821-38-5

Basic information

• Product Name: Tetradecanedioic acid
• Synonyms: 1,12-DODECANEDICARBOXYLIC ACID;DODECANEDICARBOXYLIC ACID;DICARBOXYLIC ACID C14;RARECHEM AL BO 1123;TETRADECANEDIOIC ACID;tetradecandioic acid;tetradecane diacid;1,12-DODECANEDICARBOXYLIC ACID ( FLAKE )
• CAS NO: 821-38-5
• Molecular Formula: C14H26O4
• Molecular Weight: 258.35
• EINECS: 212-476-9
• Product Categories: alpha,omega-Alkanedicarboxylic Acids;alpha,omega-Bifunctional Alkanes;Monofunctional & alpha,omega-Bifunctional Alkanes;tetradecane diacid
• Mol File: 821-38-5.mol
• Article Data: 12

Chemical Properties

• Melting Point: 124-127 °C(lit.)
• Boiling Point: 427.81°C (rough estimate)
• Flash Point: 230.5 °C
• Appearance: /Liquid
• Density: 1.0768 (rough estimate)
• Vapor Pressure: 9.48E-09mmHg at 25°C
• Refractive Index: 1.4650 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 4.48±0.10(Predicted)
• Water Solubility: SLIGHTLY SOLUBLE
• BRN: 1788202
• CAS DataBase Reference: Tetradecanedioic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Tetradecanedioic acid(821-38-5)
• EPA Substance Registry System: Tetradecanedioic acid(821-38-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 821-38-5(Hazardous Substances Data)

Usage

Chemical Properties

white fine powder

Uses

Tetradecanedioic acid is used as an organic chemical synthesis intermediate.

Definition

ChEBI: An alpha,omega-dicarboxylic acid that is tetradecane in which the methyl groups have been oxidised to the corresponding carboxylic acids.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C14H26O4/c15-13(16)11-9-7-5-3-1-2-4-6-8-10-12-14(17)18/h1-12H2,(H,15,16)(H,17,18)/p-2

Synthetic route

C22H34O8 (81393-28-4) → 1,14-tetradecanedioic acid (821-38-5)

Conditions	Yield
With hydrogenchloride In water Heating;	96%

2,2':5',2"-terthiophene-5,5"-dicarboxylic acid (87145-86-6) → 1,14-tetradecanedioic acid (821-38-5)

Conditions	Yield
With nickel In water for 20h; Heating;	85%

carbon monoxide (201230-82-2) + dodec-2-en-1-ol (22104-81-0) → 1,14-tetradecanedioic acid (821-38-5)

Conditions	Yield
With HeMaRaphos; water; toluene-4-sulfonic acid; palladium dichloride In tetrahydrofuran at 125℃; under 30003 Torr; for 24h; Autoclave; Green chemistry; regioselective reaction;	60%

1,10-decadiene (1647-16-1) + acetic anhydride (108-24-7) → 11-dodecenoic acid (65423-25-8) + 1,14-tetradecanedioic acid (821-38-5)

Conditions	Yield
With oxygen; cobalt(II) acetate; manganese(II) acetate In acetic acid at 130℃; for 5h;	A 18% B 8%

1,4-dibromo-butane (110-52-1) → 1,14-tetradecanedioic acid (821-38-5)

Conditions	Yield
With diethyl ether; magnesium Behandeln des Reaktionprodukts mit CO2;

1,12-diiodododecane (24772-65-4) + potassium cyanide (151-50-8) → 1,14-tetradecanedioic acid (821-38-5)

Conditions	Yield
With ethanol Erwaermen des Reaktionsgemisches mit aethanol.Kalilauge;

pentadec-14-enoic acid (17351-34-7) → 1,14-tetradecanedioic acid (821-38-5)

Conditions	Yield
With ozone

14-hydroxymyristic acid (17278-74-9) → 1,14-tetradecanedioic acid (821-38-5)

Conditions	Yield
With chromic acid; acetic acid

docos-14-enoic acid (45281-27-4) → Octanoic acid (124-07-2) + 1,14-tetradecanedioic acid (821-38-5)

Conditions	Yield
Ozonspaltung;

4,11-dioxo-tetradecanedioic acid (3860-19-3) → 1,14-tetradecanedioic acid (821-38-5)

Conditions	Yield
With potassium hydroxide; hydrazine hydrate; diethylene glycol
With sodium hydroxide; hydrazine hydrate In diethylene glycol at 200 - 220℃;

7-semicarbazono-tetradecanedioic acid (101108-19-4) → 1,14-tetradecanedioic acid (821-38-5)

