[ CAS No. 1068471-18-0 ]

Name: 1068471-18-0|Methyl 3-(4-Ethynylphenyl)propanoate|95%
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Quality Control of [ 1068471-18-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1068471-18-0 ]

SDS Specification

Alternatived Products of [ 1068471-18-0 ]

Product Details of [ 1068471-18-0 ]

CAS No. :	1068471-18-0	MDL No. :	MFCD26398532
Formula :	C₁₂H₁₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	AEQLLXBBEQSUNW-UHFFFAOYSA-N
M.W :	188.22 g/mol	Pubchem ID :	25150216
Synonyms :

Calculated chemistry of [ 1068471-18-0 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	4
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	55.05
TPSA :	26.3 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.62 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.73
Log Po/w (XLOGP3) :	2.57
Log Po/w (WLOGP) :	1.85
Log Po/w (MLOGP) :	2.77
Log Po/w (SILICOS-IT) :	3.08
Consensus Log Po/w :	2.6

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.68
Solubility :	0.394 mg/ml ; 0.00209 mol/l
Class :	Soluble
Log S (Ali) :	-2.77
Solubility :	0.319 mg/ml ; 0.0017 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.37
Solubility :	0.0807 mg/ml ; 0.000429 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.66

Safety of [ 1068471-18-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501	UN#:	N/A
Hazard Statements:	H302-H312-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1068471-18-0 ]

* 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 [ 1068471-18-0 ]

[ 1068471-18-0 ] Synthesis Path-Downstream 1~58

1
[ 1082059-14-0 ]
[ 1068471-18-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	With methanol; potassium carbonate; at 20.0℃; for 2.5h;	Methyl 3-(4-ethynylphenyl)propanoate.; Methyl 3-(4-((trimethylsilyl)ethynyl)phenyl)- propanoate (225 mg, 0.86 mmol) and potassium carbonate (234 mg, 1.69 mmol) was dissolved in MeOH (9 ml.) and stirred vigorously for 2.4 hours at room temperature. The reaction was added water and extracted with EtOAc. The organic phases were combined, washed with brine, dried over MgSO4 before concentrated under vacuum to give 138 mg (90%) of a brown, oily product. Rf: 0.31 (EtOAc: hexanes, 1 :5); 1HNMR(CDCI3) delta 7.43-7.40 (m, 2H), 7.17-7.14 (m, 2H), 3.66 (s, 3H), 3.04 (s, 1 H), 2.97-2.92 (t, 2H, J = 7.7 Hz), 2.65-2.59 (t, 2H, J = 7.8 Hz); 13CNMR (CDCI3) delta 173.0, 141.4, 132.3,128.3, 120.2, 83.5, 76.8, 51.6, 35.3, 30.8; ESI-MS m/z 287.1 (MNa+).
243 mg	With potassium carbonate; In methanol; at 20.0℃;	Crude methyl 3-(4-((trimethylsilyl)ethynyl)phenyl)propanoate (1b) (740mg) andpotassium carbonate 780 mg were added to 10 ml of methanol and stirred at roomtemperature until all the starting material was consumed, as was monitored by TLC.After water was added to the solution, the aqueous phase was extracted three times withethyl acetate. The combined organic layers were dried with magnesium sulfate andevaporated under reduced pressure. The residue was purified by columnchromatography (hexane : ethyl acetate=5:1(v/v)) to yield the product (243 mg, 31%over 2 steps); 1H-NMR (400 MHz, CDCl3, ): 7.40 (d, 2H), 7.14 (d, 2 H), 3.64 (s, 3H),3.06 (s, 1H) 2.90 (t, 2H), 2.61 (t, 2H)

Reference： [1]Patent: WO2010/12650,2010,A1 .Location in patent: Page/Page column 41
[2]Journal of Medicinal Chemistry,2008,vol. 51,p. 7061 - 7064
[3]Journal of Organic Chemistry,2010,vol. 75,p. 1301 - 1304
[4]Molecules,2020,vol. 25

2
[ 645-00-1 ]
[ 1068471-18-0 ]
[ 1082059-27-5 ]

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 7061 - 7064

3
[ 615-37-2 ]
[ 1068471-18-0 ]
[ 1082059-32-2 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 1301 - 1304
[2]Journal of Medicinal Chemistry,2008,vol. 51,p. 7061 - 7064

4
[ 3132-99-8 ]
[ 1068471-18-0 ]
[ 1082059-24-2 ]

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 7061 - 7064

5
[ 625-95-6 ]
[ 1068471-18-0 ]
[ 1082059-31-1 ]

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 7061 - 7064

6
[ 624-31-7 ]
[ 1068471-18-0 ]
[ 1082059-33-3 ]

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 7061 - 7064

7
[ 90-11-9 ]
[ 1068471-18-0 ]
[ 1082059-35-5 ]

