151978-50-6

Usage

Uses

Used in Organic Synthesis:
Carbamic acid, 4-pentynyl-, 1,1-dimethylethyl ester (9CI) is used as a reagent in organic synthesis for its ability to participate in various chemical reactions. Its unique structure allows it to be a versatile building block in the creation of more complex organic compounds.
Used in Pharmaceutical Production:
In the pharmaceutical industry, Carbamic acid, 4-pentynyl-, 1,1-dimethylethyl ester (9CI) is used as a key intermediate in the synthesis of certain drugs. Its involvement in the production process contributes to the development of new and innovative pharmaceuticals.
Used in Agrochemical Production:
Similarly, in the agrochemical industry, Carbamic acid, 4-pentynyl-, 1,1-dimethylethyl ester (9CI) is utilized as a reagent in the synthesis of various agrochemicals. Its application in this field aids in the development of effective and targeted agrochemicals for agricultural use.

Upstream product

• 6097-07-0 N-(pent-4-ynyl)phthalimide 
• 199276-58-9 pent-4-ynyl-1-azide 
• 5390-04-5 pent-1-yn-5-ol 
• 68275-03-6 pent-4-yn-1-yl methanesulfonate 
• 53293-00-8 hex-5-ynoic acid 
• 75-65-0 tert-butyl alcohol 
• 19596-07-7 pent-4-ynenitrile 
• 24424-99-5 di-tert-butyl dicarbonate 
• 15252-44-5 1-amino-pent-4-yne 
• 1360804-76-7 C₁₄H₂₁NO₅ 

Downstream Products

• 1312304-11-2 tert-butyl 3-(5-(3,4-dimethoxyphenylcarbamoyl)-1H-indol-2-yl)propylcarbamate 
• 1312304-12-3 2-(3-amino-propyl)-1H-indole-5-carboxylic acid (3,4-dimethoxy-phenyl)-amide 
• 1312304-15-6 {5-[2-amino-5-(3,4-dimethoxy-phenylcarbamoyl)-phenyl]-pent-4-ynyl}-methyl-carbamic acid tert-butyl ester 
• 1312304-16-7 tert-butyl 3-(5-(3,4-dimethoxyphenylcarbamoyl)-1H-indol-2-yl)propyl(methyl)carbamate 
• 1312304-17-8 2-(3-methylamino-propyl)-1H-indole-5-carboxylic acid (3,4-dimethoxy-phenyl)-amide 
• 1312304-10-1 {5-[2-amino-5-(3,4-dimethoxy-phenylcarbamoyl)-phenyl]-pent-4-ynyl}-carbamic acid tert-butyl ester 
• 1360804-75-6 benzyl 4-(5-tert-butoxycarbonylaminopent-1-yn-1-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate 
• 1360804-80-3 tert-butyl 5-[1-(3-(2-o-tolyl-1,3-dioxolan-2-yl)propyl)piperidin-4-yl]pentylcarbamate 
• 1445985-50-1 tert-butyl 5-(2,5-dichloro-4-formylphenyl)pentylcarbamate 
• 1445985-51-2 tert-butyl 5-(2,5-dichloro-4-(hydroxymethyl)phenyl)pentylcarbamate 
• 1445985-52-3 tert-butyl 5-(4-(bromomethyl)-2,5-dichlorophenyl)pentylcarbamate 
• 1445985-53-4 (R)-tert-butyl 5-(2,5-dichloro-4-((4-(4-cyclopropyl-1,2,3,4-tetrahydroquinoxaline-1-carbonyl)thiazolidin-3-yl)methyl)phenyl)pentylcarbamate 

Relevant academic research and scientific papers

Substituted Tetraethynylethylene–Tetravinylethylene Hybrids

A general synthetic approach to molecular structures that are hybrids of tetraethynylethylene (TEE) and tetravinylethylene (TVE) is reported. The synthesis permits the controlled preparation of many previously inaccessible structures, including examples w

Hexayne Amphiphiles and Bolaamphiphiles

Oligoynes with two or more conjugated carbon–carbon triple bonds are useful precursors for carbon-rich nanomaterials. However, their range of applications has so far been severely limited by the challenging syntheses, particularly in the case of oligoynes

A Commercially Available and User-Friendly Catalyst for Hydroamination Reactions under Technical Conditions

The activity of a simple, commercially available copper salt, [Cu(NCMe)4](BF4) in intramolecular hydroamination reactions of alkynes and allenes is presented. Reactions were successfully carried out in technical acetonitrile in the presence of air. While attempts of alkene hydroamination failed, this catalyst was also found active in intermolecular aza-Michael reactions.

