6-Acetonyldihydrochelerythrine

Base Information

• Chemical Name: 6-Acetonyldihydrochelerythrine
• CAS No.: 22864-92-2
• Molecular Formula: C₂₄H₂₃NO₅
• Molecular Weight: 405.45
• Mol file: 22864-92-2.mol

Synonyms:2-Propanone,1-[(13S)-12,13-dihydro-1,2-dimethoxy-12-methyl[1,3]benzodioxolo[5,6-c]phenanthridin-13-yl]-(9CI); Chelerythrine, 13b-acetonyl-12,13-dihydro- (8CI); [1,3]Benzodioxolo[5,6-c]phenanthridine,2-propanone deriv.; 13-(2-Oxopropyl)dihydrochelerythrine;13-Acetonyldihydrochelerythrine; Acetonylchelerythrine;Acetonyldihydrochelerythrine; Chelerythrine acetonate

Chemical Property of 6-Acetonyldihydrochelerythrine

Chemical Property:

• Vapor Pressure: 3.72E-14mmHg at 25°C
• Melting Point: 199 °C
• Boiling Point: 595.7°C at 760 mmHg
• PKA: 1.67±0.40(Predicted)
• Flash Point: 314.1°C
• PSA: 57.23000
• Density: 1.26g/cm³
• LogP: 4.78770

Purity/Quality:

98%min ^*data from raw suppliers

6-Acetonyldihydrochelerythrine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 6-Acetonyldihydrochelerythrine

There total 16 articles about 6-Acetonyldihydrochelerythrine 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: 66.6%

chelerythrinium (34316-15-9) + acetone (67-64-1) → 6-acetonyldihydrochelerythrine (15575-49-2,22864-92-2,128778-79-0)

Guidance literature:

With sodium carbonate; In water; for 7h; Reflux;

DOI:10.1080/14786419.2010.482055

Reference yield:

6-bromonaphtho[2,3-d][1,3]dioxol-5-ol (180411-11-4) → 6-acetonyldihydrochelerythrine (15575-49-2,22864-92-2,128778-79-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: sodium hydroxide; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 0.25 h / 20 °C / Inert atmosphere

1.2: 5 h / 20 °C / Inert atmosphere

2.1: 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium hydride / N,N-dimethyl-formamide / 2 h / 100 °C / Inert atmosphere

3.1: sodium hydroxide / water; methanol / 48 h / Inert atmosphere; Reflux

4.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere

4.2: 0 - 20 °C / Inert atmosphere

5.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere

5.2: 5 h / 0 - 20 °C / Inert atmosphere

6.1: bis(pinacol)diborane; potassium acetate; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / dimethyl sulfoxide / 16 h / Inert atmosphere

7.1: sodium acetate; iodine / ethanol / 2 h / Inert atmosphere; Reflux

8.1: sodium carbonate / water / 6 h / Inert atmosphere; Reflux

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; palladium bis[bis(diphenylphosphino)ferrocene] dichloride; iodine; potassium acetate; sodium acetate; sodium hydride; sodium carbonate; bis(pinacol)diborane; sodium hydroxide; In methanol; ethanol; water; dimethyl sulfoxide; N,N-dimethyl-formamide; 2.1: |Smiles Aromatic Rearrangement;

DOI:10.1016/j.bmc.2016.04.059

Reference yield:

6-bromo-N-(6-bromo-2,3-dimethoxybenzyl)naphtho[2,3-d][1,3]dioxol-5-amine → 6-acetonyldihydrochelerythrine (15575-49-2,22864-92-2,128778-79-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere

1.2: 5 h / 0 - 20 °C / Inert atmosphere

2.1: bis(pinacol)diborane; potassium acetate; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / dimethyl sulfoxide / 16 h / Inert atmosphere

3.1: sodium acetate; iodine / ethanol / 2 h / Inert atmosphere; Reflux

4.1: sodium carbonate / water / 6 h / Inert atmosphere; Reflux

With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; iodine; potassium acetate; sodium acetate; sodium hydride; sodium carbonate; bis(pinacol)diborane; In ethanol; water; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2016.04.059

upstream raw materials:

chelerythrinium

acetone

6-bromonaphtho[2,3-d][1,3]dioxol-5-ol

12,13-dihydrochelerythrine

Refernces

• 1、 Yang, Xin-Juan,Miao, Fang,Yao, Yao,Cao, Fang-Jun,Yang, Rui,Ma, Yan-Ni,Qin, Bao-Fu,Zhou, Le. "In vitro antifungal activity of sanguinarine and chelerythrine derivatives against phytopathogenic fungi". . p. 13026 - 13035. Retrieved 2013/02/23.