7597-68-4

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl 2-(1-benzothiophen-3-yl)acetate is used as a key intermediate in the synthesis of pharmaceutical drugs for its aromatic properties and ability to contribute to the development of new medicinal compounds.
Used in Organic Synthesis Industry:
In the field of organic synthesis, Ethyl 2-(1-benzothiophen-3-yl)acetate is utilized as a building block for the creation of various organic compounds, leveraging its chemical structure to form new molecules with potential applications in different areas.
Used in Medicinal Chemistry:
Ethyl 2-(1-benzothiophen-3-yl)acetate is employed in medicinal chemistry for its potential to exhibit a range of biological activities, contributing to the discovery and development of new therapeutic agents.
Used in Drug Development:
Ethyl 2-(1-benzothiophen-3-yl)acetate plays a role in drug development, where its aromatic properties and potential biological activities are harnessed to create novel pharmaceutical entities that address unmet medical needs.

InChI:InChI=1/C12H12O2S/c1-2-14-12(13)7-9-8-15-11-6-4-3-5-10(9)11/h3-6,8H,2,7H2,1H3

Upstream product

• 106-95-6 allyl bromide 
• 149682-18-8 diethyl 3-benzothiophenemalonate 
• 188610-79-9 ethyl 2,3-dihydrobenzo[b]thiene-3-acetate 
• 84-58-2 2,3-dicyano-5,6-dichloro-p-benzoquinone 
• 36748-88-6 3-iodobenzo[b]thiophene 

Downstream Products

• 87894-75-5 1-phenyl-3H-thiopyrano<3,4-b><1>benzothiophen-3-one 
• 87894-73-3 1-phenyl-3H-<1>benzothieno<2,3-c>pyran-3-one 
• 87894-74-4 1-phenyl-3H-<1>benzothieno<2,3-c>pyran-3-thione 
• 87894-77-7 1-phenyl-3H-<1>benzothieno<2,3-c>pyran-3-one 9,9-dioxide 
• 87894-79-9 1-phenyl-3H-<1>benzothieno<2,3-c>pyran-3-thione 9,9-dioxide 

Relevant academic research and scientific papers

Antidepressant 1-arylalkyl-4-(alkoxy pyridinyl)-and 4-(alkoxypyrimidinyl) piperazine derivatives

Novel compound of formula I and pharmaceutically acceptable salts thereof are useful CNS agents: STR1 wherein X is CH or N; X' is CH or a direct covalent link; Y is CH, CH2 or N; Y' is N, NH, O or S; R1 is H, Br, Cl, F, C1-4 alkyl, C1-4 alkoxy, C1-4 alkoxycarbonyl, CN, CONH2 or CH3 SO2 NH; n is 2 or 3; R2 is H or C1-4 alkyl; R3 is C1-4 alkoxy; R4 is H, Br, Cl, or F; and Z is CH or N.

Antidepressant 1-arylalkyl-4-(alkoxypyridinyl)- or 4-(alkoxypyrimidinyl)piperazine derivatives

Novel compound of formula I and pharmaceutically acceptable salts thereof are useful CNS agents: wherein X is CH or N; X'is CH or a direct covalent link; Y is CH, CH2or N; Y'is N, NH, O or S; R1is H, Br, Cl, F, C1-4alkyl,

Cope Rearrangements in the Benzothiophene Series

The inability to observe Cope rearrangement products at elevated temperatures for diethyl α-allyl-2-naphthalenemalonate (1) and diethyl α-allyl-9-phenanthrenemalonate (2) does not extend to the analogous systems resulting from replacement of the aromatic units by 2- and 3-benzothiophene nuclei.Thermal rearrangement of diethyl α-allyl-3-benzothiophenemalonate (5) at 215-255 deg C for 11 h produces the expected Cope rearrangement product diethyl 2-allyl-3-benzothiophenemalonate (10) (8percent) accompanied by trans- and cis-ethyl 2,3-dihydro-1-(ethoxycarbonyl)-1H-benzocyclopentathiophene-2-acetate (9a) (10percent) and (9b) (5percent), respectively.The structure elucidation of 10, 9a, and 9b was done by spectroscopy.The attempted structure verification of 10 by an independent route gave diethyl 2-(1-propenyl)-3-benzothiophenemalonate (12) which when heated at 230-240 deg C for 18 h gave 1-carbethoxy-2-hydroxy-3-methyldibenzothiophene (16) as a major product.Similar results were observed with 2-substituted analogues of 5, both diethyl 3-allyl-2-benzothiophenemalonate (24) and ethyl 1,2-dihydro-3-(ethoxycarbonyl)-3H-benzocyclopentathiophene-2-acetate (25) being formed.In this case the structure of 24 was verified by synthesis.An extension of this involved a study of thermal rearrangement of analogous compound ethyl α-allyl-α-cyano-3-benzothiopheneacetate (30).Thermal rearrangement of 30 at 235-245 deg C for 8 h gave the expected Cope rearrangement product ethyl α-cyano-2-allyl-3-benzothiopheneacetate (32) (6percent) along with an unexpected diastereomeric mixture of 1-cyano-1-(ethoxycarbonyl)-2-methyl-2,3-dihydro-1H-benzocyclopentathiophenes (33) (18percent).Speculative mechanistic considerations are offered regarding the mode of transformation of 12 to 16 and 32 to 33.