(OH)2, H₂ / methanol / 96 h

12: 71 percent / aq. HCl / methanol / 3 h / Ambient temperature

With hydrogenchloride; palladium dihydroxide; potassium hydroxide; oxalyl dichloride; diethyl cyanophosphonate; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; sodium carbonate; dimethyl sulfoxide; periodic acid; triethylamine; palladium dichloride; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo9518258

Reference yield:

: 173425-06-4
<2S,2(2R),2(3S)>-2-(2,3-dihydroxy-4-methylpentyl)piperidine

: 21008-79-7
Oncinotin

Guidance literature:: Multi-step reaction with 9 steps

1: 85 percent / Na₂CO₃ / CH₂Cl₂; H₂O / 14 h / Ambient temperature

2: 84 percent / HIO₄ / tetrahydrofuran; H₂O / 2 h / 0 °C

3: 56 percent / potassium tert-butoxide / tetrahydrofuran / 0.33 h / 0 °C

4: 96 percent / aq. KOH / methanol / 5 h / Ambient temperature

5: 95 percent / (EtO)2P(O)CN, Et₃N / dimethylformamide / 14 h / Ambient temperature

6: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

7: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1) CH₂Cl₂, -78 deg C, 2 h; 2) CH₂Cl₂, -78 deg C - rt

8: 66 percent / Pd(OH)2, H₂ / methanol / 96 h

9: 71 percent / aq. HCl / methanol / 3 h / Ambient temperature

With hydrogenchloride; palladium dihydroxide; potassium hydroxide; oxalyl dichloride; diethyl cyanophosphonate; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; sodium carbonate; dimethyl sulfoxide; periodic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jo9518258