Conditions	Yield
With potassium hydroxide; hydrazine hydrate; diethylene glycol

13-cyclopent-2-enyl-tridecanoic acid (502-30-7) → 1,14-tetradecanedioic acid (821-38-5)

Conditions	Yield
With permanganate(VII) ion

cyclotetradecanone (3603-99-4) → 1,14-tetradecanedioic acid (821-38-5)

Conditions	Yield
With chromium(VI) oxide; acetic acid

2,2'-ethanediyl-bis-cyclohexane-1,3-dione (855359-65-8) → 1,14-tetradecanedioic acid (821-38-5)

Conditions	Yield
With sodium hydroxide; hydrazine hydrate; diethylene glycol at 125℃; Reagens 4: Methanol; anschliessend auf 195grad;

acetic acid tert-butyl ester (540-88-5) + 1,10-dibromodecane (4101-68-2) → 1,14-tetradecanedioic acid (821-38-5)

Conditions	Yield
With lithium amide; ammonia at -40℃; Erhitzen des Reaktionsprodukts mit Dioxan und konz. wss. Salzsaeure;

sodium ethyl acetylacetate enolate (1007476-32-5) + 1,10-dibromodecane (4101-68-2) → 1,14-tetradecanedioic acid (821-38-5)

Conditions	Yield
With ethanol Erwaermen des Reaktionsprodukts mit konz.wss.Kalilauge;

Tetradecandisaeuredinitril (7735-44-6) → 1,14-tetradecanedioic acid (821-38-5)

Conditions	Yield
With sulfuric acid; acetic anhydride In water Heating;

dimethyl tetradecanedioate (5024-21-5) → 1,14-tetradecanedioic acid (821-38-5)

Conditions	Yield
With sodium hydroxide In methanol
saponification;
With potassium hydroxide In methanol for 24h; Heating;

cyclopentadeca-1,2-diene (14108-92-0) → 1,14-tetradecanedioic acid (821-38-5)

Conditions	Yield
(i) O3, (ii) AcOOH; Multistep reaction;

carboxy-methyl sodium ; sodium-salt + 1,10-dibromodecane (4101-68-2) → 1,14-tetradecanedioic acid (821-38-5)

Conditions	Yield
With sodium isopropylate

2-(3-Methylbut-2-enyliden)-cyclododecanon (32400-35-4) → 1,14-tetradecanedioic acid (821-38-5)

Conditions	Yield
With ozone

β-Propiolactone (57-57-8) + 1,8-octanediyldimagnesium dibromide (45037-87-4) → 1,14-tetradecanedioic acid (821-38-5)

Conditions	Yield
With dilithium tetrachlorocuprate In tetrahydrofuran at 0℃; for 3h;

1-(tert-Butyl-dimethyl-silanyloxy)-cycloheptyl-hydroperoxide (88739-43-9) → 1,14-tetradecanedioic acid (821-38-5)

Conditions	Yield
With sulfuric acid; water; iron(II) sulfate 1.) 0 deg C, methanol 2.) RT; Yield given. Multistep reaction;

cycloheptanone (502-42-1) → heptanedioic acid (111-16-0) + oenanthic acid (111-14-8) + 1,14-tetradecanedioic acid (821-38-5) + (1,1'-bicycloheptyl)-2,2'-dione (55311-03-0) + 7-(2-Oxo-cycloheptyl)-heptanoic acid (55311-13-2)

Conditions	Yield
With dihydrogen peroxide at 120 - 140℃; Product distribution; oxidative cleavage of cycloalkanones by hydrogen peroxide;

cycloheptanone (502-42-1) → heptanedioic acid (111-16-0) + oenanthic acid (111-14-8) + 1,14-tetradecanedioic acid (821-38-5) + 7-(2-Oxo-cycloheptyl)-heptanoic acid (55311-13-2)

Conditions	Yield
With dihydrogen peroxide at 120 - 140℃; Yield given. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;

cycloheptanone (502-42-1) → oenanthic acid (111-14-8) + 1,14-tetradecanedioic acid (821-38-5) + (1,1'-bicycloheptyl)-2,2'-dione (55311-03-0) + 7-(2-Oxo-cycloheptyl)-heptanoic acid (55311-13-2)

Conditions	Yield
With dihydrogen peroxide at 120 - 140℃; Yield given. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;

2,3,17-Trioxabicyclo<12.2.1>heptadecane → 1,14-tetradecanedioic acid (821-38-5) + 14-oxotetradecanoic acid

