10-Ethyl-2-propyl-6,14-dioxatricyclo[10.3.0.0^{4,8}]pentadeca-1(12),4(8)-diene-5,7,13,15-tetrone

Base Information

Chemical Name:10-Ethyl-2-propyl-6,14-dioxatricyclo[10.3.0.0^{4,8}]pentadeca-1(12),4(8)-diene-5,7,13,15-tetrone
CAS No.:743-51-1
Molecular Formula:C18H20 O6
Molecular Weight:332.353
Hs Code.:
Metabolomics Workbench ID:46459
Mol file:743-51-1.mol

$10-Ethyl-2-propyl-6,14-dioxatricyclo[10.3.0.0^{4,8}]pentadeca-1(12),4(8)-diene-5,7,13,15-tetrone$

Synonyms:10-ethyl-2-propyl-6,14-dioxatricyclo[10.3.0.0^{4,8}]pentadeca-1(12),4(8)-diene-5,7,13,15-tetrone

Suppliers and Price of 10-Ethyl-2-propyl-6,14-dioxatricyclo[10.3.0.0^{4,8}]pentadeca-1(12),4(8)-diene-5,7,13,15-tetrone

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of 10-Ethyl-2-propyl-6,14-dioxatricyclo[10.3.0.0^{4,8}]pentadeca-1(12),4(8)-diene-5,7,13,15-tetrone

Chemical Property:

PSA：86.74000
LogP:2.37280
XLogP3:3.1
Hydrogen Bond Donor Count:0
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:3
Exact Mass:332.12598835
Heavy Atom Count:24
Complexity:696

Purity/Quality:: 99% ^*data from raw suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:CCCC1CC2=C(CC(CC3=C1C(=O)OC3=O)CC)C(=O)OC2=O

Technology Process of 10-Ethyl-2-propyl-6,14-dioxatricyclo[10.3.0.0^{4,8}]pentadeca-1(12),4(8)-diene-5,7,13,15-tetrone

There total 35 articles about 10-Ethyl-2-propyl-6,14-dioxatricyclo[10.3.0.0^{4,8}]pentadeca-1(12),4(8)-diene-5,7,13,15-tetrone 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:

: 5441-51-0
4-ethylcyclohexanone

: 743-51-1
(+)-byssochlamic acid

Guidance literature:: Multi-step reaction with 16 steps

1.1: 93 percent / NaH / benzene / 1.5 h / Heating

2.1: Br₂ / diethyl ether / 2.17 h / 0 °C

3.1: 39 percent / methanol / 0 - 20 °C

4.1: 98 percent / porcine liver esterase; aq. Na₂HPO₄; aq. K₂HPO₄ / acetone / 3 h / 20 °C / pH 7

5.1: triethylamine / tetrahydrofuran / 0.5 h / 0 °C

5.2: 89 percent / NaBH₄ / H₂O / 0.5 h / 0 °C

6.1: 93 percent / TsOH monohydrate / CH₂Cl₂ / 1 h / 20 °C

7.1: DIBAL-H / CH₂Cl₂; hexane / 1 h / -78 °C

7.2: 91 percent / Rochelle's salt / CH₂Cl₂ / 0.33 h

8.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

9.1: 71 percent / MgBr₂ / diethyl ether / 5 h / 20 °C

10.1: 60 percent / EDCl; DMAP / CH₂Cl₂ / 4 h / 20 °C

11.1: aq. HF / acetonitrile / 1.5 h / 20 °C

12.1: 23.6 mg / DCC; DMAP*HCl / CHCl₃ / 20 h / Heating

13.1: CH₂Cl₂ / Photolysis

14.1: aq. LiOH / dioxane / 1.5 h / 50 °C

15.1: KMnO₄ / H₂O; dioxane / 1 h / 40 °C

16.1: aq. HCl

With 2,6-dimethylpyridine; hydrogenchloride; porcine liver esterase; dmap; lithium hydroxide; potassium permanganate; dipotassium hydrogenphosphate; disodium hydrogenphosphate; hydrogen fluoride; bromine; 4-(dimethylamino)pyridine hydrochloride; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; dicyclohexyl-carbodiimide; magnesium bromide; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; hexane; dichloromethane; chloroform; water; acetone; acetonitrile; benzene; 1.1: Condensation / 2.1: Bromination / 3.1: Favorski rearrangement-elimination / 4.1: asymmetric hydrolysis / 5.1: Addition / 5.2: Reduction / 6.1: Addition / 7.1: Reduction / 7.2: Reduction / 8.1: silylation / 9.1: acetal cleavage / 10.1: Esterification / 11.1: desilylation / 12.1: Keck-Steglich lactonization / 13.1: Cycloaddition / 14.1: Hydrolysis / 15.1: Oxidation / 16.1: dehydrative cyclization;
DOI:10.1021/ja001898v

