(S,S)-Hexestrol

Base Information

• Chemical Name: (S,S)-Hexestrol
• CAS No.: 84-16-2
• Molecular Formula: C18H22O2
• Molecular Weight: 270.371
• European Community (EC) Number: 227-082-2
• Nikkaji Number: J2.196.427A
• Wikipedia: Hexestrol
• NCI Thesaurus Code: C545
• Mol file: 84-16-2.mol

Synonyms:hexestrol;Hormoestrol;Mesohexestrol;Syntrogene;Estrifar;Estronal;Synthovo;Hexron;Erythrohexestrol;NSC 9894

Chemical Property of (S,S)-Hexestrol

Chemical Property:

• Appearance/Colour: crystalline solid
• Melting Point: 186 °C
• Refractive Index: 1.4800 (estimate)
• Boiling Point: 399.5 °C at 760 mmHg
• PKA: 9.80±0.26(Predicted)
• Flash Point: 181.6 °C
• PSA: 40.46000
• Density: 1.093 g/cm³
• LogP: 4.78520
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: almost transparency in Methanol
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 270.161979940
• Heavy Atom Count: 20
• Complexity: 235

Purity/Quality:

99% ^*data from raw suppliers

Hexestrol >98.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 45
• Safety Statements: 53-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C1=CC=C(C=C1)O)C(CC)C2=CC=C(C=C2)O
• Isomeric SMILES: CC[C@H](C1=CC=C(C=C1)O)[C@H](CC)C2=CC=C(C=C2)O
• Uses: Nonsteroidal synthetic estrogen Estrogen; antineoplastic (hormonal).
• Therapeutic Function: Estrogen

Technology Process of (S,S)-Hexestrol

There total 72 articles about (S,S)-Hexestrol 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: 86.0%

rac-4,4'-[(3R,4R)-hexa-1,5-diyne-3,4-diyl]diphenol → dl-hexestrol (84-16-2,5635-50-7,5776-72-7,29555-62-2,53625-22-2,26614-21-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; at 20 ℃; for 48h;

DOI:10.1016/S0022-328X(03)00539-4

Reference yield:

racem.-3,4-bis-(4-methoxy-phenyl)-hexane (130-78-9,28199-75-9,28231-25-6,53584-73-9) → dl-hexestrol (84-16-2,5635-50-7,5776-72-7,29555-62-2,53625-22-2,26614-21-1)

Guidance literature:

With potassium hydroxide; at 200 ℃;

DOI:10.1080/713678000

Reference yield:

Diethylstilbestrol dimethyl ether (130-79-0) → dl-hexestrol (84-16-2,5635-50-7,5776-72-7,29555-62-2,53625-22-2,26614-21-1)

Guidance literature:

Multi-step reaction with 2 steps

1: methanol; Raney nickel / 210 °C / 194910 Torr / Hydrogenation

2: aqueous HI; acetic acid / 135 - 140 °C

With methanol; hydrogen iodide; nickel; acetic acid;

DOI:10.1021/ja01225a506

upstream raw materials:

4-n-Propylphenol

Dienol

dienestrol

diethylstilbestrol

Downstream raw materials:

(RS,SR)-α,α'-diethyl-4,4'-bis-((Ξ)-tetrahydropyran-2-yloxy)-bibenzyl

3,4-bis-(4-butyryloxy-phenyl)-hexane

Cytostatin

3,3'-Diiodohexestrol

Refernces

• 1、 Frota, Carlise,Polo, Ellen Christine,Esteves, Henrique,Correia, Carlos Roque Duarte. "Regioselective and Stereoselective Heck-Matsuda Arylations of Trisubstituted Allylic Alkenols and Their Silyl and Methyl Ether Derivatives to Access Two Contiguous Stereogenic Centers: Expanding the Redox-Relay Process and Application in the Total Synthesis of meso-Hexestrol". . p. 2198 - 2209. Retrieved 2018/02/23.
• 2、 Melikyan, Gagik G.,Sepanian, Steve,Riahi, Bobby,Villena, Ferdinand,Jerome, John,Ahrens, Brian,McClain, Randolph,Matchett, John,Scanlon, Stephanie,Abrenica, Edwin,Paulsen, Kevin,Hardcastle, Kenneth I.. "Tetrahydrofuran-mediated radical processes: Stereoselective synthesis of d,l-hexestrol". . p. 324 - 330. Retrieved 2007/10/03.