Heptelidic acid

Base Information

• Chemical Name: Heptelidic acid
• CAS No.: 57710-57-3
• Molecular Formula: C15H20 O5
• Molecular Weight: 280.321
• UNII: 6H8EDV2NKQ
• DSSTox Substance ID: DTXSID901105608
• Nikkaji Number: J39.310J
• Wikipedia: Koningic_acid
• Wikidata: Q48791494
• Metabolomics Workbench ID: 108746
• ChEMBL ID: CHEMBL3585922
• Mol file: 57710-57-3.mol

Synonyms:heptelidic acid;koningic acid

Chemical Property of Heptelidic acid

Chemical Property:

• Boiling Point: 501.1°Cat760mmHg
• PKA: 3.68±0.40(Predicted)
• Flash Point: 189.1°C
• PSA: 76.13000
• Density: 1.27g/cm³
• LogP: 1.62160
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 280.13107373
• Heavy Atom Count: 20
• Complexity: 481

Purity/Quality:

97% ^*data from raw suppliers

Heptelidic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C1CCC2(CO2)C3C1C=C(COC3=O)C(=O)O
• Isomeric SMILES: CC(C)[C@H]1CC[C@@]2(CO2)[C@@H]3[C@@H]1C=C(COC3=O)C(=O)O
• Uses: Heptalidic acid is a?sesquiterpene lactone and found to inhibit etoposide-induced apoptosis in human leukemia U937 cells. In addition, it also?inhibit mammalian DNA polymerases and terminal deoxynucleotidyl transferase.

Technology Process of Heptelidic acid

There total 10 articles about Heptelidic acid 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: 96.0%

(5aS,6R,9S,9aS)-1,3,5a,6,7,8,9,9a-octahydro-6-(1-methylethyl)-1-oxospiro-(2-benzoxepine-9,2'-oxirane)-4-carbaldehyde (191987-13-0) → 1,5a,6,7,8,9a-hexahydro-6-(1-methyl-ethyl)-1-oxo-spiro<2-benzoxepin-9(3H),2'oxirane>-4-carboxylic acid (heptelidic acid) (57710-57-3)

Guidance literature:

With sodium chlorite;

DOI:10.1007/BF00807894

Reference yield:

(1S,2S,3R)-2-[3-(tert-Butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-propenyl]-3-isopropyl-6-oxo-cyclohexanecarboxylic acid methyl ester (179601-53-7) → 1,5a,6,7,8,9a-hexahydro-6-(1-methyl-ethyl)-1-oxo-spiro<2-benzoxepin-9(3H),2'oxirane>-4-carboxylic acid (heptelidic acid) (57710-57-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 91 percent / NaH

2: 89 percent / Ni(acac)2 / tetrahydrofuran; diethyl ether / 66 h / 20 °C

3: 81 percent / FeCl₃ / 0.12 h / 0 °C

4: 84 percent / TFA / CH₂Cl₂ / 48 h / 0 °C

5: 1) aq. NaOH, 2) bis(2-oxo-1,3-oxazolidin-3-yl)chlorophosphane

6: 86 percent / CrO₃

7: 54 percent / tBuOOH, Mo(CO)6

8: 96 percent / NaClO₂

With chromium(VI) oxide; tert.-butylhydroperoxide; sodium hydroxide; sodium chlorite; bis(2-oxo-1,3-oxazolidin-3-yl)phosphinous chloride; hexacarbonyl molybdenum; iron(III) chloride; sodium hydride; trifluoroacetic acid; bis(acetylacetonate)nickel(II); In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1007/BF00807894

Reference yield:

(5R,6S)-6-[3-(tert-Butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-propenyl]-2-(diethoxy-phosphoryloxy)-5-isopropyl-cyclohex-1-enecarboxylic acid methyl ester (191987-07-2) → 1,5a,6,7,8,9a-hexahydro-6-(1-methyl-ethyl)-1-oxo-spiro<2-benzoxepin-9(3H),2'oxirane>-4-carboxylic acid (heptelidic acid) (57710-57-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 89 percent / Ni(acac)2 / tetrahydrofuran; diethyl ether / 66 h / 20 °C

2: 81 percent / FeCl₃ / 0.12 h / 0 °C

3: 84 percent / TFA / CH₂Cl₂ / 48 h / 0 °C

4: 1) aq. NaOH, 2) bis(2-oxo-1,3-oxazolidin-3-yl)chlorophosphane

5: 86 percent / CrO₃

6: 54 percent / tBuOOH, Mo(CO)6

7: 96 percent / NaClO₂

With chromium(VI) oxide; tert.-butylhydroperoxide; sodium hydroxide; sodium chlorite; bis(2-oxo-1,3-oxazolidin-3-yl)phosphinous chloride; hexacarbonyl molybdenum; iron(III) chloride; trifluoroacetic acid; bis(acetylacetonate)nickel(II); In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1007/BF00807894

upstream raw materials:

(5aS,6R,9S,9aS)-1,3,5a,6,7,8,9,9a-octahydro-6-(1-methylethyl)-1-oxospiro-(2-benzoxepine-9,2'-oxirane)-4-carbaldehyde

(1S,2S,3R)-2-[3-(tert-Butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-propenyl]-3-isopropyl-6-oxo-cyclohexanecarboxylic acid methyl ester

(5aS,6R,9aS)-4-Hydroxymethyl-6-isopropyl-9-methylene-5a,6,7,8,9,9a-hexahydro-3H-benzo[c]oxepin-1-one

(5aR,6S,9aS)-1,3,5a,6,7,8,9,9a-octahydro-6-(1-methylethyl)-9-methylene-1-oxo-2-benzoxepine-4-carbaldehyde

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