154188-75-7

Basic information

• Product Name: 1H-Isoindole-1,3(2H)-dione, 2-(5-phenyl-4-pentynyl)-
• CAS NO: 154188-75-7
• Molecular Formula: C19H15NO2
• Molecular Weight: 289.334
• Mol File: 154188-75-7.mol

Chemical Properties

• CAS DataBase Reference: 1H-Isoindole-1,3(2H)-dione, 2-(5-phenyl-4-pentynyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Isoindole-1,3(2H)-dione, 2-(5-phenyl-4-pentynyl)-(154188-75-7)
• EPA Substance Registry System: 1H-Isoindole-1,3(2H)-dione, 2-(5-phenyl-4-pentynyl)-(154188-75-7)

Safety Data

• Hazardous Substances Data: 154188-75-7(Hazardous Substances Data)

Upstream product

• 108-86-1 bromobenzene 
• 6097-07-0 N-(pent-4-ynyl)phthalimide 
• 136918-14-4 phthalimide 
• 28077-72-7 1-bromo-4-pentyne 
• 591-50-4 iodobenzene 
• 4440-01-1 lithium phenylacetylide 
• 24595-58-2 5-phenylpent-4-yn-1-ol 
• 92994-35-9 2-(5-phenylpent-4-ynyloxy)tetrahydro-2H-pyran 
• 14267-92-6 1-chloro-4-pentyne 
• 57718-13-5 (5-bromo-pent-1-ynyl)-benzene 
• 24463-87-4 (5-chloropent-1-ynyl)benzene 
• 1074-82-4 potassium phtalimide 

Downstream Products

• 127808-49-5 5-phenylpent-4-yn-1-amine 

Relevant articles and documents

Cobalt-Catalyzed Regioselective Carboamidation of Alkynes with Imides Enabled by Cleavage of C-N and C-C Bonds

Through the oxidative addition of cobalt into the N-C(O) bond of phthalimide and the subsequent decarbonylation, we describe an efficient cobalt-catalyzed intermolecular decarbonylative carboamidation of alkynes. High regioselectivities have been achieved for unsymmetrical alkynes (including aryl-alkyl or aryl-aryl) to deliver polysubstituted isoquinolones. To facilitate step economy, a three-component decarbonylative carboamidation of alkynes with phthalic anhydrides and amines has been demonstrated using the current cobalt catalysis.

A Drastic Effect of TEMPO in Zinc-Catalyzed Stannylation of Terminal Alkynes with Hydrostannanes via Dehydrogenation and Oxidative Dehydrogenation

With a system consisting of a catalytic zinc Lewis acid, pyridine, and TEMPO in a nitrile medium, terminal alkynes coupled with HSnBu3, providing alkynylstannanes with structural diversity. The resulting alkynylstannane, without being isolated, could be directly used for Pd- and Cu-catalyzed transformations to deliver internal alkynes and more intricate tin-atom-containing molecules. Mechanistic studies indicated that TEMPOSnBu3 formed in situ from TEMPO and HSnBu3 works to stannylate the terminal alkyne in collaboration with the zinc catalyst, and that both of dehydrogenation and oxidative dehydrogenation processes are uniquely involved in a single reaction. (Figure presented.).

Facile one-pot synthesis of 2,3-dihydro-1H-indolizinium derivatives by rhodium(iii)-catalyzed intramolecular oxidative annulation via C-H activation: application to ficuseptine synthesis

Various substituted indolizidinium, quinolizinium and pyrido[1,2-a]azepinium salts synthesized from benzaldehydes (or α,β-unsaturated aldehydes) and alkyne-amines catalyzed by rhodium complexes via C-H activation are demonstrated. The reaction was carried

Direct Conversion of Internal Alkynes into α-Iodoenones: One-Step Collaborative Iodination and Oxidation

The reaction of an internal alkyne with 2,6-dichloropyridine N-oxide, a nucleophilic oxidant, and electrophilic N-iodosuccinimide (NIS) simultaneously enables the direct access to versatile α-iodoenones. Electronically biased internal alkynes undergo the one-step transformation with excellent regioselectivities and with practical Z/E ratios. In comparison to the related oxidative gold catalysis using pyridine N-oxides, this reaction employs NIS as the stoichiometric ynophile instead of the soft acidic noble metal catalyst and affords products featuring an additional versatile C-I bond. Similar strategies for replacing ynophilic cationic gold(I) complexes in oxidative gold catalysis with likewise ynophilic stoichiometric electrophiles would enable the development of new synthetic methods.

