10601-99-7|3-Ethynylbenzoic acid| Ambeed

Abstract: Human epidermal growth factor receptor 2 (HER2)-targeted agents have proven to be effective, however, the development of resistance to these agents has become an obstacle in treating HER2+ breast cancer. Evidence implicates HUNK as an anti-cancer target for primary and resistant HER2+ breast cancers. In this study, a selective inhibitor of HUNK is characterized alongside a phosphorylation event in a downstream substrate of HUNK as a marker for HUNK activity in HER2+ breast cancer. Rubicon has been established as a substrate of HUNK that is phosphorylated at serine (S) 92. Findings indicate that HUNK-mediated phosphorylation of Rubicon at S92 promotes both autophagy and tumorigenesis in HER2/neu+ breast cancer. HUNK inhibition prevents Rubicon S92 phosphorylation in HER2/neu+ breast cancer models and inhibits tumorigenesis. This study characterizes a downstream phosphorylation event as a measure of HUNK activity and identifies a selective HUNK inhibitor that has meaningful efficacy toward HER2+ breast cancer.

Purchased from AmBeed: 10601-99-7 ; 67967-17-3 ; 694499-26-8 ; 148893-10-1

Product Details of [ 10601-99-7 ]

CAS No. :	10601-99-7
Formula :	C₉H₆O₂
M.W :	146.14
SMILES Code :	O=C(O)C1=CC=CC(C#C)=C1
MDL No. :	MFCD06658448
InChI Key :	PHPIMLZTBYCDSX-UHFFFAOYSA-N
Pubchem ID :	15897047

Safety of [ 10601-99-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H317-H319
Precautionary Statements:	P280-P305+P351+P338

Computational Chemistry of [ 10601-99-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	6
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	41.34
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	37.3 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.93
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.25
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.45
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	2.16
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	1.84
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.73

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.5
Solubility	0.461 mg/ml ; 0.00315 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.67
Solubility	0.313 mg/ml ; 0.00214 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-1.83
Solubility	2.15 mg/ml ; 0.0147 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.59 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.56

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.65

Application In Synthesis of [ 10601-99-7 ]

* 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 [ 10601-99-7 ]

[ 10601-99-7 ] Synthesis Path-Downstream 1~54

1
[ 10602-06-9 ]
[ 10601-99-7 ]

References: [1]Journal of Organic Chemistry,1966,vol. 31,p. 2585 - 2593.
[2]Journal of Medicinal Chemistry,2015,vol. 58,p. 9228 - 9237.

2
[ 870245-85-5 ]
[ 10601-99-7 ]

References: [1]Journal of Organic Chemistry,1966,vol. 31,p. 2585 - 2593.

3
[ 10601-99-7 ]
[ 231303-75-6 ]
C₄₃H₃₄O₈ [ No CAS ]

References: [1]Chemistry Letters,1999,p. 431 - 432.

4
[ 10601-99-7 ]
C₁₀H₁₃BrSe [ No CAS ]
3-(4-<i>tert</i>-butyl-phenylselanylethynyl)-benzoic acid [ No CAS ]

References: [1]Tetrahedron Letters,2000,vol. 41,p. 5193 - 5197.

5
[ 10601-99-7 ]
C₁₉H₂₉BrOSe [ No CAS ]
[ 1066-54-2 ]
3-(5,5,8,8-tetramethyl-3-pentyloxy-5,6,7,8-tetrahydro-naphthalen-2-ylselanylethynyl)-benzoic acid [ No CAS ]

References: [1]Tetrahedron Letters,2000,vol. 41,p. 5193 - 5197.

6
[ 10601-99-7 ]
[ 86966-98-5 ]
3-(5-<i>tert</i>-butylperoxy-5-methyl-hexa-1,3-diynyl)-benzoic acid [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2000,vol. 36,p. 1105 - 1109.

7
[ 10601-99-7 ]
[ 96183-71-0 ]
3-[5-(1,1-dimethyl-propylperoxy)-5-methyl-hexa-1,3-diynyl]-benzoic acid [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2000,vol. 36,p. 1105 - 1109.

8
[ 10601-99-7 ]
[ 116507-92-7 ]
3-[5-(1,1-dimethyl-butylperoxy)-5-methyl-hexa-1,3-diynyl]-benzoic acid [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2000,vol. 36,p. 1105 - 1109.

