74639-50-2

Basic information

• Product Name: N-benzyloxycarbonyl-indole-3-carbaldehyde
• Synonyms: N-benzyloxycarbonyl-indole-3-carbaldehyde
• CAS NO: 74639-50-2
• Molecular Formula: C₁₇H₁₃NO₃
• Molecular Weight: 279
• Mol File: 74639-50-2.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-benzyloxycarbonyl-indole-3-carbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: N-benzyloxycarbonyl-indole-3-carbaldehyde(74639-50-2)
• EPA Substance Registry System: N-benzyloxycarbonyl-indole-3-carbaldehyde(74639-50-2)

Safety Data

• Hazardous Substances Data: 74639-50-2(Hazardous Substances Data)

Upstream product

• 487-89-8 Indole-3-carboxaldehyde 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 103871-33-6 N-carbobenzoxy-3-(l-chloroethyl)indole 
• 13786-41-9 (+/-) indolmycin 
• 61-54-1 tryptamine 
• 214541-53-4 (S)-3-(3-indolyl)butanoic acid 
• 74639-51-3 3-[(2R,3S)-3,4-Dimethyl-5,7-dioxo-2-phenyl-[1,4]oxazepan-(6E)-ylidenemethyl]-indole-1-carboxylic acid benzyl ester 
• 21200-24-8 (5S)-5-[(1R)-1-(1H-indol-3-yl)ethyl]-2-methylamino-2-oxazolin-4-one 
• 473918-94-4 N-carbobenzyloxy-4-iodo-indole-3-carboxaldehyde 

Relevant articles and documents

Diastereoselective synthesis of functionalised carbazoles via a sequential Diels-Alder/ene reaction strategy

An operationally simple one-pot, three-component, diastereoselective synthesis of saturated carbazoles and related pyridazino[3,4-b]indoles, based on two sequential intermolecular pericyclic reactions, is described. The reaction sequence involves an intermolecular Diels-Alder (D-A) reaction of a 3-vinyl-1H-indole, containing an electron withdrawing N-protecting group, with a suitable dienophile. Due to the electron withdrawing nature of the N-protecting group the resultant D-A cycloadducts are sufficiently stabilised to allow for a subsequent in situ diastereospecific intermolecular ene reaction to take place with an added enophile, generating functionalised carbazoles with relative stereocontrol of up to four stereocentres.

Unusual reactivity of nitronates with an aryl alkyl carbonate: Synthesis of α-amino esters

The monoanions of nitroalkanes are ambident nucleophiles that react with carbonate electrophiles through the oxygen atom. Products arising from reactivity at the carbon atom will yield α-nitro esters, which are precursors for α-amino esters. We demonstrate this in the reactions of nitroalkanes with benzyl phenyl carbonate and DABCO where α-nitro esters are obtained instead of nitrile oxides. The products are readily reduced to α-amino esters. This pathway could be a safe alternative to the Strecker reaction.

Structure-activity dependency of new bacterial tryptophanyl tRNA synthetase inhibitors

Analogues of the aminoacyl tRNA synthetase inhibitor, indolmycin, have been synthesised in which the side chain methyl group is replaced by a wide range of substituents. Their antibacterial and enzyme inhibitory potency is related to steric properties and