Conditions	Yield
In benzene-d6 at 80℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

1,12-dodecandiol (5675-51-4) + carbon monoxide → 1,14-tetradecanedioic acid (821-38-5)

Conditions	Yield
With iodine; tetracarbonyl nickel at 260℃; under 147102 Torr;

dodecane-tetracarboxylic acid-(1.1.12.12) → 1,14-tetradecanedioic acid (821-38-5)

1,14-tetradecanedioic acid (821-38-5) → 1,14-tetradecanediol (19812-64-7)

Conditions	Yield
With borane In tetrahydrofuran Reflux;	100%
With dimethylsulfide borane complex In tetrahydrofuran at 50℃; for 4h; Reduction;	98%
With dimethylsulfide borane complex In tetrahydrofuran at 0 - 20℃; for 7h;	97%

methanol (67-56-1) + 1,14-tetradecanedioic acid (821-38-5) → dimethyl tetradecanedioate (5024-21-5)

Conditions	Yield
With thionyl chloride for 24h; Inert atmosphere;	100%
With sulfuric acid Heating;
With thionyl chloride at 20℃; for 6h;
With thionyl chloride at 20℃;

1,14-tetradecanedioic acid (821-38-5) → tetradecanedioyl dichloride (21646-49-1)

Conditions	Yield
With oxalyl dichloride In chloroform at 20℃; Heating / reflux;	99%
With oxalyl dichloride In chloroform at 20℃; Heating / reflux;	99%
With oxalyl dichloride In dichloromethane at 20℃; for 24h; Inert atmosphere;	91%

n-butyl formate (592-84-7) + 1,14-tetradecanedioic acid (821-38-5) → Tetradecanedioic acid dibutyl ester (15805-82-0) + Tetradecanedioic acid monobutyl ester

Conditions	Yield
With Dowex 50W-X2 (50-100 mesh) In octane at 100℃; for 12.5h;	A 6% B 89%
With Dowex 50Wx2 In octane at 100℃; for 12.5h; Esterification;	A 6% B 89%

1,14-tetradecanedioic acid (821-38-5) + cholesterol (57-88-5) → tetradecanedioic acid bis-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] ester

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 12h;	87%

thallium salt of Δ2-1,3-thiazoline-2-thiol (63987-96-2) + 1,14-tetradecanedioic acid (821-38-5) → 1,14-Bis-(2-thioxo-thiazolidin-3-yl)-tetradecane-1,14-dione (74058-86-9)

Conditions	Yield
In tetrahydrofuran Ambient temperature;	85%

1,14-tetradecanedioic acid (821-38-5) + Tetradecanoic acid (R)-4-[(2-tert-butoxycarbonylamino-ethoxy)-methoxy-phosphoryloxy]-3-hydroxy-butyl ester → Tetradecanedioic acid bis-{(R)-1-[(2-tert-butoxycarbonylamino-ethoxy)-methoxy-phosphoryloxymethyl]-3-tetradecanoyloxy-propyl} ester

Conditions	Yield
With dicyclohexyl-carbodiimide; dmap In dichloromethane at 0 - 24℃; for 12h;	84%

1,14-tetradecanedioic acid (821-38-5) + 3β-hydroxy-14β,16β-O-(4-methoxybenzylidene)card-20(22)-enolide (190579-30-7) → hydrogen 14β,16β-O-(4-methoxybenzylidene)card-20(22)-enolide-3β-yl 1,12-dodecanedicarboxylate (190579-40-9)

Conditions	Yield
With pyridine; p-toluenesulfonyl chloride for 4h; Ambient temperature;	81%

acetic acid butyl ester (123-86-4) + 1,14-tetradecanedioic acid (821-38-5) → Tetradecanedioic acid dibutyl ester (15805-82-0) + Tetradecanedioic acid monobutyl ester

Conditions	Yield
With Dowex 50Wx2 In octane at 110℃; for 25h; Esterification;	A 4% B 80%

1,14-tetradecanedioic acid (821-38-5) + (S)-(5-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propylamine hydrochloride (101403-24-1) → N1,N14-bis((S)-5-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-N1,N14-dipropyltetradecanediamide (1403823-09-5)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 24h;	80%

1,14-tetradecanedioic acid (821-38-5) + 2-Amino-2-methyl-1-propanol (124-68-5) → C22H40N2O2 (1194063-44-9)

Conditions	Yield
at 170℃; for 0.416667h; Microwave irradiation; Neat (no solvent); open vessel;	78%

