[ CAS No. 6089-09-4 ]

Name: 6089-09-4|4-Pentynoic acid|98%
Brand: Ambeed
SKU: A391230
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{[proInfo.proName]} (Synonyms:4-Pentynoic acid) ,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

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Quality Control of [ 6089-09-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 6089-09-4 ]

Product Details of [ 6089-09-4 ]

CAS No. :	6089-09-4	MDL No. :	MFCD00004407
Formula :	C₅H₆O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MLBYLEUJXUBIJJ-UHFFFAOYSA-N
M.W :	98.10	Pubchem ID :	22464
Synonyms :	4-Pentynoic acid

Calculated chemistry of [ 6089-09-4 ]

Physicochemical Properties

Num. heavy atoms :	7
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.4
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	26.08
TPSA :	37.3 Å²

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) :	-6.69 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.13
Log Po/w (XLOGP3) :	0.3
Log Po/w (WLOGP) :	0.56
Log Po/w (MLOGP) :	0.79
Log Po/w (SILICOS-IT) :	0.35
Consensus Log Po/w :	0.63

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-0.51
Solubility :	30.7 mg/ml ; 0.312 mol/l
Class :	Very soluble
Log S (Ali) :	-0.65
Solubility :	22.2 mg/ml ; 0.226 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.06
Solubility :	84.7 mg/ml ; 0.863 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.94

Safety of [ 6089-09-4 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	3261
Hazard Statements:	H314	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 6089-09-4 ]

* 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.

Upstream synthesis route of [ 6089-09-4 ]
Downstream synthetic route of [ 6089-09-4 ]

[ 6089-09-4 ] Synthesis Path-Upstream 1~20

1
[ 5390-04-5 ]
[ 6089-09-4 ]

Yield	Reaction Conditions	Operation in experiment
82%	With Jones reagent In acetone at 0 - 20℃; for 1 h;	23d (lmL, 10.7 mmol) was dissolved in Acetone and cooled to 0°C. Jones reagent was added dropwise to the solution, under vigorous stirring, until the reaction mixture remained orange. The mixture was allowed to reach r.t., and more Jones reagent wasadded to maintain the orange colour. The reaction mixture was stirred at r.t. for lh, then water was added, and was extracted with Et20 several times, washed with Brine and dried over anhydrous Na2504. The solvent was removed at reduced pressure and the resulting oil purified by flash chromatography on silica gel (Hexane/Et20 8:2). Yield 82percent, colourless oil. 1HNMR (400 MHz CDC13-d): ö 2.61-2.59 (m, 2H), 2.52-2.48 (m, 2H), 1.98-1.95 (m, 1H) ppm.
82%	With Jones reagent In acetone at 0 - 20℃; for 1 h;	23d (lmL, 10.7 mmol) was dissolved in Acetone and cooled to 0°C. Jones reagent was added dropwise to the solution, under vigorous stirring, until the reaction mixture remained orange. The mixture was allowed to reach r.t., and more Jones reagent was added to maintain the orange colour. The reaction mixture was stirred at r.t. for 1 h, then water was added, and was extracted with Et20 several times, washed with Brine and dried over anhydrous Na2SO4. The solvent was removed at reduced pressure and the resulting oil purified by flash chromatography on silica gel (Hexane/Et20 8:2). Yield 82percent, colourless oil. 1HNMR (400 MHz CDC13-d): ö 2.61-2.59 (m, 2H), 2.52-2.48 (m, 2H), 1.98-1.95 (m, 1H) ppm.

Reference： [1] Organic Letters, 2016, vol. 18, # 11, p. 2600 - 2603
[2] Patent: WO2016/128541, 2016, A1, . Location in patent: Page/Page column 53
[3] Patent: WO2017/162834, 2017, A1, . Location in patent: Page/Page column 45
[4] Tetrahedron, 2009, vol. 65, # 24, p. 4664 - 4670
[5] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 15, p. 2976 - 2979
[6] Journal of the American Chemical Society, 1988, vol. 110, # 22, p. 7419 - 7434
[7] Journal of the American Chemical Society, 2016, vol. 138, # 27, p. 8344 - 8347
[8] Chemistry - A European Journal, 2014, vol. 20, # 46, p. 15131 - 15143
[9] Journal of the Chemical Society, 1953, p. 3052,3055
[10] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1974, p. 1981 - 1987
[11] Synthetic Communications, 1974, vol. 4, p. 203 - 210
[12] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981, p. 582 - 587
[13] Organic Mass Spectrometry, 1989, vol. 24, p. 909 - 916
[14] Journal of Chemical Research, Miniprint, 1995, # 11, p. 2642 - 2657
[15] Tetrahedron Letters, 2012, vol. 53, # 14, p. 1695 - 1698
[16] ChemPlusChem, 2016, vol. 81, # 11, p. 1160 - 1165
[17] Patent: WO2018/132326, 2018, A1, . Location in patent: Page/Page column 20

