105748-58-1

Basic information

• Product Name: 2-(methylsulfanyl)-4,9-dihydro[1,3]thiazino[6,5-b]indole
• Synonyms: 1,3-thiazino[6,5-b]indole, 4,9-dihydro-2-(methylthio)-
• CAS NO: 105748-58-1
• Molecular Formula: C₁₁H₁₀N₂S₂
• Molecular Weight: 234.3405
• Mol File: 105748-58-1.mol

Chemical Properties

• Boiling Point: 448.5°C at 760 mmHg
• Flash Point: 225°C
• Density: 1.44g/cm³
• Vapor Pressure: 8.18E-08mmHg at 25°C
• Refractive Index: 1.769
• CAS DataBase Reference: 2-(methylsulfanyl)-4,9-dihydro[1,3]thiazino[6,5-b]indole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(methylsulfanyl)-4,9-dihydro[1,3]thiazino[6,5-b]indole(105748-58-1)
• EPA Substance Registry System: 2-(methylsulfanyl)-4,9-dihydro[1,3]thiazino[6,5-b]indole(105748-58-1)

Safety Data

• Hazardous Substances Data: 105748-58-1(Hazardous Substances Data)

Upstream product

• 105748-59-2 brassinin 
• 188988-51-4 9-Boc-cyclobrassinin 
• 22259-53-6 3-aminomethylindole 
• 188988-43-4 1-(tert-butoxycarbonyl)indole-3-carboxaldehyde oxime 
• 188988-49-0 [1-(tert-butoxycarbonyl)indol-3-yl]methylisothiocyanate 
• 188988-50-3 1-(tert-butoxycarbonyl)brassinin 
• 487-89-8 Indole-3-carboxaldehyde 
• 2592-05-4 1H-indole-3-carboxaldehyde oxime 
• 188988-46-7 tert-butyl 3-(aminomethyl)-1H-indole-1-carboxylate 
• 57476-50-3 1-tert-butoxycarbonyl-3-formylindole 
• 68769-69-7 2-((1H-indol-3-yl)methyl)isoindoline-1,3-dione 

Downstream Products

• 119752-76-0 brassilexin 
• 1417888-91-5 9-[(1R,2S,5R)-menthoxycarbonyl]cyclobrassinin 
• 1417888-92-6 9-[(1R,2S,5R)-8-phenylmenthoxycarbonyl]cyclobrassinin 
• 1417888-93-7 9-[(1S)-phenylethoxycarbonyl]cyclobrassinin 

Relevant articles and documents

Spirocyclization strategy toward indole phytoalexins. The first synthesis of (±)-1-methoxyspirobrassinin, (±)-1-methoxyspirobrassinol, and (±)-1-methoxyspirobrassinol methyl ether

The first syntheses of cruciferous indole phytoalexins (±)-1-methoxyspirobrassinin, (±)-1-methoxyspirobrassinol, (±)-1-methoxyspirobrassinol methyl ether as well as a new syntheses of phytoalexins (±)-spirobrassinin and cyclobrassinin were achieved by dioxane dibromide (DDB)-mediated spirocyclization of brassinin and its 1-substituted derivatives.

Novel Sulfur-Containing Phytoalexins from the Chinese Cabbage Brassica campestris L. ssp. pekinensis (Cruciferae)

The first isolation and structure elucidation of four sulfur-containing indole phytoalexins from Chinese cabbage inoculated with Pseudomonas cichorii are described.

A facile method for the synthesis of indole phytoalexin rutalexin

Novel methods for the preparation of the indole phytoalexin rutalexin (8) in high yields are presented. The synthesis of rutalexin (8) was achieved from previously synthesized 9-tert-butoxycarbonyl-2-methoxy-4-oxo-[1,3]thiazino[6,5-b]indole (5) by its hydrolysis, methylation, and deprotection. A second method starting from 9-Boc-cyclobrassinin (9) involved oxidation, methylation, and deprotection.

Isolation of Three Novel Sulphur-containing Phytoalexins from the Chinese Cabbage Brassica campestris L. ssp. pekinensis (Cruciferae)

Inoculation of Chinese cabbage heads with the bacterium Pseudomonas cichorii induced the production of three major phytoalexins named methoxybrassinin (1), brassinin (2), and cyclobrassinin (3), whose structures have been elucidated on the basis of spectroscopic studies and synthesis.

A concise synthesis of cyclobrassinin and its analogues via a thiyl radical aromatic substitution

A simple and concise approach for the synthesis of cyclobrassinin has been developed through a thiyl radical-mediated intramolecular aromatic substitution, with benzoyl peroxide as an efficient initiator and oxidant. The current method can also be utilized in the synthesis of 6 and 7-membered ring cyclobrassinin analogues in moderate to good yields. The transformation involves a formal radical 6 and 7-endo-trig cyclization of the corresponding dithiocarbamate derivatives, which were generated from indole-3-methanamines and tryptophan.

Synthesis of thiazino[6,5-b]indole derivatives, analogues of the phytoalexin cyclobrassinin. A new method for preparation of 3-aminomethylindole

An efficient non-reductive synthesis of 3-aminomethylindole (6) was developed from gramine (1) via 3-phthalimidomethylindole (2). The reactions of amine 6 with substituted methyl dithiobenzoates gave 3- (arylthiocarbonylaminomethyl)indoles. The Hugerschoff ring-closure reactions of the thiobenzamide intermediates (11a-f) with phenyltrimethylammonium tribromide and subsequent basic treatment furnished 2-arylthiazino[6,5-b]indole derivatives (14a-f). By use of the latter bromine source, the phytoalexin cyclobrassinin (8) was prepared in a considerably higher yield than described previously. The structures of the novel products were elucidated by IR, 1H and 13C NMR spectroscopy, including 2D-HMQC, 2D-HMBC and DEPT measurements.

New syntheses of indole phytoalexins and related compounds

Synthesis of indole phytoalexins brassinin, brassitin, cyclobrassinin and related compounds via 3-aminomethylindole and its 1-substituted derivatives obtained by nickel boride catalyzed reduction of corresponding aldoximes with sodium borohydride and via [1-(t-butoxycarbonyl)-indol-3-yl]methyl isothiocyanate, the first stable derivative of indol-3-ylmethyl isothiocyanate is described. Antifungal activity of the prepared compounds was examined by using the fungus Bipolaris leersiae by t.l.c. bioassay and quantitative screening was carried out with the selected compounds.

Synthesis of Indole Phytoalexins Brassinin and Cyclobrassinin via [1-(tert-Butoxycarbonyl)indol-3-yl]-methyl Isothiocyanate as the Key Biomimetic Intermediate

A four-step synthesis of 1-protected indol-3-ylmethyl isothiocyanates from indole-3-carboxaldehyde has been elaborated. [1-(tert-Butoxycarbonyl)indol-3-yl]methyl isothiocyanate appeared to be a suitable biomimetic intermediate for the synthesis of protected phytoalexins brassinin and cyclobrassinin. Removing of the tert-butoxycarbonyl protecting group under specific conditions afforded phytoalexins identical with previously described compounds.