Regioselectivity Influences in Platinum-Catalyzed Intramolecular Alkyne O-H and N-H Additions

The steric and electronic drivers of regioselectivity in platinum-catalyzed intramolecular hydroalkoxylation are elucidated. A branch point is found that divides the process between 5-exo and 6-endo selective processes, and enol ethers can be accessed in good yields for both oxygen heterocycles. The main influence arises from an electronic effect, where the alkyne substituent induces a polarization of the alkyne that leads to preferential heteroatom attack at the more electron-deficient carbon. The electronic effects are studied in other contexts, including hydroacyloxylation and hydroamination, and similar trends in directionality are predominant although not uniformly observed.

Photocatalytic Oxyamination of Alkenes: Copper(II) Salts as Terminal Oxidants in Photoredox Catalysis

A photocatalytic method for the oxyamination of alkenes using simple nucleophilic nitrogen atom sources in place of prefunctionalized electrophilic nitrogen atom donors is reported. Copper(II) is an inexpensive, practical, and uniquely effective terminal oxidant for this process. In contrast to oxygen, peroxides, and similar oxidants commonly utilized in non-photochemical oxidative methods, the use of copper(II) as a terminal oxidant in photoredox reactions avoids the formation of reactive heteroatom-centered radical intermediates that can be incompatible with electron-rich functional groups. As a demonstration of the generality of this concept, it has been shown that diamination and deoxygenation reactions can also be accomplished using similar photooxidative conditions.

Design of Gut-Restricted Thiazolidine Agonists of G Protein-Coupled Bile Acid Receptor 1 (GPBAR1, TGR5)

Bile acid signaling and metabolism in the gastrointestinal tract have wide-ranging influences on systemic disease. G protein-coupled bile acid receptor 1 (GPBAR1, TGR5) is one of the major effectors in bile acid sensing, with demonstrated influence on metabolic, inflammatory, and proliferative processes. The pharmacologic utility of TGR5 agonists has been limited by systemic target-related effects such as excessive gallbladder filling and blockade of gallbladder emptying. Gut-restricted TGR5 agonists, however, have the potential to avoid these side effects and consequently be developed into drugs with acceptable safety profiles. We describe the discovery and optimization of a series of gut-restricted TGR5 agonists that elicit a potent response in mice, with minimal gallbladder-related effects. The series includes 12 (TGR5 EC50: human, 143 nM; mouse, 1.2 nM), a compound with minimal systemic availability that may have therapeutic value to patients with type 2 diabetes mellitus, nonalcoholic steatohepatitis, or inflammatory bowel disease.

Ruthenium-catalyzed hydroamination of aminoallenes: An approach to vinyl substituted heterocycles

Heterosubstituted aminoallenes underwent smooth ruthenium-catalyzed intramolecular exo-hydroamination reactions yielding the corresponding five-, six-, or seven-membered 1,3-diaza- or 1,3-oxaza-heterocyclic structures. This procedure is a valuable and less expensive alternative to the already known transition metal-catalyzed hydroamination reactions of aminoallenes.

NON-SYSTEMIC TGR5 AGONISTS

Compounds of structure (I), or a stereoisomer, tautomer, pharmaceutically acceptable salt or prodrug thereof, wherein R1, R2, R3, R4, R8, R9, R10, R11, R12, A1, A2, X, Y and Z are as defined herein. Uses of such compounds as TGR5 antagonists and for treatment of various indications, including Type II diabetes meletus are also provided.

Fluorescent derivatives of AC-42 to probe bitopic orthosteric/allosteric binding mechanisms on muscarinic M1 receptors

Two fluorescent derivatives of the M1 muscarinic selective agonist AC-42 were synthesized by coupling the lissamine rhodamine B fluorophore (in ortho and para positions) to AC42-NH2. This precursor, prepared according to an original seven-step procedure, was included in the study together with the LRB fluorophore (alone or linked to an alkyl chain). All these compounds are antagonists, but examination of their ability to inhibit or modulate orthosteric [3H]NMS binding revealed that para-LRB-AC42 shared several properties with AC-42. Carefully designed experiments allowed para-LRB-AC42 to be used as a FRET tracer on EGFP-fused M1 receptors. Under equilibrium binding conditions, orthosteric ligands, AC-42, and the allosteric modulator gallamine behaved as competitors of para-LRB-AC42 binding whereas other allosteric compounds such as WIN 51,708 and N-desmethylclozapine were noncompetitive inhibitors. Finally, molecular modeling studies focused on putative orthosteric/allosteric bitopic poses for AC-42 and para-LRB-AC42 in a 3D model of the human M1 receptor.

Propylphosphonic anhydride (T3P)-mediated one-pot rearrangement of carboxylic acids to carbamates

A simple one-pot conversion of carboxylic acids to carbamates is achieved by propylphosphonic anhydride (T3P) in combination with azidotrimethylsilane and an alcohol via the Curtius rearrangement. Besides diverse primary to tertiary alcohols, t