54299-80-8

Basic information

• Product Name: 2-Hexen-4-ynedioic acid, dimethyl ester, (2E)-
• Synonyms: dimethyl (E)-hex-2-en-4-yne dioate;dimethyl trans-but-1-en-3-yne-1,4-dicarboxylate;dimethyl (E)-hex-2-en-4-yne-1,6-dioate;2-hexen-4-ynedioic acid dimethyl ester;dimethyl but-1-en-3-yne-1,4-dicarboxylate;Dimethyl (E)-1-buten-3-yne-1,4-dicarboxylate;2-Hexen-4-ynedioic acid,dimethyl ester,(2E);(E)-MeO2CCHCHCCCO2Me
• CAS NO: 54299-80-8
• Molecular Formula: C8H8O4
• Molecular Weight: 168.149
• Mol File: 54299-80-8.mol
• Article Data: 3

Chemical Properties

• Melting Point: 52 °C (petroleum ether)
• Boiling Point: 250.9±32.0 °C(Predicted)
• Density: 1.163±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 2-Hexen-4-ynedioic acid, dimethyl ester, (2E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Hexen-4-ynedioic acid, dimethyl ester, (2E)-(54299-80-8)
• EPA Substance Registry System: 2-Hexen-4-ynedioic acid, dimethyl ester, (2E)-(54299-80-8)

Safety Data

• Hazardous Substances Data: 54299-80-8(Hazardous Substances Data)

Upstream product

• 922-67-8 propynoic acid methyl ester 
• 66022-00-2 1-hydroxy-2-(prop-1-ynyl)benzene 
• 853193-61-0 (-)-(3S,5E)-1-benzyloxyhept-5-en-3-ol 

Relevant articles and documents

Unified Approach to Furan Natural Products via Phosphine-Palladium Catalysis

Polyalkyl furans are widespread in nature, often performing important biological roles. Despite a plethora of methods for the synthesis of tetrasubstituted furans, the construction of tetraalkyl furans remains non-trivial. The prevalence of alkyl groups in bioactive furan natural products, combined with the desirable bioactivities of tetraalkyl furans, calls for a general synthetic protocol for polyalkyl furans. This paper describes a Michael–Heck approach, using sequential phosphine-palladium catalysis, for the preparation of various polyalkyl furans from readily available precursors. The versatility of this method is illustrated by the total syntheses of nine distinct polyalkylated furan natural products belonging to different classes, namely the furanoterpenes rosefuran, sesquirosefuran, and mikanifuran; the marine natural products plakorsins A, B, and D and plakorsin D methyl ester; and the furan fatty acids 3D5 and hydromumiamicin.

Total synthesis of the marine natural product (-)-clavosolide A

The total synthesis of the marine metabolite clavosolide A is reported which confirms the structure and absolute configuration of the natural product as the symmetrical diolide glycosylated by permethylated D-xylose moieties, 2.