9
[ 10601-99-7 ]
[ 61946-89-2 ]
3-(4-ethoxyphenyl)-5-(3-cyanophenyl)-isoxazole [ No CAS ]

References: [1]Tetrahedron Letters,2004,vol. 45,p. 2277 - 2279.
[2]Tetrahedron,2007,vol. 63,p. 652 - 665.

10
[ 10601-99-7 ]
[ 61946-93-8 ]
3-(4-butoxyphenyl)-5-(3-cyanophenyl)-isoxazole [ No CAS ]

References: [1]Tetrahedron Letters,2004,vol. 45,p. 2277 - 2279.
[2]Tetrahedron,2007,vol. 63,p. 652 - 665.

11
[ 10601-99-7 ]
[ 925692-67-7 ]
3-(4-propoxyphenyl)-5-(3-cyanophenyl)-isoxazole [ No CAS ]

References: [1]Tetrahedron Letters,2004,vol. 45,p. 2277 - 2279.
[2]Tetrahedron,2007,vol. 63,p. 652 - 665.

12
[ 10601-99-7 ]
[ 925692-68-8 ]
3-(4-pentyloxyphenyl)-5-(3-cyanophenyl)-isoxazole [ No CAS ]

References: [1]Tetrahedron Letters,2004,vol. 45,p. 2277 - 2279.
[2]Tetrahedron,2007,vol. 63,p. 652 - 665.

13
[ 10601-99-7 ]
[ 925692-69-9 ]
3-(4-hexyloxyphenyl)-5-(3-cyanophenyl)-isoxazole [ No CAS ]

References: [1]Tetrahedron Letters,2004,vol. 45,p. 2277 - 2279.
[2]Tetrahedron,2007,vol. 63,p. 652 - 665.

14
[ 10601-99-7 ]
[ 925692-70-2 ]
3-(4-heptyloxyphenyl)-5-(3-cyanophenyl)-isoxazole [ No CAS ]

References: [1]Tetrahedron Letters,2004,vol. 45,p. 2277 - 2279.
[2]Tetrahedron,2007,vol. 63,p. 652 - 665.

15
[ 10601-99-7 ]
[ 925692-71-3 ]
3-(4-octyloxyphenyl)-5-(3-cyanophenyl)-isoxazole [ No CAS ]

References: [1]Tetrahedron Letters,2004,vol. 45,p. 2277 - 2279.
[2]Tetrahedron,2007,vol. 63,p. 652 - 665.

16
[ 10601-99-7 ]
[ 925692-72-4 ]
3-(4-nonyloxyphenyl)-5-(3-cyanophenyl)-isoxazole [ No CAS ]

References: [1]Tetrahedron Letters,2004,vol. 45,p. 2277 - 2279.
[2]Tetrahedron,2007,vol. 63,p. 652 - 665.

17
[ 10601-99-7 ]
[ 925692-73-5 ]
3-(4-decyloxyphenyl)-5-(3-cyanophenyl)-isoxazole [ No CAS ]

References: [1]Tetrahedron Letters,2004,vol. 45,p. 2277 - 2279.
[2]Tetrahedron,2007,vol. 63,p. 652 - 665.

18
[ 10601-99-7 ]
[ 698-16-8 ]
3-(3-phenyl-isoxazol-5-yl)-benzonitrile [ No CAS ]

References: [1]Tetrahedron Letters,2004,vol. 45,p. 2277 - 2279.

19
[ 10601-99-7 ]
[ 38435-51-7 ]
3-(4-methoxyphenyl)-5-(3-cyanophenyl)-isoxazole [ No CAS ]

References: [1]Tetrahedron Letters,2004,vol. 45,p. 2277 - 2279.
[2]Tetrahedron,2007,vol. 63,p. 652 - 665.

20
[ 375853-65-9 ]
[ 10601-99-7 ]
[ 375853-73-9 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3370 - 3376.
[2]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 2859 - 2872.

21
[ 1025054-94-7 ]
[ 10601-99-7 ]
[ 1025053-27-3 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 1804 - 1809.

