65026-54-2

Upstream product

• 17324-35-5 (E)-2,3-di(4-methoxyphenyl)-2-butene 
• 64-19-7 acetic acid 
• 123-11-5 4-methoxy-benzaldehyde 
• 13366-36-4 trans-2,3-bis(4-hydroxyphenyl)-2-butene 
• 3319-15-1 rac-1-(4-methoxyphenyl)-ethanol 

Downstream Products

• 15624-00-7 (+/-)-threo-2-<4-(2-Diethylamino-ethoxy)-phenyl>-3-(4-hydroxy-phenyl)-butan 
• 15515-43-2 (+/-)-erythro-2-<4-(2-Dimethylamino-ethoxy)-phenyl>-3-(4-methoxy-phenyl)-butan 
• 2962-14-3 racem.-2,3-bis-(4-hydroxy-phenyl)-butane 

Relevant academic research and scientific papers

Organomolybdenum and Organotungsten Reagents, V. - On the Additive, Reductive Carbonyl Dimerization (ARCD Reaction)

Reagents of the type R4(PrO)4(μ-PrO)2W2 (3; R = Me, Et, Pr, Bu, sBu, iBu, Hex, Me3SiCH2, Ph) prepared in situ by the action of organolithium or Grignard compounds on (PrO)4(μ-PrO)2W2Cl4 (2), react with aromatic aldehydes or ketones and with the α,β-unsaturated ketone benzylidene acetone in a novel reaction, called the ARCD reaction, to give products 4 of the type RR'R''C-CRR'R'' with mostly good yields.In the case of benzylidene acetone and furfural besides the ARCD products the rearranged products 27 and 29 are formed.With the reagent Ph4(PrO)4(μ-PrO)2W2 (3b) ARCD reactions are also possible in moderate yields with aliphatic aldehydes and ketones.The more closely investigated reagent Me4(PrO)4(μ-PrO)2W2 (3a; decomposition at about -45 deg C) tolerates the aromatic bound functional groups Cl, F, OH, OMe, and NMe2 in the substrates, but not the NO2 and CO2Et substituents.It reacts with PhCOX (X = OEt, Cl, OCOPh) via acetophenone to give PhCMe2-CMe2Ph. - For the ARCD reactions a radical mechanism (Scheme 7) is postulated. - Key Words: Tungsten complexes/ Carbonyl dimerization

Ring-substituted 1,2-dialkylated 1,2-bis(hydroxyphenyl)ethanes. 3. Synthesis, estrogen receptor binding affinity, and evaluation of antiestrogenic and mammary tumor inhibiting activity of 2,2'-disubstituted butestrols and 6,6'-disubstituted metabutestrols

The syntheses of symmetrically 2,2'-disubstituted butestrols [meso-2,3-bis(4-hydroxyphenyl)butanes] and of 6,6'-disubstituted metabutestrols [meso-2,3-bis(3-hydroxyphenyl)butanes] are described [2,2'-substituents: H (1), OH (2), F (3), Cl (4), Br (5), CH3 (6), and C2H5 (7); 6,6'-substituents: H (8), OH (9), Cl (10), and CH3 (11)]. Compounds 1-11 were obtained by reductive coupling of the corresponding 1-phenylethanols with TiCl3/LiAlH4 and separation of the meso diastereomers. The binding affinity of the test compounds to the calf uterine estrogen receptor was measured relative to that of [3H]estradiol by a competitive binding assay. With the exception of 9, all other compounds showed remarkably high relative binding affinity (RBA) values between 1.0 and 29% that of estradiol. Compounds 3 and 6 (RBA values: 15 and 29), as well as 10 and 11 (1.7 and 5.2), exceeded those of the corresponding unsubstituted compounds 1 and 8 (12 and 1.0). The compounds exhibited strong (3, 4, 6, and 7), moderate (1, 2, and 10), weak (11), or no (8) estrogenic activity in the uterine weight test of the immature mouse. Compounds 1, 2, 8, 10 and 11 showed antiestrogenic activity inhibiting the estrone-stimulated uterine growth (25-35% inhibition). Compound 11 led to a significant inhibition of the tumor growth when tested on the 9,10-dimethyl-1,2-benzanthracene induced, hormone-dependent mammary carcinoma of the Sprague-Dawley rat.