1-Methoxy-2-(3-methylbut-2-en-1-yl)-9H-carbazole-3-carbaldehyde

Base Information

Chemical Name:1-Methoxy-2-(3-methylbut-2-en-1-yl)-9H-carbazole-3-carbaldehyde
CAS No.:54313-18-7
Molecular Formula:C19H19NO2
Molecular Weight:293.36
Hs Code.:
DSSTox Substance ID:DTXSID40558434
Nikkaji Number:J12.394C
Wikidata:Q82440739
Mol file:54313-18-7.mol

Synonyms:54313-18-7;Indizoline;1-Methoxy-2-(3-methylbut-2-en-1-yl)-9H-carbazole-3-carbaldehyde;DTXSID40558434;1-Methoxy-2-(3-methyl-2-butenyl)-9H-carbazole-3-carbaldehyde;1-methoxy-2-(3-methylbut-2-enyl)-9H-carbazole-3-carbaldehyde;1-meth-oxy-2-(3-methyl-but-2-en-yl)-9h-carbazole-3-carbaldehyde

Suppliers and Price of 1-Methoxy-2-(3-methylbut-2-en-1-yl)-9H-carbazole-3-carbaldehyde

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of 1-Methoxy-2-(3-methylbut-2-en-1-yl)-9H-carbazole-3-carbaldehyde

Chemical Property:

Melting Point:169-170 °C(Solv: chloroform (67-66-3); hexane (110-54-3))
Boiling Point:496.1±40.0 °C(Predicted)
PKA:16.58±0.30(Predicted)
PSA：42.09000
Density:1.185±0.06 g/cm3(Predicted)
LogP:4.65090
XLogP3:4.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:4
Exact Mass:293.141578849
Heavy Atom Count:22
Complexity:429

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:CC(=CCC1=C(C2=C(C=C1C=O)C3=CC=CC=C3N2)OC)C
General Description 1-Methoxy-2-(3-methyl-2-butenyl)-9H-carbazole-3-carbaldehyde is a key synthetic intermediate in the divergent synthesis of carbazole alkaloids such as clausenapin, indizoline, claulansine M, and clausenaline D. It serves as a common precursor that undergoes transformations like Claisen rearrangement and intramolecular cyclizations to access these bioactive natural products. 1-Methoxy-2-(3-methyl-2-butenyl)-9H-carbazole-3-carbaldehyde is structurally characterized by a methoxy group at position 1, a prenyl (3-methyl-2-butenyl) substituent at position 2, and a formyl group at position 3 on the carbazole core, making it a versatile building block for further functionalization.

Technology Process of 1-Methoxy-2-(3-methylbut-2-en-1-yl)-9H-carbazole-3-carbaldehyde

There total 8 articles about 1-Methoxy-2-(3-methylbut-2-en-1-yl)-9H-carbazole-3-carbaldehyde 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: 95.0%

: [1-methoxy-2-(3'-methylbut-2'-en-1'-yl)-9H-carbazol-3-yl]-methanol

: 54313-18-7
indizoline

Guidance literature:: With silica gel; pyridinium chlorochromate; In dichloromethane; at 25 ℃; for 0.5h; Inert atmosphere;
DOI:10.1021/acs.joc.6b00702

Reference yield: 78.0%

: methyl 1-methoxy-2-(3′-methylbut-2′-en-1′-yl)-9H-carba-zole-3-carboxylate

: 54313-18-7
indizoline

Guidance literature:: methyl 1-methoxy-2-(3′-methylbut-2′-en-1′-yl)-9H-carba-zole-3-carboxylate; With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃; for 2h; Inert atmosphere;

With Dess-Martin periodane; In tetrahydrofuran; dichloromethane; at 0 ℃; for 0.5h; Inert atmosphere;
DOI:10.3998/ark.5550190.p009.836

Reference yield:

: 182261-83-2
methyl 1-hydroxy-9H-carbazole-3-carboxylate

: 54313-18-7
indizoline

Guidance literature:: Multi-step reaction with 5 steps

1.1: potassium carbonate / acetone / 15 h / 20 °C

2.1: N,N-dimethyl-formamide / 5 h / Reflux

2.2: 15 h / 20 °C

3.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / Reflux

4.1: lithium aluminium tetrahydride / tetrahydrofuran / 15 h / 0 °C

5.1: Dess-Martin periodane / dichloromethane / 5 h / 20 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; lithium aluminium tetrahydride; potassium carbonate; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone; 2.1: |Claisen Rearrangement;
DOI:10.1021/acs.joc.6b00729