38867-17-3

Usage

Chemical compound

2,6-Heptadienoic acid

Purity

96%

Composition

Predominantly trans isomer

Physical state

Clear, colorless liquid

Odor

Characteristic and pungent

Uses

Production of pharmaceuticals, fragrances, organic compounds, flavoring agent in food products

Stability

Predominantly trans isomer makes it stable

Industrial applications

Suitable for various industrial applications

Caution

Should be handled and stored with caution due to potential hazards if not properly managed

InChI:InChI=1/C7H10O2/c1-2-3-4-5-6-7(8)9/h2,5-6H,1,3-4H2,(H,8,9)/b6-5+

Upstream product

• 592-42-7 1,5-Hexadien 
• 2100-17-6 4-pentenal 
• 141-82-2 malonic acid 
• 556-56-9 allyl iodid 
• 107-93-7 (E)-but-2-enoic acid 
• 80-59-1 Tiglic acid 
• 106-95-6 allyl bromide 
• 270901-71-8 tert-butyl (E)-hepta-2,6-dienoate 
• 821-09-0 n-Pent-4-enyl alcohol 
• 38872-58-1 3,7-Dichloro-heptanoic acid 

Downstream Products

• 910215-36-0 (4R,5S,6S)-6-methoxy-5-(4-methoxybenzyloxy)-2,4-dimethylocta-2,7-dienyl hepta-2,6-dienoate 
• 872513-16-1 C₁₄H₁₁Cl₃O₃ 
• 99285-31-1 (S)-3-(4-Methoxy-phenyl)-hept-6-enoic acid ((S)-1-naphthalen-1-yl-ethyl)-amide 
• 99285-27-5 N-(3-p-methoxyphenyl-6-heptenoyl)-l-ephedrine 
• 99285-28-6 N-(3-isopropenyl-6-heptenoyl)-l-ephedrine 
• 99285-26-4 N-(E-2,6-heptanedienoyl)-l-ephedrine 
• 215389-45-0 (2'E,5S)-1-(Hepta-2',6'-dienoyl)-5-triphenylmethoxymethylpyrrolidin-2-one 
• 637330-84-8 (3'R,4S)-3-(3-isopropenylhept-6-enoyl)-4-phenyl-5,5-dimethyloxazolidin-2-one 
• 637330-83-7 (S)-3-(hepta-2',6'-dienoyl)-4-phenyl-5,5-dimethyloxazolidin-2-one 

Relevant academic research and scientific papers

METHOD FOR PRODUCING BICYCLIC GAMMA-AMINO ACID DERIVATIVE

The problem to be solved is to provide a method for producing a compound having excellent activity as an α2δ ligand. The solution thereto is a method for producing a compound represented by the general formula (I) or a salt thereof by optical resolution: [in the formula, R1: a hydrogen atom or a C1-C6 alkyl group, and R2: a hydrogen atom or a protective group for the carboxy group]

BICYCLIC -AMINO ACID DERIVATIVE

It is intended to provide a bicyclic γ-amino acid derivative having excellent activity as an α2δ ligand. The present invention provides a compound represented by the general formula (I): wherein R1, R2, R2', R4, R5, R6, R7, R8, and R8' are a hydrogen atom or the like; and R3 is a hydrogen atom, a halogen atom, a C1-C6 alkyl group, or the like.

MIGRASTATIN ANALOGS IN THE TREATMENT OF CANCER

In one aspect, the present invention provides a method for treating colon and/or ovarian cancer in a subject comprising administering to a subject in need thereof a compound of general formula (I): wherein R1-R6, R, ,-R,, Q, Y1, Y2 and n are as defined herein, wherein the compound is present in an amount effective to inhibit colon and/or ovarian tumor metastasis.

The migrastatin family: Discovery of potent cell migration inhibitors by chemical synthesis

The first asymmetric total synthesis of (+)-migrastatin (1), a macrolide natural product with antimetastatic properties, has been accomplished. Our concise and flexible approach utilized a Lewis acid-catalyzed diene aldehyde condensation (LACDAC) to install the three contiguous stereocenters and the trisubstituted (Z)-alkene of migrastatin (2 + 3 → 21). Construction of the two remaining stereocenters and incorporation of the glutarimide-containing side chain was achieved by an anti-selective aldol addition of propionyl oxazolidinone 28 to angelic aldehyde 27, followed by a Horner-Wadsworth-Emmons (HWE) coupling of 32 with glutarimide aldehyde 5. Finally, the assembly of the macrocycle was realized by a highly (E)-selective ring-closing metathesis (35 → 37). Utilizing the power of diverted total synthesis (DTS), a series of otherwise inaccessible analogues was prepared and evaluated for their potential as tumor cell migration inhibitors in several in vitro assays. These studies revealed a dramatic increase in activity when the natural motif was considerably simplified, presenting macrolactones 45 and 48, as well as macrolactam 55, macroketone 60, and CF3-alcohol 71 as promising anti-metastatic agents.

