7-(1-Aziridinyl)-2,3-dihydro-6,9-dimethyl-1H-pyrrolo(1,2-a)indole-1,5,8-triol 1-acetate

Base Information

• Chemical Name: 7-(1-Aziridinyl)-2,3-dihydro-6,9-dimethyl-1H-pyrrolo(1,2-a)indole-1,5,8-triol 1-acetate
• CAS No.: 155474-43-4
• Molecular Formula: C₁₇H₂₀N₂O₄
• Molecular Weight: 316.357
• DSSTox Substance ID: DTXSID40935221
• Mol file: 155474-43-4.mol

Synonyms:7-(1-azidirinyl)-2,3-dihydro-1-acetoxy-5,8-dihydroxy-6,9-dimethyl-1H-pyrrolo(1,2-a)indole;7-ADAD-1H-PID

Chemical Property of 7-(1-Aziridinyl)-2,3-dihydro-6,9-dimethyl-1H-pyrrolo(1,2-a)indole-1,5,8-triol 1-acetate

Chemical Property:

• Boiling Point: 574.3±50.0 °C(Predicted)
• PKA: 10.61±0.40(Predicted)
• PSA: 74.70000
• Density: 1.50±0.1 g/cm3(Predicted)
• LogP: 2.56220
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 316.14230712
• Heavy Atom Count: 23
• Complexity: 497

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C2C(CCN2C3=C(C(=C(C(=C13)O)N4CC4)C)O)OC(=O)C

Technology Process of 7-(1-Aziridinyl)-2,3-dihydro-6,9-dimethyl-1H-pyrrolo(1,2-a)indole-1,5,8-triol 1-acetate

There total 6 articles about 7-(1-Aziridinyl)-2,3-dihydro-6,9-dimethyl-1H-pyrrolo(1,2-a)indole-1,5,8-triol 1-acetate 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:

7-(1-aziridinyl)-2,3-dihydro-1-acetoxy-6,9-dimethyl-1H-pyrrolo<1,2-a>indole-5,8-dione (155474-45-6) → 7-(1-azaridinyl)-2,3-dihydro-1-acetoxy-5,8-dihydroxy-6,9-dimethyl-1H-pyrrolo<1,2-a>indole (155474-43-4)

Guidance literature:

With pH 7.4 tris buffer; hydrogen; palladium on activated charcoal; In dimethyl sulfoxide; for 0.0833333h;

DOI:10.1021/jm00037a013

Reference yield:

2,3,5,8-tetrahydro-1-hydroxy-7-methoxy-6,9-dimethyl-1H-pyrrolo<1,2-a>indole-5,8-dione (120386-42-7) → 7-(1-azaridinyl)-2,3-dihydro-1-acetoxy-5,8-dihydroxy-6,9-dimethyl-1H-pyrrolo<1,2-a>indole (155474-43-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / pyridine / 10 h / Ambient temperature

2: 72 percent / methanol / 1.) 0 deg C, 30 min, 2.) RT, 1 h

3: H₂, pH 7.4 Tris buffer / 5percent Pd/C / dimethylsulfoxide / 0.08 h

With pyridine; pH 7.4 tris buffer; hydrogen; palladium on activated charcoal; In methanol; dimethyl sulfoxide;

DOI:10.1021/jm00037a013

Reference yield:

3-(acetyloxy)-2,3-dihydro-7-methoxy-6,9-dimethyl-1H-pyrrolo<1,2-a>indole-5,8-dione (120386-54-1) → 7-(1-azaridinyl)-2,3-dihydro-1-acetoxy-5,8-dihydroxy-6,9-dimethyl-1H-pyrrolo<1,2-a>indole (155474-43-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / methanol / 1.) 0 deg C, 30 min, 2.) RT, 1 h

2: H₂, pH 7.4 Tris buffer / 5percent Pd/C / dimethylsulfoxide / 0.08 h

With pH 7.4 tris buffer; hydrogen; palladium on activated charcoal; In methanol; dimethyl sulfoxide;

DOI:10.1021/jm00037a013

upstream raw materials:

7-(1-aziridinyl)-2,3-dihydro-1-acetoxy-6,9-dimethyl-1H-pyrrolo<1,2-a>indole-5,8-dione

2,3,5,8-tetrahydro-1-hydroxy-7-methoxy-6,9-dimethyl-1H-pyrrolo<1,2-a>indole-5,8-dione

3-(acetyloxy)-2,3-dihydro-7-methoxy-6,9-dimethyl-1H-pyrrolo<1,2-a>indole-5,8-dione

2,3-dihydro-7-methoxy-6,9-dimethyl-1H-pyrrolo<1,2-a>indol-1-one