84590-48-7

Basic information

• Product Name: (2R,5R)-5-(hydroxymethyl)-1-methyl-2-(propan-2-yl)-1,2,4,5,6,8-hexahydro-3H-[1,4]diazonino[7,6,5-cd]indol-3-one
• CAS NO: 84590-48-7
• Molecular Formula: C₁₇H₂₃N₃O₂
• Molecular Weight: 301.3834
• Mol File: 84590-48-7.mol
• Article Data: 24

Chemical Properties

• Boiling Point: 584°C at 760 mmHg
• Flash Point: 307°C
• Density: 1.166g/cm³
• Vapor Pressure: 1.75E-14mmHg at 25°C
• Refractive Index: 1.589
• CAS DataBase Reference: (2R,5R)-5-(hydroxymethyl)-1-methyl-2-(propan-2-yl)-1,2,4,5,6,8-hexahydro-3H-[1,4]diazonino[7,6,5-cd]indol-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,5R)-5-(hydroxymethyl)-1-methyl-2-(propan-2-yl)-1,2,4,5,6,8-hexahydro-3H-[1,4]diazonino[7,6,5-cd]indol-3-one(84590-48-7)
• EPA Substance Registry System: (2R,5R)-5-(hydroxymethyl)-1-methyl-2-(propan-2-yl)-1,2,4,5,6,8-hexahydro-3H-[1,4]diazonino[7,6,5-cd]indol-3-one(84590-48-7)

Safety Data

• Hazardous Substances Data: 84590-48-7(Hazardous Substances Data)

Upstream product

• 148114-79-8 4-[((S)-1-tert-Butoxycarbonyl-2-methyl-propyl)-methyl-amino]-3-hydroxymethyl-indole-1-carboxylic acid tert-butyl ester 
• 148114-80-1 3-Bromomethyl-4-[((S)-1-tert-butoxycarbonyl-2-methyl-propyl)-methyl-amino]-indole-1-carboxylic acid tert-butyl ester 
• 148114-81-2 4-[((S)-1-tert-Butoxycarbonyl-2-methyl-propyl)-methyl-amino]-3-((2S,5R)-5-isopropyl-3,6-dimethoxy-2,5-dihydro-pyrazin-2-ylmethyl)-indole-1-carboxylic acid tert-butyl ester 
• 7524-52-9 (S)-tryptophan methyl ester hydrochloride 
• 50-00-0 formaldehyd 
• 606-22-4 2,6-dinitroaniline 
• 84590-47-6 (S)-13-Hydroxymethyl-10-isopropyl-3,9,12-triaza-tricyclo[6.6.1.0^4,15]pentadeca-1,4⁽¹⁵⁾,5,7-tetraen-11-one 
• 74-88-4 methyl iodide 
• 84590-47-6 (+)-N¹³-desmethylindolactam-V 
• 84590-47-6 (10S,13R)-13-Hydroxymethyl-10-isopropyl-3,9,12-triaza-tricyclo[6.6.1.0^4,15]pentadeca-1,4⁽¹⁵⁾,5,7-tetraen-11-one 
• 132292-21-8 2-[3-(2-Methoxycarbonyl-2-nitro-ethyl)-1H-indol-4-ylamino]-3-methyl-butyric acid 

Downstream Products

• 107783-16-4 blastmycetin A 
• 119375-01-8 (-)-pendolmycin 
• 70497-14-2 Lyngbyatoxin A 
• 112775-93-6 14-O-acetyl-7-styrylindolactam-V 
• 112775-94-7 14-O-acetyl-7-phenetylindolactam-V 

Relevant articles and documents

Exploiting a C–N Bond Forming Cytochrome P450 Monooxygenase for C–S Bond Formation

C–S bond formation reactions are widely distributed in the biosynthesis of biologically active molecules, and thus have received much attention over the past decades. Herein, we report intramolecular C–S bond formation by a P450 monooxygenase, TleB, which normally catalyzes a C?N bond formation in teleocidin biosynthesis. Based on the proposed reaction mechanism of TleB, a thiol-substituted substrate analogue was synthesized and tested in the enzyme reaction, which afforded the unprecedented sulfur-containing thio-indolactam V, in addition to an unusual indole-fused 6/5/8-tricyclic product whose structure was determined by the crystalline sponge method. Interestingly, conformational analysis revealed that the SOFA conformation is stable in thio-indolactam V, in sharp contrast to the major TWIST form in indolactam V, resulting in differences in their biological activities.

11-Step Total Synthesis of Teleocidins B-1-B-4

A unified and modular approach to the teleocidin B family of natural products is presented that proceeds in 11 steps and features an array of interesting strategies and methods. Indolactam V, the known biosynthetic precursor to this family, was accessed through electrochemical amination, Cu-mediated aziridine opening, and a remarkable base-induced macrolactamization. Guided by a desire to minimize concession steps, the tactical combination of C-H borylation and a Sigman-Heck transform enabled the convergent, stereocontrolled synthesis of the teleocidins.

Modular Total Synthesis of Protein Kinase C Activator (-)-Indolactam v

A concise, eight-step total synthesis of (-)-indolactam V, a nanomolar agonist of protein kinase C, is reported. The synthesis relies upon an efficient copper-catalyzed amino acid arylation to establish the indole C4-nitrogen bond. This cross-coupling met