dendroxine

Base Information

• Chemical Name: dendroxine
• CAS No.: 7668-77-1
• Molecular Formula: C₁₇H₂₅NO₃
• Molecular Weight: 291.39
• Mol file: 7668-77-1.mol

Synonyms:Dendroban-12-one,14,10-(methyleneoxy)-; Dendroxine (7CI,8CI);7,10-Methano-7H-6,8-dioxa-3a-azadicyclopent[cd,j]azulene, dendroban-12-onederiv.

Chemical Property of dendroxine

Chemical Property:

• PSA: 38.77000
• LogP: 1.82630

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of dendroxine

There total 11 articles about dendroxine 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: 68.0%

Iodoethanol (624-76-0) + C15H21NO2 → Dendroxin (7668-77-1)

Guidance literature:

With triphenylphosphine; In acetonitrile; for 24h; Reflux; Inert atmosphere;

DOI:10.1021/acs.orglett.8b01782

Reference yield:

3-(4-methyl-2-pentenoyl)-2-oxazolidinone (564472-38-4) → Dendroxin (7668-77-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: silver tetrafluoroborate; ferric(III) bromide; (4R,4'R)-2,2'-(propane-2,2'diyl)bis(4-phenyl-4,5-dihydrooxazole) / dichloromethane / 7 h / -40 °C / Schlenk technique; Sealed tube; Inert atmosphere

1.2: 0.5 h / 0 - 20 °C / Schlenk technique; Sealed tube; Inert atmosphere

2.1: lithium hydroxide; tert.-butylhydroperoxide / tetrahydrofuran; water / 24 h / 20 °C

3.1: tetrahydrofuran / 0.08 h

3.2: 20 °C

3.3: 1 h

4.1: copper(II) bis(trifluoromethanesulfonate); triphenylphosphine; pyrrolidine / tetrahydrofuran / 72 h / 90 °C / Schlenk technique; Sealed tube; Inert atmosphere

5.1: N,N-dimethyl-formamide / dichloromethane / 5 h / 0 °C / Inert atmosphere; Reflux

6.1: di-tert-butoxydiazene; phenylsulfonyl azide / N,N-dimethyl-formamide / 3 h / 80 °C

7.1: triphenylphosphine / tetrahydrofuran / 12 h / 20 °C

8.1: triphenylphosphine / acetonitrile / 24 h / Reflux; Inert atmosphere

With pyrrolidine; tert.-butylhydroperoxide; phenylsulfonyl azide; ferric(III) bromide; silver tetrafluoroborate; di-tert-butoxydiazene; copper(II) bis(trifluoromethanesulfonate); N,N-dimethyl-formamide; triphenylphosphine; (4R,4'R)-2,2'-(propane-2,2'diyl)bis(4-phenyl-4,5-dihydrooxazole); lithium hydroxide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/acs.orglett.8b01782

Reference yield:

C13H17NO4 (1061567-18-7) → Dendroxin (7668-77-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: lithium hydroxide; tert.-butylhydroperoxide / tetrahydrofuran; water / 24 h / 20 °C

2.1: tetrahydrofuran / 0.08 h

2.2: 20 °C

2.3: 1 h

3.1: copper(II) bis(trifluoromethanesulfonate); triphenylphosphine; pyrrolidine / tetrahydrofuran / 72 h / 90 °C / Schlenk technique; Sealed tube; Inert atmosphere

4.1: N,N-dimethyl-formamide / dichloromethane / 5 h / 0 °C / Inert atmosphere; Reflux

5.1: di-tert-butoxydiazene; phenylsulfonyl azide / N,N-dimethyl-formamide / 3 h / 80 °C

6.1: triphenylphosphine / tetrahydrofuran / 12 h / 20 °C

7.1: triphenylphosphine / acetonitrile / 24 h / Reflux; Inert atmosphere

With pyrrolidine; tert.-butylhydroperoxide; phenylsulfonyl azide; di-tert-butoxydiazene; copper(II) bis(trifluoromethanesulfonate); N,N-dimethyl-formamide; triphenylphosphine; lithium hydroxide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/acs.orglett.8b01782

upstream raw materials:

1β-(3-methyl-but-2-enyl)-12-oxo-dihydro-oxazolo[3',2':1,10]-14-nor-dendrobanium; chloride

C₁₃H₁₇NO₄

3-(4-methyl-2-pentenoyl)-2-oxazolidinone

(1S,2S,6R,8R,11S)-11-isopropyl-6-methyl-5-methylene-9-oxatricyclo[6.2.1.0^2,6]undecan-7,10-dione