Benzoic acid (1S,15S)-15-isopropyl-3,14-dioxo-bicyclo[10.2.1]pentadec-12-en-13-yl ester

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Chemical Name:Benzoic acid (1S,15S)-15-isopropyl-3,14-dioxo-bicyclo[10.2.1]pentadec-12-en-13-yl ester
CAS No.:368423-72-7
Molecular Formula:C₂₅H₃₂O₄
Molecular Weight:396.527
Hs Code.:

Synonyms:Benzoic acid (1S,15S)-15-isopropyl-3,14-dioxo-bicyclo[10.2.1]pentadec-12-en-13-yl ester

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Chemical Property of Benzoic acid (1S,15S)-15-isopropyl-3,14-dioxo-bicyclo[10.2.1]pentadec-12-en-13-yl ester

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Technology Process of Benzoic acid (1S,15S)-15-isopropyl-3,14-dioxo-bicyclo[10.2.1]pentadec-12-en-13-yl ester

There total 14 articles about Benzoic acid (1S,15S)-15-isopropyl-3,14-dioxo-bicyclo[10.2.1]pentadec-12-en-13-yl ester 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: 89.0%

: 368423-71-6
Benzoic acid (Z)-(1S,15S)-15-isopropyl-3,14-dioxo-bicyclo[10.2.1]pentadeca-8,12-dien-13-yl ester

: 368423-72-7
Benzoic acid (1S,15S)-15-isopropyl-3,14-dioxo-bicyclo[10.2.1]pentadec-12-en-13-yl ester

Guidance literature:: With hydrogen; palladium on activated charcoal; In tetrahydrofuran; at 20 ℃; for 8.5h;
DOI:10.1021/ja011242h

Reference yield:

: 2-[2-Methyl-prop-(E)-ylidene]-hex-5-enal

: 368423-72-7
Benzoic acid (1S,15S)-15-isopropyl-3,14-dioxo-bicyclo[10.2.1]pentadec-12-en-13-yl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: NaClO₂; KH₂PO₄; 2-methyl-2-butene

2.1: CBr₄; PPh₃

3.1: n-BuLi; LiCl / tetrahydrofuran / -78 °C

3.2: tetrahydrofuran / 1 h / -78 - -45 °C

3.3: HCl / various solvent(s) / 0 °C

4.1: 90 percent / pyridine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 6.5 h / 20 °C

5.1: 77 percent / 3-benzyl-5-(hydroxyethyl)-4-methylthiazolium chloride; Et₃N / dioxane / 23 h / 70 °C

6.1: 91 percent / Grubbs' catalyst / CH₂Cl₂ / 30 h / Heating

7.1: 89 percent / H₂ / Pd/C / tetrahydrofuran / 8.5 h / 20 °C

With pyridine; dmap; sodium chlorite; potassium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; 3-benzyl-4-methyl-5-hydroxyethylthiazolium chloride; carbon tetrabromide; hydrogen; triethylamine; triphenylphosphine; lithium chloride; palladium on activated charcoal; Grubbs catalyst first generation; In tetrahydrofuran; 1,4-dioxane; dichloromethane; 5.1: Stetter reaction;
DOI:10.1021/ja011242h

Reference yield:

: 764-59-0
hex-5-en-1-al

: 368423-72-7
Benzoic acid (1S,15S)-15-isopropyl-3,14-dioxo-bicyclo[10.2.1]pentadec-12-en-13-yl ester

Guidance literature:: Multi-step reaction with 11 steps

1.1: 94 percent / 20 °C

2.1: LDA / tetrahydrofuran / -78 - 10 °C

3.1: LDA / -78 - 10 °C

4.1: (COOH)2 / tetrahydrofuran; H₂O

5.1: NaClO₂; KH₂PO₄; 2-methyl-2-butene

6.1: CBr₄; PPh₃

7.1: n-BuLi; LiCl / tetrahydrofuran / -78 °C

7.2: tetrahydrofuran / 1 h / -78 - -45 °C

7.3: HCl / various solvent(s) / 0 °C

8.1: 90 percent / pyridine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 6.5 h / 20 °C

9.1: 77 percent / 3-benzyl-5-(hydroxyethyl)-4-methylthiazolium chloride; Et₃N / dioxane / 23 h / 70 °C

10.1: 91 percent / Grubbs' catalyst / CH₂Cl₂ / 30 h / Heating

11.1: 89 percent / H₂ / Pd/C / tetrahydrofuran / 8.5 h / 20 °C

With pyridine; dmap; sodium chlorite; potassium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; 3-benzyl-4-methyl-5-hydroxyethylthiazolium chloride; carbon tetrabromide; hydrogen; oxalic acid; triethylamine; triphenylphosphine; lithium chloride; lithium diisopropyl amide; palladium on activated charcoal; Grubbs catalyst first generation; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; 9.1: Stetter reaction;
DOI:10.1021/ja011242h