6617-37-4

Basic information

• Product Name: (5Z)-5-[(E)-2-Methyl-5-(3-furyl)-2-pentene-4-ynylidene]-3-methyl-2(5H)-furanone
• Synonyms: (5Z)-5-[(E)-2-Methyl-5-(3-furyl)-2-pentene-4-ynylidene]-3-methyl-2(5H)-furanone;5-[(1Z,2E)-5-(3-Furyl)-2-methyl-2-penten-4-ynylidene]-3-methylfuran-2(5H)-one;Freelingyne
• CAS NO: 6617-37-4
• Molecular Formula: C₁₅H₁₂O₃
• Molecular Weight: 240.25
• Mol File: 6617-37-4.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (5Z)-5-[(E)-2-Methyl-5-(3-furyl)-2-pentene-4-ynylidene]-3-methyl-2(5H)-furanone(CAS DataBase Reference)
• NIST Chemistry Reference: (5Z)-5-[(E)-2-Methyl-5-(3-furyl)-2-pentene-4-ynylidene]-3-methyl-2(5H)-furanone(6617-37-4)
• EPA Substance Registry System: (5Z)-5-[(E)-2-Methyl-5-(3-furyl)-2-pentene-4-ynylidene]-3-methyl-2(5H)-furanone(6617-37-4)

Safety Data

• Hazardous Substances Data: 6617-37-4(Hazardous Substances Data)

Upstream product

• 193478-02-3 (2Z,6E)-9-Furan-3-yl-2,6-dimethyl-nona-2,6-diene-4,8-diyn-1-ol 
• 193478-00-1 (E)-5-Furan-3-yl-2-methyl-pent-2-en-4-ynoic acid methyl ester 
• 193478-01-2 (E)-6-(3-furanyl)-3-methyl-3-hexene-1,5-diyne 
• 147675-99-8 3-(2,2-dibromovinyl)furan 
• 193478-07-8 (3E)-1,1-dibromo-6-(3-furanyl)-3-methyl-1,3-hexadien-5-yne 
• 53768-17-5 (E)-5-(3-furanyl)-2-methyl-2-penten-4-ynal 
• 53768-06-2 (E)-5-(3-furanyl)-2-methyl-1-[(tetrahydropyranyl)oxy]-2-penten-4-yne 
• 53768-16-4 (E)-5-(3-furanyl)-2-methyl-2-penten-4-yn-1-ol 
• 53768-03-9 (E)-2-methyl-1-[(tetrahydro-2H-pyran-2-yl)oxy]-2-penten-4-yne 
• 51061-85-9 3-ethynylfuran 
• 616-02-4 citraconic acid anhydride 
• 22122-36-7 3-methyl-5H-furan-2-one 
• 61550-03-6 2-trimethylsilyloxy-3-methylfurane 
• 498-60-2 furan-3-carboxaldehyde 

Downstream Products

• 104049-40-3 2-methyl-3-<2'-(furan-3-yl)-3'-hydroxy-5'-methylphenyl>propenoic acid 

Relevant articles and documents

Stereoselective synthesis of freelingyne and related γ-alkylidenebutenolides via vinylogous Mukaiyama aldol additions

Following the strategy of Scheme 1, a Mukaiyama aldol addition/anti-elimination route to stereopure γ-alkylidenebutenolides 4 was established. The addition giving 27 was only moderately diastereoselective but the products lk- and ul-27 were chromatographically separable (Scheme 4). They underwent highly selective anti-eliminations in the presence of triflic anhydride-pyridine or Burgess' reagent, furnishing the thiophene-containing butenolides Z- and E-28, respectively (Scheme 5). The Mukaiyama aldol addition leading to compound 29 was 100% lk-selective when mediated by BF3 etherate and 87 : 13 ul-selective in the presence of ZnBr2 (Scheme 6). Stephens-Castro couplings of the resulting butenolides lk- and ul-29 with 3-ethynylfuran proceeded with complete conservation of the stereochemical integrity (Scheme 7). The subsequent anti-eliminations of water were best realized by treatment with DEAD-PPh3. They provided freelingyne (Z-9) with ds = 92 : 8 and its isomer E-9 with ds = 98 : 2 (Scheme 8). Analogously, the differently substituted (trimethylsiloxy)furans 15 or 16 provided the freelingyne analogs Z-10, E-10 and Z-11 (Schemes 6-8).

Efficient and Stereoselective Synthesis of Freelingyne via Pd-Catalyzed Cross Coupling and Lactonization

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