22
[ 3524-32-1 ]
[ 10601-99-7 ]
[ 1027730-01-3 ]

Yield	Reaction Conditions	Operation in experiment
78%	With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 50℃; for 3h;	Example 478(S)-5-[(3-[(l,3-dimethyl-lH-pyrazol-5-yl)amino]carbonyl}phenyl)ethynyl]-N- [methyl(oxido)phenyl-lambda4-sulfanylidene]nicotinamideStep 1 N-(2,5-Dimethyl-2H-pyrazol-3-yl)-3-ethynyl-benzamide 3-Ethynylbenzoic acid (0.1 g, 0.685 mmol) was added to a dry 50 mL round bottom flask and dissolved in DMF (6.85 mL). To the resulting solution was added l,3-dimethyl-lH-pyrazol-5- amine (0.076 g, 0.685 mmol), followed by BOP (0.393 g, 0.890 mmol), and 0.238 mL of DIPEA (1.37 mmol). This reaction mixture was heated to 50 0C for 3 h. After allowing the reaction to cool to room temperature it was taken up in EtOAc (15 mL) and extracted with brine (3 x 15 mL). The EtOAc layer was then washed with saturated aqueous NaHCtheta3 (2 x 15 mL). The organics were dried over anhydrous Na2SO^8), filtered and concentrated in vacuo. The crude residue was purified via column chromatography (silica gel, gradient eluant mixture of EtOAc in Hexanes: 0% to 100% EtOAc) affording N-(l,3-dimethyl-lH-pyrazol-5-yl)-3-ethynylbenzamide (0.128 g,

References: [1]Patent: WO2008/61236,2008,A2 .Location in patent: Page/Page column 83.

23
[ 10601-99-7 ]
[ 143587-37-5 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; In Ar;	Reference Example 4 (Synthesis of 3-ethynyl-N,N-diethylbenzamide) Air in a 20 ml Schlenk tube was replaced by Ar gas and 1.02 g (7 mmol) of <strong>[10601-99-7]m-ethynylbenzoic acid</strong> and 5 g (42 mmol) of thionyl chloride were added to the tube and the mixture was stirred at 50C for 2 hours and then excess thionyl chloride was removed by distillation under reduced pressure to obtain m-ethynylbenzoyl chloride.
	With thionyl chloride; In Ar;	Reference Example 5 (Synthesis of 3-ethynyl-N,N-diphenylbenzamide) Air in a 20 ml Schlenk tube was replaced by Ar gas and 1.02 g (7 mmol) of <strong>[10601-99-7]m-ethynylbenzoic acid</strong> and 5 g (42 mmol) of thionyl chloride were added to the tube and the mixture was stirred at 50C for 2 hours and then excess thionyl chloride was removed by distillation under reduced pressure to obtain m-ethynylbenzoyl chloride.
	With thionyl chloride; In Ar;	Reference Example 6 (Synthesis of ethyl 3-ethynylbenzoate) Air in a 20 ml Schlenk tube was replaced by Ar gas and 1.02 g (7 mmol) of <strong>[10601-99-7]m-ethynylbenzoic acid</strong> and 5 g (42 mmol) of thionyl chloride were added to the tube and the mixture was stirred at 50C for 2 hours and then excess thionyl chloride was removed by distillation under reduced pressure to obtain m-ethynylbenzoyl chloride.

	With thionyl chloride; In Ar;	Reference Example 7 (Synthesis of phenyl 3-ethynylbenzoate) Air in a 20 ml Schlenk tube was replaced by Ar gas and 1.02 g (7 mmol) of <strong>[10601-99-7]m-ethynylbenzoic acid</strong> and 5 g (42 mmol) of thionyl chloride were added to the tube and the mixture was stirred at 50C for 2 hours and then excess thionyl chloride was removed by distillation under reduced pressure to obtain m-ethynylbenzoyl chloride.
	With thionyl chloride; In Ar;	Reference Example 8 (Synthesis of S-methyl 3-ethynyl-thiobenzoate) Air in a 20 ml Schlenk tube was replaced by Ar gas and 1.02 g (7 mmol) of <strong>[10601-99-7]m-ethynylbenzoic acid</strong> and 5 g (42 mmol) of thionyl chloride were added to the tube and the mixture was stirred at 50C for 2 hours and then excess thionyl chloride was removed by distillation under reduced pressure to obtain m-ethynylbenzoyl chloride. To the m-ethynylbenzoyl chloride obtained was added 7 ml of dichloromethane and the resultant mixture was ice-cooled.
	With thionyl chloride; In Ar;	Reference Example 9 (Synthesis of S-phenyl 3-ethynyl-thiobenzoate) Air in a 20 ml Schlenk tube was replaced by Ar gas and 1.02 g (7 mmol) of <strong>[10601-99-7]m-ethynylbenzoic acid</strong> and 5 g (42 mmol) of thionyl chloride were added to the tube and the mixture was stirred at 50C for 2 hours and then excess thionyl chloride was removed by distillation under reduced pressure to obtain m-ethynylbenzoyl chloride. To the m-ethynylbenzoyl chloride obtained was added 7 ml of THF and the resultant mixture was ice-cooled.

