2,6-Dimethyl-9-(phenylthio)-2,6-undecadien-10 yne

Base Information

Chemical Name:2,6-Dimethyl-9-(phenylthio)-2,6-undecadien-10 yne
CAS No.:79499-66-4
Molecular Formula:C₁₉H₂₄S
Molecular Weight:284.466
Hs Code.:

Synonyms:

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Chemical Property of 2,6-Dimethyl-9-(phenylthio)-2,6-undecadien-10 yne

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Technology Process of 2,6-Dimethyl-9-(phenylthio)-2,6-undecadien-10 yne

There total 1 articles about 2,6-Dimethyl-9-(phenylthio)-2,6-undecadien-10 yne 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:

: 6138-90-5
trans-geranyl bromide

: 5651-88-7
phenyl propargyl sulfide

: 79499-66-4
2,6-Dimethyl-9-(phenylthio)-2,6-undecadien-10 yne

Guidance literature:: With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; Yield given. Multistep reaction; 1) THF, -60 to -50 deg C, 1 h, 2) THF, -50 to 25 deg C, a few h;
DOI:10.1021/jo00337a057

Reference yield:

: 79499-66-4
2,6-Dimethyl-9-(phenylthio)-2,6-undecadien-10 yne

: C₂₂H₃₀O₅

Guidance literature:: Multi-step reaction with 10 steps

1.1: lithium; naphthalene / tetrahydrofuran / 1.5 h / 0 °C / Inert atmosphere

2.1: zirconocene dichloride / 1,2-dichloro-ethane; water / 0.25 h / 0 - 20 °C / Inert atmosphere

2.2: -20 °C / Inert atmosphere

3.1: zinc(II) chloride; bis(acetylacetonate)nickel(II); triphenylphosphine; diisobutylaluminium hydride / tetrahydrofuran; toluene; 1-methyl-pyrrolidin-2-one / 0.08 h / -45 - 0 °C / Inert atmosphere

3.2: 0.75 h / -45 - 20 °C / Inert atmosphere

4.1: potassium carbonate; potassium hexacyanoferrate(III); methanesulfonamide; tetrabutylammonium acetate; potassium osmate(VI) dihydrate; C₆₅H₈₃N₆O₄⁽¹⁺⁾*I^(1-) / tetrahydrofuran; water; tert-butyl alcohol / 17 h / 0 °C

5.1: pyridine; methanesulfonyl chloride / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere

5.2: 4 h / 20 °C / Inert atmosphere

6.1: manganese; 2,4,6-trimethyl-pyridine; bis(cyclopentadienyl)titanium dichloride / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere

7.1: potassium carbonate / methanol; dichloromethane / 24 h / 20 °C

8.1: lithium; naphthalene / tetrahydrofuran / 0.08 h / -21 °C / Inert atmosphere

9.1: bis-[(trifluoroacetoxy)iodo]benzene / N,N-dimethyl-formamide; water / 0.5 h / 0 °C / Inert atmosphere

10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

With pyridine; 2,4,6-trimethyl-pyridine; bis(cyclopentadienyl)titanium dichloride; potassium osmate(VI) dihydrate; bis(acetylacetonate)nickel(II); manganese; zirconocene dichloride; naphthalene; methanesulfonamide; C₆₅H₈₃N₆O₄⁽¹⁺⁾*I^(1-); tetrabutyl ammonium fluoride; tetrabutylammonium acetate; lithium; diisobutylaluminium hydride; potassium carbonate; methanesulfonyl chloride; triphenylphosphine; potassium hexacyanoferrate(III); bis-[(trifluoroacetoxy)iodo]benzene; zinc(II) chloride; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 3.1: |Negishi Coupling / 3.2: |Negishi Coupling / 4.1: |Sharpless Dihydroxylation;
DOI:10.1002/ejoc.201500815

Reference yield:

: 79499-66-4
2,6-Dimethyl-9-(phenylthio)-2,6-undecadien-10 yne

: {3,5-bis(benzyloxy)-4-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl]benzyloxy}triisopropylsilane

Guidance literature:: Multi-step reaction with 3 steps

1.1: lithium; naphthalene / tetrahydrofuran / 1.5 h / 0 °C / Inert atmosphere

2.1: zirconocene dichloride / 1,2-dichloro-ethane; water / 0.25 h / 0 - 20 °C / Inert atmosphere

2.2: -20 °C / Inert atmosphere

3.1: zinc(II) chloride; bis(acetylacetonate)nickel(II); triphenylphosphine; diisobutylaluminium hydride / tetrahydrofuran; toluene; 1-methyl-pyrrolidin-2-one / 0.08 h / -45 - 0 °C / Inert atmosphere

3.2: 0.75 h / -45 - 20 °C / Inert atmosphere

With bis(acetylacetonate)nickel(II); zirconocene dichloride; naphthalene; lithium; diisobutylaluminium hydride; triphenylphosphine; zinc(II) chloride; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; water; 1,2-dichloro-ethane; toluene; 3.1: |Negishi Coupling / 3.2: |Negishi Coupling;
DOI:10.1002/ejoc.201500815