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Chemical Structure| 432027-96-8
Chemical Structure| 432027-96-8
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Product Details of [ 432027-96-8 ]

CAS No. :432027-96-8 MDL No. :N/A
Formula : C8H10O Boiling Point : -
Linear Structure Formula :- InChI Key :QCQDXFLZGCVLTR-UHFFFAOYSA-N
M.W : 122.16 Pubchem ID :86204217
Synonyms :

Calculated chemistry of [ 432027-96-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.5
Num. rotatable bonds : 3
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 38.06
TPSA : 20.23 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.37 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.11
Log Po/w (XLOGP3) : 0.95
Log Po/w (WLOGP) : 0.8
Log Po/w (MLOGP) : 1.97
Log Po/w (SILICOS-IT) : 1.63
Consensus Log Po/w : 1.49

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.0
Solubility : 12.3 mg/ml ; 0.1 mol/l
Class : Very soluble
Log S (Ali) : -0.96
Solubility : 13.3 mg/ml ; 0.109 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.69
Solubility : 25.1 mg/ml ; 0.206 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.65

Safety of [ 432027-96-8 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 432027-96-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 432027-96-8 ]

[ 432027-96-8 ] Synthesis Path-Downstream   1~40

  • 1
  • [ 432027-96-8 ]
  • [ 3282-30-2 ]
  • [ 432027-68-4 ]
YieldReaction ConditionsOperation in experiment
40% With dmap; triethylamine In dichloromethane at 20℃; for 10h;
  • 2
  • [ 432027-96-8 ]
  • [ 18162-48-6 ]
  • [ 432027-69-5 ]
YieldReaction ConditionsOperation in experiment
37% With triethylamine In dichloromethane at 20℃; for 10h;
  • 3
  • [ 181478-00-2 ]
  • [ 432027-96-8 ]
YieldReaction ConditionsOperation in experiment
82% With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 0.0833333h;
78% With lithium aluminium tetrahydride In tetrahydrofuran at -10 - 25℃; for 12h; Inert atmosphere;
78% With lithium aluminium tetrahydride In tetrahydrofuran at -10 - 25℃; for 12h; 43.3 Step 3: Synthesis of ethyl 2-(prop-2-yn-1-yl)pent-4-yn-1-ol. To a suspension of lithium aluminum hydride (1.25 g, 33.0 mmol) in dry THF (40 mL) stirring at -10 °C was added a solution of methyl 2-(2-propynyl)-4-pentynoate (3.06 g, 20.4 mmol) in dry THF (10 mL). The reaction mixture was allowed to warm to 25 °C and stirred for 12 h. The reaction mixture was then quenched through the dropwise addition of H2O (1.25 mL), an aq 10% NaOH solution (1.25 mL), and then additional H2O (3.75 mL). The reaction mixture was then stirred for 30 min until the suspended solids turned white. The mixture was then filtered, and the solids were washed with diethyl ether (100 mL). The resulting solution was concentrated on a rotary evaporator yielding a pale yellow oil. The crude oil was purified by flash chromatography on a silica gel column using 10% EtOAc in hexanes as the eluent, resulting in 1.95 g of a clear oil (78% yield).
  • 4
  • [ 432027-96-8 ]
  • 4-hydroxymethyl-1-methylene-2-(triethylsilyl)methylenecyclopentane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 37 percent / Et3N / CH2Cl2 / 10 h / 20 °C 2.1: B(C6F5)3 / [PhN=C(Me)-C(Me)=NPh]PtMe2 / toluene / 0.25 h / 110 °C 2.2: 58 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.17 h / 20 °C
  • 5
  • [ 432027-96-8 ]
  • 4-hydroxymethyl-1-methylene-2-(triethylsilyl)methylenecyclopentane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 37 percent / Et3N / CH2Cl2 / 10 h / 20 °C 2.1: B(C6F5)3 / [PhN=C(Me)-C(Me)=NPh]PtMe2 / toluene / 0.25 h / 110 °C 2.2: tetrabutylammonium fluoride / tetrahydrofuran / 0.17 h / 20 °C
  • 6
  • [ 432027-96-8 ]
