8-Hydroxy-5a,7a-dimethyl-4,5,5a,5b,6,7,7a,8,9,10,10a,10b,11,12-tetradecahydrocyclopenta[5,6]naphtho[1,2-d]azepin-2(3H)-one

Base Information

• Chemical Name: 8-Hydroxy-5a,7a-dimethyl-4,5,5a,5b,6,7,7a,8,9,10,10a,10b,11,12-tetradecahydrocyclopenta[5,6]naphtho[1,2-d]azepin-2(3H)-one
• CAS No.: 21058-56-0
• Molecular Formula: C₁₉H₂₉NO₂
• Molecular Weight: 303.445
• NSC Number: 137003
• DSSTox Substance ID: DTXSID60300437
• Pharos Ligand ID: T4K19VY7VB57
• ChEMBL ID: CHEMBL386857
• Mol file: 21058-56-0.mol

Synonyms:CHEMBL386857;21058-56-0;NSC-627265;1-hydroxy-10a,12a-dimethyl-2,3,3a,3b,4,5,8,9,10,10b,11,12-dodecahydro-1H-indeno[4,5-i][3]benzazepin-7-one;NSC627265;8-Hydroxy-5a,7a-dimethyl-4,5,5a,5b,6,7,7a,8,9,10,10a,10b,11,12-tetradecahydrocyclopenta[5,6]naphtho[1,2-d]azepin-2(3H)-one;DTXSID60300437;BDBM50200091;NSC137003;NSC-137003;8-hydroxy-7a-methyl-4,5,5a,5b,6,7,7a,8,9,10,10a,10b,11,12-tetradecahydro-3H-cyclopenta[5,6]naphtho[1,2-d]azepin-2-one

Chemical Property of 8-Hydroxy-5a,7a-dimethyl-4,5,5a,5b,6,7,7a,8,9,10,10a,10b,11,12-tetradecahydrocyclopenta[5,6]naphtho[1,2-d]azepin-2(3H)-one

Chemical Property:

• Vapor Pressure: 4E-12mmHg at 25°C
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 303.219829168
• Heavy Atom Count: 22
• Complexity: 528

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2O)CCC4=CC(=O)NCCC34C

Technology Process of 8-Hydroxy-5a,7a-dimethyl-4,5,5a,5b,6,7,7a,8,9,10,10a,10b,11,12-tetradecahydrocyclopenta[5,6]naphtho[1,2-d]azepin-2(3H)-one

There total 5 articles about 8-Hydroxy-5a,7a-dimethyl-4,5,5a,5b,6,7,7a,8,9,10,10a,10b,11,12-tetradecahydrocyclopenta[5,6]naphtho[1,2-d]azepin-2(3H)-one 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: 92.0%

3-aza-17β-acetoxy-A-homo-4α-androsten-4-one (21058-55-9) → 8-hydroxy-5a,7a-dimethyl-3,4,5,5a,5b,6,7,7a,8,9,10,10a,11,12-tetradecahydrocyclopenta-[5,6]naphtho[1,2-d]azepin-2(10bH)-one (21058-56-0)

Guidance literature:

With lithium hydroxide; In methanol; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.steroids.2016.07.009

Reference yield:

17β-acetoxy-3-hydroximinoandrost-4-ene (59285-18-6) → 8-hydroxy-5a,7a-dimethyl-3,4,5,5a,5b,6,7,7a,8,9,10,10a,11,12-tetradecahydrocyclopenta-[5,6]naphtho[1,2-d]azepin-2(10bH)-one (21058-56-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 55 percent / thionyl chloride / dioxane / 1 h / Ambient temperature

2: 4N LiOH

With lithium hydroxide; thionyl chloride; In 1,4-dioxane;

DOI:10.1002/jhet.5570200449

Reference yield:

testosterone acetate (1045-69-8) → 8-hydroxy-5a,7a-dimethyl-3,4,5,5a,5b,6,7,7a,8,9,10,10a,11,12-tetradecahydrocyclopenta-[5,6]naphtho[1,2-d]azepin-2(10bH)-one (21058-56-0)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine; hydroxylamine hydrochloride / 6 h / Reflux

2: thionyl chloride / 1,4-dioxane / 3 h / 0 - 20 °C

3: methanol; lithium hydroxide / 2 h / 20 °C

With pyridine; methanol; thionyl chloride; hydroxylamine hydrochloride; lithium hydroxide; In 1,4-dioxane; 2: |Beckmann Rearrangement;

upstream raw materials:

3-aza-17β-acetoxy-A-homo-4α-androsten-4-one

17β-acetoxy-3-hydroximinoandrost-4-ene

testosterone acetate

Downstream raw materials:

17β-hydroxy-3-aza-A-homo-4a-androsten-4-one pphenylbutyrate

17β-hydroxy-3-aza-A-homo-4a-androsten-4-one pphenylthioacetate

17β-hydroxy-3-aza-A-homo-4a-androsten-4-one p-phenylacetate

3-aza-A-homo-4α-androstene-4,17-dione