1,14-tetradecanedioic acid (821-38-5) + 1,2-diamino-benzene (95-54-5) → C26H34N4 (158076-61-0)

Conditions	Yield
With hydrogenchloride at 135℃; for 20h;	76%

1,14-tetradecanedioic acid (821-38-5) + alovudine (25526-93-6) → 3'-fluoro-2′,3′-dideoxy-5'-O-(13-carboxyltridecanoate)thymidine

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 4h;	75%

1,14-tetradecanedioic acid (821-38-5) + phorbol 13-acetate 20-tritylether (82389-25-1) → Tetradecanedioic acid mono-((1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-9a-acetoxy-4a,7b-dihydroxy-1,1,6,8-tetramethyl-5-oxo-3-trityloxymethyl-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-1H-cyclopropa[3,4]benzo[1,2-e]azulen-9-yl) ester (561063-36-3)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at -78 - 20℃;	73%

1,14-tetradecanedioic acid (821-38-5) + phorbol 12-acetate-20-trityl (92590-31-3) → Tetradecanedioic acid mono-((1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-9-acetoxy-4a,7b-dihydroxy-1,1,6,8-tetramethyl-5-oxo-3-trityloxymethyl-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl) ester (561063-48-7)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃;	73%

1,14-tetradecanedioic acid (821-38-5) + 1,3-diaminoguanidine hydrochloride (36062-19-8) → 1,12-bis(3,4-diamino-1,2,4-triazol-5-yl)dodecane (1338484-49-3)

Conditions	Yield
Stage #1: 1,14-tetradecanedioic acid; 1,3-diaminoguanidine hydrochloride at 50 - 120℃; for 4.5h; Stage #2: With sodium hydroxide In water pH=8;	72%

1,14-tetradecanedioic acid (821-38-5) + rac-α-aminoglutarimide hydrochloride (24666-56-6) → N1,N14-bis(2,6-dioxopiperidin-3-yl)tetradecanediamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃;	72%

1,14-tetradecanedioic acid (821-38-5) + (+)-D-glucosamine hydrochloride (1078691-95-8) → C20H37NO8

Conditions	Yield
With 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; sodium hydroxide In methanol; water at 20℃;	70%
Stage #1: 1,14-tetradecanedioic acid With sodium hydroxide In methanol at 20℃; Stage #2: (+)-D-glucosamine hydrochloride With 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride at 20℃; for 30h;	64%

1,14-tetradecanedioic acid (821-38-5) + (-)-N4-(4,4'-dimethoxytrityl)-5-fluoro-2',3'-dideoxy-3'-thiacytidine (1365246-86-1) → C43H52FN3O8S

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;	68%

1,14-tetradecanedioic acid (821-38-5) + ciprofloxacin (85721-33-1) → C48H58F2N6O8 (1350462-69-9)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 4h;	66%

1,14-tetradecanedioic acid (821-38-5) + 3'-azido-2',3'-deoxythymidine (30516-87-1) → C34H48N10O10 (1396742-25-8)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; for 12h;	61%
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;	30%

4'-demethyl-4-deoxypodophyllotoxin (3590-93-0, 85440-15-9, 123287-54-7, 123287-57-0) + 1,14-tetradecanedioic acid (821-38-5) → Tetradecanedioic acid mono-[2,6-dimethoxy-4-((5R,5aR,8aR)-6-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl)-phenyl] ester

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 2h;	60%

1,14-tetradecanedioic acid (821-38-5) + 1-(2-nitrophenyl)ethan-1-ol (80379-10-8, 108530-03-6, 142631-59-2, 3205-25-2) → N-(2-{1-[(13-carboxytridecanoyl)oxy]ethyl}phenyl)-N-oxohydroxylammonium

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 0 - 25℃; Inert atmosphere;	58%

1,14-tetradecanedioic acid (821-38-5) + metronidazole (443-48-1) → C20H33N3O6

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dimethyl sulfoxide at 40℃; for 24h;	57.4%

1,14-tetradecanedioic acid (821-38-5) → tetradecanedioyl difluoride

Conditions	Yield
With sodium fluoride; ethanaminium,N-(difluoro-λ4-sulfanylidene)-N-ethyl-,tetrafluoroborate at 20℃; for 24h; Inert atmosphere;	57%

7-[4-(2-chloroacetyl) piperazin-1-yl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid + 1,14-tetradecanedioic acid (821-38-5) → C52H62F2N6O12 (1350462-75-7)