  • [ 1026080-93-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 40 percent / DMAP; Et3N / CH2Cl2 / 10 h / 20 °C 2: 78 percent / B(C6F5)3 / [PhN=C(Me)-C(Me)=NPh]PtMe2 / toluene / 0.25 h / 110 °C
  • 7
  • [ 432027-96-8 ]
  • 4-(trimethylacetoxy)methyl-1-methylene-2-(tributylsilyl)methylenecyclopentane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 40 percent / DMAP; Et3N / CH2Cl2 / 10 h / 20 °C 2: B(C6F5)3 / [PhN=C(Me)-C(Me)=NPh]PtMe2 / toluene / 0.25 h / 110 °C
  • 8
  • [ 432027-96-8 ]
  • 2,2-Dimethyl-propionic acid (3aS,4S,8aR)-1,3-dioxo-2-phenyl-4-triethylsilanyl-1,2,3,3a,4,5,6,7,8,8a-decahydro-cyclopenta[f]isoindol-6-ylmethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 40 percent / DMAP; Et3N / CH2Cl2 / 10 h / 20 °C 2: 78 percent / B(C6F5)3 / [PhN=C(Me)-C(Me)=NPh]PtMe2 / toluene / 0.25 h / 110 °C 3: toluene / 15 h / 110 °C
  • 9
  • [ 432027-96-8 ]
  • 2,2-Dimethyl-propionic acid (3aR,4S,8aS)-1,3-dioxo-2-phenyl-4-triethylsilanyl-1,2,3,3a,4,5,6,7,8,8a-decahydro-cyclopenta[f]isoindol-6-ylmethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 40 percent / DMAP; Et3N / CH2Cl2 / 10 h / 20 °C 2: 78 percent / B(C6F5)3 / [PhN=C(Me)-C(Me)=NPh]PtMe2 / toluene / 0.25 h / 110 °C 3: toluene / 15 h / 110 °C
  • 10
  • [ 432027-96-8 ]
  • [ 591-50-4 ]
  • [ 1049012-25-0 ]
YieldReaction ConditionsOperation in experiment
95% With tetrakis(triphenylphosphine) palladium(0); triethylamine; copper(l) chloride at 50℃; Inert atmosphere;
  • 11
  • [ 432027-96-8 ]
  • [ 124-63-0 ]
  • 2-(prop-2-yn-1-yl)pent-4-yn-1-yl methanesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In dichloromethane at 0℃; for 2h; Inert atmosphere;
  • 12
  • [ 432027-96-8 ]
  • [ 930092-19-6 ]
YieldReaction ConditionsOperation in experiment
91% With methanesulfonic acid; AgNO<SUB>3</SUB>(PPh<SUB>3</SUB>); water In methanol at 70℃; for 3h; Ionic liquid; Inert atmosphere;
  • 13
  • [ 432027-96-8 ]
  • C13H18O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap; triethylamine / dichloromethane 2: toluene-4-sulfonic acid / methanol
  • 14
  • [ 432027-96-8 ]
  • C23H34O10 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: dmap; triethylamine / dichloromethane 2: toluene-4-sulfonic acid / methanol 3: dmap; 2,2-dipropargyl-1,3-propandiol / dichloromethane 4: toluene-4-sulfonic acid / methanol
  • 15
  • [ 432027-96-8 ]
  • [ 1313763-78-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: dmap; triethylamine / dichloromethane 2: toluene-4-sulfonic acid / methanol 3: dmap; 2,2-dipropargyl-1,3-propandiol / dichloromethane
  • 16
  • [ 432027-96-8 ]
  • [ 1313763-80-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: dmap; triethylamine / dichloromethane 2: toluene-4-sulfonic acid / methanol 3: dmap; 2,2-dipropargyl-1,3-propandiol / dichloromethane 4: toluene-4-sulfonic acid / methanol 5: dmap; 2,2-dipropargyl-1,3-propandiol / dichloromethane
  • 17
  • [ 432027-96-8 ]
  • [ 994-30-9 ]
  • [ 1313763-76-6 ]
YieldReaction ConditionsOperation in experiment
98.5% With pyridine; dmap In dichloromethane at 0 - 20℃; for 7h;
  • 18
  • [ 432027-96-8 ]
  • [ 408322-03-2 ]
  • [ 1313763-83-5 ]
YieldReaction ConditionsOperation in experiment
99.4% With dmap; triethylamine In dichloromethane
  • 19
  • [ 432027-96-8 ]
  • [ 760-67-8 ]
  • 4-(2-ethylhexanoyloxy)-methyl-1,6-heptadiyne [ No CAS ]
YieldReaction ConditionsOperation in experiment
94.5% With dmap; triethylamine In dichloromethane at 0 - 20℃; for 4h;
  • 20
  • [ 432027-96-8 ]
  • [ 24131-32-6 ]
  • C29H28O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
79.1% Stage #1: 4-(hydroxymethyl)-1,6-heptadiyne With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.5h; Stage #2: 3,5-bis(benzyloxy)benzyl bromide In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil at 20℃; for 1h;