Reference yield:

: 114862-60-1
methyl 5-ethyl-2-oxo-cyclohexancarboxylate

: 743-51-1
(+)-byssochlamic acid

Guidance literature:: Multi-step reaction with 15 steps

1.1: Br₂ / diethyl ether / 2.17 h / 0 °C

2.1: 39 percent / methanol / 0 - 20 °C

3.1: 98 percent / porcine liver esterase; aq. Na₂HPO₄; aq. K₂HPO₄ / acetone / 3 h / 20 °C / pH 7

4.1: triethylamine / tetrahydrofuran / 0.5 h / 0 °C

4.2: 89 percent / NaBH₄ / H₂O / 0.5 h / 0 °C

5.1: 93 percent / TsOH monohydrate / CH₂Cl₂ / 1 h / 20 °C

6.1: DIBAL-H / CH₂Cl₂; hexane / 1 h / -78 °C

6.2: 91 percent / Rochelle's salt / CH₂Cl₂ / 0.33 h

7.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

8.1: 71 percent / MgBr₂ / diethyl ether / 5 h / 20 °C

9.1: 60 percent / EDCl; DMAP / CH₂Cl₂ / 4 h / 20 °C

10.1: aq. HF / acetonitrile / 1.5 h / 20 °C

11.1: 23.6 mg / DCC; DMAP*HCl / CHCl₃ / 20 h / Heating

12.1: CH₂Cl₂ / Photolysis

13.1: aq. LiOH / dioxane / 1.5 h / 50 °C

14.1: KMnO₄ / H₂O; dioxane / 1 h / 40 °C

15.1: aq. HCl

With 2,6-dimethylpyridine; hydrogenchloride; porcine liver esterase; dmap; lithium hydroxide; potassium permanganate; dipotassium hydrogenphosphate; disodium hydrogenphosphate; hydrogen fluoride; bromine; 4-(dimethylamino)pyridine hydrochloride; diisobutylaluminium hydride; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; dicyclohexyl-carbodiimide; magnesium bromide; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; hexane; dichloromethane; chloroform; water; acetone; acetonitrile; 1.1: Bromination / 2.1: Favorski rearrangement-elimination / 3.1: asymmetric hydrolysis / 4.1: Addition / 4.2: Reduction / 5.1: Addition / 6.1: Reduction / 6.2: Reduction / 7.1: silylation / 8.1: acetal cleavage / 9.1: Esterification / 10.1: desilylation / 11.1: Keck-Steglich lactonization / 12.1: Cycloaddition / 13.1: Hydrolysis / 14.1: Oxidation / 15.1: dehydrative cyclization;
DOI:10.1021/ja001898v

Reference yield:

: 144226-91-5
3-n-propylcyclobut-1-en-1,2-dicarboxylic acid

: 743-51-1
(+)-byssochlamic acid

Guidance literature:: Multi-step reaction with 9 steps

1: 59 percent / NaI; DIPEA / 1,2-dimethoxy-ethane / 4 h / 20 - 70 °C

2: pig liver esteraze; Na₂HPO₄; K₂HPO₄ / acetone / 3 h / 20 °C / pH 7

3: 60 percent / EDCl; DMAP / CH₂Cl₂ / 4 h / 20 °C

4: aq. HF / acetonitrile / 1.5 h / 20 °C

5: 23.6 mg / DCC; DMAP*HCl / CHCl₃ / 20 h / Heating

6: CH₂Cl₂ / Photolysis

7: aq. LiOH / dioxane / 1.5 h / 50 °C

8: KMnO₄ / H₂O; dioxane / 1 h / 40 °C

9: aq. HCl

With hydrogenchloride; dmap; lithium hydroxide; potassium permanganate; dipotassium hydrogenphosphate; disodium hydrogenphosphate; hydrogen fluoride; 4-(dimethylamino)pyridine hydrochloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; sodium iodide; In 1,4-dioxane; 1,2-dimethoxyethane; dichloromethane; chloroform; water; acetone; acetonitrile; 1: Alkylation / 2: enzymatic hydrolysis / 3: Esterification / 4: desilylation / 5: Keck-Steglich lactonization / 6: Cycloaddition / 7: Hydrolysis / 8: Oxidation / 9: dehydrative cyclization;
DOI:10.1021/ja001898v