Yield	Reaction Conditions	Operation in experiment
24%	With triethylamine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In N,N-dimethyl-formamide; at 90.0℃;Inert atmosphere;	General procedure IB for the Sonogashira reaction; A dry Schlenk flask charged with 3-(4-ethynylphenyl)propanoate (1 equiv), aryl halide (1.1 equiv), CuI (0.02 equiv) and Et3N (3 equiv) in DMF (-10 mL/g aryl halide) under inert atmosphere was added Pd(PPh3)2CI2 (0.01 equiv). The reaction was heated to 90 0C and stirred until consumption of the starting material as indicated by TLC. The reaction mixture was cooled to room temperature, added water, and extracted with EtOAc. The organic phases were combined, washed with brine, dried over MgSO4 and concentrated under vacuum before purification by flash chromatography.; Example E6; Methyl 3-(4-(1-naphthylethynyl)phenyl)propanoate.; The title compound was prepared from methyl 3-(4-((2-chloropyridin-4-yl)ethynyl)phenyl)propanoate (80 mg, 0.27 mmol) and 1-bromonaphthalene (53 mul_, 0.38 mmol) according to the general procedure IB to give 26 mg (24%) of an orange oil after purification by flash chromatography (SiO2, EtOAc/hexanes, 1 :30?1 :10). Rf: 0.25 (EtOAc: hexanes, 1 :5); 1HNMR (CDCI3) delta 8.44- 8.41 (m, 1 H), 7.87-7.73 (m, 3H), 7.58-7.44 (m, 5H), 7.24-7.21 (m, 2H), 3.00-2.96 (t, 2H, J = 7.5 Hz), 2.68-2.63 (t, 2H, J = 7.5 Hz); 13CNMR (CDCI3) delta 173.1 , 141.0, 133.2, 133.2, 131.8, 130.3, 128.7, 128.4, 128.3, 126.7, 126.4, 126.2, 125.3, 121.3, 121.0, 94.2, 87.2, 51.6, 35.4, 30.8; MALDI-MS m/z 314.1 (M+).

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 1301 - 1304
[2]Journal of Medicinal Chemistry,2008,vol. 51,p. 7061 - 7064
[3]Patent: WO2010/12650,2010,A1 .Location in patent: Page/Page column 32; 41

8
[ 69113-59-3 ]
[ 1068471-18-0 ]
[ 1082059-28-6 ]

Yield	Reaction Conditions	Operation in experiment
58%	With triethylamine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In N,N-dimethyl-formamide; at 50.0℃;Inert atmosphere;	General procedure IC for the Sonogashira reaction; A dry Schlenk flask charged with phenyl acetylene (1 equiv), aryl halide (1.1 equiv), CuI (0.02 equiv) and Et3N (2.4 equiv) in DMF (-10 mL/g aryl halide) under inert atmosphere was added Pd(PPh3)2CI2 (0.01 equiv). The reaction was heated to 50 0C and stirred until consumption of the starting material indicated by TLC the reaction was cooled to room temperature, added water and extracted with EtOAc. The organic phases were combined, washed with brine and dried over MgSO4 and concentrated under vacuum before purification by flash chromatography.; Example E11; Methyl 3-(4-((3-cyanophenyl)ethynyl)phenyl)propanoate.; The title compound was prepared from <strong>[1068471-18-0]methyl 3-(4-ethynylphenyl)propanoate</strong> (103 mg, 0.55 mmol) and 3- iodobenzonitrile (134 mg, 0.59 mmol) according to the general procedure IC to give 68 mg (58%) of an orange-brown solid after purification by flash chromatography (SiO2,EtOAc/hexanes, 1 :5). Rf: 0.26 (EtOA?hexanes, 1 :5); 1HNMR (CDCI3) delta 7.79-7.78 (m,1 H), 7.73-7.70 (m, 1 H), 7.61-7.57 (m, 1 H), 7.48-7.43 (m, 3H), 7.22-7.18 (m, 2H), 3.67 (s, 3H), 3.00-2.95 (t, 2H, J = 7.8 Hz), 2.67-2.62 (t, 2H, J = 7.8 Hz); 13CNMR (CDCI3) delta 173.0,141.7, 135.5, 134.8, 131.9, 131.3, 129.2, 128.5, 125.0, 120.2, 118.1 , 116.7, 1 12.8, 91.7,86.6, 51.7, 35.3, 30.8; EI-MS m/z 289 (M+).

