7-beta-(2-Chloroethyl-N-nitroso-N-carbonylamino)cholesterol

Base Information

• Chemical Name: 7-beta-(2-Chloroethyl-N-nitroso-N-carbonylamino)cholesterol
• CAS No.: 164120-30-3
• Molecular Formula: C₃₀H₅₀ClN₃O₃
• Molecular Weight: 536.198
• DSSTox Substance ID: DTXSID60936912
• Mol file: 164120-30-3.mol

Synonyms:7-beta-(2-Chloroethyl-N-nitroso-N-carbonylamino)cholesterol;N-(2-Chloroethyl)-N'-((3-beta,7-beta)-3-hydroxycholest-5-en-7-yl)-N-nitrosourea;Urea, N-(2-chloroethyl)-N'-((3-beta,7-beta)-3-hydroxycholest-5-en-7-yl)-N-nitroso-;164120-30-3;C30H50ClN3O3;DTXSID60936912;C30-H50-Cl-N3-O3;LS-159408;N-(2-Chloroethyl)-N'-(3-hydroxycholest-5-en-7-yl)-N-nitrosocarbamimidic acid

Chemical Property of 7-beta-(2-Chloroethyl-N-nitroso-N-carbonylamino)cholesterol

Chemical Property:

• Density: 1.25g/cm³
• XLogP3: 8.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 535.3540702
• Heavy Atom Count: 37
• Complexity: 865

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CCCC(C)C1CCC2C1(CCC3C2C(C=C4C3(CCC(C4)O)C)NC(=O)N(CCCl)N=O)C
• Isomeric SMILES: C[C@H](CCCC(C)C)[C@H]1CCC2[C@@]1(CCC3C2[C@H](C=C4[C@@]3(CC[C@@H](C4)O)C)NC(=O)N(CCCl)N=O)C

Technology Process of 7-beta-(2-Chloroethyl-N-nitroso-N-carbonylamino)cholesterol

There total 8 articles about 7-beta-(2-Chloroethyl-N-nitroso-N-carbonylamino)cholesterol 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: 64.0%

7β-aminocholesterol (122241-89-8) + N-(chloro-2 ethyl)N-nitrosocarbamate de trichloro-2,4,5 phenyle (80354-51-4) → 7β-(2-chloroethyl-N-nitroso-N-carbonylamino)cholesterol (164120-30-3)

Guidance literature:

In pyridine; at -10 ℃; for 3h;

Reference yield:

cholesterol (57-88-5) → 7β-(2-chloroethyl-N-nitroso-N-carbonylamino)cholesterol (164120-30-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 95 percent / pyridinium p-toluene sulfonate / CH₂Cl₂ / 1.5 h / Ambient temperature

2: 65 percent / pyridine, chromic anhydride / CH₂Cl₂ / 12 h / Ambient temperature

3: 78 percent / 1 mol/l L-Selectride / tetrahydrofuran / 0.25 h / -78 °C

4: pyridine / 36 h / Ambient temperature

5: NaN₃ / dimethylformamide / 72 h / 60 °C

6: 85 percent / pyridinium p-toluene sulfonate / ethanol / 12 h / Heating

7: 70 percent / LiAlH₄ / tetrahydrofuran / 4 h / Heating

8: 64 percent / pyridine / 3 h / -10 °C

With pyridine; chromium(VI) oxide; lithium aluminium tetrahydride; sodium azide; pyridinium p-toluenesulfonate; L-Selectride; In tetrahydrofuran; pyridine; ethanol; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

3-O-(tetrahydro-2H-pyran-2-yl)cholesterol (6252-45-5) → 7β-(2-chloroethyl-N-nitroso-N-carbonylamino)cholesterol (164120-30-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 65 percent / pyridine, chromic anhydride / CH₂Cl₂ / 12 h / Ambient temperature

2: 78 percent / 1 mol/l L-Selectride / tetrahydrofuran / 0.25 h / -78 °C

3: pyridine / 36 h / Ambient temperature

4: NaN₃ / dimethylformamide / 72 h / 60 °C

5: 85 percent / pyridinium p-toluene sulfonate / ethanol / 12 h / Heating

6: 70 percent / LiAlH₄ / tetrahydrofuran / 4 h / Heating

7: 64 percent / pyridine / 3 h / -10 °C

With pyridine; chromium(VI) oxide; lithium aluminium tetrahydride; sodium azide; pyridinium p-toluenesulfonate; L-Selectride; In tetrahydrofuran; pyridine; ethanol; dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

7β-aminocholesterol

N-(chloro-2 ethyl)N-nitrosocarbamate de trichloro-2,4,5 phenyle

cholesterol

3-O-(tetrahydro-2H-pyran-2-yl)cholesterol

Refernces