106352-19-6

Usage

InChI:InChI=1/C10H14O4/c1-4-13-8(11)10(6-7(10)3)9(12)14-5-2/h3-6H2,1-2H3

Upstream product

• 13830-91-6 diethyl bromoisopropylidenemalonate 
• 865-47-4 potassium tert-butylate 
• 75-65-0 tert-butyl alcohol 
• 841275-59-0 diethyl 1-(phenylselenyl)methylcyclopropane-2,2-dicarboxylate selenium oxide 
• 144296-42-4 2-iodomethyl-cyclopropane-1,1-dicarboxylic acid diethyl ester 
• 167401-82-3 diethyl 1-(phenylselenyl)methylcyclopropane-2,2-dicarboxylate 
• 6802-75-1 diethyl isopropylidenemalonate 

Relevant academic research and scientific papers

Catalytic [3 + 2] Cycloaddition through Ring Cleavage of Simple Cyclopropanes with Isocyanates

The catalytic synthesis of γ-butyrolactams was established via [3 + 2]-cycloaddition of cyclopropanes with isocyanates. An organotin iodide ate complex, MgBr+[Bu2SnBrI2]-, was employed as an effective catalyst. Simple cyclopropanes that lack aryl or vinyl substituents were useful precursors. Even acyl cyclopropanes were applicable. The hybrid characteristics of a tin complex, acidic MgBr+ with nucleophilic tin iodide, was responsible for the catalytic reaction.

Synthesis and Antiviral Activity of (Z)- and (E)-2,2-[Bis(hydroxymethyl)cyclopropylidene]methylpurines and -pyrimidines: Second-Generation Methylenecyclopropane Analogues of Nucleosides

The second generation of methylenecyclopropane analogues of nucleosides 5a-5i and 6a-6i was synthesized and evaluated for antiviral activity. The 2,2-bis(hydroxymethyl)methylenecyclopropane (11) was converted to dibromo derivative 7 via acetate 12. Alkylation-elimination of adenine (16) with 7 afforded the Z/E mixture of acetates 17 + 18, which was deacetylated to give analogues 5a and 6a separated by chromatography. A similar reaction with 2-amino-6-chloropurine (19) afforded acetates 20 + 21 and, after deprotection and separation, isomers 5f and 6f. The latter served as starting materials for synthesis of analogues 5b, 5e, 5g-5i and 6b, 6e, 6g-6i. Alkylation-elimination of N4-acetylcytosine (22) with 7 afforded a mixture of isomers 5c + 6c which were separated via N4-benzoyl derivatives 23 and 24. Deprotection furnished analogues 5c and 6c. Alkylation of 2,4-bis(trimethylsilyloxy)-5-methylpyrimidine (25) with 7 led to bromo derivative 26. Elimination of HBr followed by deacetylation and separation gave thymine analogues 5d and 6d. The guanine Z-isomer 5b was the most effective against human and murine cytomegalovirus (HCMV and MCMV) with EC50 = 0.27-0.49 μM and no cytotoxicity. The 6-methoxy analogue 5g was also active (EC50 = 2.0-3.5 μM) whereas adenine Z-isomer 5a was less potent (EC50 = 3.6-11.7 μM). Cytosine analogue 5c was moderately effective, but 2-amino-6-cyclopropylamino derivative 5e was inactive. All E-isomers were devoid of anti-CMV activity, and none of the analogues was significantly active against herpes simplex viruses (HSV-1 or HSV-2). The potency against Epstein-Barr virus (EBV) was assay-dependent. In Daudi cells, the E-isomers of 2-amino-6-cyclopropylamino- and 2,6-diaminopurine derivatives 6e and 6h were the most potent (EC50 ≈ 0.3 μM), whereas only the thymine Z-isomer 5d was active (EC50 = 4.6 μM). Guanine Z-derivative 5b was the most effective compound in H-1 cells (EC50 = 7 μM). In the Z-series, the 2-amino-6-methoxypurine analogue 5g was the most effective against varicella zoster virus (VZV, EC50 = 3.3 μM) and 2,6-diaminopurine 5h against hepatitis B virus (HBV, EC50 = 4 μM). Adenine analogues 5a and 6a were moderately active as substrates for adenosine deaminase.

Catalytic Annulation of Diethyl Methylenecyclopropane-1,1-dicarboxylate with 1,1-Dicyanoalkenes

The catalytic annulation of methylenecyclopropane 1 with 1,1-dicyanoalkenes 2 using a Mg-Sn catalytic system was developed. Selective formation of cyclopentylidenemalonates 3 and spiro[2,3]hexane-1,1-dicarboxylates 4 was accomplished via the choice of a proper solvent and an effective catalytic system.

Diastereoselective Synthesis of Spiro[2.3]hexanes from Methylenecyclopropane and Cyanoalkenes Catalyzed by a Tin-Ate Complex

A diastereoselective synthesis of spiro[2.3]hexane catalyzed by Sn and Mg halides was developed from a combination of methylenecyclopropane and cyanoalkene bearing an ester group. The selectivity was affected by the size of the halogen in the catalyst and

Magnesium Halide-Catalyzed Synthesis of Oxaspiro[2.5]octenes from a Methylenecyclopropane and Acyl Cyanoalkenes

MgX2-catalyzed annulation of methylenecyclopropanes with acyl cyanoalkenes was accomplished to give oxaspiro[2.5]octenes in excellent yields. The reaction proceeded through a rare intramolecular oxa-Michael addition of Mg enolate. The oxaspiro

Nucleotides and pronucleotides of 2,2-bis(hydroxymethyl) methylenecyclopropane analogues of purine nucleosides: Synthesis and antiviral activity

Phenylmethylphosphor-L-alaninate pronucleotides 7a, 7b, 8a, and 8b, cyclic phosphates 10a and 10b, and phosphates 11a and 11b derived from 2,2-bis(hydroxymethyl)methylenecyclopropane analogues 1a, 1b, 2a, and 2b were synthesized and evaluated for their an

2,2-bis-(hydroxymethyl)cyclopropylidenemethyl-purines and pyrmindines as antiviral agents

Compounds which are active against viruses have the following formulas: wherein B is a purine or pyrimidine heterocyclic ring or base. In a preferred embodiment, the purine include 6-aminopurine (adenine), 6-hydroxypurine (hypoxanthine), 2-amino-6-hydroxypurine (guanine), 2,6-diamino-purine, 2-amino-6-azidopurine, 2-amino-6-halo substituted purines such as 2-amino-6-chloropurine, 2-amino-6-fluoropurine, 2-amino-6-alkoxypurines such as 2-amino-6-methoxypurine, 2-amino-6-cyclopropylaminopurine, 2-amino-6-alkylamino or 2-amino-6-dialkylamino substituted purines, 2-amino-6-thiopurine, 2-amino-6-alkylthio substituted purines, 3-deazapurines, 7-deazapurines and 8-azapurines. The pyrimidine incorporates cytosine, uracil and thymine, 5-halo substituted cytosines and uracils, 5-alkyl substituted cytosines and uracils including derivatives with a saturated or unsaturated alkyl group and 6-azapyrimidines.