  • 21
  • [ 432027-96-8 ]
  • [ 2345-34-8 ]
  • 2-(prop-2-yn-1-yl)pent-4-yn-1-yl 4-hydroxybenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 46 h / 0 - 20 °C 2: ammonium acetate; water / methanol / 76 h / 20 °C
  • 22
  • [ 432027-96-8 ]
  • [ 2345-34-8 ]
  • 2-(prop-2-yn-1-yl)pent-4-yn-1-yl 4-acetoxybenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 46h; 3 Example 3: 2-(prop-2-yn-1-yl)pent-4-yn-1-yl 4-hydroxybenzoate [41 1] Example 3: 2-(Pro -yl 4-hydroxybenzoate [412] To a solution of 2-(prop-2-yn-1-yl)pent-4-yn-1 -ol (J. Org. Chem. 2002, 67, 2778) (380 mg, 3.1 1 mmol), 4-acetoxybenzoic acid (619 mg, 3.43 mmol) and DMAP (36.9 mg, 0.30 mmol) in DCM at 0°C was added EDC HCI (663 mg, 3.46 mmol) and the resulting solution stirred at 0°C for 1h before allowing to warm to rt. The mixture was stirred for an additional 21 h before further EDC HCI (652 mg, 3.40 mmol) was added. The resultant mixture was stirred at rt for an additional 24h before Et20 and H20 were added. The product was extracted (Et20), washed (H20, then brine), dried (Na2S04), filtered and concentrated under reduced pressure. Flash chromatography (0 - 100% EtOAc / petrol gradient elution) gave 2-(prop-2-yn-1-yl)pent-4-yn-1-yl 4-acetoxybenzoate (427 mg, 1.50 mmol, 48%) as a colourless oil. 2-(prop-2-yn-1-yl)pent-4-yn-1-yl 4-acetoxybenzoate (423.3 mg, 1.49 mmol) was dissolved in a 3:1 mixture of MeOH:H20 (16 mL) before NH4OAc (583.6 mg, 7.57 mmol) was added. The resultant mixture was stirred at rt for 76 h before EtOAc and H20 were added. The product was extracted (EtOAc), washed (H20, then brine), dried (Na2S04), filtered and concentrated under reduced pressure. Flash chromatography (0 - 100% EtOAc / petrol gradient elution) gave the title compound (295.1 mg, 1.22 mmol, 82%) as a white solid. ESI-MS: m/z 243 ([M+Hf). 1H NMR (400 MHz CDCI3): δ 7.95 (m, 2H), 6.86 (m, 2H), 4.38 (d, J = 6.1 Hz, 2H), 2.47 (dd, J = 6.2, 2.7 Hz, 4H), 2.28 (m, 1 H), 2.03 (t, J = 2.7 Hz, 2H).
  • 23
  • [ 432027-96-8 ]
  • (Z)-isopropyl 7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((R)-5-phenyl-3-((((2-(prop-2-yn-1-yl)pent-4-yn-1-yl)oxy)carbonyl)oxy)pentyl)cyclopentyl)hept-5-enoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: pyridine / dichloromethane / -40 - 20 °C 2.1: pyridine / 0 - 20 °C 2.2: 16 h / 20 °C
  • 24
  • [ 432027-96-8 ]
  • (S)-1-(tert-butylamino)-3-((4-morpholino-1,2,5-thiadiazol-3-yl)oxy)propan-2-yl (2-(prop-2-yn-1-yl)pent-4-yn-1-yl) carbonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine / dichloromethane / -40 - 20 °C 2: triethylamine / dichloromethane / 24 h / 0 - 20 °C
  • 25
  • [ 432027-96-8 ]
  • [ 41639-83-2 ]
  • (Z)-2-(prop-2-yn-1-yl)pent-4-yn-1-yl 7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((R)-3-hydroxy-5-phenylpentyl)cyclopentyl)hept-5-enoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In dichloromethane at 20℃; Inert atmosphere; Darkness; 12 Example 12: (Z)-2-(Prop-2-yn-1-yl)pent-4-yn-1-yl 7-((1R,2R,3R,5S)- 3,5-dihydroxy-2-((R)-3-hydroxy-5-phenylpentyl)cyclopentyl)hept-5-enoate General procedure: [399] Method 2: HBTU mediated ester formation [400] A solution of the carboxylic acid substrate (1.0 eq.) in anhydrous THF is added dropwise into a stirring solution of HBTU (-1.2 eq.), the alcohol derivative (-1.6 eq.) and triethylamine (-4.3 eq.) in anhydrous THF under nitrogen atmosphere. The mixture is stirred at room temperature for 3 days, with the exclusion of light, or until the reaction is complete. The reaction is quenched with 1 M aqueous citric acid and extracted with ethyl