29279-66-1

Usage

Uses

Used in Organic Synthesis:
(2-methylenecyclopropyl)methanol is used as a chemical intermediate for the synthesis of various larger molecules. Its unique structure allows it to be incorporated into complex organic compounds, making it a valuable component in the creation of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (2-methylenecyclopropyl)methanol is used as a building block for the development of new drugs. Its reactivity and structural features contribute to the synthesis of bioactive molecules with potential therapeutic applications.
Used in Agrochemical Industry:
(2-methylenecyclopropyl)methanol is also utilized in the agrochemical industry for the synthesis of pesticides and other crop protection agents. Its ability to form stable and effective compounds makes it a valuable asset in the development of innovative agrochemical products.
Safety Considerations:
As a flammable liquid, (2-methylenecyclopropyl)methanol requires careful handling to prevent accidents and ensure the safety of personnel and equipment. Exposure to (2-methylenecyclopropyl)methanol can result in skin and eye irritation, necessitating the implementation of appropriate safety measures and precautions during its use in any industry. Proper handling procedures, including the use of personal protective equipment and adherence to safety guidelines, are crucial when working with (2-methylenecyclopropyl)methanol.

InChI:InChI=1/C5H8O/c1-4-2-5(4)3-6/h5-6H,1-3H2

Upstream product

• 60329-10-4 2,2,2-triphenyl-3-oxa-2λ⁵-phosphabicyclo[3.1.0]hexane 
• 50-00-0 formaldehyd 
• 18941-94-1 2-methylene-cyclopropanecarboxylic acid ethyl ester 

Downstream Products

• 1012886-10-0 (E)-1-methylene-2-(3-phenylprop-2-enyl)cyclopropane 
• 86951-67-9 (R*)-<(1R*)-(Methylidenecyclopropyl)>cyclohexylmethanol 
• 86951-67-9 (R*)-<(1S*)-(Methylidenecyclopropyl)>cyclohexylmethanol 
• 2517-07-9 (2-methylenecyclopropyl)glycine 
• 502150-92-7 5-(2-methylenecyclopropyl)imidazolidine-2,4-dione 

Relevant academic research and scientific papers

Design of spiro[2.3]hex-1-ene, a genetically encodable double-strained alkene for superfast photoclick chemistry

Reactive yet stable alkene reporters offer a facile route to studying fast biological processes via the cycloaddition-based bioorthogonal reactions. Here, we report the design and synthesis of a strained spirocyclic alkene, spiro[2.3]hex-1-ene (Sph), for an accelerated photoclick chemistry, and its site-specific introduction into proteins via amber codon suppression using the wild-type pyrrolysyl-tRNA synthetase/tRNACUA pair. Because of its high ring strain and reduced steric hindrance, Sph exhibited fast reaction kinetics (k2 up to 34 000 M-1 s-1) in the photoclick chemistry and afforded rapid (10 s) bioorthogonal protein labeling.

Fluorinated methylenecyclopropane analogues of nucleosides. Synthesis and antiviral activity of (Z)- and (E)-9-{[(2-fluoromethyl-2-hydroxymethyl)-cyclopropylidene]methyl}adenine and -guanine

Synthesis and antiviral activity of the title fluoromethylenecyclopropane analogues 15a, 15b, 16a, and 16b is described. Methylenecyclopropane carboxylate was first transformed to 2,2-bis-hydroxymethylmethylenecyclopropane. Selective monoacetylation followed by introduction of fluorine gave 2-acetoxymethyl-2-fluoromethylmethylenecyclopropane as the key intermediate. The synthesis of analogues 15a, 15b, 16a, and 16b then followed alkylation-elimination procedure as described previously for other methylenecyclopropane analogues. The adenine Z-isomer 15a was found to be a potent inhibitor of Epstein-Barr virus (EBV) in vitro with EC50/CC50 (μM) 0.5/55.7. Compounds 15b, 16a, and 16b were also active but at higher concentrations, EC50/CC50 (μM) 3.2-7.5/53.6-64.1. Analogue 15a inhibited hepatitis C virus by virtue of its cytotoxicity and it moderately inhibited replication of the Towne strain of human cytomegalovirus (HCMV). The E-isomer 16a was a substrate for adenosine deaminase, whereas the Z-isomer 15a was not deaminated.

Bu2SnIH-promoted proximal bond cleavage of methylenecyclopropanes and successive radical cyclization and/or Pd-catalyzed coupling reaction

The unprecedented regioselective hydrostannation of methylenecyclopropanes to give vinyltins was achieved using dibutyliodotin hydride (Bu2SnIH), which could be applied to intramolecular radical cyclization. Copyright

Spiropentane Mimics of Nucleosides: Analogues of 2′-Deoxyadenosine and 2′-Deoxyguanosine. Synthesis of All Stereoisomers, Isomeric Assignment, and Biological Activity

Synthesis of spirocyclic analogues of 2′-deoxyadenosine and 2′-deoxyguanosine (12a-15a and 12b-15b) is described. Rhodium-catalyzed reaction of ethyl diazoacetate with methylenecyclopropane 19, obtained from 2-bromo-2-bromomethylcyclopropane 17 via debromination (16), reduction (18), and acetylation (19), gave a mixture of all four isomeric spiropentanes 20a-20d. Hydrolysis afforded hydroxy carboxylic acids 21a-21d. Acetylation of separated proximal + medial-syn isomers 21a + 21b and medial anti + distal isomers 21c + 21d furnished acetates 22a + 22b and 22c + 22d. Curtius rearrangement effected by diphenylphosphoryl azide in tert-butyl alcohol performed separately with mixtures 22a + 22b and 22c + 22d led to BOC-amino spiropentanes 23a + 23b and 23c + 23d. After deacetylation all isomers 24a-24d were separated and deprotected to give aminospiropentane hydrochlorides 25a-25d. Free bases were of limited stability. The heterocyclic moieties were introduced into individual isomers 25a-25d via 6-chloropurine derivatives 26a-26d or 30a-30d. Ammonolysis of 26a-26d furnished the adenine isomeric series 12a-15a, whereas guanine derivatives 12b-15b were obtained by hydrolysis of 30a-30d with formic acid. The isomeric assignments followed from IR spectra of BOC-aminospiropentanes 24a-24d and NMR spectra of 12a-15a including NOE and (H,H) COSY. The proximal and medial-syn isomers 12a and 12b were modest inhibitors of human cytomegalovirus (HCMV) and Epstein-Barr virus (EBV) in culture, whereas the medial-anti isomer 12c was a substrate for adenosine deaminase. The distal isomer 15b was an anti-EBV agent. The medial-syn phosphoralaninate 34 was an effective inhibitor of HCMV replication in vitro. It was also active against herpes simplex virus type 1 (HSV-1), varicella zoster virus (VZV), human immunodeficiency virus (HIV-1), hepatitis B virus (HBV), and EBV with a varying degree of cytotoxicity.