(13S,17R)-17-ethynyl-3-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-ol

Base Information

• Chemical Name: (13S,17R)-17-ethynyl-3-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-ol
• CAS No.: 72-33-3
• Molecular Formula: C21H26O2
• Molecular Weight: 310.436
• Hs Code.: 29372900
• NSC Number: 757100
• Wikidata: Q27163376
• Mol file: 72-33-3.mol

Synonyms:(13S,17R)-17-ethynyl-3-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-ol;17-Ethynyl-3-methoxyestra-1,3,5(10)-trien-17-ol;CHEBI:91543;HMS2091B22;HMS3371B13;HMS3393J22;Pharmakon1600-01500388;NSC757100;AKOS030490045;CCG-212682;NSC-757100;SBI-0206693.P002;AB01563267_01;SR-05000001669;SR-05000001669-1;BRD-A14798026-001-01-8;Q27163376

Chemical Property of (13S,17R)-17-ethynyl-3-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-ol

Chemical Property:

• Appearance/Colour: crystalline solid
• Vapor Pressure: 2.38E-08mmHg at 25°C
• Melting Point: 153-155 °C(lit.)
• Refractive Index: 1.49
• Boiling Point: 464.1ºC at 760 mmHg
• PKA: 13.10±0.40(Predicted)
• Flash Point: 224.1ºC
• PSA: 29.46000
• Density: 0.905g/cm3
• LogP: 3.91560
• Storage Temp.: -20°C Freezer
• XLogP3: 4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 310.193280068
• Heavy Atom Count: 23
• Complexity: 519

Purity/Quality:

98% ^*data from raw suppliers

Mestranol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 36/37/38-40-48-68
• Safety Statements: 22-26-36/37/39-45-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2(C#C)O)CCC4=C3C=CC(=C4)OC
• Isomeric SMILES: C[C@]12CCC3C(C1CC[C@]2(C#C)O)CCC4=C3C=CC(=C4)OC
• Uses: Mestranol is an orally active estrogenic steroid. It was the estrogen used in many of the first oral contraceptives Pharmacological estrogen molecule
• Therapeutic Function: Estrogen

Technology Process of (13S,17R)-17-ethynyl-3-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-ol

There total 19 articles about (13S,17R)-17-ethynyl-3-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-ol 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: 98.0%

estrone 3-methyl ether (1624-62-0) + acetylene (74-86-2,25067-58-7) → mestranol (72-33-3)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1021/op4003533

Reference yield: 93.0%

estrone 3-methyl ether (1624-62-0) + acetylenemagnesium bromide (4301-14-8) → mestranol (72-33-3)

Guidance literature:

In tetrahydrofuran; Reflux;

DOI:10.1002/anie.201502086

Reference yield: 90.0%

estrone 3-methyl ether (1624-62-0) + trimethylsilylacetylene (1066-54-2) → mestranol (72-33-3)

Guidance literature:

trimethylsilylacetylene; With n-butyllithium; In tetrahydrofuran; hexane; at -40 - -20 ℃; for 1h; Inert atmosphere;

estrone 3-methyl ether; In tetrahydrofuran; hexane; at -40 ℃; for 1h; Further stages; Inert atmosphere;

DOI:10.1016/j.tet.2010.04.008

upstream raw materials:

estrone 3-methyl ether

acetylene

ethinyl estradiol

methyl iodide

Downstream raw materials:

1,3,5(10)-estratrien-17α-(E-1'-phenylseleno-2'-chloroethenyl)-3β,17β-diol 3-methyl ether

17α-ethinyl-3-methoxy-1,3,5(10),9(11)-estratetraen-17-ol

ethinyl estradiol

2-hydroxy-mestranol

Refernces

• 1、 Alotaibi, Faez,Halaweish, Fathi,Halaweish, Hossam,Iram, Surtaj,Kasten, Abigail,Kyeremateng, Jennifer,Ostlund, Trevor. "Triazole-estradiol analogs: A potential cancer therapeutic targeting ovarian and colorectal cancer". . . Retrieved 2021/12/27.
• 2、 Hosseini, Abolfazl,Seidel, Daniel,Miska, Andreas,Schreiner, Peter R.. "Fluoride-assisted activation of calcium carbide: A simple method for the ethynylation of aldehydes and ketones". supporting information. p. 2808 - 2811. Retrieved 2015/06/16.