Irofulven

Base Information

• Chemical Name: Irofulven
• CAS No.: 158440-71-2
• Molecular Formula: C15H18 O3
• Molecular Weight: 246.306
• NSC Number: 683863
• UNII: 6B799IH05A
• DSSTox Substance ID: DTXSID50166423
• Nikkaji Number: J805.233F
• Wikipedia: Irofulven
• Wikidata: Q6072197
• NCI Thesaurus Code: C1717
• Metabolomics Workbench ID: 149561
• ChEMBL ID: CHEMBL118218
• Mol file: 158440-71-2.mol

Synonyms:6-(hydroxymethyl)acylfulvene;6-hydroxymethylacylfulvene;HMAF cpd;irofulven;MGI 114;MGI-114;MGI.114

Chemical Property of Irofulven

Chemical Property:

• Melting Point: 127-129°
• Boiling Point: 501oC at 760 mmHg
• Flash Point: 270.9oC
• PSA: 57.53000
• Density: 1.28g/cm3
• LogP: 1.66560
• Storage Temp.: -20°C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 246.125594432
• Heavy Atom Count: 18
• Complexity: 558

Purity/Quality:

99%, ^*data from raw suppliers

(R)-Irofulven ^*data from reagent suppliers

Safty Information:

• Pictogram(s): A poison.
• Hazard Codes: A poison.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C2=C(C3(CC3)C(C(=O)C2=C1)(C)O)C)CO
• Isomeric SMILES: CC1=C(C2=C(C3(CC3)[C@@](C(=O)C2=C1)(C)O)C)CO
• Recent ClinicalTrials: Irofulven in AR-targeted and Docetaxel-Pretreated mCRPC Patients With Drug Response Predictor (DRP?)
• Recent EU Clinical Trials: Allocation of patients with pre-treated solid tumors to anti-cancer therapy based on gene expression drug response prediction - a phase II basket trial
• Uses: Semi-synrhetic antitumor agent derived from Illudin S. Inhibits DNA synthesis and induces apoptosis in tumor cells. Antineoplastic.

Technology Process of Irofulven

There total 4 articles about Irofulven 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: 73.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (R)-6’-hydroxy-2’,4’,6’-trimethylspiro[cyclopropane-1,5’-inden]-7’(6’H)-one (33781-60-1,125392-76-9) → [14C]-Irofulven (158440-71-2,187277-46-9)

Guidance literature:

With sulfuric acid;

DOI:10.1039/a607077i

Reference yield:

(4R)-4,8-dimethyl-7-((2E)-2-methyl-3-phenylallyl)-6-vinylspiro[2.5]oct-7-ene-4,5-diyl carbonate → [14C]-Irofulven (158440-71-2,187277-46-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: PhCH=Ru(1,3-Mes₂-4,5-dihydroimidazol-2-ylidene)(PCy₃)Cl₂ / benzene / 0.5 h / 80 °C

1.2: NaOMe / methanol; benzene / 24 h / 23 °C

1.3: 30 percent / DDQ; AcOH / benzene; methanol; acetonitrile / 13 h

2.1: 63 percent / aq. H₂SO₄ / acetone; H₂O / 144 h / 23 °C

With sulfuric acid; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In water; acetone; benzene;

DOI:10.1002/anie.200602011

Reference yield:

illudin S (1149-99-1) → [14C]-Irofulven (158440-71-2,187277-46-9)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. H₂SO₄

2: 0.2 mg / aq. H₂SO₄ / tetrahydrofuran / 24 h

With sulfuric acid; In tetrahydrofuran;

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

upstream raw materials:

formaldehyd

(R)-6’-hydroxy-2’,4’,6’-trimethylspiro[cyclopropane-1,5’-inden]-7’(6’H)-one

illudin S

Downstream raw materials:

6-ethyl-2,5,7-trimethyl-1-methylene-1H-inden-4-ol

Refernces

A rapid synthesis of hydroxymethylacylfulvene (HMAF) using the allenic Pauson-Khand reaction. A synthetic approach to either enantiomer of this illudane structure

10.1021/ja000546l

Kay M. Brummond, Jianliang Lu, and Jeffrey Petersen detail a novel synthetic approach to Irofulven (HMAF), an anticancer agent in Phase II clinical trials. The synthesis involves 11 steps from commercially available materials and utilizes an allenic Pauson-Khand reaction to construct the illudane skeleton. The authors also developed an asymmetric route to produce enantiomerically pure HMAF by integrating an enantiomerically pure intermediate synthesized via Sharpless asymmetric dihydroxylation. The study optimizes conditions for stereospecific synthesis of E or Z trisubstituted enynes using Peterson olefination or Horner-Wadsworth-Emmons protocols. This method provides access to both enantiomers of HMAF by altering ligands in the Sharpless reaction, offering a versatile approach for synthesizing HMAF and its derivatives for further antitumor activity studies.

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