17|A,18-Norestradiol

Base Information

• Chemical Name: 17|A,18-Norestradiol
• CAS No.: 15093-14-8
• Molecular Formula: C₁₇H₂₂O₂
• Molecular Weight: 258.36
• DSSTox Substance ID: DTXSID40450565
• Nikkaji Number: J1.065.680J
• Wikidata: Q82270350
• Mol file: 15093-14-8.mol

Synonyms:17|A,18-Norestradiol;15093-14-8;18-Nor-17beta-estradiol;(8S,9S,13S,14S,17S)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol;18-Norestradiol;SCHEMBL17400404;DTXSID40450565

Chemical Property of 17|A,18-Norestradiol

Chemical Property:

• Melting Point: 251-253 °C(Solv: ethanol (64-17-5))
• Boiling Point: 451.0±45.0 °C(Predicted)
• PKA: 10.27±0.40(Predicted)
• Density: 1.185±0.06 g/cm3(Predicted)
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 258.161979940
• Heavy Atom Count: 19
• Complexity: 342

Purity/Quality:

95% ^*data from raw suppliers

18-Nor-17β-estradiol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CC2C(CCC3=C2C=CC(=C3)O)C4C1C(CC4)O
• Isomeric SMILES: C1C[C@H]2[C@@H](CCC3=C2C=CC(=C3)O)[C@H]4[C@H]1[C@H](CC4)O
• Uses: A novel Estradiol (E888000) intermediate as selectively active estrogens. The specificity of the estrogen-receptor in human breast carcinoma was determine by incubating the cytosol fraction with 17β-estradiol-3H alone or in the presence of other steroids.

Technology Process of 17|A,18-Norestradiol

There total 13 articles about 17|A,18-Norestradiol 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: 99.0%

3-methoxy-gona-1,3,5(10)-trien-17β-ol (15206-28-7) → 17β-estradiol (15093-14-8)

Guidance literature:

With diisobutylaluminium hydride; In benzene; Heating;

DOI:10.1002/(SICI)1522-2675(19990113)82:1<30::AID-HLCA30>3.0.CO;2-T

Reference yield:

(8S,9S,14S)-3-Methoxy-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene (207504-01-6) → 17β-estradiol (15093-14-8)

Guidance literature:

Multi-step reaction with 2 steps

1: catecholborane, LiBH₄ / benzene / 24 h / Heating

2: 99 percent / DIBAH / benzene / Heating

With lithium borohydride; diisobutylaluminium hydride; benzo[1,3,2]dioxaborole; In benzene;

DOI:10.1002/(SICI)1522-2675(19990113)82:1<30::AID-HLCA30>3.0.CO;2-T

Reference yield:

3-((1S,4aS,10aS)-7-methoxy-2-methylene-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)propanenitrile (25062-42-4) → 17β-estradiol (15093-14-8)

Guidance literature:

Multi-step reaction with 10 steps

1: NaOH, H₂O / ethanol / 135 °C

2: diethyl ether / 0 °C

3: 98 percent / LiAlH₄ / tetrahydrofuran

4: 83 percent / Et₃N / CH₂Cl₂ / 0 °C

5: 100 percent / LiBr / acetone

6: 80 percent / O₃ / CH₂Cl₂; methanol / -78 °C

7: 100 percent / 85 °C

8: 8 percent / MeSOCH₂Na / dimethylsulfoxide / 1.) RT, 2.) 75 deg C

9: catecholborane, LiBH₄ / benzene / 24 h / Heating

10: 99 percent / DIBAH / benzene / Heating

With sodium hydroxide; lithium aluminium tetrahydride; lithium borohydride; dimsylsodium; water; diisobutylaluminium hydride; ozone; triethylamine; lithium bromide; benzo[1,3,2]dioxaborole; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; acetone; benzene;

DOI:10.1002/(SICI)1522-2675(19990113)82:1<30::AID-HLCA30>3.0.CO;2-T

upstream raw materials:

3-methoxy-gona-1,3,5(10)-trien-17β-ol

(8S,9S,14S)-3-Methoxy-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene

3-((1S,4aS,10aS)-7-methoxy-2-methylene-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)propanenitrile

(1S,4aS,10aR)-1-(3-Bromo-propyl)-7-methoxy-3,4,4a,9,10,10a-hexahydro-1H-phenanthren-2-one