(Z)-beta-((4-(2-(Dimethylamino)ethoxy)phenyl)phenylmethylene)-alpha-methylbenzeneethanol

Base Information

• Chemical Name: (Z)-beta-((4-(2-(Dimethylamino)ethoxy)phenyl)phenylmethylene)-alpha-methylbenzeneethanol
• CAS No.: 97170-41-7
• Molecular Formula: C₂₆H₂₉NO₂
• Molecular Weight: 387.522
• Hs Code.: 2922509090
• DSSTox Substance ID: DTXSID801343982
• Nikkaji Number: J947.260F
• Mol file: 97170-41-7.mol

Synonyms:(Z)-beta-((4-(2-(Dimethylamino)ethoxy)phenyl)phenylmethylene)-alpha-methylbenzeneethanol;97170-41-7;(Z)-4-[4-[2-(dimethylamino)ethoxy]phenyl]-3,4-diphenylbut-3-en-2-ol;Benzeneethanol, beta-((4-(2-(dimethylamino)ethoxy)phenyl)phenylmethylene)-alpha-methyl-, (Z)-;Benzeneethanol,b-[[4-[2-(dimethylamino)ethoxy]phenyl]phenylmethylene]-a-methyl-,(bE)-;-Hydroxytamoxifen;(E)--Hydroxy tamoxifen;-OHTAM;DTXSID801343982;LS-30270

Chemical Property of (Z)-beta-((4-(2-(Dimethylamino)ethoxy)phenyl)phenylmethylene)-alpha-methylbenzeneethanol

Chemical Property:

• Vapor Pressure: 3.17E-12mmHg at 25°C
• Melting Point: 112-114掳C
• Boiling Point: 533.8°Cat760mmHg
• Flash Point: 276.6°C
• PSA: 32.70000
• Density: 1.094g/cm³
• LogP: 4.96690
• Storage Temp.: -20?C Freezer
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol
• XLogP3: 5.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 8
• Exact Mass: 387.219829168
• Heavy Atom Count: 29
• Complexity: 495

Purity/Quality:

95% ^*data from raw suppliers

(Z)-α-HydroxyTamoxifen ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(=C(C1=CC=CC=C1)C2=CC=C(C=C2)OCCN(C)C)C3=CC=CC=C3)O
• Isomeric SMILES: CC(/C(=C(/C1=CC=CC=C1)\C2=CC=C(C=C2)OCCN(C)C)/C3=CC=CC=C3)O
• Uses: A hydroxylated analogue of tamoxifen with anti-estrogenic properties

Technology Process of (Z)-beta-((4-(2-(Dimethylamino)ethoxy)phenyl)phenylmethylene)-alpha-methylbenzeneethanol

There total 5 articles about (Z)-beta-((4-(2-(Dimethylamino)ethoxy)phenyl)phenylmethylene)-alpha-methylbenzeneethanol 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: 29.0%

(E,Z)-4-[4-(2-dimethylaminoethoxy)phenyl]-3,4-diphenyl-but-3-en-2-one (556834-76-5) → (E)-(+/-)-alpha-Hydroxytamoxifen (97151-02-5) + (Z)-(+/-)-alpha-Hydroxytamoxifen (97170-41-7)

Guidance literature:

(E,Z)-4-[4-(2-dimethylaminoethoxy)phenyl]-3,4-diphenyl-but-3-en-2-one; With methanol; cerium(III) chloride heptahydrate; at 25 ℃; for 0.5h;

With sodium tetrahydroborate; at 25 ℃; for 1h;

DOI:10.1021/acs.orglett.7b03223

Reference yield:

E,Z-1-bromo-1,2-diphenyl-2-(4-hydroxyphenyl)ethene (61923-53-3,97151-00-3) → (Z)-(+/-)-alpha-Hydroxytamoxifen (97170-41-7)

Guidance literature:

Multi-step reaction with 2 steps

1: NaH / dimethylformamide / 0.25 h / 60 °C

2: 1.) n-butyllithium, 2.) acetaldehyde / 1.) THF, hexane, -78 deg C, 5 min, 2.) THF, hexane, -78 deg C to 0 deg C, 20 min

With n-butyllithium; sodium hydride; acetaldehyde; In N,N-dimethyl-formamide;

DOI:10.1021/jm00148a020

Reference yield:

trans-(E)-1-bromo-2-<4-<2-(dimethylamino)ethoxy>phenyl>-1,2-diphenylethene (19118-19-5) → E,Z-1-<4-<2-(dimethylamino)ethoxy>phenyl>-1,2-diphenylethene (19957-51-8) + (E)-(+/-)-alpha-Hydroxytamoxifen (97151-02-5) + (Z)-(+/-)-alpha-Hydroxytamoxifen (97170-41-7)

Guidance literature:

With n-butyllithium; acetaldehyde; Yield given. Multistep reaction. Yields of byproduct given; 1.) THF, hexane, -78 deg C, 5 min, 2.) THF, hexane, -78 deg C to 0 deg C, 20 min;

DOI:10.1021/jm00148a020

upstream raw materials:

trans-(E)-1-bromo-2-<4-<2-(dimethylamino)ethoxy>phenyl>-1,2-diphenylethene

acetaldehyde

trans-α-acetoxytamoxifen

E,Z-1-bromo-1,2-diphenyl-2-(4-hydroxyphenyl)ethene

Downstream raw materials:

[2-{(Z)-4-(4-(2-dimethylaminoethoxy)phenyl)-3,4-diphenyl but-3-enyl}]amine

2-[2-{(Z)-4-(4-(2-dimethylaminoethoxy)phenyl)-3,4-diphenyl-but-3-enyl}]isoindole-1,3-dione

Refernces

• 1、 Wang, Quannan,Yang, Xiaoge,Wu, Ping,Yu, Zhengkun. "Photoredox-Catalyzed C-H Arylation of Internal Alkenes to Tetrasubstituted Alkenes: Synthesis of Tamoxifen". supporting information. p. 6248 - 6251. Retrieved 2017/11/24.