Copper-catalyzed highly selective semihydrogenation of non-polar carbon-carbon multiple bonds using a silane and an alcohol

A copper catalyst bearing a suitable Xantphos derivative or NHC ligand was found to be highly efficient for the selective semihydrogenation of non-polar unsaturated compounds using a mixture of a silane and an alcohol as reducing agent. The catalytic system was useful for the selective semihydrogenation of internal alkynes to (Z)-alkenes with suppression of overreduction to the corresponding alkanes. Furthermore, semihydrogenations of terminal alkyne, 1,2-diene, 1,3-diene, 1,3-enyne and 1,3-diyne systems were also achieved selectively. Copyright

Rh(I)-catalyzed CO gas-free cyclohydrocarbonylation of alkynes with formaldehyde to α,β-butenolides

The rhodium(I)-catalyzed reaction of alkynes with formaldehyde proceeds via the double incorporation of a carbonyl moiety from formaldehyde, resulting in a CO gas-free cyclohydrocarbonylation leading to α,β-butenolides. The Royal Society of Chemistry 2005.

Induced chain alignment, efficient energy transfer, and enhanced light emission in functional poly acetylene-perovskite hybrids

The hybridization of functional polyacetylenes with lead bromide perovskite was investigated. It was observed that the perovskite induces the nonmesogenic polyactylene chains to align like liquid crystals within the inorganic layers. It was shown that pho

Organolanthanide-catalyzed intramolecular hydroamination/cyclization of aminoalkynes

This contribution reports the efficient and regiospecific Cp'2LnCH(SiMe3)2 (Ln = La, Nd, Sm, Lu; Cp' = η5-Me5C5)- and Me2SiCp''2LnCH(SiMe3)2 (Ln = Nd, Sm; Cp'' = η5-Me4C5)-catalyzed hydroamination/cyclization of aliphatic and aromatic aminoalkynes of the formula RC≡C(CH2)(n)NH2 to yield the corresponding cyclic imines RCH2C=N(CH2)(n-1)CH2, where R, n, N(t) h-1 (°C) = Ph, 3, 77 (21°C); Ph, 3, 2830 (60°C); Me, 3, 96 (21°C); CH2=CMeCH2, 3, 20 (21°C); H, 3, 580 (21°C); Ph, 4, 4 (21°C); Ph, 4, 328 (60°C); Ph, 5, 0.11 (60°C); and SiMe3, 3, >7600 (21°C), and of aliphatic secondary amino-alkynes of the formula RC≡C(CH2)3NHR1 to generate the corresponding cyclic enamines RCH=CNR1(CH2)2CH2 where R, R1, N(t) h-1 (°C) = SiMe3, CH2=CHCH2, 56 (21°C); H, CH2=CHCH2, 27 (21°C); SiMe3, CH2=CH(CH2)3, 129 (21°C); and H, CH2=CH(CH2)3, 47 (21°C). Kinetic and mechanistic evidence is presented arguing that the turnover-limiting step is an intramolecular alkyne insertion into the Ln-N bond followed by rapid protonolysis of the resulting Ln-C bond. The use of larger metal ionic radius Cp'2LnCH(SiMe3)2 and more open Me2SiCp''2LnCH(SiMe3)2 complexes as the precatalysts results in a decrease in the rate of hydroamination/cyclization, arguing that the steric demands in the -C≡C- insertive transition state are relaxed compared to those of the analogous aminoolefin hydroamination/cyclization.