N-[4-ethylidene-2-(2-hydroxy-ethyl)-cyclohex-2-enyl]-N-(2-iodo-phenyl)-methanesulfonamide

Base Information

Chemical Name:N-[4-ethylidene-2-(2-hydroxy-ethyl)-cyclohex-2-enyl]-N-(2-iodo-phenyl)-methanesulfonamide
CAS No.:311309-60-1
Molecular Formula:C₁₇H₂₂INO₃S
Molecular Weight:447.337
Hs Code.:

<i>N</i>-[4-ethylidene-2-(2-hydroxy-ethyl)-cyclohex-2-enyl]-<i>N</i>-(2-iodo-phenyl)-methanesulfonamide

Synonyms:N-[4-ethylidene-2-(2-hydroxy-ethyl)-cyclohex-2-enyl]-N-(2-iodo-phenyl)-methanesulfonamide

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Chemical Property of N-[4-ethylidene-2-(2-hydroxy-ethyl)-cyclohex-2-enyl]-N-(2-iodo-phenyl)-methanesulfonamide

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Technology Process of N-[4-ethylidene-2-(2-hydroxy-ethyl)-cyclohex-2-enyl]-N-(2-iodo-phenyl)-methanesulfonamide

There total 9 articles about N-[4-ethylidene-2-(2-hydroxy-ethyl)-cyclohex-2-enyl]-N-(2-iodo-phenyl)-methanesulfonamide 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: 91.0%

: 311309-59-8
methanesulfonic acid 1-{3-(2-hydroxy-ethyl)-4-[(2-iodo-phenyl)-methanesulfonyl-amino]-cyclohex-2-enyl}-ethyl ester

: 311309-60-1
N-[4-ethylidene-2-(2-hydroxy-ethyl)-cyclohex-2-enyl]-N-(2-iodo-phenyl)-methanesulfonamide

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; Heating;
DOI:10.1021/ol006477x

Reference yield:

: 143675-84-7
3-isobutoxy-2-(2-propenyl)-2-cyclohexenone

: 311309-60-1
N-[4-ethylidene-2-(2-hydroxy-ethyl)-cyclohex-2-enyl]-N-(2-iodo-phenyl)-methanesulfonamide

Guidance literature:: Multi-step reaction with 9 steps

1: 72 percent / LDA

2: 83 percent / Et₃N; DMAP / CH₂Cl₂

3: 67 percent / DIBAL-H / CH₂Cl₂

4: 67 percent / NaBH₄; CeCl₃*7H₂O / methanol

5: 51 percent / Me₃P; DIAD; pyridine / tetrahydrofuran

6: 78 percent / OsO₄; NMO / acetone; H₂O; 2-methyl-propan-2-ol

7: 65 percent / NaIO₄ / H₂O; diethyl ether; ethanol

8: 95 percent / NaBH₄ / methanol / 0.33 h

9: 91 percent / DBU / toluene / Heating

With pyridine; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; cerium(III) chloride; di-isopropyl azodicarboxylate; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium diisopropyl amide; trimethylphosphane; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; acetone; toluene; tert-butyl alcohol; 1: aldol condensation / 2: Substitution / 3: Reduction / 4: Reduction / 5: Mitsunobu reaction / 6: Oxidation / 7: Oxidation / 8: Reduction / 9: Elimination;
DOI:10.1021/ol006477x

Reference yield:

: 311309-55-4
methanesulfonic acid 1-(3-allyl-4-hydroxy-cyclohex-2-enyl)-ethyl ester

: 311309-60-1
N-[4-ethylidene-2-(2-hydroxy-ethyl)-cyclohex-2-enyl]-N-(2-iodo-phenyl)-methanesulfonamide

Guidance literature:: Multi-step reaction with 5 steps

1: 51 percent / Me₃P; DIAD; pyridine / tetrahydrofuran

2: 78 percent / OsO₄; NMO / acetone; H₂O; 2-methyl-propan-2-ol

3: 65 percent / NaIO₄ / H₂O; diethyl ether; ethanol

4: 95 percent / NaBH₄ / methanol / 0.33 h

5: 91 percent / DBU / toluene / Heating

With pyridine; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; di-isopropyl azodicarboxylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; trimethylphosphane; In tetrahydrofuran; methanol; diethyl ether; ethanol; water; acetone; toluene; tert-butyl alcohol; 1: Mitsunobu reaction / 2: Oxidation / 3: Oxidation / 4: Reduction / 5: Elimination;
DOI:10.1021/ol006477x