1740-74-5

Usage

Uses

Used in Pharmaceutical Industry:
1,1-Diethoxy-3-methyl-2-butene is used as a synthetic intermediate for the production of complex organic molecules, specifically in the synthesis of bioactive compounds such as 6,6,10-trimethyl-4-propyl-10,11-dihydro-2H,6H,12H-dipyrano[2,3-f:2′,3′-h]chromene-2,12-dione and angular pyranocoumarins. These compounds hold potential applications in the development of new drugs and therapeutic agents.
Used in Chemical Research:
In the field of chemical research, 1,1-Diethoxy-3-methyl-2-butene is utilized as a starting material for the synthesis of various organic compounds, including 6-cyano-2,2-dimethyl-2-H-1-benzopyran. 1 1-DIETHOXY-3-METHYL-2-BUTENE 97 can be further modified or used as a building block in the creation of novel chemical entities with potential applications in various industries.
Overall, 1,1-Diethoxy-3-methyl-2-butene plays a significant role in the synthesis of complex organic molecules and contributes to the advancement of pharmaceuticals, chemical research, and other related industries.

InChI:InChI=1/C9H18O2/c1-5-10-9(11-6-2)7-8(3)4/h7,9H,5-6H2,1-4H3

Upstream product

• 64-17-5 ethanol 
• 17466-13-6 1-ethoxy-3-methyl-buta-1,3-diene 
• 7463-52-7 2-bromo-1,1-diethoxy-3-methyl-butane 
• 865-47-4 potassium tert-butylate 
• 107-86-8 3,3-dimethyl acrylaldehyde 
• 122-51-0 orthoformic acid triethyl ester 
• 3017-69-4 2-methyl-1-propenylbromide 
• 14444-77-0 diethyl phenyl orthoformate 
• 5344-23-0 diethoxyacetaldehyde 
• 1530-33-2 isopropyltriphenylphosphonium bromide 
• 1825-62-3 ethyl trimethylsilyl ether 
• 3842-03-3 isovaleraldehyde diethyl acetal 
• 5329-14-6 aminosulfonic acid 
• 590-86-3 isovaleraldehyde 

Downstream Products

• 167482-50-0 1,2-O-Isopropylidene-3-O-(p-phenylbenzyl)-4,5-O-<(1'R)-3'-methyl-2'-buten-1'-yl>-β-D-fructopyranose 
• 107-86-8 3,3-dimethyl acrylaldehyde 
• 22927-97-5 6-methoxy-2,2-dimethyl-2H-chromene 
• 19013-07-1 desmethoxyencecalin 
• 67667-62-3 8-hydroxy-6-acetyl-2,2-dimethylchromene 
• 922-63-4 ethylacrolein 
• 1005322-18-8 3-benzyl-4,6,6,10-tetramethyl-10,11-dihydro-2H,6H,12H-dipyrano[2,3-f:2',3'-h]chromene-2,12-dione 
• 1005322-33-7 6,6,10-trimethyl-4-p-nitrophenyl-2H,6H,12H-benzo[1,2-b:3,4-b':5,6-b'']tripyranyl-2,12-dione 
• 1005322-35-9 6,6,10-trimethyl-4-(3,4,5-trimethoxylphenyl)-2H,6H,12H-benzo[1,2-b:3,4-b':5,6-b'']tripyranyl-2,12-dione 
• 1005322-28-0 6,6-dimethyl-4-n-propyl-10-phenyl-2H,6H,12H-benzo[1,2-b:3,4-b':5,6-b'']tripyranyl-2,12-dione 
• 1005322-29-1 6,6-dimethyl-4-n-propyl-10-(p-methylphenyl)-2H,6H,12H-benzo[1,2-b:3,4-b':5,6-b'']tripyranyl-2,12-dione 
• 303007-22-9 2,2-dimethyl-8-oxo-10-propyl-2H,8H-pyrano[2,3-f]chromen-5-yl 4-methylbenzenesulfonate 
• 523-59-1 seseline 
• 57103-57-8 (+)-Glyceollin I 

Relevant academic research and scientific papers

Synthesis of 6-Cyano-2,2-dimethyl-2H-1-benzopyran and Other Substituted 2,2-dimethyl-2H-1-benzopyrans

A practical synthesis of 6-cyano-2,2-dimethyl-2H-1-benzopyran (1) has been developed.This process involves the pyridine-catalyzed condensation of 1,1-diethoxy-3-methyl-2-butene (6) with 4-cyanophenol (3) in toluene or xylene at elevated temperatures.The development of this process, including an evaluation of solvents, bases, acid catalysts, and alterantive acetals, along with an improved synthesis of 1,1-diethoxy-3-methyl-2-butene, is discussed.Using this method, a variety of other substituted 2,2-dimethyl-2H-1-benzopyrans were synthesized.

Green synthesis of 6-cyano-2,2-dimethyl-2-H-1-benzopyran and its subsequent enantioselective epoxidation

The clean synthesis of 6-cyano-2,2-dimethyl-2-H-1-benzopyran epoxide starting from 3-methyl-2-butenal is reported using recyclable catalysts. H4PMo11VO40 (PMo11V) and (PyH)3HPMo11VO40 (Py3-PMo11V) Keggin-type heteropolyacids were used to synthesize 6-cyano-2,2-dimethyl-2-H-1-benzopyran in two steps with 35% yield. This is an alternative procedure to the traditional methodology with pyridine or picoline as catalyst, where 6-cyano-2,2-dimethyl-2-H-1-benzopyran is obtained by condensation of 4-cyanophenol with 1,1-diethoxy-3-methyl-2-butene. The 6-cyano-2,2-dimethyl-2-H-1-benzopyran epoxide was obtained using Jacobsen-type catalysts, and in situ generated dimethyldioxirane (DMD) as oxidizing agent, that in comparison to m-CPBA/4-NMO and NaOCl/4-PPNO did not degrade the catalyst. In presence of 4-phenylpyridine N-oxide (4-PPNO) at 4 °C, enantioselectivities of 87% for 3S,4S-epoxide and 68% for 3R,4R-epoxide were obtained with the S,S- and R,R-Jacobsen catalysts, respectively. Overall yield was approximately 17% for 3S,4S-epoxide.

