74500-50-8

Basic information

• Product Name: trans-Cyclopentanon-3,4-dicarbonsaeure-dimethylester
• CAS NO: 74500-50-8
• Molecular Weight: 200.191
• Mol File: 74500-50-8.mol

Chemical Properties

• CAS DataBase Reference: trans-Cyclopentanon-3,4-dicarbonsaeure-dimethylester(CAS DataBase Reference)
• NIST Chemistry Reference: trans-Cyclopentanon-3,4-dicarbonsaeure-dimethylester(74500-50-8)
• EPA Substance Registry System: trans-Cyclopentanon-3,4-dicarbonsaeure-dimethylester(74500-50-8)

Safety Data

• Hazardous Substances Data: 74500-50-8(Hazardous Substances Data)

Upstream product

• 16631-27-9 rac-trans-3,4-bis(methoxycarbonyl)hexanedioic acid 
• 16631-27-9 meso-3,4-bis(methoxycarbonyl)hexanedioic acid 
• 186581-53-3 diazomethane 
• 92334-74-2 trans(3,4)-3-Hydroxymethyl-4-(1',2'-dihydroxy-ethyl)-cyclopentanol-⁽¹⁾ 
• 104636-81-9 (1S,2S)-2-((R)-2,2-Di-tert-butyl-[1,3,2]dioxasilolan-4-yl)-4-methylene-cyclopentanecarboxylic acid methyl ester 
• 104636-80-8 (E)-3-((S)-2,2-Di-tert-butyl-[1,3,2]dioxasilolan-4-yl)-acrylic acid methyl ester 
• 4841-84-3 dimethyl cis-1,2,3,6-tetrahydrophthalate 
• 17673-68-6 dimethyl trans-cyclohex-4-ene-1,2-dicarboxylate 
• 99837-73-7 4(S),1'(RS),2'(RS)-2,2-dimethyl-4-(2-carbomethoxy-4-methylenecyclopentyl)-1,3-dioxolane 
• 4373-15-3 1,2,3,4-butanetetracarboxylic acid tetraethyl ester 
• 4534-68-3 1,2,3,4-butanetetracarboxylic acid 
• 67-56-1 methanol 
• 1703-61-3 racemic trans-cyclopentanone-3,4-dicarboxylic acid 
• 37575-81-8 methyl trans-2-(methoxycarbonyl)-4-methylenecyclopentane-1-carboxylate 

Downstream Products

• 35079-19-7 trans-(1R,2R)-1,2-Bis(methoxycarbonyl)-4-oxocyclopentane 
• 115694-82-1 (1S,2S)-2-(methoxycarbonyl)-4-oxocyclopentanecarboxylic acid 
• 115794-30-4 (+)-(1S,2S)-dimethyl-4-oxocyclopentane 1,2-dicarboxylate 
• 194918-80-4 2,4-Dioxo-1,3-diaza-spiro[4.4]nonane-7,8-dicarboxylic acid 
• 195209-04-2 ACPT-II 
• 146144-68-5 trans-(3R,4R)-bis(benzoyloxymethyl)cyclopentanone 
• 138804-29-2 3(S)-trans-3,4-Bis<(benzoyloxy)methyl>cyclopentanone 

Relevant articles and documents

The Synthesis of Novel Trans-Oxabicyclo[3,3,0]octane Systems as Potential Inhibitors of HIV Protease

The novel trans-3-oxabicyclo[3,3.0]octan-7-one system has been prepared by intramolecular ring closure of the corresponding cyclopentane diol. Peralkylation and benzylidene substitution of the octanone has allowed the preparation of tetra-alkylated potential inhibitors of HIV protease. Weak activity against HIV protease (IC50's 70-100μM) was observed.

PROCESSES AND INTERMEDIATES FOR PREPARING A MACROCYCLIC PROTEASE INHIBITOR OF HCV

Disclosed is a process for the preparation of certain intermediates, e.g. those in the scheme below: which intermediates and processes are useful in the preparation of the macrocyclic HVC inhibitor Simeprevir.

Synthesis and pharmacological characterization of aminocyclopentanetricarboxylic acids: New tools to discriminate between metabotropic glutamate receptor subtypes

The four stereoisomers of 1-aminocyclopentane-1,3,4-tricarboxylic acid {ACPT-I (18) and -II (19), (3R,4R)-III [(-)-20], and (3S,4S)-III [(+)-20]} have been synthesized and evaluated for their effects at glutamate receptors subtypes. ACPTs are ACPD analogues in which a third carboxylic group has been added at position 4 in the cyclopentane ring. None of the ACPT isomers showed a significant effect on ionotropic NMDA, KA, and AMPA receptors. On the other hand, ACPT-III (19) was found to be a general competitive antagonist for metabotropic receptors (mGluRs) and exhibited a similar affinity for mGluR1a (K(B) = 115 ± 2 μM), mGluR2 (K(B) = 88 ± 21 μM), and mGluR4a (K(B) = 77 ± 9 μM), the representative members of group I, II and III mGluRs, respectively. Two other isomers, ACPT-I (18) and (+)-(3S,4S)-ACPT-III [(+)- 20], were potent agonist at the group III receptors mGluR4a (EC50 = 7.2 ± 2.3 and 8.8 ± 3.2 μM) and competitive antagonists with low affinity for mGluR1a and mGluR2 (K(B) > 300 μM). Finally, (-)-(3R,4R)-ACPT-III [(-)-20] was a competitive antagonist with poor but significant affinity for mGluR4a (K(B) = 220 μM). These results demonstrate that the addition of a third carboxylic group to ACPD can change its activity (from agonist to antagonist) and either increase or decrease its selectivity and/or affinity for the various mGluR subtypes.

SYNTHESIS OF RING-ENLARGED CYCLOBUT-A AND CYCLOBUT-G ANALOGUES AS HIV INHIBITORS. PART 4

Two ring-expanded analogues (compounds 13 and 14) of the anti-HIV agents Cyclobut-A and Cyclobut-G are described.They were synthesized from trans-3,4-bis(hydroxymethyl)cyclobutylamine which was obtained from threo-3,4-bis(methoxycarbonyl)hexane dioic acid.Neither compound (13,14) was able to provide protection to CEM cells against HIV-1-infection.

Enzyme-Catalyzed Asymmetric Synthesis. 8. Enantioselectivity of Pig Liver Esterase Catalyzed Hydrolyses of 4-Substituted Meso Cyclopentane 1,2-Diesters

Hydrolyses of meso-1,2-cyclopentanedicarboxylic acid bis(methyl esters) bearing in the 4-position an oxo, methylene, cis-hydroxy, trans-hydroxy,cis-acetoxy, trans-acetoxy, cis-methoxy, cis-tert-butoxy, ethylenedioxy, propylenedioxy, dimethyl propylenediox

Diastereoselectivity of a Annulation. On the Question of a Dipole Effect on Diastereoselectivity of Olefin Addition

The stereochemistry of addition to γ-alkoxy-α,β-unsaturated carbonyl systems is examined in the context of a palladium catalyzed cycloaddition.

A SYNTHESIS OF (+/-)-BREFELDIN A

A macrolide antibiotic, brefeldin A, was synthesized from trans-4-oxocyclopentane-1,2-dicarboxylic acid in a stereoselective manner, the intermediary hydroxyl acid being lactonized by the mixed 2,4,6-trichlorobenzoic acid anhydride - 4-dimethylaminopyridi