33781-60-1

Basic information

• Product Name: acylfulvene
• Synonyms: acylfulvene
• CAS NO: 33781-60-1
• Molecular Formula: C14H16O2
• Molecular Weight: 216.27564
• Product Categories: Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 33781-60-1.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 437.0±34.0 °C(Predicted)
• Appearance: /
• Density: 1.21±0.1 g/cm3(Predicted)
• Solubility: Chloroform, Ethyl Acetate
• PKA: 12.53±0.60(Predicted)
• CAS DataBase Reference: acylfulvene(CAS DataBase Reference)
• NIST Chemistry Reference: acylfulvene(33781-60-1)
• EPA Substance Registry System: acylfulvene(33781-60-1)

Safety Data

• Hazardous Substances Data: 33781-60-1(Hazardous Substances Data)

Usage

Chemical Properties

Thick Orange Oil

Uses

Antitumor agent derived from Illudin S.

Upstream product

• 203390-34-5 C₁₄H₁₈O₂ 
• 652134-50-4 (1S,2R)-8,9-dihydroxy-3,6,8-trimethyl-7-spiro-cyclopropylbicyclo[4.3.0]nona-1,3,5-triene 
• 1149-99-1 illudin S 

Downstream Products

• 158440-71-2 [14C]-Irofulven 
• 187277-46-9 (+/-)-hydroxymethylacylfulvene 

Relevant articles and documents

ILLUDIN ANALOGS, USES THEREOF, AND METHODS FOR SYNTHESIZING THE SAME

This invention provides illudin derivatives, intermediates, preparation methods, pharmaceutical compositions and uses thereof. Specific examples include novel synthetic routes to prepare illudin derivatives and an illudin derivative having a positive optical rotation, which has therapeutic value.

Enantioselective total synthesis of (-)-acylfulvene and (-)-irofulven

(Chemical Equation Presented) We report our full account of the enantioselective total synthesis of (-)-acylfulvene (1) and (-)-irofulven (2), which features metathesis reactions for the rapid assembly of the molecular framework of these antitumor agents. We discuss (1) the application of an Evans Cu-catalyzed aldol addition reaction using a strained cyclopropyl ketenethioacetal, (2) an efficient enyne ring-closing metathesis cascade reaction in a challenging setting, (3) the reagent IPNBSH for a late-stage reductive allylic transposition reaction, and (4) the final RCM/dehydrogenation sequence for the formation of (-)-acylfulvene (1) and (-)-irofulven (2).

Investigating the role of stereochemistry in the activity of anticancer acylfulvenes: Synthesis, reductase-mediated bioactivation, and cellular toxicity

Acylfulvenes comprise a family of semisynthetic natural product derivatives with potent antitumor activities. Previous studies indicated that acylfulvenes are bioactivated by NADPH-dependent alkenal/one reductase (AOR), presumably generating intermediates