Isoflavone type compound as well as preparation method and application thereof

The invention provides an isoflavone type compound and a preparation method thereof. A structural formula of the isoflavone type compound is shown as a formula and the formula is shown in the description, wherein R is a formula shown in the description, a

Highly selective carbamate-based butyrylcholinesterase inhibitors derived from a naturally occurring pyranoisoflavone

This current study described the design and synthesis of a series of derivatives based on a natural pyranoisaflavone, which was obtained from the seeds of Millettia pachycarpa and displayed attractive BChE inhibition and high selectivity in our previous study. The inhibitory potential of all derivatives against two cholinesterases was evaluated. Only a few compounds demonstrated AChE inhibitory activity at the tested concentrations, while 26 compounds showed significant inhibition on BChE (the IC50 values varied from 9.34 μM to 0.093 μM), most of them presented promising selectivity to ward BChE. Prediction of ADME properties for 7 most active compounds was performed. Among them, 9g (IC50 = 222 nM) and 9h (IC50 = 93 nM) were found to be the most potent BChE inhibitors with excellent selectivity over AChE (SI ratio = 1339 and 836, respectively). The kinetic analysis demonstrated both of them acted as mixed-type BChE inhibitors, while the molecular docking results indicated that they interacted with both residues in the catalytic active site. A cytotoxicity test on PC12 cells showed that both 9g and 9h had a therapeutic safety range similar to tacrine. Overall, the results indicate that 9h could be a good candidate of BChE inhibitors.

Asymmetric epoxidation of chromenes mediated by iminium salts: Synthesis of mollugin and (3S,4R)-trans-3,4-dihydroxy-3,4-dihydromollugin

Organocatalytic asymmetric epoxidation of chromenes mediated by iminium salt catalysts under non-aqueous conditions provided ees as high as 99%. Contrastingly, reaction under aqueous conditions can form the corresponding diol products with ees as high as 71%. The process has been used for the synthesis of the East African medicinal plant metabolite (3S,4R)-trans-3,4-dihydroxy-3,4-dihydromollugin.

Method for producing 3-methyl 2-butenal acetals

A process for preparing acetals of the formula I where a) the Rs are, independently of one another, a C1-C20-alkyl or C3-C20-alkenyl radical, or b) the two R radicals together form the members of an unsubstituted or C1-C10-alkyl-substituted 5- to 7-membered cyclic acetal, by reacting 3-methyl-2-butenal in the presence of sulfamic acid, of a N-(C1-C8-alkyl)sulfamic acid or of a N,N-di(C1-C8-alkyl)sulfamic acid as catalyst with: an alcohol of the formula R—OH (IIa), or an orthoester of the formula HC—(OR)3(III) or a mixture of an alcohol of the formula (IIa) and an orthoester of the formula (III), or an alcohol of the formula HO—(CH2)m—OH (IIb), where m is a number from 2 to 4, and (CH2)mgroup in the alcohol IIb may be substituted by a C1-C10-alkyl group.

Process for the production of 2H-1-benzopyrans

There is provided a 2-stage process for making 2H-1-benzopyrans wherein an alpha,beta-unsaturated aldehyde is reacted with an alkanol or an alkane-diol in the presence of a dehydrating compound which is an orthoformate and an aluminum oxide/silicon oxide catalyst to form an aliphatic acetal, which is then condensed in a second stage with a phenol in the presence of base in an organic solvent.

Process for the preparation of intermediates useful in the preparation of pyranyl cyanoguanidine derivatives

A process for preparing compounds of the formula STR1 where a, b d, R1, R2, R3 and R4 are as defined herein including condensation of a phenol of formula STR2 with an acetal of formula STR3 in the presence of a catalytic amount of a tertiary amine. The compounds of formula I are intermediates useful in the preparation of pyranyl cyanoguanidine derivatives.

Alkylation of Enol Ethers Obtained by Treatment of α,β-Unsaturated Acetals with Organopotassium Reagents: An Inverse Polarity Approach

The reaction of α,β-unsaturated acetals 1-4 with sec-butyllithium (2 equiv.) in the presence of potassium tert-butoxide in tetrahydrofuran at -95 deg C gave, as a result of 1,4-elimination, α-metallated enol ethers.The latter react with alkyl halides and carbonyl compounds to afford substitution and addition products.In particular, for the reaction with the acetal 1 and D2O as the electrophile, the α-deuteriated enol ether 5 cyclizes to -2-(prop-1-enyl)-1,3-dioxane.

Structure - Odor Correlation,IV.- Synthesis and Fragrance of Compounds Related to Rose Oxide

For the systematic investigation of the odor of analogues of rose oxide (1),the seco-ethers 2-6, the cyclic nor-ethers 7-10,and the functionally varied compounds 11 and 12 were prepared.- For the typical spicy-herbaceous fragrance of 1 particularly the st