References: [1]Patent: EP2042506,2009,A1 .
[2]Patent: EP2042506,2009,A1 .
[3]Patent: EP2042506,2009,A1 .
[4]Patent: EP2042506,2009,A1 .
[5]Patent: EP2042506,2009,A1 .
[6]Patent: EP2042506,2009,A1 .
[7]Beilstein Journal of Organic Chemistry,2009,vol. 5.
[8]Journal of Medicinal Chemistry,2015,vol. 58,p. 9228 - 9237.
[9]Chemistry - A European Journal,2014,vol. 20,p. 13143 - 13145.

24
[ 1138342-10-5 ]
[ 10601-99-7 ]
[ 1138342-06-9 ]

Yield	Reaction Conditions	Operation in experiment
33%	With triphenyl-arsane; triethylamine;tris-(dibenzylideneacetone)dipalladium(0); In tetrahydrofuran; for 24h;Inert atmosphere of nitrogen; Reflux;	A mixture of porphyrin 27 (24 mg), <strong>[10601-99-7]3-ethynylbenzoic acid</strong> (29.2 mg) in dry THF (10 mL) and Et3N (2 mL) was deoxygenated with nitrogen for 10 minutes, followed by adding Pd2(dba)3 (9.2 mg) and AsPh3 (24.5 mg). The mixture was refluxed under nitrogen for 24 hours, and then purified according to a method similar to that for ZnP-11 to obtain photosensitizer dye 12 (ZnP-12, 8.3 mg, 33%).

References: [1]Chemistry - A European Journal,2009,vol. 15,p. 1403 - 1412.
[2]Patent: US2010/125136,2010,A1 .Location in patent: Page/Page column 13.

25
[ 1198118-73-8 ]
[ 10601-99-7 ]
[ 1198118-78-3 ]

References: [1]Beilstein Journal of Organic Chemistry,2009,vol. 5.

26
[ 17356-09-1 ]
[ 10601-99-7 ]
[ 1206102-98-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium azide; sodium L-ascorbate; triethylamine;copper(l) iodide; N,N`-dimethylethylenediamine; In water; dimethyl sulfoxide; at 20℃; for 2h;	Example 5a: 3-[l-(4-isopropylphenyl)-l/f-l,2,3-triazol-4-yl]benzoic acid (5-3); [000233] A mixture of l-iodo-4-isopropylbenzene (5-1) (123 mg, 0.5 mmol), sodium azide (34 mg, 0.52 mmol), <strong>[10601-99-7]3-ethynylbenzoic acid</strong> (5-2) (73 mg, 0.5 mmol), CuI (10 mg), MeNHCH2CH2NHMe (11 muL), Et3N (51 mg, 0.5 mmol), sodium ascorbate (10 mg), DMSO-H2O (v/v 5: l, 1.5 mL) is stirred at room temperature for 2 hours followed by the addition of 2 mL of IM HCl. The resulting mixture is poured into ethyl acetate (100 mL), washed with water (10 mL) and brine (10 mL), dried over Na2SO4, filtered and evaporated. The residue is purified on slilica gel (0-100% ethyl acetate in hexane) to give 3-[l-(4-isopropylphenyl)-l/f- l,2,3-triazol-4-yl]benzoic acid (5-3) as a white solid. 1H NMR (DMSO-d6) delta (ppm) 9.42 (s, IH), 8.53 (dd, J=1.6, 1.6 Hz, IH), 8.20 (ddd, J=8.0, 1.6, 1.2 Hz, IH), 7.95 (ddd, J=8.0, 1.6, 1.2 Hz, IH), 7.89 (dm, J=8.8 Hz, 2H), 7.64 (dd, J=8.4, 8.0 Hz, IH), 7.51 (dm, J=8.8 Hz, 2H), 3.00 (septet, J=6.8 Hz, IH), 1.26 (d, J=6.8 Hz, 6H). HPLC-MS calculated for Ci8H17N3O2 (M +H+) 308.13, found 308.10.

References: [1]Patent: WO2010/8831,2010,A2 .Location in patent: Page/Page column 53-54.

27
[ 10601-99-7 ]
[ 21103-33-3 ]
3-ethynyl-N-{4-[4-(2-methoxyphenyl)piperazin-1-yl]butyl}benzamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 6860 - 6870.