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 7061 - 7064
[2]Patent: WO2010/12650,2010,A1 .Location in patent: Page/Page column 32; 46

9
[ 1068471-18-0 ]
[ 22445-41-6 ]
[ 1082059-36-6 ]

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 7061 - 7064

10
[ 1068471-18-0 ]
[ 576-23-8 ]
[ 1082059-34-4 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 1301 - 1304
[2]Journal of Medicinal Chemistry,2008,vol. 51,p. 7061 - 7064

11
[ 1068471-18-0 ]
[ 401-81-0 ]
[ 1082059-30-0 ]

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 7061 - 7064

12
[ 1068471-18-0 ]
[ 57455-06-8 ]
[ 1082059-20-8 ]

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 7061 - 7064

14
[ 1973-22-4 ]
[ 1068471-18-0 ]
[ 1206629-01-7 ]

Yield	Reaction Conditions	Operation in experiment
87%	With N,N,N,N,-tetramethylethylenediamine;copper(l) iodide; sodium tetrachloropalladate(II); 2-[bis(1,1-dimethylethyl)phosphino]-1-phenyl-1H-indole; at 80.0℃;Inert atmosphere;	General procedure IF for the Sonogashira reaction; A dry Schlenk flask was charged with Na2[PdCI4] (1 mol%), 2-(di-tert-butylphosphino)-1- phenylindole (2 mol%), CuI (2 mol%), <strong>[1068471-18-0]methyl 3-(4-ethynylphenyl)propanoate</strong> (1 equiv), tetramethylethylenediamine (2 mL/mmol) and aryl halide (1 .1-1.5 equiv). The mixture was evacuated and backfilled with Ar (3x), and heated to 80 0C. After consumption of the starting material, the reaction mixture was cooled to room temperature, quenched with water and extracted with EtOAc (3x). The combined extracts were washed with brine, dried over MgSO4 and concentrated under vacuum and the residue was purified by flash chromatography.; Example E30; Methyl 3-(4-((2-ethylphenyl)ethynyl)phenyl)propanoate.; The title compound was prepared from <strong>[1068471-18-0]methyl 3-(4-ethynylphenyl)propanoate</strong> (95 mg, 0.51 mmol) and 1-bromo- 2-ethylbenzene (0.10 ml_, 0.73 mmol) according to the general procedure IF to give 130 mg (87%) of a clear oil after purification by flash chromatography (SiO2, EtOAcPE, 1 :7): Rf = 0.28 (EtOAcPE, 1 :4); 1H NMR (CDCI3) delta 7.50-7.48 (m, 1 H), 7.46-7.44 (m, 2H), 7.26-7.22 (m, 2H), 7.20-7.14 (m, 3H), 3.67 (s, 3H), 2.96 (t, J = 7.8 Hz, 2H), 2.88 (q, J = 7.2 Hz, 2H), 2.63 (t, J = 7.6 Hz, 2H), 1.29 (t, J = 7.6 Hz, 3H); 13C NMR (CDCI3) delta 173.2, 146.3, 140.9, 132.2, 131.8, 128.6, 128.5, 128.1 , 125.8, 122.5, 121.7, 92.9, 88.0, 51.8, 35.6, 31.0, 27.9, 14.9; ESI-MS m/z 315.1 (M+Na+).

Reference： [1]Patent: WO2010/12650,2010,A1 .Location in patent: Page/Page column 33; 66
[2]Journal of Organic Chemistry,2010,vol. 75,p. 1301 - 1304

15
[ 1003-09-4 ]
[ 1068471-18-0 ]
[ 1206629-37-9 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 1301 - 1304
[2]Journal of Medicinal Chemistry,2011,vol. 54,p. 6691 - 6703

16
1-bromo-3-(isocyanomethyl)benzene [ No CAS ]
[ 1068471-18-0 ]
[ 1206629-28-8 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 1301 - 1304

17
[ 98027-84-0 ]
[ 1068471-18-0 ]
[ 1206629-07-3 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 1301 - 1304

18
[ 591-18-4 ]
[ 1068471-18-0 ]
[ 1207950-02-4 ]
[ 1226954-55-7 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 1301 - 1304

19
[ 583-55-1 ]
[ 1068471-18-0 ]
[ 1206629-22-2 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 1301 - 1304

20
[ 95-46-5 ]
[ 1068471-18-0 ]
[ 1082059-32-2 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 1301 - 1304

21
[ 2252-44-0 ]
[ 1068471-18-0 ]
[ 1207950-04-6 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 1301 - 1304

22
[ 1068471-18-0 ]
[ 553-94-6 ]
[ 1206629-03-9 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 1301 - 1304

23
[ 1068471-18-0 ]
[ 15115-60-3 ]
[ 1206629-26-6 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 1301 - 1304

24
[ 1068471-18-0 ]
[ 2142-70-3 ]
[ 1206629-49-3 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 1301 - 1304
[2]Journal of Medicinal Chemistry,2013,vol. 56,p. 982 - 992

25
[ 1068471-18-0 ]
[ 99-90-1 ]
[ 1207950-03-5 ]