2
[ 24342-04-9 ]
[ 6089-09-4 ]

Yield	Reaction Conditions	Operation in experiment
51%	With copper(I) iodide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide	4-Pentynoic acid, 5-(2,5-dimethoxy-4-methylphenyl)-, methyl ester (4.2) To 3.88 g. (14.0 mmol) of the aryl iodide 4.1 and 1.88 g methyl pentynoate (16.7 mmol) in 50 mL of dry DMF was added 0.277 g. (1.45 mmol) of cuprous iodide and 0.80 g. (0.69 mmol) of tetrakis (triphenylphosphine palladium (0) (Lancaster). The flask was flushed with argon and sealed with a septum, and 3.6 mL of N,N-diisopropylethylamine was added to the flask. After stirring overnight, TLC showed a trace of unreacted starting material. The solution was evaporated and the residue was purified by flash chromatography (5*40 cm silica) using a gradient of 1:1 hexanes-methylene chloride to 100percent methylene chloride. Evaporation gave a dark brown solid. Despite good NMR purity, a second silica gel column was run using an eluent of 4:1 hexanes-ethyl acetate to eliminate color. Appropriate fractions were collected and evaporated to give 1.88 g (51percent yield) of the desired product 4.2 as an off-white solid: mp=66-67 C; TLC (2:1 hexanes-ethyl acetate) Rf=0.63; ¹ H NMR (CDCl₃), 6.77 (s, 1H), 6.62 (s, 1H), 3.78 (s, 3H), 3.73 (s, 3H), 3.67 (s, 3H), 2.75 (t, 2H, J=6.3 Hz), 2.63 (t, 2H, J=6.3 Hz), 2.16 (s, 3H). Anal. Calcd for C₁₅ H₁₈ O₄: C, 68.69; H: 6.92. Found: C: 68.59; H: 6.53.

Reference： [1] Patent: US6072046, 2000, A,

3
[ 185986-76-9 ]
[ 6089-09-4 ]

Reference： [1] Journal of the American Chemical Society, 1998, vol. 120, # 36, p. 9228 - 9236

4
[ 18498-59-4 ]
[ 6089-09-4 ]

Reference： [1] ChemCatChem, 2018, vol. 10, # 6, p. 1253 - 1257
[2] ChemPlusChem, 2016, vol. 81, # 11, p. 1160 - 1165

5
[ 78181-02-9 ]
[ 6089-09-4 ]

Reference： [1] Russian Chemical Bulletin, 2001, vol. 50, # 5, p. 833 - 837
[2] Chemische Berichte, 1938, vol. 71, p. 570

6
[ 128545-15-3 ]
[ 6089-09-4 ]

Reference： [1] Patent: JP2005/112734, 2005, A, . Location in patent: Page/Page column 7

7
[ 78181-02-9 ]
[ 6089-09-4 ]
[ 36781-65-4 ]
[ 88663-49-4 ]
[ 88663-50-7 ]

Reference： [1] Russian Chemical Bulletin, 2001, vol. 50, # 5, p. 833 - 837

8
[ 21565-82-2 ]
[ 6089-09-4 ]

Reference： [1] European Journal of Medicinal Chemistry, 2015, vol. 105, p. 289 - 296

9
[ 63093-41-4 ]
[ 6089-09-4 ]

Reference： [1] Revue Roumaine de Chimie, 1995, vol. 40, # 3, p. 253 - 258

10
[ 1431618-30-2 ]
[ 64-18-6 ]
[ 6089-09-4 ]

Reference： [1] Chemical Communications, 2013, vol. 49, # 38, p. 4012 - 4014

11
[ 122181-86-6 ]
[ 145071-97-2 ]
[ 6089-09-4 ]

