[ CAS No. 53293-00-8 ]

Name: 53293-00-8|5-Hexynoic acid|97%
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Quality Control of [ 53293-00-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 53293-00-8 ]

Product Details of [ 53293-00-8 ]

CAS No. :	53293-00-8	MDL No. :	MFCD00066346
Formula :	C₆H₈O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VPFMEXRVUOPYRG-UHFFFAOYSA-N
M.W :	112.13	Pubchem ID :	143036
Synonyms :

Calculated chemistry of [ 53293-00-8 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.5
Num. rotatable bonds :	3
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	30.89
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) :	-6.52 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.37
Log Po/w (XLOGP3) :	0.66
Log Po/w (WLOGP) :	0.95
Log Po/w (MLOGP) :	1.17
Log Po/w (SILICOS-IT) :	0.76
Consensus Log Po/w :	0.98

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.75
Solubility :	19.8 mg/ml ; 0.177 mol/l
Class :	Very soluble
Log S (Ali) :	-1.02
Solubility :	10.7 mg/ml ; 0.0956 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.49
Solubility :	36.2 mg/ml ; 0.323 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.06

Safety of [ 53293-00-8 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P280-P301+P330+P331-P280-P305+P351+P338-P310-P302+P352-P301+P312-P304+P340	UN#:	3265
Hazard Statements:	H302-H312-H332-H314	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 53293-00-8 ]

* 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.

Upstream synthesis route of [ 53293-00-8 ]
Downstream synthetic route of [ 53293-00-8 ]

[ 53293-00-8 ] Synthesis Path-Upstream 1~2

1
[ 53293-00-8 ]
[ 928-90-5 ]

Reference： [1] Journal of the American Chemical Society, 2011, vol. 133, # 49, p. 19976 - 19981
[2] Patent: US2002/49244, 2002, A1,

2
[ 53293-00-8 ]
[ 75-65-0 ]
[ 151978-50-6 ]

Reference： [1] Synthesis, 2011, # 9, p. 1477 - 1483
[2] Organic Letters, 2018, vol. 20, # 22, p. 7345 - 7350

[ 53293-00-8 ] Synthesis Path-Downstream 1~69

1
[ 31608-22-7 ]
[ 53293-00-8 ]
10-Hydroxy-5-decinsaeure [ No CAS ]

Reference： [1]Liebigs Annalen der Chemie,1993,p. 153 - 160

2
[ 53293-00-8 ]
[ 154590-66-6 ]
N-({(5S)-3-[3-Fluoro-4-(4-hex-5-ynoylpiperazin-1-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With diphenyl phosphoryl azide; N-ethyl-N,N-diisopropylamine; at 0 - 20℃; for 14h;	Amine 3 (U.S. Patent Application Publication 2002/86900) (3.0 g, 5.36 mmol), 5-hexynoic acid (0.66 g, 5.90 mmol), and Hunig's base (5 mL) were cooled to 0 C. in an ice bath and then diphenylphosphoryl azide (1.62 g, 5.90 mmol) was added dropwise via syringe. The reaction mixture was allowed to warm slowly to rt and then stirred 14 h. The reaction mixture was diluted with EtOAc and water added. The water layer was extracted five times with EtOAc, the organic layers were combined and washed with water, saturated aqueous NaHCO3, brine and dried over MgSO4. The extract was concentrated in vacuo and then triturated with Et2O to afford the desired amide 4; 1H NMR (300 MHz, DMSO-d6) delta 8.24 (m, 1H), 7.50 (dd, J=16, 2 Hz, 1H), 7.18 (dd, J=2, 8 Hz, 1H), 7.07 (dd, J=12, 12 Hz, 1H), 4.71 (m, 1H), 4.08 (m, 1H), 3.70 (dd, J=8, 6 Hz, 1H), 3.60 (m, 4H), 3.40 (m, 2H), 2.98-2.89 (m, 4H), 2.81 (m, 1H), 2.44 (t, J=4 Hz, 2H), 2.21 (dt, J=4, 8 Hz, 2H), 1.83 (s, 3H), 1.69 (m, 2H).

Reference： [1]Patent: US2004/204463,2004,A1 .Location in patent: Page 6

3
N-9-fluorenylmethyloxycarbonyl-4-benzoyl-D-phenylalanine [ No CAS ]
[ 53293-00-8 ]
[ 164470-64-8 ]
[ 1011719-34-8 ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 2184 - 2194

4
N-9-fluorenylmethyloxycarbonyl-4-benzoyl-D-phenylalanine [ No CAS ]
[ 53293-00-8 ]
[ 164470-64-8 ]
C₃₀H₂₈N₂O₅ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 2184 - 2194

5
N-9-fluorenylmethyloxycarbonyl-4-benzoyl-D-phenylalanine [ No CAS ]
[ 53293-00-8 ]
[ 185116-43-2 ]
[ 1011719-40-6 ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 2184 - 2194