acetate. The organic phase is then washed with saturated aqueous sodium hydrogen carbonate, followed by brine. The organic phase is then dried over Na2S04, filtered, concentrated and dried in vacuo. [424] Example 12: (Z)-2-(Prop-2-yn-1-yl)pent-4-yn-1-yl 7-((1R,2R,3R,5S)- 3,5-dihydroxy-2-((R)-3-hydroxy-5-phenylpentyl)cyclopentyl)hept-5-enoate [425] A solution of latanoprost free acid {0.3989 g, 1.02 mmol) in anhydrous DCM (10 mL) was added dropwise into a solution mixture of 2-(prop-2-yn-1 - yl)pent-4-yn-1 -ol (0.1405 g, 1.15 mmol), HBTU (0.4391 g, 1 .16 mmol) and triethylamine (0.60 mL, 0.4362 g, 4.31 mmol) in anhydrous DCM (5 mL) according to the procedure outlined in Method 2 above. The crude residue was purified on the automated flash chromatography using 0%-20% MeOH in DCM gradient elution to give the title compound as a clear colourless viscous oil (0.2251 g, 45% yield). ESI-MS: m/z 540 ([M+2Na]+). H NMR (400 MHz, CDCI3) δ 7.33 - 7.24 (m, 2H), 7.24 - 7.14 (m, 3H), 5.56 - 5.32 (m, 2H), 4.23 - 4.06 (m, 3H), 4.01 - 3.88 (m, 1 H), 3.73 - 3.60 (m, 1 H), 2.88 - 2.58 (m, 3H), 2.44 - 2.27 (m, 8H), 2.25 - 2.05 (m, 4H), 2.01 (t, J = 2.7 Hz, 2H), 1.90 - 1.84 (m, 2H), 1.84 - 1.46 (m, 9H), 1.46 - 1.18 (m, 2H). 3C NMR (101 MHz, CDCI3) δ 173.79, 142.20, 129.63, 129.57, 128.56, 128.55, 125.98, 81.04, 78.94, 74.88, 71.45, 70.63, 65.28, 53.06, 52.03, 42.68, 39.22, 36.38, 35.94, 33.70, 32.26, 29.79, 27.09, 26.76, 24.96, 20.00.
  • 26
  • [ 432027-96-8 ]
  • [ 108-30-5 ]
  • 4-oxo-4-((2-(prop-2-yn-1-yl)pent-4-yn-1-yl)oxy)butanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With pyridine; dmap In dichloromethane at 45℃; for 16h; 19 Example 19: (R)-1-((1 R,2R,3S,5R)-3,5-Dihydroxy-2-((Z)-7-isopropoxy- 7-oxohept-2-en-1 -yl)cyclopentyl)-5-phenylpentan-3-yl (2-(prop-2-yn-1 -yl)pent-4- yn-1-yl) succinate [438] Example 19: (R)-1-((1 R,2R,3S,5R)-3,5-Dihydroxy-2-((Z)-7-isopropoxy- 7-oxohept-2-en-1 -yl)cyclopentyl)-5-phenylpentan-3-yl (2-(prop-2-yn-1 -yl)pent-4- yn-1-yl) succinate [439] 2-(Prop-2-yn-1-yl)pent-4-yn-1-ol (552.3 mg, 4.52 mmol) in anhydrous DCM (20 mL)was added succinic anhydride (5.99 mg, 5.99 mmol), DMAP (23.0 mg, 0.19 mmol) and pyridine (0.36 mL, 28.0 mmol). The mixture was heated at 45°C for 16 h. The reaction mixture was washed with 1 M HCI, followed by brine. The organic phase is then dried over a2S04, filtered, concentrated and dried in vacuo to give 4-oxo-4-((2-(prop-2-yn-1-yl)pent-4-yn-1 -yl)oxy)butanoic acid as a clear colourless oii (quantitative yield). A solution of example 9 (117.7 mg, 0.24 mmol) in anhydrous DCM (1 mL) was added dropwise to a solution of 4-oxo-4-((2- (prop-2-yn-1-yl)pent-4-yn-1-yl)oxy)butanoic acid (60.6 mg, 0.27 mmol), DCC (62.2 mg, 0.30 mmol) and DMAP (3.8 mg, 0.03 mmol) in anhydrous DCM (5 mL) according to Method 1 b outlined above. The residue was dissolved in methanol (2 mL) and stirred at room temperature for 3 days. The crude residue was purified on the automated flash chromatography using 0%-100% EtOAc in pet. spirit gradient elution to give the title compound as a clear colourless oil (81.9 mg, 54% yield) 1H NMR (400 MHz, CDCI3) δ 7.24 - 7.17 (m, 2H), 7.14 - 7.07 (m, 3H), 5.43 - 5.25 (m, 2H), 4.97 - 4.83 (m, 2H), 4.15 - 4.03 (m, 3H), 3.83 (s, 1 H), 2.67 - 2.43 (m, 7H), 2.35 - 2.17 (m, 7H), 2.15 - 1.96 (m, 4H), 1.95 (t, J = 2.6 Hz, 2H), 1.91 - 1.75 (m, 4H), 1.75 - 1.50 (m, 6H), 1.43 - 1.23 (m, 3H), 1.16 (s, 3H), 1.15 (s, 3H). 3C NMR (101 MHz, CDCI3) δ 173.48, 172.18, 172.05, 141.56, 129.62, 129.37, 128.44, 128.37, 125.95, 78.69, 74.60, 74.47, 70.58, 67.65, 65.48, 52.80, 51.63, 42.50, 36.26, 35.85, 34.09, 32.76, 31.76, 29.32, 29.27, 29.07, 26.95, 26.68, 24.96, 21.88, 19.85.