Reference： [1] Tetrahedron Letters, 1992, vol. 33, # 42, p. 6231 - 6234

12
[ 92975-31-0 ]
[ 6089-09-4 ]

Reference： [1] Synthetic Communications, 1984, vol. 14, # 9, p. 805 - 816

13
[ 5390-04-5 ]
[ 6089-09-4 ]

Reference： [1] Journal of the Chemical Society, 1953, p. 3052,3055

14
[ 98198-39-1 ]
[ 6089-09-4 ]

Reference： [1] Angewandte Chemie, 1955, vol. 67, p. 516
[2] Bulletin de la Societe Chimique de France, 1954, p. 797
[3] Chemische Berichte, 1954, vol. 87, p. 964,969
[4] Journal of Organic Chemistry USSR (English Translation), 1971, vol. 7, p. 2568 - 2572[5] Zhurnal Organicheskoi Khimii, 1971, vol. 7, p. 2471 - 2476
[6] Collection of Czechoslovak Chemical Communications, 1987, vol. 52, # 4, p. 995 - 1005
[7] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1986, p. 1215 - 1224
[8] Bulletin des Societes Chimiques Belges, 1986, vol. 95, # 7, p. 535 - 546

15
[ 17920-23-9 ]
[ 6089-09-4 ]

Reference： [1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1965, p. 1197 - 1201[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1965, p. 1237 - 1241

16
[ 106-96-7 ]
[ 105-53-3 ]
[ 6089-09-4 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981, p. 582 - 587

17
[ 627-15-6 ]
[ 105-53-3 ]
[ 6089-09-4 ]
[ 88663-49-4 ]
[ 88663-50-7 ]

Reference： [1] Steroids, 1983, vol. 41, # 3, p. 277 - 284

18
[ 6089-09-4 ]
[ 38330-80-2 ]
[ 100330-50-5 ]

Reference： [1] Synthesis (Germany), 2012, vol. 44, # 13, p. 2005 - 2012

19
[ 6089-09-4 ]
[ 100330-50-5 ]

Reference： [1] Journal of Organic Chemistry, 1997, vol. 62, # 16, p. 5327 - 5332

20
[ 6089-09-4 ]
[ 75-65-0 ]
[ 149990-27-2 ]

Yield	Reaction Conditions	Operation in experiment
53%	at 0 - 85℃;	Preparation 16; But-3-ynyl-carbamic acid tert-butyl ester; Add triethylamine (3 mL) to a solution of 4-pentynoic acid (1.96 g, 20 mmol) in tert-butanol (6 mL) at O⁰C and then add diphenyl phosphoryl azide (CAUTION: reaction starts violently a short period after the addition). Heat the reaction mixture at 85⁰C overnight under nitrogen. Concentrate in vacuo and purify the crude mixture by chromatography on silica gel eluting with dichloromethane to obtain the title compound as a white solid (1.81g, 53percent).

Reference： [1] Patent: WO2007/28131, 2007, A1, . Location in patent: Page/Page column 49

[ 6089-09-4 ] Synthesis Path-Downstream 1~68

1
[ 6089-09-4 ]
[ 3417-91-2 ]
3-(4-hydroxy-phenyl)-2-pent-4-ynoylamino-propionic acid methyl ester [ No CAS ]

Reference： [1]Organic Letters,2005,vol. 7,p. 1513 - 1515

2
[ 13993-61-8 ]
[ 6089-09-4 ]
1-(4-pentynoyl)-1,2,3,4-tetrahydro-1,5-naphthyridine [ No CAS ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 5649 - 5655

3
[ 6089-09-4 ]
[ 75-65-0 ]
[ 149990-27-2 ]

Yield	Reaction Conditions	Operation in experiment
53%	With diphenyl phosphoryl azide; triethylamine; at 0 - 85℃;	Preparation 16; But-3-ynyl-carbamic acid tert-butyl ester; Add triethylamine (3 mL) to a solution of 4-pentynoic acid (1.96 g, 20 mmol) in tert-butanol (6 mL) at O0C and then add diphenyl phosphoryl azide (CAUTION: reaction starts violently a short period after the addition). Heat the reaction mixture at 850C overnight under nitrogen. Concentrate in vacuo and purify the crude mixture by chromatography on silica gel eluting with dichloromethane to obtain the title compound as a white solid (1.81g, 53%).

