2-(hydroxyimino)-5,6-(methylenedioxy)-1-indanone

Base Information

• Chemical Name: 2-(hydroxyimino)-5,6-(methylenedioxy)-1-indanone
• CAS No.: 38489-93-9
• Molecular Formula: C10H7NO4
• Molecular Weight: 205
• Hs Code.: 2932999099
• Mol file: 38489-93-9.mol

Synonyms:2-(hydroxyimino)-5,6-(methylenedioxy)-1-indanone;5H-Indeno[5,6-d]-1,3-dioxole-5,6(7H)-dione 6-OxiMe;6-(HydroxyiMino)-6,7-dihydro-5H-indeno[5,6-d][1,3]dioxol-5-one

Chemical Property of 2-(hydroxyimino)-5,6-(methylenedioxy)-1-indanone

Chemical Property:

• PSA: 68.12000
• LogP: 0.98430
• Storage Temp.: Hygroscopic, Refrigerator, Under Inert Atmosphere
• Solubility.: DMSO

Purity/Quality:

99%, ^*data from raw suppliers

6-(Hydroxyimino)-6,7-dihydro-5H-indeno[5,6-d][1,3]dioxol-5-one 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 5H-Indeno[5,6-d]-1,3-dioxole-5,6(7H)-dione 6-oxime can be used in the preparation of nonneurotoxic tetralin, indan analogues and in the total synthesis of Papilistatin. Papilistatin is a unique phenanthrene-1,10-dicarboxylic acid having good anticancer and antibacterial activity. Can be used in the preparation of nonneurotoxic tetralin and indan analogues.

Technology Process of 2-(hydroxyimino)-5,6-(methylenedioxy)-1-indanone

There total 11 articles about 2-(hydroxyimino)-5,6-(methylenedioxy)-1-indanone 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: 90.0%

5,6-methylenedioxy-1-indanone (6412-87-9) → 2-(hydroxyimino)-5,6-(methylenedioxy)-1-indanone (38489-93-9)

Guidance literature:

With isopentyl nitrite;

DOI:10.1016/S0040-4020(01)87039-3

Reference yield: 75.0%

5,6-methylenedioxy-1-indanone (6412-87-9) → 2-(hydroxyimino)-5,6-(methylenedioxy)-1-indanone (38489-93-9)

Guidance literature:

With hydrogenchloride; n-Amyl nitrite; In methanol; water;

DOI:10.1039/c0ob01214a

Reference yield:

3-benzo[1,3]dioxol-5-yl-propionyl chloride (68996-81-6) → 2-(hydroxyimino)-5,6-(methylenedioxy)-1-indanone (38489-93-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / SnCl₄ / CH₂Cl₂ / 1.) 0 deg C, 10 min, 2.) 0.5 h

2: 86.9 percent / isoamyl nitrite, conc. HCl / methanol / 1.25 h

With hydrogenchloride; tin(IV) chloride; isopentyl nitrite; In methanol; dichloromethane;

DOI:10.1021/jm00164a037

upstream raw materials:

5,6-methylenedioxy-1-indanone

isopentyl nitrite

piperonal

3-benzo[1,3]dioxol-5-yl-propionyl chloride

Downstream raw materials:

(Z/E)-3-(2-bromo-6-methoxyphenyl)-2-(2-carboxy-4,5-methylenedioxyphenyl)acrylic acid methyl ester

6,7-dihydro-5H-cyclopenta[f][1,3]benzodioxol-6-amine

Refernces

• 1、 Wu, Meng,Li, Ling,Feng, An-Zheng,Su, Bo,Liang, De-Min,Liu, Yu-Xiu,Wang, Qing-Min. "First total synthesis of Papilistatin". scheme or table. p. 2539 - 2542. Retrieved 2011/05/06.
• 2、 Nichols, David E.,Brewster, William K.,Johnson, Michael P.,Oberlender, Robert,Riggs, Robert M.. "Nonneurotoxic Tetralin and Indian Analogues of 3,4-(Methylenedioxy)amphetamine (MDA)". . p. 703 - 710. Retrieved 2007/10/02.