89% With dmap In dichloromethane at 20℃; for 24h; Inert atmosphere; Schlenk technique; 3.2. Synthesis of Compound 1 To a solution of 4-hydroxymethyl-1,6-heptadiyne (6.1 g, 50 mmol) in 60 mL of CH2Cl2, succinicanhydride (6 g, 60 mmol) and DMAP (1.22 g, 10 mmol) were added and stirred under anN2 atmosphere for 24 h at room temperature. The CH2Cl2 phase was washed with 1 M HCl and saturated saltwateruntil the water phase reached neutrality. After that, the CH2Cl2 solvent was evaporated, and the crudeproduct was purified by column chromatography on silica gel using petroleum ether/ethyl acetate (1:5)as eluent. The compound 1 was obtained as a yellow sticky liquid (10.2 g, 89%); 1H NMR (500 MHz,CDCl3, ppm): 8.87 (s, 1H, -COOH), 4.21 (d, 2H, -CH2OC-), 2.72 (m, 2H, -CH2COOH), 2.65 (m, 2H,-CH2CH2COO-), 2.39 (m, 4H, -CHCH2CCH), 2.15 (m, 1H, -CH2CHCH2-), 2.03 (t, 2H, CCH).
88.3% With dmap In dichloromethane for 24h; Inert atmosphere;
  • 27
  • [ 432027-96-8 ]
  • [ 32315-10-9 ]
  • 2-(prop-2-yn-1-yl)pent-4-yn-1-yl carbonochloridate [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With pyridine In dichloromethane at -40 - 20℃; 20 Example 20: (Z)-isopropyl 7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((R)-5-phenyl-3-((((2-(prop-2-yn-1-yl)pent-4-yn-1-yl)oxy)carbonyl)oxy)pentyl)cyclopentyl)hept-5-enoate General procedure: [403] Method 4: Formation of chloroformate [404] To a solution of the alcohol derivative (1.0 eq) and triphosgene (0.5 eq.) in anhydrous DCM, pyridine (1.3 eq) is added dropwise at -40°C. The reaction mixture is stirred at -40°C for 2 h, then slowly warm to room temperature and stirred for 4 h or until the reaction is complete. The reaction mixture is filtered through a thin layer of silica gel, concentrated and dried in vacuo. [440] Example 20: (Z)-lsopropyl 7-(( R,2R,3R,5S)-3,5-dihydroxy-2-((R)-5- phenyl-3-((((2-(prop-2-yn-1 -yl)pent-4-yn-1 - yl)oxy)carbonyl)oxy)pentyl)cyclopentyl)hept-5-enoate [441] To a solution of 2-(prop-2-yn-1-yl)pent-4-yn-1 -ol (716.9 mg, 5.87 mmol) and triphosgene (877.3 mg, 2.96 mmol) in anhydrous DCM (10 mL), pyridine (0.62 mL, 608.8 mg, 7.70 mmol) was added according to Method 4 outline above to give 2-(prop-2-yn-1-yl)pent-4-yn-1-yl carbonochloridate as a clear colourless oil (897.7 mg, 83% yield). [442] To a solution of example 9 (82.6 mg, 0.17 mmol) in anhydrous pyridine (3 mL), 2-(prop-2-yn-1 -yl)pent-4-yn-1 -yl carbonochloridate (68.4 mg, 0.37 mmol) was added according to Method 5 outlined above. The crude mixture was dissolved in methanol (5 mL) and stirred at room temperature for 16 h. The residue was purified on the automated flash chromatography using 0%-100% EtOAc in pet. spirit gradient elution to give the title compound as a clear colourless oil (21.9 mg, 23% yield). 1H NMR (400 MHz, CDCI3) δ 7.34 - 7.24 (m, 2H), 7.23 - 7.11 (m, 3H), 5.48 - 5.30 (m, 2H), 4.99 (hept, J = 6.3 Hz, 1 H), 4.83 - 4.71 (m, 1 H), 4.22 (dd, J = 6.2, 1.3 Hz, 2H), 4.15 (bs, 1 H), 3.91 (bs, 1 H), 2.80 - 2.54 (m, 2H), 2.47 - 2.38 (m, 4H), 2.38 - 2.24 (m, 7H), 2.21 - 2.05 (m, 4H), 2.02 (t, J = 2.7 Hz, 2H), 2.00 - 1.75 (m, 5H), .75 - 1.61 (m, 4H), 1.55 - 1.24 (m, 3H), 1.23 (s, 3H), 1.21 (s, 3H). 13C NMR (101 MHz, CDCI3) δ 173.60, 155.07, 141.39, 129.85, 129.31 , 128.58, 128.52, 128.44, 126.14, 78.84, 78.68, 74.79, 70.70, 68.50, 67.78, 66.48, 52.99, 51.83, 42.60, 36.45, 35.91 , 34.15, 32.85, 31.73, 29.37, 27.02, 26.77, 25.03, 21.96, 21.76, 19.84.