Reference： [1]Journal of the American Chemical Society,2019,vol. 141,p. 13772 - 13777
[2]Patent: WO2007/28131,2007,A1 .Location in patent: Page/Page column 49

4
[ 254-60-4 ]
methanolic HCl [ No CAS ]
[ 312263-07-3 ]
[ 6089-09-4 ]
[ 312263-08-4 ]

Yield	Reaction Conditions	Operation in experiment
	With CuI; triethylamine;PtO2; Pd(PPh3)2Cl2; In tetrahydrofuran; ethanol; ethyl acetate; N,N-dimethyl-formamide;	Step D 5-(3-Cyclopropyl-5,6,7,8-tetrahydro[1,8]naphthyridin-2-yl)-pentanoic acid methyl ester (2-7) A mixture of naphthyridine 2-5 (15.8 g, 77.2 mmol), ester 2-6 (prepared from 4-pentynoic acid and methanolic HCl solution, 11.3 g, 100.4 mmol), CuI (0.7 g, 3.9 mmol), 100 mL Et3N and 100 mL DMF was gently degassed with argon for 10 min. Then Pd(PPh3)2Cl2 was added in one portion. The reaction mixture was heated at 53 C. for 20 hr, cooled to room temperature and quenched with 500 mL water and 100 mL NaHCO3 (sat.). The aqueous mixture was extracted three times with ethyl acetate. The combined organic layer was washed with brine and dried over MgSO4. After solvent removal, the residue was purified by silica gel flash chromatography (EtOAc/Hexane=1/4 to 100% EtOAc over 30 min) to afford an oil, which was subsequently dissolved in 150 mL THF and 50 mL EtOH. Et3N (15 mL, 104 mmol) and PtO2 (0.7 g) were added. The mixture was degassed under moderate vacuum and subjected to balloon hydrogenation condition for 6 hrs. It was then filtered and concentrated to provide the desired product 2-7 as an oil. 1H NMR (400 MHz, CDCl3): delta6.80 (s, 1H), 4.75 (s, 1H), 3.62 (s, 3H), 3.36 (m, 2H), 2.76(t, 2H), 2.64 (t, 2H), 2.36 (t, 2H), 1.88 (m, 2H), 1.78 (m, 5H), 0.86 (m, 2H), 0,50 (m, 2H).

Reference： [1]Patent: US2004/38963,2004,A1

5
[ 6089-09-4 ]
[ 100-63-0 ]
[ 4578-58-9 ]

Reference： [1]Tetrahedron Letters,2008,vol. 49,p. 4607 - 4609

6
[ 6089-09-4 ]
[ 611-98-3 ]
[ 1085399-09-2 ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 15766 - 15767

7
[ 6089-09-4 ]
[ 1201149-19-0 ]
[ 1201149-21-4 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In N,N-dimethyl-formamide; at 20 - 80℃;Inert atmosphere; Microwave irradiation;	Description for D160; 3-(5-bromo-7-fluoro-1H-indol-2-yl)propanoic acid (D160); To a solution of <strong>[1201149-19-0](4-bromo-2-fluoro-6-iodophenyl)amine</strong> (D159) (2 g), 4-pentynoic acid (0.62 g) and copper(l) iodide (0.60 g) in DMF (4 ml.) stirred under nitrogen at room temperature was added bis(triphenylphosphine)palladium(ll) chloride (0.222 g), then triethylamine (2.2 ml.) was added in a portion. The reaction mixture was stirred at 80 0C in microwave reactor for 2 hrs. The solid in the mixture was filtered, the filtrate was diluted with EtOAc (30 ml_), washed with brine (80 ml.) and water(50 ml_ x 2). The organic layer was dried over anhydrous sodium sulfate. The dried solution was concentrated. The residue was purified by column chromatography to afford 3- (5-bromo-7-fluoro-1 H-indol-2-yl)propanoic acid (D160) (700 mg) as a yellow solid. MS (ES): C11H9BrFNO2 requires 285; found 286.0 (M+H+). deltaH (CDCI3, 400 MHz): 2.75 (2H, t), 3.07 (2H, t), 5.45 (1 H, s), 7.05 (1 H, d), 7.41 (1 H, s).
	With triethylamine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In N,N-dimethyl-formamide; at 80℃; for 2.0h;Inert atmosphere;	Description for D160; 3-(5-bromo-7-fluoro-1H-indol-2-yl)propanoic acid (D160); To a solution of <strong>[1201149-19-0](4-bromo-2-fluoro-6-iodophenyl)amine</strong> (D159) (2 g), 4-pentynoic acid (0.62 g) and copper(I) iodide (0.60 g) in DMF (4 mL) stirred under nitrogen at room temperature was added bis(triphenylphosphine)palladium(II) chloride (0.222 g), then triethylamine (2.2 mL) was added in a portion. The reaction mixture was stirred at 80 C. in microwave reactor for 2 hrs. The solid in the mixture was filtered, the filtrate was diluted with EtOAc (30 mL), washed with brine (80 mL) and water (50 mL×2). The organic layer was dried over anhydrous sodium sulfate. The dried solution was concentrated. The residue was purified by column chromatography to afford 3-(5-bromo-7-fluoro-1H-indol-2-yl)propanoic acid (D160) (700 mg) as a yellow solid. MS (ES): C11H9BrFNO2 requires 285. found 286.0 (M+H+). deltaH (CDCl3, 400 MHz): 2.75 (2H, t), 3.07 (2H, t), 5.45 (1H, s), 7.05 (1H, d), 7.41 (1H, s).

