Estrone 3-methyl ether

Base Information

• Chemical Name: Estrone 3-methyl ether
• CAS No.: 1624-62-0
• Molecular Formula: C19H24O2
• Molecular Weight: 284.398
• Hs Code.: 2914509090
• European Community (EC) Number: 216-613-3
• NSC Number: 88911
• UNII: 4SMZ4A51IJ,59359RSB8X
• DSSTox Substance ID: DTXSID40167368
• Nikkaji Number: J22.730G
• Wikipedia: Estrone_methyl_ether
• Wikidata: Q63392002
• ChEMBL ID: CHEMBL1409077
• Mol file: 1624-62-0.mol

Synonyms:estrone 3-methyl ether;estrone 3-methyl ether, (+-)-isomer

Chemical Property of Estrone 3-methyl ether

Chemical Property:

• Appearance/Colour: White crystalline powder
• Vapor Pressure: 1.65E-07mmHg at 25°C
• Melting Point: 170.0 to 174.0 °C
• Refractive Index: 1.556
• Boiling Point: 427.4 °C at 760 mmHg
• Flash Point: 183.6 °C
• PSA: 26.30000
• Density: 1.103 g/cm³
• LogP: 4.12040
• Storage Temp.: Refrigerator
• Solubility.: Acetonitrile (Slightly), Chloroform (Sparingly), Ethyl Acetate (Slightly), Metha
• Water Solubility.: 1.8mg/L at 20℃
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 284.177630004
• Heavy Atom Count: 21
• Complexity: 431

Purity/Quality:

99% ^*data from raw suppliers

3-O-MethylEstrone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-40
• Safety Statements: 22-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2=O)CCC4=C3C=CC(=C4)OC
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CCC4=C3C=CC(=C4)OC
• Uses: An estrogenic hormone.

Technology Process of Estrone 3-methyl ether

There total 192 articles about Estrone 3-methyl ether 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%

Estrone (53-16-7) + methyl iodide (74-88-4) → estrone 3-methyl ether (1624-62-0)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydroxide; In dichloromethane; at 70 ℃; for 3h;

DOI:10.1016/j.bmc.2018.02.018

Reference yield: 99.0%

Estrone (53-16-7) + carbonic acid dimethyl ester (616-38-6) → estrone 3-methyl ether (1624-62-0)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 130 ℃; for 16h;

Reference yield: 98.3%

17,17-ethylenedioxy-3-methoxyoestra-1,3,5(10)-triene (28336-29-0) → estrone 3-methyl ether (1624-62-0)

Guidance literature:

With hydrogenchloride; In water; at 20 ℃; for 2h;

DOI:10.1016/j.steroids.2018.11.018

upstream raw materials:

(+-)-estrone

carbonic acid dimethyl ester

estrone

methyl iodide

Downstream raw materials:

3-methoxy-17β-hydroxyestra-1,3,5(10)-triene-17α-carbonitrile

3-methoxy-1,3,5(10)-estratriene

norethisterone

17-hydroxyimino-3-methoxy-estra-1,3,5⁽¹⁰⁾-triene

Refernces

• 1、 Poirier, Donald,Berthiaume, David,Boivin, Roch P.. "Unexpected formation of O-methoxycarbonyl cyanohydrin showing potential as a protective group of ketones". . p. 1423 - 1425. Retrieved 1999.
• 2、 Tserfas,Kuznetsov, Yu. V.,Levina,Zavarzin. "Key structures for the synthesis of steroid antitumor agents. Synthesis of 16-dehydro-17-carbaldehydes of 13β- and 13α-estratriene series". . p. 2350 - 2354. Retrieved 2019.
• 3、 Climent, M. S.,Marinas, J. M.,Sinisterra, J. V.. "INFLUENCE OF THE CHEMICAL AND TEXTURAL PORPERTIES OF K2Cr2O7 SUPPORTED ON SOLIDS, IN THE OXIDATION OF CHOLESTEROL". . p. 3303 - 3308. Retrieved 1987.
• 4、 Lu, He-Lin,Wu, Zong-Wen,Song, Shu-Yong,Liao, Xiao-Dan,Zhu, Yan,Huang, Yun-Sheng. "An improved synthesis of nomegestrol acetate". . p. 431 - 436. Retrieved 2014.
• 5、 Solyom,Szilagyi,Toldy. "New 17-Spirosteroids, III. Synthesis of steroid-17-spiro-5'-(1',2',3'-oxathiazolidine) 2'-oxides". . p. 1001 - 1019. Retrieved 1983.
• 6、 Brito,Campos,Salgado-Zamora,Fabbro. "Copper bromide mediated A-ring dehydrogenation of 19-norsteroids". . p. 623 - 629. Retrieved 1996.
• 7、 Litvinovskaya,Drach,Lapchinskaya,Khripach. "Synthesis of 17-dihydroisoxazolyl steroids of the androstane and estrone series". . p. 46 - 51. Retrieved 2001.
• 8、 Xie, Wenge,Peng, Hairuo,Kim, Deog-Il,Kunkel, Mark,Powis, Garth,Zalkow, Leon H.. "Structure - Activity relationship of Aza-steroids as PI-PLC inhibitors". . p. 1073 - 1083. Retrieved 2001.
• 9、 Arora, Amandeep,Weaver, Jimmie D.. "Photocatalytic Generation of 2-Azolyl Radicals: Intermediates for the Azolylation of Arenes and Heteroarenes via C-H Functionalization". . p. 3996 - 3999. Retrieved 2016.
• 10、 Shi, Shasha,Yang, Xianyu,Tang, Man,Hu, Jiefeng,Loh, Teck-Peng. "Direct Synthesis of α-Amino Nitriles from Sulfonamides via Base-Mediated C-H Cyanation". supporting information. p. 4018 - 4022. Retrieved 2021/05/26.