MIGRASTATIN ANALOG COMPOSITIONS AND USES THEREOF

In one aspect, the present invention provides pharmaceutical compositions comprising a therapeutically effective amount of a compound of general formula (I), wherein R1-R6, Ra-RC, Q, Y1, Y2 and n are as defined herein, whereby the composition is formulated for administration to a subject at a dosage between about 0.1 mg/kg to about 50 mg/kg of body weight. In another aspect, the present invention provides a method for treating breast tumor metastasis in a subject comprising administering to a subject in need thereof a therapeutically effective amount of the inventive composition described directly above and a pharmaceutically acceptable carrier, adjuvant or vehicle.

Stereocontrol in organic synthesis using silicon-containing compounds. A synthesis of methyl (+)-nonactate

(3Z,2S)-7,7-Ethylenedioxyhex-3-en-2-yl N-phenylcarbamate 7 gave the allylsilane 8, (2E,4S)-7,7-ethylenedioxy-4-dimethyl(phenyl)silylhept-2-ene, introducing one stereogenic centre carrying a silyl group. Hydroboration-oxidation gave (2S,4S)-7,7-ethylenedioxy-4-dimethyl(phenyl)silylheptan-2-ol 9, controlling a second stereogenic centre. Conjugate addition of the phenyldimethylsilylcuprate reagent to the α,β-unsaturated imide (2′E,6′S,8′R,5S)-1-[8′-benzyloxy-6′- dimethyl(phenyl)silylnon-2′-enoyl]-5-triphenylmethoxymethylpyrrolidin-2- one 11 introduced a third stereogenic centre, and methylation of the ester derived from the product introduced a fourth. Ester hydrolysis and a double silyl-to-hydroxy conversion gave (25,3S,6S,8R)-8-benzyloxy-3)6-dihydroxy-2-methylnonanoic acid 16, from which methyl (+)-nonactate 2 was prepared by differentiating the hydroxy groups with the selective formation of a β-lactone 17 rather than a seven-membered lactone.

Alkylation of lithium dienediolates of butenoic acids. Regioselectivity effects of structure and leaving group of the alkylating agent

Regioselectivity of alkylation of but-2-enoic acids I and 2 by alkyl halides strongly depends on the reactivity of the electrophile. High α selectivity results for saturated alkyl halides, whereas poor α-selectivity is obtained for highly reactive allyl and benzyl halides. For reactive alkylating halides selectivity is partly governed by the ion pairing aggregates of the dienediolates. Lithium bromide and the carboxylate generated in the ongoing reaction cause opposite effects on regioselectivity.

Asymmetric synthesis towards (3Z,6R)-3-methyl-6-isopropenyl-3,9-decadien-1-yl acetate, a component of the California red scale pheromone

The key chiral synthons, (R)-3-isopropenyl-6-heptenoic acid and (R)-3-isopropenyl-6-heptenal, needed for the synthesis of (3Z,6R)-3-methyl-6-isopropenyl-3,9-decadien-1-yl acetate, a component of the sex pheromone of the California red scale, Aonidiella aurantii, have been prepared by asymmetric synthesis.The chiral acid was synthesized in 86percent ee by an asymmetric 1,4-addition of isopropenylmagnesium bromide to the l-ephedrine amide derived from (E)-2,6-heptadienoic acid, followed by base hydrolysis.Acid hydrolysis gave the chiral 3-(3-buten-1-yl)-4,4-dimethylbutyrolactone.The chiral aldehyde was prepared in greater than 99percent ee by an asymmetric 1,4-addition of isopropenylmagnesium bromide to the imine derived from (S)-(+)-tert-butyl 2-amino-3,3-dimethylbutyrate and (E)-2,6-heptadienal.The 1,4-addition reactions of n-butyllithium or isopropenyllithium to (4S,5S)-(+)-2--4-methoxymethyl-5-phenyl-2-oxazoline gave the addition products, and sequential mild hydrolysis and reduction of these adducts yielded chiral 3-n-butyl-6-hepten-1-ol for the former adduct but a mixture of products was obtained from the latter adduct.