Reference： [1]Patent: WO2009/153307,2009,A1 .Location in patent: Page/Page column 122
[2]Patent: US2010/29729,2010,A1 .Location in patent: Page/Page column 59

8
[ 31608-22-7 ]
[ 6089-09-4 ]
C₁₄H₂₂O₄ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 5069 - 5075

9
[ 6089-09-4 ]
[ 72080-83-2 ]
[ 1228573-50-9 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 0 - 25℃; for 12h;	Intermediate 10 Benzyl N-r2-(pent-4-vnamido) ethyll carbamate Pentynoic acid (0.590 g, 6 mmol) was added to a suspension of Intermediate 9 ( 1.8 g, 9 mmol), EDCI- HCI ( 1.72 g, 9 mmol) and HOBt. H20 ( 1.21 g, 9 mmol) in dry DCM (30 mL) . The resulting mixture was cooled to 0C and TEA ( 1.25 mL, 9 mmol) was added dropwise. The reaction mixture was stirred at 25C for 12h . The DCM solution was washed with NH4CI solution ( 15 mL) and NaHC03 solution (15 mL), the organic phase was filtered through a phase sepa rator and evaporated to dryness to give the title compound as a white solid ( 1.97 g) . The crude product was used in the next step without further purification. JH NMR (400 M Hz, CDCI3) delta ppm 7.40-7.34 (m, 5H), 6.15 (br s, IH), 5.17 (br s, I H), 5.12 (s, 2H), 3.46-3.34 (m, 4H), 2.52 (dt 2H), 2.38 (t, 2H), 2.0 (br s, I H) . UPLC-MS : Rt=0.75; m/z (ES+) : 275 [M + H] + .

Reference： [1]Synthesis,2010,p. 971 - 978
[2]Patent: WO2013/124286,2013,A1 .Location in patent: Page/Page column 65; 66

10
[ 57772-50-6 ]
[ 6089-09-4 ]
[ 1224428-53-8 ]

Reference： [1]Advanced Synthesis and Catalysis,2010,vol. 352,p. 373 - 378

11
[ 6089-09-4 ]
[ 37585-16-3 ]
[ 1224428-49-2 ]

Reference： [1]RSC Advances,2016,vol. 6,p. 62742 - 62746
[2]Advanced Synthesis and Catalysis,2010,vol. 352,p. 373 - 378

12
[ 6089-09-4 ]
[ 20712-12-3 ]
[ 1224428-50-5 ]

Reference： [1]Advanced Synthesis and Catalysis,2010,vol. 352,p. 373 - 378
[2]RSC Advances,2016,vol. 6,p. 62742 - 62746

13
[ 6089-09-4 ]
[ 748805-85-8 ]
[ 1224428-47-0 ]

Reference： [1]Advanced Synthesis and Catalysis,2010,vol. 352,p. 373 - 378
[2]RSC Advances,2016,vol. 6,p. 62742 - 62746

14
[ 6089-09-4 ]
[ 29022-11-5 ]
[ 35661-60-0 ]
[ 85157-21-7 ]
[ 1138-80-3 ]
[ 204777-78-6 ]
[ 1201896-27-6 ]

