1,5-dihydroxy-2,2,5,7-tetramethylspiro[1H-indene-6,1'-cyclopropane]-4-one

Base Information

• Chemical Name: 1,5-dihydroxy-2,2,5,7-tetramethylspiro[1H-indene-6,1'-cyclopropane]-4-one
• CAS No.: 1146-04-9
• Molecular Formula: C15H20 O3
• Molecular Weight: 248.322
• NSC Number: 626370
• Wikidata: Q104196256
• Mol file: 1146-04-9.mol

Synonyms:NSC626370;1,5-dihydroxy-2,2,5,7-tetramethylspiro[1H-indene-6,1'-cyclopropane]-4-one;NSC-626370;Neuro_000257;Spiro[cyclopropane-1, 2',3'-dihydro-3',6'-dihydroxy-2',2',4',6'-tetramethyl-,(3'S,6'R)-;Spiro[cyclopropane-1, 2',3'-dihydro-3',6'-dihydroxy-2',2',4',6'-tetramethyl-,(3'S-trans)-;Spiro[cyclopropane-1, 2',3'-dihydro-3'.beta.,6'.alpha.-dihydroxy- 2',2',4',6'-tetramethyl-;NCI60_008312;Illudine M;UNII-0ASO6A4L61;(-)-Illudin M;1,5-dihydroxy-2,2,5,7-tetramethyl-spiro[1H-indene-6,1'-cyclopropane]-4-one;3',6'-dihydroxy-2',2',4',6'-tetramethyl-2',3'-dihydrospiro[cyclopropane-1,5'-inden]-7'(6'H)-one;Spiro[cyclopropane-1,5'-[5H]inden]-7'(6'H)-one, 2',3'-dihydro-3',6'-dihydroxy-2',2',4',6'-tetramethyl-

Chemical Property of 1,5-dihydroxy-2,2,5,7-tetramethylspiro[1H-indene-6,1'-cyclopropane]-4-one

Chemical Property:

• Vapor Pressure: 4.36E-10mmHg at 25°C
• Melting Point: 120-122.5° (Matsumoto); mp 128-130° (McMorris)
• Boiling Point: 452.4°Cat760mmHg
• PKA: 12.57±0.70(Predicted)
• Flash Point: 241.5°C
• PSA: 57.53000
• Density: 1.24g/cm³
• LogP: 1.74390
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 248.14124450
• Heavy Atom Count: 18
• Complexity: 520

Purity/Quality:

97% ^*data from raw suppliers

IlludinM ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C2C(C(C=C2C(=O)C(C13CC3)(C)O)(C)C)O
• Description: Illudin M is a cytotoxic sesquiterpene from the fungus O. illudens that alkylates DNA. It is cytotoxic to HL-60 human leukemia cells at 6-100 nM. Illudin M was used as a base structure for the development of potential anticancer agents with less toxicity and improved efficacy. It is closely related to illudin S , which has been the focus of additional studies.
• Uses: Illudin M is a cytotoxic sesquiterpene from Omphalotus illudens and Granulobasidium vellereum. It acts as an alkylating agent that can cause inhibition of cell growth or replication.

Technology Process of 1,5-dihydroxy-2,2,5,7-tetramethylspiro[1H-indene-6,1'-cyclopropane]-4-one

There total 6 articles about 1,5-dihydroxy-2,2,5,7-tetramethylspiro[1H-indene-6,1'-cyclopropane]-4-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: 23.0%

Dihydroilludin M → (+/-)-Illudin M (1146-04-9,19903-66-3) + C15H20O3

Guidance literature:

With pyridine; N-Bromosuccinimide; In dichloromethane; at 25 ℃; for 1.5h;

DOI:10.1021/jo00102a020

Reference yield:

sodium acetate (127-09-3) → illudin M (1146-04-9) + dehydroilludin M (28282-65-7) + illudin S (1149-99-1)

Guidance literature:

With Omphalotus illudens strain 4435; In ethanol; water; for 504h;

DOI:10.1002/(SICI)1099-1344(199804)41:4<279::AID-JLCR86>3.0.CO;2-J

Reference yield:

(3S,4S,7R)-dihydroilludin M → (3S,7R)-illudin M (1146-04-9,19903-66-3)

Guidance literature:

With pyridine; N-Bromosuccinimide; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1021/acs.jnatprod.5b00500

upstream raw materials:

sodium acetate

Downstream raw materials:

dehydroilludin M

Dihydroilludin M

(R)-4,6,6,8a-Tetramethyl-2,3,6,8a-tetrahydro-indeno[5,6-b]furan-8-one

Deoxyilludin M