28
[ 10601-99-7 ]
[ 613-94-5 ]
[ 1198602-62-8 ]

References: [1]Tetrahedron Letters,2009,vol. 50,p. 6435 - 6439.

29
C₁₈H₁₉N₄O₃Pol [ No CAS ]
[ 10601-99-7 ]
C₂₇H₂₅N₄O₅Pol [ No CAS ]

References: [1]Organic Letters,2010,vol. 12,p. 5414 - 5417.

30
[ 1115614-25-9 ]
[ 10601-99-7 ]
[ 1115614-26-0 ]

References: [1]Journal of Organic Chemistry,2011,vol. 76,p. 5219 - 5228.

31
[ 1219717-59-5 ]
[ 10601-99-7 ]
[ 1310827-38-3 ]

References: [1]Journal of Organic Chemistry,2011,vol. 76,p. 5219 - 5228.

32
[ 375853-65-9 ]
[ 10601-99-7 ]
[ 1374037-23-6 ]
[ 1374037-22-5 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3370 - 3376.

33
[ 10601-99-7 ]
[ 1374037-19-0 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3370 - 3376.

34
[ 10601-99-7 ]
[ 1374037-20-3 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3370 - 3376.

35
(1'S,2'R,3'S,4'S,5'S)-4'-[6-(3-chlorobenzylamino)-2-iodopurin-9-yl]-2',3'-O-isopropylidenebicyclo[3.1.0]hexane-1'-carboxylic acid N-methylamine [ No CAS ]
[ 10601-99-7 ]
[ 1388186-79-5 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 4847 - 4860.

36
[ 573982-80-6 ]
[ 10601-99-7 ]
[ 1400887-92-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 5966 - 5970.

37
[ 10601-99-7 ]
[ 95-54-5 ]
[ 1316652-57-9 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 9562 - 9575.

38
[ 618-51-9 ]
[ 10601-99-7 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 9562 - 9575.
[2]Patent: JP5725475,2015,B2 .

39
[ 618-91-7 ]
[ 10601-99-7 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 9562 - 9575.
[2]Patent: JP5725475,2015,B2 .

40
[ 77123-59-2 ]
[ 10601-99-7 ]

Yield	Reaction Conditions	Operation in experiment
99%	With sodium hydroxide; In methanol; water; at 20℃; for 7h;Cooling with ice;	Obtained in Step 2 3-[(trimethylsilyl)ethynyl]benzoic acid methyl ester(105) (2.42 g) was dissolved in methanol (30 mL), under ice cooling 2N aqueous sodium hydroxide solution (10.4 mL) was added, 7 hours and stirred at room temperature. The reaction mixture was acidified (pH 3 ~ 4) with 2N hydrochloric acid, and concentrated under reduced pressure. The residue Water (100 mL) was added, followed by extraction with ethyl acetate (100mL). The organic layer was washed with saturated brine (100 mL), dried over anhydrous sodium sulfate, and filtered. Thefiltrate was concentrated under reduced pressure to give 3-ethynylbenzoic acid (106) and (1.50 g, 99% yield) as a white solid.
0.26 g	With lithium hydroxide; In tetrahydrofuran; water; at 50℃;	Preparation 18Synthesis of 3-ethynylbenzoic acid.Place methyl 3-(2-trimethylsilylethynyl)benzoate (0.399 g, 1.55 mmoles) and tetrahydrofuran (3.68 mL) in a round bottom flask. Add lithium hydroxide (0.162 g, 3.86 mmoles) and water (3.68 mL) and heat at 50C. Quench the reaction with 1.3 mL 5N hydrochloric acid and extract three times with ethyl acetate. Wash one time with brine and dry over sodium sulfate, filter and concentrate under reduced pressure to give the title compound (0.26g, >100%).]H NMR (400 MHz, DMSO-d6) ppm: 4.39 (s, 3H), 7.50 (m, 2H), 7.70 (m, 1H), 7.94 (m, 1H) 13.22 (s, 1H).

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 9562 - 9575.
[2]Patent: JP5725475,2015,B2 .Location in patent: Paragraph 0028; 0031.
[3]Patent: WO2014/168824,2014,A1 .Location in patent: Page/Page column 19.

41
[ 10601-99-7 ]
[ 1316649-89-4 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 9562 - 9575.
[2]Patent: JP5725475,2015,B2 .