83% With pyridine In dichloromethane at -40 - 20℃; 11 To a solution of 2-(prop-2-yn-1-yl)pent-4-yn-1-ol (716.9 mg, 5.87 mmol) and triphosgene ((877.3 mg, 2.96 mmol).) in anhydrous DCM (10 ml_), pyridine (0.62 ml_, 608.8 mg, 7.70 mmol)) was added dropwise at -40°C. The reaction mixture was stirred at -40°C for 2 h, then slowly warmed to room temperature and stirred for 4 h or until the reaction is complete. The reaction mixture was filtered through a thin layer of silica gel, concentrated and dried in vacuo to give 2-(prop-2-yn-1-yl)pent-4-yn-1-yl carbonochloridate as a clear colourless oil (897.7 mg, 83% yield).
  • 28
  • [ 432027-96-8 ]
  • [ 1388697-73-1 ]
  • C15H19N2O2(1+)*F6P(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% Stage #1: 4-(hydroxymethyl)-1,6-heptadiyne; [1-(2-carboxylpropyl)-1-methylimidazolium] hexafluorophosphate With dmap In acetonitrile at 0℃; for 0.166667h; Inert atmosphere; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 20℃; for 72h; Inert atmosphere;
  • 29
  • [ 65994-70-9 ]
  • [ 432027-96-8 ]
YieldReaction ConditionsOperation in experiment
91% With lithium aluminium tetrahydride In tetrahydrofuran at 10 - 20℃; 2-(2-Propynyl)-pent-4-yn-1-ol (5): LiAlH4 (0.27 g, 7.5 mmol) was added to stirred solution of 1d (1.1 g, 7.2 mmol) in anhydrous THFat 10 °C. The reaction mixture was allowed to warm to room temperature and stirred overnight.Water (1.2 mL) was added carefully to destroy excess reagent, followed by 10% NaOH aq (1.2 mL)and more water (3.6 mL). Precipitating aluminates were filtered off and rinsed with CH2Cl2. Theaqueous phase was extracted with CH2Cl2 and the combined organic phases were dried over MgSO4and concentrate to leave 55 (0.8 g, 91 %) as colorless oil.
  • 30
  • [ 63104-44-9 ]
  • [ 432027-96-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: lithium chloride / dimethyl sulfoxide; water / 1 h / Reflux 2: sodium hydroxide; water / ethanol / 9 h / Reflux 3: lithium aluminium tetrahydride / tetrahydrofuran / 10 - 20 °C
Multi-step reaction with 2 steps 1: lithium chloride; water / dimethyl sulfoxide / 1 h / Reflux 2: lithium aluminium tetrahydride / tetrahydrofuran / 12 h / -10 - 25 °C
  • 31
  • [ 432027-96-8 ]
  • C60H94N12O19 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap / dichloromethane / 24 h / Inert atmosphere 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 96 h / 0 - 20 °C / Inert atmosphere
  • 32
  • [ 432027-96-8 ]
  • [ 50893-53-3 ]
  • 1-chloroethyl (2-(prop-2-yn-1-yl)pent-4-yn-1-yl) carbonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With dmap In dichloromethane at 20℃; for 18h; 9 I -Chioroethyl (2-(prop-2-yn- I -yi)pent-4-yn- 1-yl) carbonate To an ice cold solution & 2-(prop-2-yn-1-yl)pent-4-yn-1-ol (2.0 g, 16.37 mmol) and DMAP (3.0 g, 24.55 mmol) in anhydrous dichloromethane (60 mL), was added 1-chloroethyl chloroformate (3.4 mL, 31.4 mmol). The reaction mixture was allowed to warm to room temperature and stirred for 18h. The solvent wasremoved under reduced pressure. The crude was slurried with ethyl acetate and passed through a plug & silica. The title compound was isolated as a dear amber coloured liquid (3.01 g, 80% yield). 1H NMR (400 MHz, CDCI3) 56.43 (q, J = 5.8 Hz, IH), 4.31 (d, J = 6.1 Hz, 2H), 2.48- 2.36 (m, 4H), 2.25-2.14 (m, IH), 2.03 (t, J=2.6Hz, 2H), 1.84(d, J=5.8 Hz, 3H).
