2-(diethylaminomethyl)-4-[(E)-4-[3-(diethylaminomethyl)-4-hydroxyphenyl]hex-3-en-3-yl]phenol

Base Information

• Chemical Name: 2-(diethylaminomethyl)-4-[(E)-4-[3-(diethylaminomethyl)-4-hydroxyphenyl]hex-3-en-3-yl]phenol
• CAS No.: 82058-16-0
• Molecular Formula: C₂₈H₄₂N₂O₂
• Molecular Weight: 438.654
• DSSTox Substance ID: DTXSID60420245
• Wikidata: Q82231469
• ChEMBL ID: CHEMBL559626
• Mol file: 82058-16-0.mol

Synonyms:82058-16-0;NSC 33994;NSC-33994;2-(diethylaminomethyl)-4-[(E)-4-[3-(diethylaminomethyl)-4-hydroxyphenyl]hex-3-en-3-yl]phenol;CHEMBL559626;(E)-4,4-(1,2-Diethyl-1,2-ethenediyl)bis[2-[(diethylamino)methyl]phenol];E-4,4'-(1,2-Diethyl-1,2-ethenediyl)bis[2-[(diethylamino)methyl]phenol;NSC33994;SCHEMBL2482865;DTXSID60420245;QFNJFVBKASKGEU-OCEACIFDSA-N;BDBM50293657;HB1430;AKOS024458101;NCGC00387166-03;AS-16870;G6;HY-18293;CS-0007398;NSC 33994, >=98% (HPLC);4,4''-(hex-3-ene-3,4-diyl)bis(2-((diethylamino)methyl)phenol);(E)-4,4'-(1,2-Diethyl-1,2-ethenediyl)bis[2-[(diethylamino)methyl]-phenol (9CI), 4,4'-(3E)-Hex-3-ene-3,4-diylbis{2-[(diethylamino)methyl]phenol}

Chemical Property of 2-(diethylaminomethyl)-4-[(E)-4-[3-(diethylaminomethyl)-4-hydroxyphenyl]hex-3-en-3-yl]phenol

Chemical Property:

• Boiling Point: 524.7±45.0 °C(Predicted)
• PKA: 9.20±0.50(Predicted)
• PSA: 46.94000
• Density: 1.040±0.06 g/cm3(Predicted)
• LogP: 6.51220
• Storage Temp.: 2-8°C
• Solubility.: DMSO: ≥25mg/mL
• XLogP3: 6.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 12
• Exact Mass: 438.324628587
• Heavy Atom Count: 32
• Complexity: 508

Purity/Quality:

≥98% by HPLC ^*data from raw suppliers

NSC 33994 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(=C(CC)C1=CC(=C(C=C1)O)CN(CC)CC)C2=CC(=C(C=C2)O)CN(CC)CC
• Isomeric SMILES: CC/C(=C(/CC)\C1=CC(=C(C=C1)O)CN(CC)CC)/C2=CC(=C(C=C2)O)CN(CC)CC
• Description: NSC-33994 (82058-16-0) is a remarkably potent and selective JAK2 inhibitor (IC50 = 60 nM). Displays no effect on Src and TYK2 tyrosine kinase activity at a concentration of 25 μM.1?Suppresses JAK2-V617F-mediated human pathological cell growth?in vitro?and?in vivo2?and is concomitant with the disruption of intracellular vimentin filaments3. NSC-33994 reduces the tumorigenic potential of T98G glioblastoma cells?in vitro?and?in vivo.4
• Uses: NSC-33994 is novel inhibitor of JAK2 tyrosine kinase (Janus kinase 2 ). Janus kinase 2 (JAK2) plays a crucial role in the pathomechanism of myeloproliferative disorders and hematological malignancies.

Technology Process of 2-(diethylaminomethyl)-4-[(E)-4-[3-(diethylaminomethyl)-4-hydroxyphenyl]hex-3-en-3-yl]phenol

There total 1 articles about 2-(diethylaminomethyl)-4-[(E)-4-[3-(diethylaminomethyl)-4-hydroxyphenyl]hex-3-en-3-yl]phenol 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:

formaldehyd (50-00-0,30525-89-4,61233-19-0) + diethylamine (109-89-7) → NSC 33994 (82058-16-0)

Guidance literature:

With ethanol;

DOI:10.1021/ja01214a008

Reference yield:

NSC 33994 (82058-16-0) → 3,3'-bis(hydroxymethyl)diethylstilbestrol (82058-18-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 3.7 g / acetic acid / 5 h / Heating

2: 450 mg / n-BuLi / tetrahydrofuran; hexane / 2 h / from -78 deg C warming up to r.t.

With n-butyllithium; In tetrahydrofuran; hexane; acetic acid;

Reference yield:

NSC 33994 (82058-16-0) → 3,3'-bis(acetoxymethyl)diethylstilbestrol (82058-19-3,82058-20-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 3.7 g / acetic acid / 5 h / Heating

2: 450 mg / n-BuLi / tetrahydrofuran; hexane / 2 h / from -78 deg C warming up to r.t.

3: 190 mg / TsOH / acetic acid / Ambient temperature

With n-butyllithium; toluene-4-sulfonic acid; In tetrahydrofuran; hexane; acetic acid;

upstream raw materials:

formaldehyd

diethylamine

Downstream raw materials:

3,3'-bis(acetoxymethyl)diethylstilbestrol diacetate

3,3'-bis(hydroxymethyl)diethylstilbestrol

3,3'-bis(acetoxymethyl)diethylstilbestrol