Reference： [1]Chemical Communications,2009,p. 6601 - 6603

15
[ 5345-47-1 ]
[ 6089-09-4 ]
[ 1227624-65-8 ]

Yield	Reaction Conditions	Operation in experiment
60%		General procedure: A suspension of alkynoic acids 1 (0.6 mmol), amine nucleophiles 2 or 3 (0.5 mmol), andAuPPh3Cl/AgSbF6 (with the amount indicated) in H2O (4.0 mL) was stirred at the temperatureindicated for 20 h. Then the reaction mixture was cooled to room temperature, and CF3COOH(0.5 mmol) was added, and the resulting mixture was stirred for another 4 h at the temperatureindicated. At ambient temperature, saturated Na2CO3 solution (25.0 mL) was added to the reactionmixture. The resulting mixture was then extracted with ethyl acetate (3 15 mL). The combinedorganic layers were washed with brine, and dried over Na2SO4. After filtration and removal of thesolvents in vacuo, the crude product was purified by flash chromatography on silica gel to yield thedesired product.

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 3274 - 3282
[2]Molecules,2019,vol. 24
[3]Advanced Synthesis and Catalysis,2019

16
[ 6089-09-4 ]
[ 50419-58-4 ]
[ 1227624-62-5 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 3274 - 3282

17
[ 6089-09-4 ]
[ 434-76-4 ]
[ 1227624-53-4 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 3274 - 3282

18
[ 6089-09-4 ]
[ 46460-73-5 ]
[ 1242190-28-8 ]

Reference： [1]Tetrahedron,2010,vol. 66,p. 5811 - 5818

19
[ 6089-09-4 ]
[ 29022-11-5 ]
[ 35661-60-0 ]
[ 35661-40-6 ]
(S)-6-[((9H-fluoren-9-yl)-methoxy)carbonylamino]-2-[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethylamino]hexanoic acid [ No CAS ]
[ 201611-92-9 ]
[ 1280211-97-3 ]

Reference： [1]Reactive and functional polymers,2011,vol. 71,p. 294 - 302

20
[ 6089-09-4 ]
[ 144-68-3 ]
C₄₅H₆₀O₃ [ No CAS ]

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 2480 - 2482

21
[ 6089-09-4 ]
[ 6305-38-0 ]
[ 863499-59-6 ]

Reference： [1]Organic and Biomolecular Chemistry,2013,vol. 11,p. 938 - 954

22
[ 6089-09-4 ]
[ 4488-22-6 ]
[ 1453458-12-2 ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 2251 - 2255
Angew. Chem.,2013,vol. 125,p. 2307 - 2311,5

23
[ 6089-09-4 ]
[ 3468-18-6 ]
[ 1453457-68-5 ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 2251 - 2255
Angew. Chem.,2013,vol. 125,p. 2307 - 2311,5

24
[ 6089-09-4 ]
[ 3228-51-1 ]
[ 1434169-46-6 ]

Reference： [1]Chemical Communications,2013,vol. 49,p. 4950 - 4952

25
[ 6089-09-4 ]
[ 3326-34-9 ]
[ 872433-76-6 ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 4270 - 4277

26
[ 6089-09-4 ]
[ 80379-10-8 ]
1-(2-nitrophenyl)ethyl 4-pentynoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 1h;	To a solution of 1-(2-nitrophenyl) ethanol (1) (940 mg, 5.6 mmol) in DCM (12 mL) was added 4-pentynoic acid (500 muL, 5.6 mmol), N,N'-dicyclohexylcarbodiimide (DCC, 2.06 g, 10.0 mmol) and 4-dimethylamiopryidine (240 mg, 2.0 mmol). The whole mixture was stirred at room temperature for 1 h, and was then poured into ethyl acetate (50 mL). The organic layer was washed with 8percent citric acid aq (2 * 50 mL), brine (2 * 50 mL), and dried over Na2SO4. After removal of ethyl acetate, the organic layer was concentrated in vacuo, and the residue was purified by short silica gel column, eluted with petroleum ether:ethyl acetate (10:1) to give 2 as a clear, yellow oil (970 mg, 3.93 mmol, yield 70percent). 1H NMR (400 MHz, CDCl3) delta 7.95 (dd, J = 8, 1 Hz, 1H), 7.66-7.60 (m, 2H), 7.43 (m, 1H), 6.36 (q, J = 6 Hz, 1H), 2.60-2.55 (m, 2H), 2.51-2.46 (m, 2H), 1.95 (t, J = 3 Hz, 1H), 1.65 (d, J = 6 Hz, 3H); 13C NMR (100 MHz, CDCl3) delta 170.71 147.88, 137.91, 133.65, 128.56, 127.38, 124.60, 82.41, 69.32, 68.67, 33.55, 22.14, 14.43.

