4969-01-1

Basic information

• Product Name: 1,4-dioxaspiro[4.5]decan-9-one
• Synonyms: 1,4-dioxaspiro[4.5]decan-9-one;1,4-Dioxaspiro[4.5]decan-7-one
• CAS NO: 4969-01-1
• Molecular Formula: C₈H₁₂O₃
• Molecular Weight: 156.18
• Mol File: 4969-01-1.mol

Chemical Properties

• Boiling Point: 261.4°C at 760 mmHg
• Flash Point: 102.5°C
• Appearance: /
• Density: 1.16g/cm³
• Vapor Pressure: 0.0116mmHg at 25°C
• Refractive Index: 1.489
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• CAS DataBase Reference: 1,4-dioxaspiro[4.5]decan-9-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-dioxaspiro[4.5]decan-9-one(4969-01-1)
• EPA Substance Registry System: 1,4-dioxaspiro[4.5]decan-9-one(4969-01-1)

Safety Data

• Hazardous Substances Data: 4969-01-1(Hazardous Substances Data)

Usage

Uses

1. Used in Pharmaceutical Industry:
1,4-dioxaspiro[4.5]decan-9-one is used as a chemical reagent for the preparation of rhodesain inhibitors. These inhibitors play a crucial role in combating trypanosoma brucei parasites, which are responsible for causing African sleeping sickness. 1,4-dioxaspiro[4.5]decan-9-one's ability to inhibit the enzyme rhodesain makes it a valuable asset in the development of treatments for this disease.
2. Used in Chemical Synthesis:
Due to its unique structure, 1,4-dioxaspiro[4.5]decan-9-one can be utilized as an intermediate in the synthesis of various complex organic compounds. Its versatility in chemical reactions allows it to be a valuable building block for the creation of new molecules with potential applications in different industries, such as pharmaceuticals, agrochemicals, and materials science.
3. Used in Research and Development:
1,4-dioxaspiro[4.5]decan-9-one's unique properties make it an interesting subject for research and development in the field of organic chemistry. Scientists and researchers can explore its potential applications in various areas, such as drug discovery, material development, and the creation of novel chemical processes.

InChI:InChI=1/C8H12O3/c9-7-2-1-3-8(6-7)10-4-5-11-8/h1-6H2

Upstream product

• 504-02-9 1,3-cylohexanedione 
• 73223-83-3 1,4-dioxaspiro[4,5]decan-9-ol 
• 107-21-1 ethylene glycol 
• 159888-59-2 2-bromo-3-oxo-cyclohexanone ethylene acetal 
• 1004-58-6 1,4-dioxa-spiro[4.5]dec-6-ene 
• 62906-51-8 2-Brom-3-hydroxycyclohexanon-ethylenketal 
• 19770-37-7 6,7-epoxy-1,4-dioxaspiro<4,5>decane 
• 1728-15-0 (R,S)-6-bromo-1,4-dioxaspiro<4.5>decane 

Downstream Products

• 25017-78-1 3-cyano-2-cyclohexenone 
• 65093-64-3 ethyl 2-(3-oxocyclohex-1-en-1-yl)acetate 
• 73223-83-3 1,4-dioxaspiro[4,5]decan-9-ol 
• 108932-40-7 3-(3'-Thienyl)-2-cyclohexen-1-one 
• 104598-81-4 7-methylene-1,4-dioxaspiro<4.5>decane 
• 504-02-9 1,3-cylohexanedione 
• 25444-79-5 3-hydroxy-3-phenylcyclohexanone 
• 885461-97-2 3-allyl-3-(tert-butyl-dimethyl-silanyloxy)-cyclohexanone 
• 868673-66-9 (+/-)-3-allyl-3-benzyloxy-cyclohexanone 
• 868673-65-8 (+/-)-3-allyl-3-(tert-butyldimethylsilanyloxy)cyclohexanone 
• 868673-64-7 (+/-)-7-allyl-7-benzyloxy-1,4-dioxaspiro[4.5]decane 
• 86437-21-0 3-hydroxy-3-prop-2-enylcyclohexan-1-one 
• 147972-79-0 Ethyl (1-hydroxy-3-oxocyclohexyl)acetate 

Relevant articles and documents

Drug delivery to the malaria parasite using an arterolane-like scaffold

Antimalarial agents artemisinin and arterolane act via initial reduction of a peroxide bond in a process likely mediated by ferrous iron sources in the parasite. Here, we report the synthesis and antiplasmodial activity of arterolane-like 1,2,4-trioxolanes specifically designed to release a tethered drug species within the malaria parasite. Compared with our earlier drug delivery scaffolds, these new arterolane-inspired systems are of significantly decreased molecular weight and possess superior metabolic stability. We describe an efficient, concise and scalable synthesis of the new systems, and demonstrate the use of the aminonucleoside antibiotic puromycin as a chemo/biomarker to validate successful drug release in live Plasmodium falciparum parasites. Together, the improved drug-like properties, more efficient synthesis, and proof of concept using puromycin, suggests these new molecules as improved vehicles for targeted drug delivery to the malaria parasite.

SPIROCYCLIC TETRAHYDROQUINAZOLINES

Provided are compounds represented by Formula I, wherein R3, A, A1, A2, A3, E, E1, E2, L, Q, Z, and (aa) are as defined in the specification, and the pharmaceutically acceptable salts and solvates thereof. Compounds of Formula (I) are KRAS inhibitors and are thus useful to treat cancer and other diseases.

Spirocyclic tetrahydroquinazolines

The invention discloses spirocyclic tetrahydroquinazolines , and particularly provide compounds represented by Formula I shown in the specification, and pharmaceutically acceptable salts and solvates thereof. In the formula, R3, A, A1, A2, A3, E, E1, E2, L, Q, Z and a structure shown in the specification are as defined in the specification,. The compounds of formula I are KRAS inhibitors and are therefore useful in the treatment of cancer and other diseases.

