5-Cyclodecen-1-one, 7-methylene-4-(1-methylethyl)-10-(phenylsulfinyl)-

Base Information

Chemical Name:5-Cyclodecen-1-one, 7-methylene-4-(1-methylethyl)-10-(phenylsulfinyl)-
CAS No.:113666-32-3
Molecular Formula:C₂₀H₂₆O₂S
Molecular Weight:330.491
Hs Code.:
Mol file:113666-32-3.mol

Synonyms:

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Chemical Property of 5-Cyclodecen-1-one, 7-methylene-4-(1-methylethyl)-10-(phenylsulfinyl)-

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Technology Process of 5-Cyclodecen-1-one, 7-methylene-4-(1-methylethyl)-10-(phenylsulfinyl)-

There total 22 articles about 5-Cyclodecen-1-one, 7-methylene-4-(1-methylethyl)-10-(phenylsulfinyl)- 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:

: 105897-86-7
(R)-3-(1-methylethyl)-6-oxo-9-decenal dimethylacetal

: 105329-29-1,105371-14-0,113666-32-3
(4S,5E)-7-methylene-4-(1-methylethyl)-10-phenylsulfinyl-5-cyclodecene-1-one

Guidance literature:: Multi-step reaction with 17 steps

1: LiAlH₄ / diethyl ether / 1 h / below 10 deg C

2: EtN(i-Pr)2 / CH₂Cl₂ / 24 h / Heating

3: OsO₄, NaIO₄ / diethyl ether; H₂O / 7 h

4: LiAlH₄ / diethyl ether / 0.5 h / below 10 deg C

5: pyridine / Ambient temperature

6: 75 percent AcOH / 1 h / 30 °C

7: 1.) LDA / 1.) THF, below -60 deg C, 20 min; 2.) THF, below -60 deg C, 30 min

8: NaOAc / 0.67 h / 130 °C

9: 1 percent NaOMe / methanol / 1 h / Ambient temperature

10: 97 percent / Et₃N, DMAP / CH₂Cl₂ / 7 h / below 0 deg C

11: 1.) NaN(TMS)2; 2.) LiAlH₄ / 1.) DME, 50 min, reflux; 2.) Et₂O, 0 deg C, 1 h

12: DMAP, pyridine / tetrahydrofuran / 24 h / Ambient temperature

13: 84 percent / TMSCl, NaI / acetonitrile / -10 °C

14: 86 percent / sodium naphtalenide / 0.08 h / -70 °C

15: 69 percent / PCC, molecular sieves 3A / CH₂Cl₂ / 0.5 h / Ambient temperature

16: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min

17: NaIO₄ / methanol; H₂O / 22 h

With pyridine; dmap; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; chloro-trimethyl-silane; 3 A molecular sieve; sodium methylate; sodium acetate; sodium hexamethyldisilazane; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; sodium naphthalenide; 1,1,1,3,3,3-hexamethyl-disilazane; pyridinium chlorochromate; sodium iodide; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetonitrile;
DOI:10.1016/S0040-4020(01)86874-5

Reference yield:

: 105897-85-6
(R)-3-(1-methylethyl)-6-oxoheptanal dimethylacetal

: 105329-29-1,105371-14-0,113666-32-3
(4S,5E)-7-methylene-4-(1-methylethyl)-10-phenylsulfinyl-5-cyclodecene-1-one

Guidance literature:: Multi-step reaction with 19 steps

1: 1.) NaH / 1.) dioxane, MeOH, reflux; 2.) reflux, 90 min

2: 62 percent / 1.) KOH / methanol; H₂O / 2 h / Heating

3: LiAlH₄ / diethyl ether / 1 h / below 10 deg C

4: EtN(i-Pr)2 / CH₂Cl₂ / 24 h / Heating

5: OsO₄, NaIO₄ / diethyl ether; H₂O / 7 h

6: LiAlH₄ / diethyl ether / 0.5 h / below 10 deg C

7: pyridine / Ambient temperature

8: 75 percent AcOH / 1 h / 30 °C

9: 1.) LDA / 1.) THF, below -60 deg C, 20 min; 2.) THF, below -60 deg C, 30 min

10: NaOAc / 0.67 h / 130 °C

11: 1 percent NaOMe / methanol / 1 h / Ambient temperature

12: 97 percent / Et₃N, DMAP / CH₂Cl₂ / 7 h / below 0 deg C

13: 1.) NaN(TMS)2; 2.) LiAlH₄ / 1.) DME, 50 min, reflux; 2.) Et₂O, 0 deg C, 1 h

14: DMAP, pyridine / tetrahydrofuran / 24 h / Ambient temperature

15: 84 percent / TMSCl, NaI / acetonitrile / -10 °C

16: 86 percent / sodium naphtalenide / 0.08 h / -70 °C

17: 69 percent / PCC, molecular sieves 3A / CH₂Cl₂ / 0.5 h / Ambient temperature

18: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min

19: NaIO₄ / methanol; H₂O / 22 h

With pyridine; dmap; potassium hydroxide; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; chloro-trimethyl-silane; 3 A molecular sieve; sodium methylate; sodium acetate; sodium hexamethyldisilazane; sodium hydride; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; sodium naphthalenide; 1,1,1,3,3,3-hexamethyl-disilazane; pyridinium chlorochromate; sodium iodide; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetonitrile;
DOI:10.1016/S0040-4020(01)86874-5

Reference yield:

: 113590-01-5
(R)-8-(2,2-Dimethoxy-ethyl)-9-methyl-dec-1-en-5-ol

: 105329-29-1,105371-14-0,113666-32-3
(4S,5E)-7-methylene-4-(1-methylethyl)-10-phenylsulfinyl-5-cyclodecene-1-one

Guidance literature:: Multi-step reaction with 16 steps

1: EtN(i-Pr)2 / CH₂Cl₂ / 24 h / Heating

2: OsO₄, NaIO₄ / diethyl ether; H₂O / 7 h

3: LiAlH₄ / diethyl ether / 0.5 h / below 10 deg C

4: pyridine / Ambient temperature

5: 75 percent AcOH / 1 h / 30 °C

6: 1.) LDA / 1.) THF, below -60 deg C, 20 min; 2.) THF, below -60 deg C, 30 min

7: NaOAc / 0.67 h / 130 °C

8: 1 percent NaOMe / methanol / 1 h / Ambient temperature

9: 97 percent / Et₃N, DMAP / CH₂Cl₂ / 7 h / below 0 deg C

10: 1.) NaN(TMS)2; 2.) LiAlH₄ / 1.) DME, 50 min, reflux; 2.) Et₂O, 0 deg C, 1 h

11: DMAP, pyridine / tetrahydrofuran / 24 h / Ambient temperature

12: 84 percent / TMSCl, NaI / acetonitrile / -10 °C

13: 86 percent / sodium naphtalenide / 0.08 h / -70 °C

14: 69 percent / PCC, molecular sieves 3A / CH₂Cl₂ / 0.5 h / Ambient temperature

15: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min

16: NaIO₄ / methanol; H₂O / 22 h

With pyridine; dmap; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; chloro-trimethyl-silane; 3 A molecular sieve; sodium methylate; sodium acetate; sodium hexamethyldisilazane; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; sodium naphthalenide; 1,1,1,3,3,3-hexamethyl-disilazane; pyridinium chlorochromate; sodium iodide; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetonitrile;
DOI:10.1016/S0040-4020(01)86874-5