6
N-9-fluorenylmethyloxycarbonyl-4-benzoyl-D-phenylalanine [ No CAS ]
[ 53293-00-8 ]
[ 185116-43-2 ]
C₂₉H₂₆N₂O₅ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 2184 - 2194

7
[ 53293-00-8 ]
[ 611-98-3 ]
[ 930772-89-7 ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 2184 - 2194
[2]MedChemComm,2014,vol. 5,p. 352 - 357
[3]ACS Chemical Biology,2020,vol. 15,p. 952 - 961

8
[ 53293-00-8 ]
[ 88574-06-5 ]
2-([(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(4-benzoylphenyl)propanoic acid [ No CAS ]
[ 185116-43-2 ]
[ 1011719-43-9 ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 2184 - 2194

9
[ 53293-00-8 ]
[ 149834-58-2 ]
2-([(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(4-benzoylphenyl)propanoic acid [ No CAS ]
[ 185116-43-2 ]
methyl-8-chloro-8-oxooctanoate [ No CAS ]
C₄₄H₅₄N₄O₇ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 2184 - 2194

10
[ 53293-00-8 ]
[ 164470-64-8 ]
2-([(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(4-benzoylphenyl)propanoic acid [ No CAS ]
[ 1011719-33-7 ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 2184 - 2194

11
[ 53293-00-8 ]
[ 164470-64-8 ]
2-([(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(4-benzoylphenyl)propanoic acid [ No CAS ]
C₃₀H₂₈N₂O₅ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 2184 - 2194

12
[ 53293-00-8 ]
2-([(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(4-benzoylphenyl)propanoic acid [ No CAS ]
[ 185116-43-2 ]
[ 1011719-39-3 ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 2184 - 2194

13
[ 53293-00-8 ]
2-([(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(4-benzoylphenyl)propanoic acid [ No CAS ]
[ 185116-43-2 ]
C₂₉H₂₆N₂O₅ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 2184 - 2194

14
[ 53293-00-8 ]
[ 69-52-3 ]
[ 1067890-47-4 ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 13400 - 13409

15
[ 53293-00-8 ]
[ 99395-88-7 ]
[ 1190391-59-3 ]

Yield	Reaction Conditions	Operation in experiment
85.4%		To a solution of 69.0 g (615 mmol) of 5-hexynoic acid and 214 mL (1540 mmol) of triethylamine in 1.0 L of anhydrous tetrahydrofuran at -25 C. under an atmosphere of nitrogen was added 83.0 mL (677 mmol) of trimethylacetyl chloride over 20 min. Upon addition a white precipitate formed and the resulting suspension was stirred for 2 h. Next, 28.7 g (677 mmol) of anhydrous lithium chloride and 100.0 g (615.0 mmol) of (4S)-4-phenyl-1,3-oxazolidin-2-one were added sequentially and the mixture was allowed to gradually warm to ambient temperature over 12 h. All volatiles were removed in vacuo and the residue was diluted with water (1 L) and extracted with ethyl acetate (3×300 mL). The combined organic layers were washed with brine (250 mL), dried over magnesium sulfate, filtered and concentrated in vacuo. The crude residue was purified by silica gel chromatography eluting with a 5-50% ethyl acetate in hexanes gradient to afford the title compound as a colorless solid (135 g, 85.4%). 1H NMR (500 MHz, CDCl3): delta 7.40-7.37 (m, 2H), 7.36-7.32 (m, 1H), 7.31-7.28 (m, 2H), 5.42 (dd, J=8.9, 3.7 Hz, 1H), 4.69 (t, J=8.9 Hz, 1H), 4.28 (dd, J=9.2, 3.7 Hz, 1H), 3.13-3.02 (m, 2H), 2.24-2.21 (m, 2H), 1.94 (t, J=2.6 Hz, 1H), 1.84 (quintet, J=7.1 Hz, 2H). LC-MS: m/z (ES) 258.2 (MH)+.
85.4%		To a solution of 69.0 g (615 mmol) of 5-hexynoic acid and 214 mL (1540 mmol) of triethylaraine in 1.0 L of ar ydrous tetrahydrofuran at -25C under an atmosphere of nitrogen was added 83.0 mL (677 mmol) of trimethylacetyl chloride over 20 min. Upon addition a white precipitate formed and the resulting suspension was stirred for 2 h. Next, 28.7 g (677 mmol) of anhydrous lithium chloride and 100.0 g (615.0 mmol) of (4S)-4-phenyl-l,3-oxazolidin-2-one were added sequentially and the mixture was allowed to gradually warm to ambient temperature over 12 h. All volatiles were removed in vacuo and the residue was diluted with water (1 L) and extracted with ethyl acetate (3 x 300 mL). The combined organic layers were washed with brine (250 mL), dried over magnesium sulfate, filtered and concentrated in vacuo. The crude residue was purified by silica gel chromatography eluting with a 5-50% ethyl acetate in hexanes gradient to afford the title compound as a colorless solid (135 g, 85.4%). 1H NMR (500 MHz, CDC13): delta 7.40-7.37 (m, 2H), 7.36-7.32 (m, 1H), 7.31-7.28 (m, 2H), 5.42 (dd, J= 8.9, 3.7 Hz, 1H), 4.69 (t, J= 8.9 Hz, IE), 4.28 (dd, J= 92, 3.7 Hz, 1H), 3.13-3.02 (m, 2H), 2.24-2.21 (m, 2H), 1.94 (t, J= 2.6 Hz, 1H), 1.84 (quintet, J- 7.1 Hz, 2H). LC-MS: m/z (ES) 258.2 (MH)+.
85.4%		INTERMEDIATE 45-({(2S, 5R)- 1 -(tert-butoxycarbonyl)-5-[(R)-hydroxy(phenyl)methyl]pyrroiidin-2- yl ) methyl)pyridine-2 -carboxylic acidStep A: (4)USD^-3-Hex-5-ynoyl-4-pheny - 1.3-oxazolidin-2-one; To a solution of 69.0 g (615 mmol) of 5-hexynoic acid and 214 mL (1540 mmol) of triethylamine in 1.0 L of anhydrous tetrahydrofuran at -25 C under an atmosphere of nitrogen was added 83.0 mL (677 mmol) of trimethylacetyl chloride over 20 min. Upon addition a white precipitate formed and the resulting suspension was stirred for 2 h. Next, 28.7 g (677 mmol) of anhydrous lithium chloride and 100.0 g (615.0 mmol) of (4S)-4-phenyl-l,3-oxazolidin-2-one were added sequentially and the mixture was allowed to gradually warm to ambient temperature'~<4'3 " over 12 h. All volatiles were removed in vacuo and the residue was diluted with water (1 L) and extracted with ethyl acetate (3 x 300 mL). The combined organic layers were washed with brine (250 mL), dried over magnesium sulfate, filtered and concentrated in vacuo. The crude residue was purified by silica gel chromatography eluting with a 5-50% ethyl acetate in hexanes gradient to afford the title compound as a colorless solid (135 g, 85.4%). 1H NMR (500 MHz, CDC13): delta 7.40-7.37 (m, 2H), 7.36-7.32 (m, 1H), 7.31-7.28 (m, 2H), 5.42 (dd, J- 8.9, 3.7 Hz, 1H), 4.69 (t, J= 8.9 Hz, 1H), 4.28 (dd, J= 9.2, 3.7 Hz, 1H), 3.13-3.02 (m, 2H), 2.24-2.21 (m, 2H), 1.94 (t, J= 2.6 Hz, 1H), 1.84 (quintet, J= 7.1 Hz, 2H). LC-MS: m/z (ES) 258.2 (MH)+.

