Spirorenone

Base Information

• Chemical Name: Spirorenone
• CAS No.: 74220-07-8
• Molecular Formula: C24H28 O3
• Molecular Weight: 364.485
• European Community (EC) Number: 277-770-1
• UNII: B8TEV07170
• DSSTox Substance ID: DTXSID501024537
• Nikkaji Number: J139.389H
• Wikipedia: Spirorenone
• Wikidata: Q25091762
• NCI Thesaurus Code: C152420
• Metabolomics Workbench ID: 155866
• ChEMBL ID: CHEMBL2107584
• Mol file: 74220-07-8.mol

Synonyms:6 beta, 7 beta, 15 beta, 16 beta-dimethylene-1,4-androstadiene-(17(beta-1')-spiro-5')-perhydrofuran-2',3-dione;spirorenone

Chemical Property of Spirorenone

Chemical Property:

• Vapor Pressure: 2.09E-12mmHg at 25°C
• Boiling Point: 556.1°C at 760 mmHg
• Flash Point: 243.7°C
• PSA: 43.37000
• Density: 1.28g/cm³
• LogP: 4.08190
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 364.20384475
• Heavy Atom Count: 27
• Complexity: 869

Purity/Quality:

99% ^*data from raw suppliers

SPIRORENONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1C4CC4C25CCC(=O)O5)C6CC6C7=CC(=O)C=CC37C
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1[C@@H]4C[C@@H]4[C@@]25CCC(=O)O5)[C@H]6C[C@H]6C7=CC(=O)C=C[C@]37C

Technology Process of Spirorenone

There total 11 articles about Spirorenone 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: 59.0%

dihydrospirorenone (90457-65-1,93920-59-3,67372-75-2,67392-87-4) → Spirorenone (74220-07-8)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; at 100 ℃; for 1.5h;

Reference yield:

3β-hydorxy-15β,16β-methylene androst-5-ene-17-one (67372-65-0) → Spirorenone (74220-07-8)

Guidance literature:

Multi-step reaction with 11 steps

1: 55 percent / Botryodiplodia malorum / 40 h

2: 65 percent / dimethylaminopyridine / pyridine / 72 h / Ambient temperature

3: 98 percent / tert-butylhydroperoxide, VO(C₅H₇O₂)2 / toluene / 2 h / 80 °C

4: 79 percent / P(C₆H₅)3 / CCl₄; CH₂Cl₂; pyridine / 2 h / 0 deg C to room temp.

5: 75 percent / Zn / acetic anhydride; tetrahydrofuran / 1.5 h / 70 °C

6: 94 percent / KOH, NaClO₄ / tetrahydrofuran; methanol / 2.5 h / Ambient temperature

7: 88 percent / Zn/Cu / 1,2-dimethoxy-ethane / 5 h / 55 °C

8: 69 percent / KOEt / tetrahydrofuran / 2 h / Ambient temperature

9: 95 percent / H₂ / Pd/CaCO₃ / tetrahydrofuran; propan-2-ol / 2 h / 750.06 Torr / Ambient temperature

10: 62 percent / pyridinium dichromate / dimethylformamide / 24 h / 70 °C

11: 59 percent / DDQ / dioxane / 1.5 h / 100 °C

With tert.-butylhydroperoxide; dmap; potassium hydroxide; dipyridinium dichromate; Botryodiplodia malorum; VO(C₅H₇O₂)2; potassium ethoxide; sodium perchlorate; hydrogen; copper; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc; Lindlar's catalyst; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; tetrachloromethane; 1,2-dimethoxyethane; dichloromethane; acetic anhydride; N,N-dimethyl-formamide; isopropyl alcohol; toluene;

Reference yield:

(2S,4aR,4bS,6aS,7aS,8aS,8bS,8cR,8dR,9aR,9bR)-2,9b-dihydroxy-4a,6a-dimethyloctadecahydro-7H-cyclopropa[4,5]cyclopenta[1,2-a]cyclopropa[l]phenanthren-7-one (82543-16-6) → Spirorenone (74220-07-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 69 percent / KOEt / tetrahydrofuran / 2 h / Ambient temperature

2: 95 percent / H₂ / Pd/CaCO₃ / tetrahydrofuran; propan-2-ol / 2 h / 750.06 Torr / Ambient temperature

3: 62 percent / pyridinium dichromate / dimethylformamide / 24 h / 70 °C

4: 59 percent / DDQ / dioxane / 1.5 h / 100 °C

With dipyridinium dichromate; potassium ethoxide; hydrogen; 2,3-dicyano-5,6-dichloro-p-benzoquinone; Lindlar's catalyst; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide; isopropyl alcohol;

upstream raw materials:

dihydrospirorenone

3β-hydorxy-15β,16β-methylene androst-5-ene-17-one

17α-(3-hydroxypropyl)-6β,7β;15β,16β-dimethylene-5β-androstane-3β,5,17β-triol

(2S,4aR,4bS,6aS,7aS,8aS,8bS,8cR,8dR,9aR,9bR)-2,9b-dihydroxy-4a,6a-dimethyloctadecahydro-7H-cyclopropa[4,5]cyclopenta[1,2-a]cyclopropa[l]phenanthren-7-one