[5a-S,10b-R]-2-(2,4,6-Trimethyl-phenyl)-2,5a,6,10b-tetrahydro-4H-5-oxa-2,3-diaza-10c-azonia-cyclopenta[c]fluorene chloride

Base Information

• Chemical Name: [5a-S,10b-R]-2-(2,4,6-Trimethyl-phenyl)-2,5a,6,10b-tetrahydro-4H-5-oxa-2,3-diaza-10c-azonia-cyclopenta[c]fluorene chloride
• CAS No.: 919102-70-8
• Molecular Formula: C21H22N3O.Cl
• Molecular Weight: 367.878
• Hs Code.: 29349990
• European Community (EC) Number: 889-806-9
• Mol file: 919102-70-8.mol

Synonyms:919102-70-8;Bode Catalyst 1;Bode Catalyst 1;[5a-S,10b-R]-2-(2,4,6-Trimethyl-phenyl)-2,5a,6,10b-tetrahydro-4H-5-oxa-2,3-diaza-10c-azonia-cyclopenta[c]fluorene chloride;(-)-(5aS,10bR)-5a,10b-Dihydro-2-(2,4,6-trimethylphenyl)-4H,6H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazinium Chloride;(1R,9S)-4-(2,4,6-Trimethylphenyl)-8-oxa-4,5-diaza-2-azoniatetracyclo[7.7.0.02,6.011,16]hexadeca-2,5,11,13,15-pentaene;chloride;rel-(5aS,10bR)-2-Mesityl-4,5a,6,10b-tetrahydroindeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-2-ium chloride;(1R,9S)-4-(2,4,6-trimethylphenyl)-8-oxa-2??,4,5-triazatetracyclo[7.7.0.0(2),?.0(1)(1),(1)?]hexadeca-2,5,11,13,15-pentaen-2-ylium chloride;2041584-05-6;MFCD09787521;AKOS037647900;AKOS040767948;(-)-(5aS,10bR)-5a,10b-Dihydro-2-mesityl-4H,6H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazinium Chloride;AS-75214;D3984;D81687;(-)-(5aS pound not10bR)-5a pound not10b-Dihydro-2-(2 pound not4 pound not6-triMethylphenyl)-4H pound not6H-indeno[2 pound not1-b][1 pound not2 pound not4]triazolo[4 pound not3-d][1 pound not4]oxaziniuM Chloride Monohydrate;(1R,9S)-4-(2,4,6-trimethylphenyl)-8-oxa-2,5-diaza-4-azoniatetracyclo[7.7.0.02,6.011,16]hexadeca-3,5,11(16),12,14-pentaene;(5aS,10bR)-5a,10b-Dihydro-2-mesityl-4H,6H-indeno[2,1-b]-1,2,4-triazolo[4,3-d]-1,4-oxazinium chloride;[5a-S,10b-R]-2-(2,4,6-Trimethyl-phenyl)-2,5a,6,10b-tetrahydro-4H-5-oxa-2,3-diaza-10c-azonia-cyclopenta[c]fluorenechloride

Chemical Property of [5a-S,10b-R]-2-(2,4,6-Trimethyl-phenyl)-2,5a,6,10b-tetrahydro-4H-5-oxa-2,3-diaza-10c-azonia-cyclopenta[c]fluorene chloride

Chemical Property:

• Melting Point: 212-216 °C
• PSA: 30.93000
• LogP: 0.13330
• Storage Temp.: Inert atmosphere,Room Temperature
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 367.1451400
• Heavy Atom Count: 26
• Complexity: 488

Purity/Quality:

98%,99%, ^*data from raw suppliers

[5a-S,10b-R]-2-(2,4,6-Trimethyl-phenyl)-2,5a,6,10b-tetrahydro-4H-5-oxa-2,3-diaza-10c-azonia-cyclopenta[c]fluoreneChloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=C(C(=C1)C)N2C=[N+]3C4C(CC5=CC=CC=C45)OCC3=N2)C.[Cl-]
• Isomeric SMILES: CC1=CC(=C(C(=C1)C)N2C=[N+]3[C@H]4[C@H](CC5=CC=CC=C45)OCC3=N2)C.[Cl-]
• Uses: (5aS,10bR)-5a,10b-Dihydro-2-(2,4,6-trimethylphenyl)-4H, 6H-indeno[2,1-b]-1,2,4-triazolo[4,3-d]-1,4-oxazinium chloride monohydrate can be used as an N-heterocyclic carbene (NHC) organocatalyst:In the synthesis of tricyclic β-lactones by reacting 2-bromoenals with 1,3-diketones.To functionalize the C2-position of 3-aminobenzofurans using 2-bromoenals as coupling partners.In the synthesis of dihydroquinoxalines from substituted bisimines.In the preparation of spiro-glutarimide derivatives by reacting cyclic β-ketoamides with α,β-unsaturated aldehydes.

Technology Process of [5a-S,10b-R]-2-(2,4,6-Trimethyl-phenyl)-2,5a,6,10b-tetrahydro-4H-5-oxa-2,3-diaza-10c-azonia-cyclopenta[c]fluorene chloride

There total 4 articles about [5a-S,10b-R]-2-(2,4,6-Trimethyl-phenyl)-2,5a,6,10b-tetrahydro-4H-5-oxa-2,3-diaza-10c-azonia-cyclopenta[c]fluorene chloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 66.0%

(Z)-2-mesityl-1-((4aR,9aS)-4,4a,9,9a-tetrahydroindeno[2,1b][1,4]oxazin-3(2H)-ylidene)hydrazine hydrochloride (1345817-96-0,955103-23-8) + orthoformic acid triethyl ester (122-51-0) → (5aS,10bR)-5a,10b-dihydro-2-(2',4',6'-trimethylphenyl)-4H,6H-indeno[2,1-b]-1,2,4-triazolo[4,3-d]-1,4-oxazinium chloride monohydrate (919102-70-8,903571-02-8)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; chlorobenzene; at 120 ℃; for 1h;

Reference yield:

indeno[2,1-b]-1,4-oxazin-3(2H)-one,4,4a,9,9a-tetrahydro-,(4aR,9aS)- (862095-79-2) → (5aS,10bR)-5a,10b-dihydro-2-(2',4',6'-trimethylphenyl)-4H,6H-indeno[2,1-b]-1,2,4-triazolo[4,3-d]-1,4-oxazinium chloride monohydrate (919102-70-8,903571-02-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: dichloromethane / 16 h / 20 °C / Inert atmosphere

1.2: 2.5 h / Cooling with ice

2.1: hydrogenchloride / 1,4-dioxane; methanol / 48 h / 60 °C / Inert atmosphere

3.1: hydrogenchloride / 1,4-dioxane; chlorobenzene / 1 h / 120 °C / Inert atmosphere; Sealed vessel

With hydrogenchloride; In 1,4-dioxane; methanol; dichloromethane; chlorobenzene;

DOI:10.15227/orgsyn.087.0362

Reference yield:

2,4,6-trimethylaniline (88-05-1) → (5aS,10bR)-5a,10b-dihydro-2-(2',4',6'-trimethylphenyl)-4H,6H-indeno[2,1-b]-1,2,4-triazolo[4,3-d]-1,4-oxazinium chloride monohydrate (919102-70-8,903571-02-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: hydrogenchloride; sodium nitrite / water / 1.25 h / -5 - 3 °C

1.2: 21 h / 0 - 20 °C

2.1: hydrogenchloride / 1,4-dioxane; methanol / 48 h / 60 °C / Inert atmosphere

3.1: hydrogenchloride / 1,4-dioxane; chlorobenzene / 1 h / 120 °C / Inert atmosphere; Sealed vessel

With hydrogenchloride; sodium nitrite; In 1,4-dioxane; methanol; water; chlorobenzene;

DOI:10.15227/orgsyn.087.0362

upstream raw materials:

(Z)-2-mesityl-1-((4aR,9aS)-4,4a,9,9a-tetrahydroindeno[2,1b][1,4]oxazin-3(2H)-ylidene)hydrazine hydrochloride

orthoformic acid triethyl ester

(4aR,9aS)-3-methoxy-2,4a,9,9a-tetrahydroindeno[2,1-b][1,4]oxazine

mesitylhydrazine hydrochloride

Downstream raw materials:

C₃₀H₂₇ClN₃O₂⁽¹⁺⁾