Reference： [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 6205 - 6211

27
[ 6089-09-4 ]
[ 139897-19-1 ]
[ 590-92-1 ]
[ 104329-69-3 ]

Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 2879 - 2887

28
[ 72-18-4 ]
[ 6089-09-4 ]
[ 35661-60-0 ]
[ 35661-39-3 ]
Fmoc-Lys(Alloc)-OH [ No CAS ]
[ 35661-40-6 ]
[ 108-24-7 ]
[ 71989-23-6 ]
[ 71989-26-9 ]
[ 103213-32-7 ]
[ 71989-28-1 ]
[ 111061-56-4 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
[ 166108-71-0 ]
Ac-K[((2-(pent-4-ynamido)ethoxy)ethoxy)acetyl]-VSIRAVCVMRFLVSKRKF-NH₂ [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2014,vol. 12,p. 8877 - 8887

29
[ 72-18-4 ]
[ 6089-09-4 ]
[ 35661-60-0 ]
[ 35661-39-3 ]
[ 35661-40-6 ]
[ 108-24-7 ]
[ 71989-23-6 ]
[ 71989-26-9 ]
[ 111061-56-4 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
[ 166108-71-0 ]
Ac-K[((2-(pent-4-ynamido)ethoxy)ethoxy)acetyl]-VSIRAVRVLRFLVSKRKF-NH₂ [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2014,vol. 12,p. 8877 - 8887

30
[ 252881-74-6 ]
[ 6089-09-4 ]
C₁₈H₃₁NO₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 24h;	[0075] 4-pentynoic acid was treated with t-Boc protected PEG amine (3) to give compound 11 and deprotected using TFA to afford compound 12, followed by activation using NHS to form its activated ester compound 13. The dendrimer was fully functionalized by amidation of a generation 1 dendrimer bearing a cleavable cystamine core (DNT-294, from Dendritic Nanotechnologies, Inc.) to generate compound 14 leaving a terminal alkyne for orthoganol conjugation through a click reaction. Compound 14 was isolated by preparative HPLC. The purity of 14 was confirmed by LC/MS deconvolution and MALDI analysis.

Reference： [1]Patent: WO2015/38493,2015,A1 .Location in patent: Paragraph 0075

31
[ 6089-09-4 ]
[ 7499-66-3 ]
N-(6-bromonaphthalen-2-yl)pent-4-ynamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%		General procedure: 4-Pentynoic acid (1.38 g, 14.01 mmol, 1 equiv.) was dissolved in DCM (2mL) then added to an ice-cold solution of EDC (4.026 g, 21 mmol, 1.5 equiv.) and HOBt (2.649 g, 19.59 mmol, 1.4 equiv.) in DCM (25mL). A solution of appropriate 2-naphthylamine (21 mmol, 1.5 equiv.) in DCM (20mL) was then added to the reaction mixture and stirred. Triethylamine (2.13 g, 21 mmol, 1.5 equiv.) was added drop-wise over 10 min. then the reaction temperature was allowed to increase gradually to room temperature. The reaction mixture was stirred for 17 h. The reaction mixture was then diluted with 20 ml DCM, washed with water, 5percent aq. HCl, saturated Aq. sodium bicarbonate solution, and brine solution. The organic layer was dried over anh. sodium sulfate, filtered and the solvent was evaporated under reduced pressure. The crude was purified by column chromatography to afford the corresponding N-(naphthalen-2-yl)pent-4-ynamides.

Reference： [1]Steroids,2015,vol. 98,p. 107 - 113

32
[ 6089-09-4 ]
[ 25691-37-6 ]
C₁₄H₂₂N₂O₅ [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2015,vol. 13,p. 4570 - 4580

33
[ 6089-09-4 ]
[ 39549-79-6 ]
2-(3-butynyl)-7-methyl-4(3H)-quinazolinone [ No CAS ]