  • 33
  • [ 432027-96-8 ]
  • 1-((((2-(prop-2-yn-1-yl)pent-4-yn-1-yl)oxy)carbonyl)oxy)ethyl 2-(2-((2,6-dichlorophenyl)amino)phenyl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap / dichloromethane / 18 h / 20 °C 2: N,N-dimethyl-formamide / 0 - 20 °C
  • 34
  • [ 432027-96-8 ]
  • 1-((((2-(prop-2-yn-1-yl)pent-4-yn-1-yl)oxy)carbonyl)oxy)ethyl (3S)-9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap / dichloromethane / 18 h / 20 °C 2: potassium carbonate / N,N-dimethyl-formamide / 96 h / 20 °C / Darkness
  • 35
  • [ 432027-96-8 ]
  • C36H34N2O8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap / dichloromethane / 24 h / 20 °C / Inert atmosphere; Schlenk technique 2: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 96 h / 20 °C / Inert atmosphere; Cooling with ice; Schlenk technique
  • 36
  • [ 432027-96-8 ]
  • [ 762-42-5 ]
  • dimethyl 2-(hydroxymethyl)-2,3-dihydro-1H-indene-5,6-dicarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
26% With Wilkinson's catalyst In ethanol for 18h; Inert atmosphere; Reflux; 43.4 Step 4: Synthesis of dimethyl 2-(hydroxymethyl)-2,3-dihydro-1H-indene-5,6- dicarboxylate. A solution of 5 and dimethyl acetylenedicarboxylate (6, 30.7 g, 216 mmol) in 110 mL of absolute EtOH was degassed by bubbling N2 through the solution for 10 min. To this was added 1.0 g (0.02 equiv) of Wilkinson’s catalyst [(Ph3P)3RhCl] at 25 °C. After being heated at reflux for 18 h, the reaction mixture was cooled to 25 °C and then concentrated in vacuo. The resulting brown residue was diluted in 200 mL of Et2O, and the precipitate was removed by filtration over Celite. The filtrate was concentrated and the crude product purified by column chromatography (20% EtOAc/hexane) to give 4.60g (26%) of compound 7.
26% With Wilkinson's catalyst In ethanol at 25℃; Inert atmosphere; Reflux; 7.4 Step 4: Synthesis of dimethyl 2-(hydroxymethyl)-2,3-dihydro-lH-indene-5,6- dicarboxylate. A solution of 5 and dimethyl acetylenedicarboxylate (6, 30.7 g, 216 mmol) in 110 mL of absolute EtOH was degassed by bubbling N2 through the solution for 10 min. To this was added 1.0 g (0.02 equiv) of Wilkinson’s catalyst ((Ph3P)3RhCl) at 25 °C. After being warmed at reflux for 18 h, the reaction mixture was cooled to 25 °C and then concentrated in vacuo. The resulting brown residue was diluted in 200 mL of Et20, and the precipitate was removed by filtration over Celite. The filtrate was concentrated and the crude product purified by column chromatography (20% EtOAc/hexane) to give 4.60g (26%) of compound 7.
26% With Wilkinson's catalyst In ethanol at 25℃; for 18h; Reflux; 22.4 Step 4: Synthesis of dimethyl 2-(hydroxymethyl)-2,3-dihydro-1H-indene-5,6- dicarboxylate. A solution of 5 and dimethyl acetylenedicarboxylate (6, 30.7 g, 216 mmol) in 110 mL of absolute EtOH was degassed by bubbling N2 through the solution for 10 min. To this was added 1.0 g (0.02 equiv) of Wilkinson’s catalyst [(Ph3P)3RhCl] at 25 °C. After being heated at reflux for 18 h, the reaction mixture was cooled to 25 °C and then concentrated in vacuo. The resulting brown residue was diluted in 200 mL of Et2O, and the precipitate was removed by filtration over Celite. The filtrate was concentrated and the crude product purified by column chromatography (20% EtOAc/hexane) to give 4.60g (26%) of compound 7.
