1-(6-Iodo-1-methoxy-3-methylenehexyl)-5-(1-oxoprop-2-enyl)-2,6,6-trimethylcyclohex-1-ene

Base Information

Chemical Name:1-(6-Iodo-1-methoxy-3-methylenehexyl)-5-(1-oxoprop-2-enyl)-2,6,6-trimethylcyclohex-1-ene
CAS No.:216978-27-7
Molecular Formula:C₂₀H₃₁IO₂
Molecular Weight:430.369
Hs Code.:

Synonyms:1-(6-Iodo-1-methoxy-3-methylenehexyl)-5-(1-oxoprop-2-enyl)-2,6,6-trimethylcyclohex-1-ene

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Chemical Property of 1-(6-Iodo-1-methoxy-3-methylenehexyl)-5-(1-oxoprop-2-enyl)-2,6,6-trimethylcyclohex-1-ene

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Technology Process of 1-(6-Iodo-1-methoxy-3-methylenehexyl)-5-(1-oxoprop-2-enyl)-2,6,6-trimethylcyclohex-1-ene

There total 26 articles about 1-(6-Iodo-1-methoxy-3-methylenehexyl)-5-(1-oxoprop-2-enyl)-2,6,6-trimethylcyclohex-1-ene 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: 93.0%

: 216978-66-4
Toluene-4-sulfonic acid 6-(5-acryloyl-2,6,6-trimethyl-cyclohex-1-enyl)-6-methoxy-4-methylene-hexyl ester

: 216978-27-7
1-(6-Iodo-1-methoxy-3-methylenehexyl)-5-(1-oxoprop-2-enyl)-2,6,6-trimethylcyclohex-1-ene

Guidance literature:: With sodium iodide; In butanone; for 1.5h; Heating;
DOI:10.1039/a805268i

Reference yield:

: 35044-52-1
ethyl 2-acetyl-3-methylbut-2-enoate

: 216978-27-7
1-(6-Iodo-1-methoxy-3-methylenehexyl)-5-(1-oxoprop-2-enyl)-2,6,6-trimethylcyclohex-1-ene

Guidance literature:: Multi-step reaction with 18 steps

1: 98 percent / tetrahydrofuran / Ambient temperature

2: 92 percent / DIBAL-H / toluene / -60 °C

3: 93 percent / PTSA / benzene / 65 °C

4: 95 percent / Et₃N, DMAP / CH₂Cl₂ / 18 h / Ambient temperature

5: 79 percent / BF₃*OEt₂ / toluene / 1.) -78 deg C, 5 min, 2.) -78 deg C, 10 h

6: 98 percent / NaBH₄ / methanol; diethyl ether / 1.) 0 deg C, 30 min, 2.) 0 deg C to r.t., 20 min

7: 94 percent / Et₃N, DMAP / CH₂Cl₂ / 12 h / 0 - 20 °C

8: 95 percent / K₂CO₃ / methanol / 14 h / Ambient temperature

9: 97 percent / tetra(n-propyl)ammonium perruthenate, NMO, 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / Ambient temperature

10: 82 percent / NaI, SnCl₂*2H₂O / dimethylformamide / 4 h / Ambient temperature

11: 97 percent / KHMDS / tetrahydrofuran / 1.) -78 deg C, 7 min, 2.) -78 deg C to r.t., 30 min

12: 88 percent / PPTS / methanol / 4.5 h / Ambient temperature

13: 94 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / Ambient temperature

14: 95 percent / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -78 deg C to r.t., 1 h

15: 86 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / Ambient temperature

16: 97 percent / TBAF, PTSA / tetrahydrofuran / 60 h / Ambient temperature

17: 79 percent / Et₃N / CH₂Cl₂ / 24 h / Ambient temperature

18: 93 percent / NaI / butan-2-one / 1.5 h / Heating

With dmap; sodium tetrahydroborate; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; sodium iodide; tin(ll) chloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; butanone; benzene;
DOI:10.1039/a805268i

Reference yield:

: 5390-04-5
pent-1-yn-5-ol

: 216978-27-7
1-(6-Iodo-1-methoxy-3-methylenehexyl)-5-(1-oxoprop-2-enyl)-2,6,6-trimethylcyclohex-1-ene

Guidance literature:: Multi-step reaction with 14 steps

1: 99 percent / DMAP, Et₃N / CH₂Cl₂ / 1.) 0 deg C, 1 h, 2.) r.t., 14 h

2: 1.) 9-BBN, 2.) NaOH, H₂O, H₂O₂ / 1.) CH₂Cl₂, 0 deg C to r.t., 14 h, 2.) 0 deg C, 3 h

3: 82 percent / t-BuLi / tetrahydrofuran; diethyl ether / 1.) -110 deg C, 1 h, 2.) -110 deg C to r.t., 1 h

4: 99 percent / NaBH₄, CeCl₃*7H₂O / methanol / 0.33 h / 0 °C

5: 99 percent / NBS, PPh₃ / CH₂Cl₂ / 0.33 h / 0 - 20 °C

6: 82 percent / NaI, SnCl₂*2H₂O / dimethylformamide / 4 h / Ambient temperature

7: 97 percent / KHMDS / tetrahydrofuran / 1.) -78 deg C, 7 min, 2.) -78 deg C to r.t., 30 min

8: 88 percent / PPTS / methanol / 4.5 h / Ambient temperature

9: 94 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / Ambient temperature

10: 95 percent / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -78 deg C to r.t., 1 h

11: 86 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / Ambient temperature

12: 97 percent / TBAF, PTSA / tetrahydrofuran / 60 h / Ambient temperature

13: 79 percent / Et₃N / CH₂Cl₂ / 24 h / Ambient temperature

14: 93 percent / NaI / butan-2-one / 1.5 h / Heating

With dmap; sodium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; 9-borabicyclo[3.3.1]nonane dimer; cerium(III) chloride; tetrabutyl ammonium fluoride; water; dihydrogen peroxide; tert.-butyl lithium; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; sodium iodide; tin(ll) chloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; butanone;
DOI:10.1039/a805268i