4-Ohimg

Base Information

• Chemical Name: 4-Ohimg
• CAS No.: 83327-20-2
• Molecular Formula: C₁₆H₂₀N₂O₁₀S₂
• Molecular Weight: 464.474
• Nikkaji Number: J390.325G
• Wikidata: Q76309502
• Mol file: 83327-20-2.mol

Synonyms:4-hydroxy-3-indolylmethylglucosinate;4-hydroxy-3-indolylmethylglucosinolate;4-OHIMG

Chemical Property of 4-Ohimg

Chemical Property:

• PKA: 9.68±0.40(Predicted)
• PSA: 235.81000
• Density: 1.89±0.1 g/cm3(Predicted)
• LogP: 0.16280
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 7
• Exact Mass: 464.05593719
• Heavy Atom Count: 30
• Complexity: 717

Purity/Quality:

98.5% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C(=C1)O)C(=CN2)CC(=NOS(=O)(=O)O)SC3C(C(C(C(O3)CO)O)O)O
• Isomeric SMILES: C1=CC2=C(C(=C1)O)C(=CN2)C/C(=N/OS(=O)(=O)O)/S[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O

Technology Process of 4-Ohimg

There total 4 articles about 4-Ohimg 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: 20.0%

2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-[(4-acetoxy-1-acetyl-1H-indol-3-yl)methyl]thiohydroxamate → 4-hydroxyglucobrassicin (83327-20-2)

Guidance literature:

2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-[(4-acetoxy-1-acetyl-1H-indol-3-yl)methyl]thiohydroxamate; With pyridine; chlorosulfonic acid; at -50 - 25 ℃; for 20h;

With sodium methylate; In methanol; at 25 ℃; for 1h;

DOI:10.1021/acs.jnatprod.6b00121

Reference yield:

1H-indol-4-ol (2380-94-1) → 4-hydroxyglucobrassicin (83327-20-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: trifluoroacetic acid / dichloromethane / 0.5 h / 0 °C

2.1: pyridine / 1 h / 25 °C

3.1: triethylsilane; titanium tetrachloride / dichloromethane / 1 h / 0 - 25 °C

4.1: triethylamine / dichloromethane / 1 h / 25 °C

5.1: chlorosulfonic acid; pyridine / 20 h / -50 - 25 °C

5.2: 1 h / 25 °C

With pyridine; triethylsilane; chlorosulfonic acid; titanium tetrachloride; triethylamine; trifluoroacetic acid; In pyridine; dichloromethane;

DOI:10.1021/acs.jnatprod.6b00121

Reference yield:

(E)-3-(2-nitroethenyl)-1H-indol-4-ol → 4-hydroxyglucobrassicin (83327-20-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: pyridine / 1 h / 25 °C

2.1: triethylsilane; titanium tetrachloride / dichloromethane / 1 h / 0 - 25 °C

3.1: triethylamine / dichloromethane / 1 h / 25 °C

4.1: chlorosulfonic acid; pyridine / 20 h / -50 - 25 °C

4.2: 1 h / 25 °C

With pyridine; triethylsilane; chlorosulfonic acid; titanium tetrachloride; triethylamine; In pyridine; dichloromethane;

DOI:10.1021/acs.jnatprod.6b00121

upstream raw materials:

1H-indol-4-ol

Refernces