  • 37
  • [ 432027-96-8 ]
  • [ 1262873-48-2 ]
  • 2-(prop-2-yn-1-yl)pent-4-yn-1-yl 4-((3S,5aR,6R,7R,8aS)-6-((R,E)-4-(2,5-difluorophenoxy)-3-hydroxybut-1-en-1-yl)-7-hydroxyoctahydro-2H-cyclopenta[b]oxepin-3-yl)butanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 72h; Inert atmosphere; 1 Method 1 : Formation of HBTU mediated esters General procedure: A solution of the carboxylic acid substrate (1.0 eq.) in anhydrous THF or DCM is added to a stirring solution of HBTU (-1.2 eq.), the alcohol derivative (-1.6 eq.) and triethylamine (-4.3 eq.) in anhydrous THF or DCM under a nitrogen atmosphere. The mixture is stirred at room temperature for 3 days, with the exclusion of light, or until the reaction is complete. The reaction is quenched with 0.5 M or 1 M aqueous citric acid and extracted with DCM or ethyl acetate. The organic phase is then washed (sat. aq. NaHCC>3, and brine), dried (Na2SC>4), filtered, concentrated, and dried in vacuo. Purification is by flash chromatography.
  • 38
  • [ 432027-96-8 ]
  • isopropyl 4-((3S,5aR,6R,7R,8aS)-6-((R,E)-4-(2,5-difluorophenoxy)-3-((((2-(prop-2-yn-1-yl)pent-4-yn-1-yl)oxy)carbonyl)oxy)but-1-en-1-yl)-7-hydroxyoctahydro-2H-cyclopenta[b]oxepin-3-yl)butanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine / dichloromethane / -40 - 20 °C 2: pyridine / 16 h / 0 - 20 °C
  • 39
  • [ 2689-88-5 ]
  • [ 432027-96-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: lithium chloride / water; dimethyl sulfoxide / 1 h / Reflux 2: lithium aluminium tetrahydride / tetrahydrofuran / 12 h / -10 - 25 °C
  • 40
  • [ 40870-15-3 ]
  • [ 432027-96-8 ]
YieldReaction ConditionsOperation in experiment
78% With lithium aluminium tetrahydride In tetrahydrofuran at -10 - 25℃; for 12h; 7.3 Step 3: Synthesis of ethyl 2-(prop-2-yn-l-yl)pent-4-yn-l-ol. To a suspension of lithium aluminum hydride (1.25 g, 33.0 mmol) in dry THF (40 mL) stirring at -10 °C was added a solution of methyl 2-(2-propynyl)-4-pentynoate (3.06 g, 20.4 mmol) in dry THF (10 mL). The reaction mixture was allowed to warm to 25 °C and stirred for 12 h. The reaction mixture was then quenched through the dropwise addition of H2O (1.25 mL), an aq 10% NaOH solution (1.25 mL), and then additional H2O (3.75 mL). The reaction mixture was then stirred for 30 min until the suspended solids turned white. The mixture was then filtered, and the solids were washed with diethyl ether (100 mL). The resulting solution was concentrated on a rotary evaporator yielding a pale yellow oil. The crude oil was purified by flash chromatography on a silica gel column using 10% EtOAc in hexanes as the eluent, resulting in 1.95 g of a clear oil (78% yield).
78% With lithium aluminium tetrahydride In tetrahydrofuran at -10 - 25℃; for 12h; 22.3 Step 3: Synthesis of ethyl 2-(prop-2-yn-1-yl)pent-4-yn-1-ol. To a suspension of lithium aluminum hydride (1.25 g, 33.0 mmol) in dry THF (40 mL) stirring at -10 °C was added a solution of methyl 2-(2-propynyl)-4-pentynoate (3.06 g, 20.4 mmol) in dry THF (10 mL). The reaction mixture was allowed to warm to 25 °C and stirred for 12 h. The reaction mixture was then quenched through the dropwise addition of H2O (1.25 mL), an aq 10% NaOH solution (1.25 mL), and then additional H2O (3.75 mL). The reaction mixture was then stirred for 30 min until the suspended solids turned white. The mixture was then filtered, and the solids were washed with diethyl ether (100 mL). The resulting solution was concentrated on a rotary evaporator yielding a pale yellow oil. The crude oil was purified by flash chromatography on a silica gel column using 10% EtOAc in hexanes as the eluent, resulting in 1.95 g of a clear oil (78% yield).
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