85.4%

To a solution of 69.0 g (615 mmol) of 5-hexynoic acid and 214 mL (1540 mmol) of triethylamine in 1.0 L of anhydrous tetrahydrofuran at -25C under an atmosphere of nitrogen was added 83.0 mL (677 mmol) of trimethylacetyl chloride over 20 min. Upon addition a white precipitate formed and the resulting suspension was stirred for 2 h. Next, 28.7 g (677 mmol) of anhydrous lithium chloride and 100.0 g (615.0 mmol) of (45)-4-phenyl-l,3-oxazolidin-2-one were added sequentially and the mixture was allowed to gradually warm to ambient temperature over 12 h. All volatiles were removed in vacuo and the residue was diluted with water (1 L) and extracted with ethyl acetate (3 x 300 mL). The combined organic layers were washed with brine (250 mL), dried over magnesium sulfate, filtered and concentrated in vacuo. The crude residue was purified by silica gel chromatography eluting with a 5-50% ethyl acetate in hexanes gradient to afford the title compound as a colorless solid (135 g, 85.4%). NMR (500 MHz, CDC13): delta 7.40-7.37 (m, 2H), 7.36-7.32 (m, 1H), 7.31-7.28 (m, 2H), 5.42 (dd, J= 8.9, 3.7 Hz, 1H), 4.69 (t, J- 8.9 Hz, 1H), 4.28 (dd, J- 9.2, 3.7 Hz, 1H), 3.13-3.02 (m, 2H), 2.24-2.21 (m, 2H), 1.94 (t, J= 2.6 Hz, 1 H), 1.84 (quintet, J- 7.1 Hz, 2H). LC-MS: m/z (ES) 258.2 (MH)+.

Reference： [1]Patent: US2009/253705,2009,A1 .Location in patent: Page/Page column 23
[2]Patent: WO2011/137054,2011,A1 .Location in patent: Page/Page column 37
[3]Patent: WO2012/12314,2012,A1 .Location in patent: Page/Page column 43-44
[4]Patent: WO2011/43942,2011,A1 .Location in patent: Page/Page column 17-18
[5]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 1094 - 1098

16
[ 6232-92-4 ]
[ 959126-16-0 ]
[ 53293-00-8 ]
[ 1215352-93-4 ]