Nigrosporalactone

Base Information

• Chemical Name: Nigrosporalactone
• CAS No.: 23790-99-0
• Molecular Formula: C8H12O3
• Molecular Weight: 156.17900
• UNII: UUX6F128HY
• Nikkaji Number: J990.641J
• Wikidata: Q105033103
• Mol file: 23790-99-0.mol

Synonyms:Nigrosporalactone;UUX6F128HY;UNII-UUX6F128HY;23790-99-0;5-(S)-(1-(1(S)-Hydroxybut-2-enyl))dihydrofuran-2-one;Dihydro-5-(1-hydroxy-2-butenyl)-2(3H)-furanone, trans-(+)-;2(3H)-Furanone, dihydro-5-((1S,2E)-1-hydroxy-2-butenyl)-, (5S)-

Chemical Property of Nigrosporalactone

Chemical Property:

• PSA: 46.53000
• LogP: 0.62900
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 156.078644241
• Heavy Atom Count: 11
• Complexity: 174

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC=CC(C1CCC(=O)O1)O
• Isomeric SMILES: C/C=C/[C@@H]([C@@H]1CCC(=O)O1)O

Technology Process of Nigrosporalactone

There total 6 articles about Nigrosporalactone 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: 68.0%

(4S,5S,6E)-4,5-O-cyclohexylidene-6-octenoic acid (846027-62-1) → (4S)-4-[(1'S,2'E)-1'-hydroxy-2'-butenyl]-4-butanolide (23790-99-0)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; at 50 ℃; for 12h;

DOI:10.1039/b415759c

Reference yield:

(2R,3S)-((E)-3-Propenyl)-1,4-dioxa-spiro[4.5]decane-2-carbaldehyde (1026153-57-0) → (4S)-4-[(1'S,2'E)-1'-hydroxy-2'-butenyl]-4-butanolide (23790-99-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: NaH / tetrahydrofuran / 0.5 h / 20 °C

1.2: tetrahydrofuran / 0.58 h / 0 °C

2.1: 93 percent / aq. KOH / ethanol / 0.75 h / 20 °C

3.1: 98 percent / NaBH₄ / ethanol / 15 h / 40 °C

4.1: 68 percent / aq. HCl / dioxane / 12 h / 50 °C

With hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; sodium hydride; In tetrahydrofuran; 1,4-dioxane; ethanol; 1.2: Horner-Wadsworth-Emmons reaction;

DOI:10.1039/b415759c

Reference yield:

(2S,3S,4E)-2,3-O-cyclohexylidene-4-hexen-1-ol (846027-56-3) → (4S)-4-[(1'S,2'E)-1'-hydroxy-2'-butenyl]-4-butanolide (23790-99-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 1.17 h / -78 - 20 °C

2.1: NaH / tetrahydrofuran / 0.5 h / 20 °C

2.2: tetrahydrofuran / 0.58 h / 0 °C

3.1: 93 percent / aq. KOH / ethanol / 0.75 h / 20 °C

4.1: 98 percent / NaBH₄ / ethanol / 15 h / 40 °C

5.1: 68 percent / aq. HCl / dioxane / 12 h / 50 °C

With hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; oxalyl dichloride; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; 1.1: Swern oxidation / 2.2: Horner-Wadsworth-Emmons reaction;

DOI:10.1039/b415759c

upstream raw materials:

(4S,5S,6E)-4,5-O-cyclohexylidene-6-octenoic acid

(2R,3S)-((E)-3-Propenyl)-1,4-dioxa-spiro[4.5]decane-2-carbaldehyde

(2S,3S,4E)-2,3-O-cyclohexylidene-4-hexen-1-ol

(4S,5S,2E,6E)-4,5-O-cyclohexylidene-2,6-octadienoic acid

Downstream raw materials:

Benzoic acid (E)-(R)-1-((S)-5-oxo-tetrahydro-furan-2-yl)-but-2-enyl ester

Refernces