4,7-Dihydroxy[1,3]dioxolo[4,5-j]phenanthridin-6(5H)-one

Base Information

• Chemical Name: 4,7-Dihydroxy[1,3]dioxolo[4,5-j]phenanthridin-6(5H)-one
• CAS No.: 28233-43-4
• Molecular Formula: C14H9 N O5
• Molecular Weight: 271.229
• Mol file: 28233-43-4.mol

Synonyms:Arolycoricidinol;NSC 624394; Narciprimin; Narciprimine

Chemical Property of 4,7-Dihydroxy[1,3]dioxolo[4,5-j]phenanthridin-6(5H)-one

Chemical Property:

• Melting Point: Decomposes 300-320°C
• PSA: 91.78000
• LogP: 1.82120

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: The fresh bulbs of many species of Narcissus yield this alkaloid, together with the preceding base. It resembles narciclasine in that although the structure is clearly related to those of the Amaryllidaceous alkaloids it shows no basic properties since the nitrogen is amidic in character. The ultraviolet spectrum in EtOH is quite complex having absorption maxima at 233, 257, 274, 295, 322, 337 and 353 mil. It contains a methylenedioxy group and two phenolic hydroxyl groups and furnishes the diacetate which crystallizes from MeOH with m.p. 247°C. The corresponding dimethyl ether is amorphous with melting point above 320°C.

Technology Process of 4,7-Dihydroxy[1,3]dioxolo[4,5-j]phenanthridin-6(5H)-one

There total 6 articles about 4,7-Dihydroxy[1,3]dioxolo[4,5-j]phenanthridin-6(5H)-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: 35.0%

(2S,5aS,2aR,5bR)-2,8-dihydroxy-4,4-dimethyl-2,6,2a,5a,5b-pentahydro-10H-1,3-dioxolano<4,5-c>1,3-dioxoleno<4,5-j>phenanthridin-7-one (40041-97-2) → 4,7-dihydroxy-[1,3]dioxolo[4,5-j]phenanthridin-6(5H)-one (28233-43-4)

Guidance literature:

(2S,5aS,2aR,5bR)-2,8-dihydroxy-4,4-dimethyl-2,6,2a,5a,5b-pentahydro-10H-1,3-dioxolano<4,5-c>1,3-dioxoleno<4,5-j>phenanthridin-7-one; With di-isopropyl azodicarboxylate; triphenylphosphine; 4-nitro-benzoic acid; In tetrahydrofuran; at 0 - 20 ℃; for 16h; Inert atmosphere;

With water; trifluoroacetic acid; In tetrahydrofuran; at 0 - 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/acs.jnatprod.8b00218

Reference yield: 3.7%

pancratistatin (96203-70-2,96281-31-1) → 4,7-dihydroxy-[1,3]dioxolo[4,5-j]phenanthridin-6(5H)-one (28233-43-4) + C14H15NO11P(1-)*Na(1+)

Guidance literature:

pancratistatin; With toluene-4-sulfonic acid; tetrabutylammonium dihydrogen phosphate; dicyclohexyl-carbodiimide; In pyridine; at 80 ℃; for 120h;

With Dowex 50WX₈-200 resin Na⁽¹⁺⁾ form; In water;

DOI:10.1021/np030299+

Reference yield:

narciclasine (29477-83-6,220751-83-7) → 4,7-dihydroxy-[1,3]dioxolo[4,5-j]phenanthridin-6(5H)-one (28233-43-4)

Guidance literature:

With hydrogenchloride; In methanol;

DOI:10.1248/cpb.16.1860

upstream raw materials:

4-benzyloxy-7-hydroxy-5H-[1,3]dioxolo[4,5-j]phenanthridin-6-one

narciclasine

pancratistatin

4-benzyloxy-6-bromo-benzo[1,3]dioxole-5-carboxylic acid 2-benzyloxy-anilide

Refernces

• 1、 Pettit, George R.,Melody, Noeleen,Herald, Delbert L.. "Antineoplastic Agents. 511. Direct Phosphorylation of Phenpanstatin and Pancratistatin". . p. 322 - 327. Retrieved 2004.
• 2、 Okamoto,Torii,Isogai. "Lycoricidinol and lycoricidine, new plant-growth regulators in the bulbs of Lycoris radiata herb.". . p. 1860 - 1864. Retrieved 2007/10/08.