154477-02-8

Basic information

• Product Name: 5-(4-methylphenyl)-4-pentyne-1-ol
• Synonyms: 5-(4-methylphenyl)-4-pentyne-1-ol
• CAS NO: 154477-02-8
• Molecular Weight: 174.243
• Mol File: 154477-02-8.mol

Chemical Properties

• CAS DataBase Reference: 5-(4-methylphenyl)-4-pentyne-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(4-methylphenyl)-4-pentyne-1-ol(154477-02-8)
• EPA Substance Registry System: 5-(4-methylphenyl)-4-pentyne-1-ol(154477-02-8)

Safety Data

• Hazardous Substances Data: 154477-02-8(Hazardous Substances Data)

Upstream product

• 5390-04-5 pent-1-yn-5-ol 
• 624-31-7 4-tolyl iodide 

Downstream Products

• 154477-04-0 5-(4-methylphenyl)pent-4-ynylamine 
• 1220285-50-6 3-(2-(4-methylphenyl)tetrahydro-2-furanyl)-1H-indole 
• 1208003-54-6 C₁₉H₂₂N₂O₂ 
• 1208003-51-3 C₁₉H₂₂N₂O₂ 
• 1379654-78-0 (Z)-5-(p-tolyl)pent-2-en-4-ynal 
• 1379654-77-9 (E)-5-(p-tolyl)pent-2-en-4-ynal 
• 1401463-80-6 1-methyl-1-(5-phenylpent-4-ynyl)-3H-imidazol-1-ium iodide 
• 1401463-74-8 1-(5-p-tolylpent-4-ynyl)-1H-imidazole 
• 1620403-85-1 C₂₁H₂₃NO₂ 
• 1620403-94-2 C₁₉H₂₁NO 
• 1620404-03-6 C₁₉H₂₀N₂O₂ 
• 1620404-12-7 C₂₀H₁₉NO₂ 
• 1620404-26-3 C₁₉H₁₉NO 
• 1620403-71-5 C₂₀H₂₁NO₂ 

Relevant articles and documents

NOVEL LYSOPHOSPHATIDIC ACID DERIVATIVE

PROBLEM TO BE SOLVED: To provide a compound that specifically activates an LPA4 receptor, and a pharmaceutical composition containing the same. SOLUTION: This invention relates to a novel lysophosphatidic acid derivative that has an agonistic action on an LPA4 receptor and is useful for the prevention and/or treatment of a disease with angiodysplasia caused by the LPA4 receptor, or a disease associated with angiopathy, or symptoms associated therewith. This invention also relates to a pharmaceutical composition containing the lysophosphatidic acid derivative. SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT

Palladium-Catalyzed Synthesis of Tricyclic Indoles via a N-S Bond Cleavage Strategy

In palladium/norbornene (Pd/NBE) chemistry, the "ortho effect"has been proven to be a key factor in the process of β-carbon elimination to extrude NBE. Herein, we found that the o-iodoaniline protected by a p-methoxybenzenesulfonyl group can recover the "

One-Pot Double-Annulation Strategy for the Synthesis of Unusual Fused Bis-Heterocycles

A novel metal-free double-annulation cascade for the construction of unusual fused heterocyclic systems is described. This simple protocol enables the sequential assembly of two rings in one pot from two simple precursors. Acidic conditions promote the condensation and the intramolecular alkynyl Prins reaction of an enyne or arenyne alcohol with a cyclic hemiaminal to form a five-, six-, or seven-membered oxacycle followed by a seven-or eight-membered azacycle. In this transformation, chemical complexity is rapidly generated with the formation of three new bonds (one C-O, one C-C, and one C-N) in one synthetic operation. The strategy is modular and relatively general, providing access to a series of unique fused bicyclic scaffolds.

Tetrahydroxydiboron-Promoted Radical Addition of Alkynols

Tetrahydroxydiboron has previously been used as a borylation or reducing reagent in organic synthesis. Herein, we present a novel tetrahydroxydiboron-promoted radical addition of internal alkynes followed by intramolecular oxidation of alcohol through 1,5-hydrogen atom transfer. Preliminary mechanistic studies showed that the process might be initiated through N,N-dimethylformamide-assisted homolytic cleavage of tetrahydroxydiboron. This process provides a convenient synthesis of fluoroalkyl-substituted alkenes with a pendant aldehyde or ketone moiety.

Enantioselective Formal C(sp3)?H Bond Activation in the Synthesis of Bioactive Spiropyrazolone Derivatives

Herein, we report the first enantioselective annulation of α-arylidene pyrazolones through a formal C(sp3)?H activation under mild conditions enabled by highly variable RhIII-Cpx catalysts. The method has a wide substrate scope and proceeds with good to excellent yields and enantioselectivities. Its synthetic utility was demonstrated by the late-stage functionalization of drugs and natural products as well as the preparation of enantioenriched [3]dendralenes. Preliminary biological investigations also identified the spiropyrazolones as a novel class of Hedgehog pathway inhibitors.

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.

Cu-catalyzed intramolecular aryl-etherification reactions of alkoxyl alkynes with diaryliodonium salts via cleavage of a stable C-O bond

A novel Cu-catalyzed intramolecular aryl-etherification reaction of alkoxyl alkynes with diaryliodonium salts is realized. The reactions proceed smoothly to produce valuable oxo-heterocycles with readily available linear starting materials via cleavage of a stable C-O bond. This journal is

Rh(III)-catalyzed intramolecular redox-neutral or oxidative cyclization of alkynes: Short, efficient synthesis of 3,4-fused indole skeletons

A Rh(III)-catalyzed intramolecular redox-neutral or oxidative annulation of a tethered alkyne has been developed to efficiently construct 3,4-fused indoles via a C-H activation pathway. The advantages of this process are (1) ready availability of annulation precursors; (2) broad substrate scope; (3) complete regioselectivity; (4) simple and mild reaction conditions; and (5) no need for an external oxidant or to employ molecular oxygen as the stoichiometric terminal oxidant.

Synthesis of bicyclic N,N-enaminals by cyclization of alk-4-ynals with aliphatic diamines in DMSO upon treatment with KOH

A cyclization of alk-4-ynals with aliphatic diamines in DMSO upon treatment with KOH was found to lead to bicyclic N,N-enaminals. The studies of this reaction showed that 1,3-diaminopropane and N-methyl-1,3-diaminopropane gave (E)-6-(arylmethylidene)octahydropyrrolo[1,2-a]pyrimidines in 45 - 78% yields, whereas 1,2-diaminoethane gave 5-(arylmethylidene)hexahydropyrrolo[1,2-a] imidazoles as mixtures of E- and Z-isomers in up to 75% total yield. The mechanism of these new cascade cyclization reactions includes formation of the equilibrium mixtures of imines and cyclic aminals with subsequent intramolecular hydroamination of the triple bond having considerable ionic character.

Intramolecular cyclization and subsequent rearrangements of alkyne-tethered N-heterocyclic carbenes

Alkyne-tethered imidazole and 1,2,4-triazole-based N-heterocyclic carbene precursors have been prepared and studies of the intramolecular reactions of carbenes are performed. Products consistent with intramolecular cyclizations and subsequent rearrangemen