Ring-opening reactions of donor-acceptor cyclopropanes with cyclic ketals and thiol ketals

1,3-Cyclohexandione derived cyclic ketals and thiol ketals were used as O- and S-nucleophiles, respectively, for the ring opening of donor-acceptor cyclopropanes catalyzed by Cu(OTf)2 and a series of functionalized alkylene glycol diethers and dithiol diethers were obtained in good to high yields under mild conditions. This journal is

TRPV4 ANTAGONIST

The present invention relates to a novel compound useful as a TRPV4 antagonist, specifically the compound 1-(((5S,7R)-3-(5-cyclopropylpyrazin-2-yl)-7-hydroxy-2-oxo-1-oxa-3-azaspiro[4.5]decan-7-yl)methyl)-1H-benzo[d]imidazole-6-carbonitrile, pharmaceutically acceptable salts thereof and pharmaceutical compositions containing the compound. The compound of the invention can be useful in the treatment of a disease state selected from: atherosclerosis, disorders related to vasogenic edema, postsurgical abdominal edema, ocular edema, cerebral edema, local and systemic edema, fluid retention, sepsis, hypertension, inflammation, bone related dysfunctions and congestive heart failure, pulmonary disorders, chronic obstructive pulmonary disorder, ventilator induced lung injury, high altitude induced pulmonary edema, acute respiratory distress syndrome, acute lung injury, pulmonary fibrosis, sinusitis/rhinitis, asthma, cough; including acute cough, sub-acute cough and chronic cough, pulmonary hypertension, overactive bladder, cystitis, pain, motor neuron disorders, genetic gain of function disorders, cardiovascular disease, renal dysfunction, stroke, glaucoma, retinopathy, endometriosis, pre-term labor, dermatitis, pruritus, pruritus in liver disease, diabetes, metabolic disorder, obesity, migraine, pancreatitis, tumor suppression, immunosuppression, osteoarthritis, crohn's disease, colitis, diarrhea, intestinal irregularity (hyperreactivity/hyporeactivity), fecal incontinence, irritable bowel syndrome (IBS), constipation, intestinal pain and cramping, celiac disease, lactose intolerance, and flatulence.

Stereoelectronic Model to Explain Highly Stereoselective Reactions of Seven-Membered-Ring Oxocarbenium-Ion Intermediates

Nucleophilic attack on seven-membered-ring oxocarbenium ions is generally highly stereoselective. The preferred mode of nucleophilic attack forms the product in a conformation that minimizes transannular interactions, thus leading to different stereoselectivity as compared to that of reactions involving six-membered-ring oxocarbenium ions.

Substituted cyclic ketoenols spiroketal

Spiroketal-substituted cyclic ketoenol compounds (I) are new. Spiroketal-substituted cyclic ketoenol compounds of formula (I) are new. W 1> : H, (halo)alkyl, alkenyl, alkynyl, (halo)alkoxy, halo, alkenyloxy or CN; X : halo, (halo)alkyl, alkenyl, alkynyl,

Optimization of Triazine Nitriles as Rhodesain Inhibitors: Structure-Activity Relationships, Bioisosteric Imidazopyridine Nitriles, and X-ray Crystal Structure Analysis with Human CathepsinL

The cysteine protease rhodesain of Trypanosoma brucei parasites causing African sleeping sickness has emerged as a target for the development of new drug candidates. Based on a triazine nitrile moiety as electrophilic headgroup, optimization studies on the substituents for the S1, S2, and S3 pockets of the enzyme were performed using structure-based design and resulted in inhibitors with inhibition constants in the single-digit nanomolar range. Comprehensive structure-activity relationships clarified the binding preferences of the individual pockets of the active site. The S1 pocket tolerates various substituents with a preference for flexible and basic side chains. Variation of the S2 substituent led to high-affinity ligands with inhibition constants down to 2nM for compounds bearing cyclohexyl substituents. Systematic investigations on the S3 pocket revealed its potential to achieve high activities with aromatic vectors that undergo stacking interactions with the planar peptide backbone forming part of the pocket. X-ray crystal structure analysis with the structurally related enzyme human cathepsinL confirmed the binding mode of the triazine ligand series as proposed by molecular modeling. Sub-micromolar inhibition of the proliferation of cultured parasites was achieved for ligands decorated with the best substituents identified through the optimization cycles. In cell-based assays, the introduction of a basic side chain on the inhibitors resulted in a 35-fold increase in antitrypanosomal activity. Finally, bioisosteric imidazopyridine nitriles were studied in order to prevent off-target effects with unselective nucleophiles by decreasing the inherent electrophilicity of the triazine nitrile headgroup. Using this ligand, the stabilization by intramolecular hydrogen bonding of the thioimidate intermediate, formed upon attack of the catalytic cysteine residue, compensates for the lower reactivity of the headgroup. The imidazopyridine nitrile ligand showed excellent stability toward the thiol nucleophile glutathione in a quantitative invitro assay and fourfold lower cytotoxicity than the parent triazine nitrile.

Bicyclo[3.2.1]Octanes via McMurry couplings

A novel approach to the synthesis of bicyclo[3.2.1]octane systems is described. The key step involves the McMurry coupling of ketoaldehyde 7 which leads to the bridgehead dihydroxybicyclo[3.2.1]octane 8.

Synthesis and structure of tetraols with convergent and divergent arrays of hydroxy groups

As hydrogen-bonding hosts with a partially flexible framework, two types of tetrahydroxy compounds with respectively convergent and divergent arrays of hydroxy groups were prepared. The structures of the tetraol with a diethyleneoxy bridge (1a), and that