109610-83-5

Upstream product

• 109610-54-0 5-(m-Methoxyphenyl)-2-phenylpentonitrile 
• 6943-97-1 (m-methoxyphenyl)propyl bromide 
• 7252-82-6 3-(3-methoxyphenyl)propan-1-ol 

Downstream Products

• 109610-86-8 1,2-cis/trans-7-Methoxy-2-phenylbenzosuber-1-ol 
• 107752-02-3 1,2-trans-1-2-phenyl-7-methoxybenzosuberan 
• 109610-89-1 1,2-trans-1-(p-Hydroxyphenyl)-7-methoxy-2-phenylbenzosuberan 
• 109610-82-4 3-methoxy-6,7-dihydro-8-phenyl-9-(4-hydroxyphenyl)-5H-benzocycloheptene 
• 109610-88-0 1,2-Epoxy-7-methoxy-2-phenylbenzosuberan 
• 109610-87-9 7-Methoxy-2-phenylbenzosuber-1-ene 
• 109610-84-6 2-methoxy-6-phenyl-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one 
• 109610-85-7 1-Cloro-7-methoxy-2-phenyl-benzosuber-1-ene 

Relevant academic research and scientific papers

Synthesis of oxygen-substituted benzocycloheptenes as valuable intermediate products for the production of tissue-selective estrogens

The invention relates to intermediate products and a new process for the production of benzocycloheptene C. The process for the production of its new intermediate products according to the invention starts from economical starting materials, provides the

Antifertility Agents: Part XLVI - Synthesis and Activity of 1,2-trans-1--2-phenyl-7-methoxybenzosuberan

Treatment of 1-bromo-3-(m-methoxyphenyl)propane (2) with p-methoxydesoxybenzoin and benzyl cyanide yields 1,5-diaryl-2-phenylpentanone (5) and 2,5-diarylpentanenitrile (6) respectively.Demethylation of 5 gives 1-(p-hydroxyphenyl)-3-(m-methoxyphenyl) (7) and 1-(p-hydroxyphenyl)-3-(m-hydroxyphenyl)-(8)-2-phenylpentanones which on acetylation afford mono- and di-acetates 9 and 10 respectively.Attempted cyclisation of 7 and 9 with p-TsOH fails to give the desired 1,2-diarylbenzosuber-1-ene (11).In another approach, 6 is hydrolysed to yield the acid 12 which on treatment with PPA gives 2-phenylbenzosuber-1-one (13) while with PCl5-SnCl4 it gives a mixture of 13 and 1-chloro-2-phenylbenzosuber-1-ene (14).Reaction of 13 and p-(trimethylsilyloxy)phenylmagnesium bromide gives 11 in a low yield.Alternatively, 13 is reduced with NaBH4 to give a cis-/trans-mixture of suberols 15a,b which on treatment with PhOH-AlCl3 yield mainly 1,2-trans-1-(p-hydroxyphenyl)-2-phenyl-7-methoxybenzosuberan (18) along with 2-phenylbenzosuber-1-ene (16) and traces of 1-(o-hydroxyphenyl)-2-phenylbenzosuberan (18a).Acetylation of 18 gives the acetate 19 and alkylation of 18 furnishes the desired compound, 1,2-trans-1--2-phenyl-7-methoxybenzosuberan (III, 20).The compound 20 prevents pregnancy in rats at 0.2 mg/kg daily oral dose on days 1-5 post-coitum or at a single oral dose of 1.5 mg/kg on day 1 post-coitum.At 0.2 mg/kg dose, it is 1000 times less estrogenic than ethinylestradiol and is antiestrogenic at single day contraceptive dose.