83803-81-0

Basic information

• Product Name: ethyl 4,4-dimethoxy-3-methyl-2-butenoate
• Synonyms: ethyl 4,4-dimethoxy-3-methyl-2-butenoate;4,4-Dimethoxy-3-methyl-2-butenoic acid ethyl ester;Einecs 280-901-5
• CAS NO: 83803-81-0
• Molecular Formula: C₉H₁₆O₄
• Molecular Weight: 188.22094
• EINECS: 280-901-5
• Mol File: 83803-81-0.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 240.4°C at 760 mmHg
• Flash Point: 97.5°C
• Appearance: /
• Density: 1.006g/cm³
• Vapor Pressure: 0.0381mmHg at 25°C
• Refractive Index: 1.435
• CAS DataBase Reference: ethyl 4,4-dimethoxy-3-methyl-2-butenoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 4,4-dimethoxy-3-methyl-2-butenoate(83803-81-0)
• EPA Substance Registry System: ethyl 4,4-dimethoxy-3-methyl-2-butenoate(83803-81-0)

Safety Data

• Hazardous Substances Data: 83803-81-0(Hazardous Substances Data)

Usage

General Description

Ethyl 4,4-dimethoxy-3-methyl-2-butenoate is an organic compound with the chemical formula C10H16O4. It is a colorless liquid with a fruity, sweet odor, and is commonly used as a flavor and fragrance ingredient in various products. This chemical is often utilized in the production of perfumes, soaps, and other personal care items, as well as in food and beverage flavorings. Additionally, it is also used as an intermediate in the synthesis of pharmaceuticals and other organic compounds. Ethyl 4,4-dimethoxy-3-methyl-2-butenoate is considered to be relatively stable under normal conditions, but may react vigorously with oxidizing agents and strong bases.

InChI:InChI=1/C9H16O4/c1-5-13-8(10)6-7(2)9(11-3)12-4/h6,9H,5H2,1-4H3/b7-6+

Upstream product

• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 6342-56-9 Pyruvic aldehyde dimethyl acetal 
• 90208-14-3 ethyl 2-(diethoxyphosphoryl)acetate lithium salt 

Downstream Products

• 40834-42-2 5-hydroxy-4-methyl-5H-furan-2-one 
• 95286-43-4 ethyl 9-(2',6',6'-trimethyl-1'-cyclohexen-1'-yl)-3,7-dimethyl-4,7-dihydroxy-(2E,8E)-nona-2,8-dien-5-ynoate 
• 118282-96-5 (1E,7E)-9-(tert-Butyl-dimethyl-silanyloxy)-3,7-dimethyl-1-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-1,7-dien-4-yne-3,6-diol 
• 118272-45-0 9-(2',6',6'-trimethyl-1'-cyclohexen-1'-yl)-3,7-dimethyl-1-<(tert-butyldimethylsilyl)oxy>-(2E,5E,8E)-nona-2,5,8-triene-4,7-diol 
• 118272-45-0 9-(2',6',6'-trimethyl-1'-cyclohexen-1'-yl)-3,7-dimethyl-1-<(tert-butyldimethylsilyl)oxy>-(2E,5Z,8E)-nona-2,5,8-triene-4,7-diol 
• 118304-71-5 (2E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,8-dien-5-yne-1,4,7-triol 
• 118353-70-1 tBDMS-retinol 
• 68-26-8 RETINOL 
• 302-79-4 all-trans-retinoic-acid 
• 116-31-4 all-trans-Retinal 
• 110625-77-9 (S)-benzyloxy-1-ethoxymethoxy-2-methylbutane 
• 966-47-2 3-methoxy-estra-1,3,5⁽¹⁰⁾,8⁽⁹⁾,14⁽¹⁵⁾-pentaene-17-one 
• 54709-94-3 5-methylpyridazin-3(2H)-one 
• 62054-49-3 ethyl (E)-3-formyl-2-butenoate 

Relevant articles and documents

Toward Leiodermatolide: Synthesis of the Core Structure

The macrocyclic core (35) of the marine natural product leiodermatolide (1) was synthesized from two key fragments, vinyl iodide 23 (C1-C11 part) and vinyl stannane 31 (C12-C18 part). A Stille coupling led to conjugated Z,Z-diene 32. The derived seco acid 34 was cyclized using a Yamaguchi macrolactonization. Key steps in the assembly of vinyl iodide 23 were a Paterson aldol reaction, and a Kumada coupling on a triflate derivative to create the C4-C5 trisubstituted double bond. The two stereocenters in fragment 31 were established by a Marshall-Tamaru reaction. The longest linear sequence comprises 20 steps.

Total synthesis of the potent antitumor macrolides pladienolide B and D

Getting cross: The total syntheses of two pladienolides (see picture), which have prominent antitumor activity based on a unique mechanism of action, have been accomplished, and their absolute configurations were verified. The 12-membered aliphatic macrolide structure was formed by ring-closing metathesis, and the side-chain moiety was coupled to the macrolide by Julia-Kocienski olefination or cross-metathesis. (Chemical Equation Presented).

Triene compounds having a chromene structure

Compounds of general formula (I): STR1 in which: R1, R2, R3 and R4, which may be identical or different, denote a hydrogen atom, a halogen atom or a lower alkyl, lower alkenyl, lower alkyloxy or lower alkenyloxy group, optionally substituted with one or more halogen atoms, R5 denotes a carboxyl, (lower alkyloxy)carbonyl, (lower alkenyloxy)carbonyl or (lower alkynyloxy)-carbonyl, their isomers, stereoisomers and diastereoisomers, and also their addition salts with a pharmaceutically acceptable base. Medicinal products.