42
[ 10601-99-7 ]
[ 1316649-90-7 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 9562 - 9575.
[2]Patent: JP5725475,2015,B2 .

43
[ 10601-99-7 ]
[ 1316652-25-1 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 9562 - 9575.
[2]Patent: JP5725475,2015,B2 .

44
[ 10601-99-7 ]
[ 1316652-41-1 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 9562 - 9575.

45
[ 10601-99-7 ]
[ 1316649-91-8 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 9562 - 9575.

46
[ 10601-99-7 ]
[ 1316649-95-2 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 9562 - 9575.

47
[ 10601-99-7 ]
[ 1316649-97-4 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 9562 - 9575.

48
[ 10601-99-7 ]
[ 1316649-98-5 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 9562 - 9575.

49
[ 10601-99-7 ]
C₂₂H₁₈N₄O₂ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 9562 - 9575.

50
[ 10601-99-7 ]
C₂₂H₁₈N₄O₂ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 9562 - 9575.

51
[ 10601-99-7 ]
[ 1316650-01-7 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 9562 - 9575.

52
[ 10601-99-7 ]
C₂₂H₁₈N₄O₃ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 9562 - 9575.

53
[ 10601-99-7 ]
[ 1316650-04-0 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 9562 - 9575.

54
[ 10601-99-7 ]
[ 1316650-05-1 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 9562 - 9575.

Historical Records

Technical Information

• Alkyl Halide Occurrence • Arndt-Eistert Homologation • Hunsdiecker-Borodin Reaction • Passerini Reaction • Preparation of Amines • Preparation of Carboxylic Acids • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Carboxylic Acids • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Ugi Reaction

Related Functional Groups of
[ 10601-99-7 ]

Aryls

A108180 [883106-26-1]

3,5-Diethynylbenzoic acid

Similarity: 1.00

A141073 [10602-00-3]

4-Ethynylbenzoic acid

Similarity: 1.00

A392045 [16819-43-5]

4,4'-(1,2-Ethynediyl)dibenzoic Acid

Similarity: 0.93

A245615 [3034-86-4]

Methyl 4-ethynylbenzoate

Similarity: 0.91

A310836 [33578-00-6]

2-Ethynylbenzoic acid

Similarity: 0.91

Alkynyls

A108180 [883106-26-1]

3,5-Diethynylbenzoic acid

Similarity: 1.00

A141073 [10602-00-3]

4-Ethynylbenzoic acid

Similarity: 1.00

A392045 [16819-43-5]

4,4'-(1,2-Ethynediyl)dibenzoic Acid

Similarity: 0.93

A245615 [3034-86-4]

Methyl 4-ethynylbenzoate

Similarity: 0.91

A310836 [33578-00-6]

2-Ethynylbenzoic acid

Similarity: 0.91

Carboxylic Acids

A108180 [883106-26-1]

3,5-Diethynylbenzoic acid

Similarity: 1.00

A141073 [10602-00-3]

4-Ethynylbenzoic acid

Similarity: 1.00

A392045 [16819-43-5]

4,4'-(1,2-Ethynediyl)dibenzoic Acid

Similarity: 0.93

A310836 [33578-00-6]

2-Ethynylbenzoic acid

Similarity: 0.91

A104474 [619-21-6]

3-Formylbenzoic acid

Similarity: 0.82

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{[proInfo.proName]}

CAS No.: 10601-99-7

{[proInfo.proName]}

CAS No.: 10601-99-7

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[ 10601-99-7 ] Synthesis Path-Downstream 1~54

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Related Functional Groups of
[ 10601-99-7 ]

Aryls

Alkynyls

Carboxylic Acids

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{[proInfo.proName]}

CAS No.: 10601-99-7

{[proInfo.proName]}

CAS No.: 10601-99-7

Product Citations

Alternative Products

Product Details of [ 10601-99-7 ]

Safety of [ 10601-99-7 ]

Computational Chemistry of [ 10601-99-7 ] Show Less

Physicochemical Properties

Lipophilicity

Water Solubility

Pharmacokinetics

Druglikeness

Medicinal Chemistry

Application In Synthesis of [ 10601-99-7 ]

[ 10601-99-7 ] Synthesis Path-Downstream 1~54

Related Products

Historical Records

Technical Information

Categories

Related Functional Groups of [ 10601-99-7 ]

Aryls

Alkynyls

Carboxylic Acids

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Molarity Calculator

Total Compounds Calculator

Dissolution Calculator

Related Functional Groups of
[ 10601-99-7 ]