(1S,2S,3R,4R,5R,6R)-2-exo-cyano-6-endo-hydroxy-5-exo-iodo-3-exo-phenylbicyclo<2.2.1>heptane-2-endo-carboxylic acid lactone

Base Information

Chemical Name:(1S,2S,3R,4R,5R,6R)-2-exo-cyano-6-endo-hydroxy-5-exo-iodo-3-exo-phenylbicyclo<2.2.1>heptane-2-endo-carboxylic acid lactone
CAS No.:142698-01-9
Molecular Formula:C₁₅H₁₂INO₂
Molecular Weight:365.17
Hs Code.:

Synonyms:(1S,2S,3R,4R,5R,6R)-2-exo-cyano-6-endo-hydroxy-5-exo-iodo-3-exo-phenylbicyclo<2.2.1>heptane-2-endo-carboxylic acid lactone

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Chemical Property of (1S,2S,3R,4R,5R,6R)-2-exo-cyano-6-endo-hydroxy-5-exo-iodo-3-exo-phenylbicyclo<2.2.1>heptane-2-endo-carboxylic acid lactone

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Technology Process of (1S,2S,3R,4R,5R,6R)-2-exo-cyano-6-endo-hydroxy-5-exo-iodo-3-exo-phenylbicyclo<2.2.1>heptane-2-endo-carboxylic acid lactone

There total 7 articles about (1S,2S,3R,4R,5R,6R)-2-exo-cyano-6-endo-hydroxy-5-exo-iodo-3-exo-phenylbicyclo<2.2.1>heptane-2-endo-carboxylic acid lactone 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:

: 14378-06-4
(E)-α-cyanocinnamic acid

: 142698-01-9
(1S,2S,3R,4R,5R,6R)-2-exo-cyano-6-endo-hydroxy-5-exo-iodo-3-exo-phenylbicyclo<2.2.1>heptane-2-endo-carboxylic acid lactone

Guidance literature:: Multi-step reaction with 3 steps

1: 91 percent / 1,3-dicyclohexylcarbodiimide, 4-dimethylaminopyridine / CH₂Cl₂ / 1.) 0 deg C, 1 h, 2.) r.t., 20 h

2: CH₂Cl₂ / 120 h / 20 °C

3: 1.) 10percent KOH, 2.) 5percent aq. NaHCO₃, I₂, KI / 1.) EtOH, reflux, 2.) MeOH

With dmap; potassium hydroxide; iodine; sodium hydrogencarbonate; dicyclohexyl-carbodiimide; potassium iodide; In dichloromethane;
DOI:10.1021/jo00043a025

Reference yield:

: 133382-26-0
(E)-2-cyanocinnamate of (S)-ethyl lactate

: 142698-01-9
(1S,2S,3R,4R,5R,6R)-2-exo-cyano-6-endo-hydroxy-5-exo-iodo-3-exo-phenylbicyclo<2.2.1>heptane-2-endo-carboxylic acid lactone

Guidance literature:: Multi-step reaction with 2 steps

1: CH₂Cl₂ / 120 h / 20 °C

2: 1.) 10percent KOH, 2.) 5percent aq. NaHCO₃, I₂, KI / 1.) EtOH, reflux, 2.) MeOH

With potassium hydroxide; iodine; sodium hydrogencarbonate; potassium iodide; In dichloromethane;
DOI:10.1021/jo00043a025

Reference yield:

: 124977-93-1,125074-48-8
(+/-)-2-exo-cyano-3-exo-phenylbicyclo<2.2.1>hept-5-ene-2-endo-carboxylic acid

: 142698-01-9
(1S,2S,3R,4R,5R,6R)-2-exo-cyano-6-endo-hydroxy-5-exo-iodo-3-exo-phenylbicyclo<2.2.1>heptane-2-endo-carboxylic acid lactone

Guidance literature:: Multi-step reaction with 2 steps

1: 24 percent / 4-dimethylaminopyridine, 1,3-dicyclohexylcarbodiimide / CH₂Cl₂ / 1.) 0 deg C, 1 h, 2.) r.t., 20 h

2: 1.) 10percent KOH, 2.) 5percent aq. NaHCO₃, I₂, KI / 1.) EtOH, reflux, 2.) MeOH

With dmap; potassium hydroxide; iodine; sodium hydrogencarbonate; dicyclohexyl-carbodiimide; potassium iodide; In dichloromethane;
DOI:10.1021/jo00043a025