Conditions	Yield
Stage #1: 1,14-tetradecanedioic acid With caesium carbonate In N,N-dimethyl-formamide at 50℃; for 1h; Stage #2: 7-[4-(2-chloroacetyl) piperazin-1-yl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid With tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide at 50℃; for 72h;	56%

1,14-tetradecanedioic acid (821-38-5) + [1-deamino,8-lysine]vasotocin → C100H154N24O26S4

Conditions	Yield
With 1-hydroxy-pyrrolidine-2,5-dione; N-ethyl-N,N-diisopropylamine; diisopropyl-carbodiimide In N,N-dimethyl-formamide for 7h;	56%

Upstream product

• 110-52-1 1,4-dibromo-butane 
• 45281-27-4 docos-14-enoic acid 
• 3860-19-3 4,11-dioxo-tetradecanedioic acid 
• 101108-19-4 7-semicarbazono-tetradecanedioic acid 
• 540-88-5 acetic acid tert-butyl ester 
• 4101-68-2 1,10-dibromodecane 
• 1007476-32-5 sodium ethyl acetylacetate enolate 
• 7735-44-6 Tetradecandisaeuredinitril 
• 5675-51-4 1,12-dodecandiol 
• 24772-65-4 1,12-diiodododecane 
• 151-50-8 potassium cyanide 
• 17351-34-7 pentadec-14-enoic acid 
• 17278-74-9 14-hydroxymyristic acid 
• 502-30-7 13-cyclopent-2-enyl-tridecanoic acid 

Downstream Products

• 5024-21-5 dimethyl tetradecanedioate 
• 19812-63-6 diethyl tetradecanedioate 
• 19812-64-7 1,14-tetradecanediol 
• 190579-40-9 hydrogen 14β,16β-O-(4-methoxybenzylidene)card-20(22)-enolide-3β-yl 1,12-dodecanedicarboxylate 
• 234082-00-9 1,12-dodecanedicarboxylic acid mono-tert-butyl ester 
• 561063-36-3 Tetradecanedioic acid mono-((1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-9a-acetoxy-4a,7b-dihydroxy-1,1,6,8-tetramethyl-5-oxo-3-trityloxymethyl-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-1H-cyclopropa[3,4]benzo[1,2-e]azulen-9-yl) ester 
• 561063-48-7 Tetradecanedioic acid mono-((1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-9-acetoxy-4a,7b-dihydroxy-1,1,6,8-tetramethyl-5-oxo-3-trityloxymethyl-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl) ester 
• 941286-74-4 N,N'-dimethyl-N,N'-diphenyl-tetradecanediamide 
• 72995-94-9 14-bromotetradecan-1-ol 
• 941286-75-5 N,N'-dimethyl-N,N'-diphenyl-1,8-tetradecanediamine 
• 907218-92-2 14-(2,5-dimethoxyphenylamino)tetradecan-1-ol 
• 907218-96-6 [14-(tert-butyl-dimethyl-silanyloxy)-tetradecyl]-(2,5-dimethoxy-phenyl)-amine 
• 887604-06-0 hexadec-15-ynyloxymethyl-benzene 
• 887604-26-4 Q₂FA₁₆ 

Relevant articles and documents

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Cytotoxic linear acetylenes from a marine sponge Pleroma sp.

Bioassay-guided fractionation of the extract of the rare deep-sea marine sponge Pleroma sp. afforded seven new linear acetylenes, yakushynols A-F (1-6) and neopetroformyne E (7). The structures of 1-7 were determined by a combination of the analysis of spectroscopic data and chemical derivatization. Compounds 1-6 are the first examples of the sponge-derived acetylenes of the size of duryne with oxidation at the sixth carbon from the terminus. Compounds 1-5 and 7 exhibited moderate cytotoxic activity. A biosynthetic route of neopetroformyne A was inferred from the structural transition among sponge-derived linear acetylenes.

cis/trans-Ozonides of Cycloolefins

Ozonolyses in pentane of the unsubstituted cycloolefins having eleven-, twelve-, fourteen- and sixteen-membered rings (1b-e) and of cyclohexadecen-8-one (12) gave the corresponding cis- (2b-e; cis-15a) and trans-ozonides (3b-e; trans-15a), whereas cyclodecene (1a) gave only the corresponding cis-ozonide (2a).Ozonolyses on polyethylene of the dimethyl-substituted cycloolefins bearing fourteen- and sixteen-membered rings (7b,c) also afforded cis- and trans-isomeric ozonides (8, 9), whereas from the twelve-membered ring (7a) only the corresponding cis-ozonide (8a) was formed. - Keywords: Ozonides; Cycloolefins