120870-47-5|2-(Hex-1-yn-1-yl)benzoic acid| Ambeed

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
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

Application In Synthesis of [ 120870-47-5 ]

* 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 [ 120870-47-5 ]

[ 120870-47-5 ] Synthesis Path-Downstream 1~54

1
[ 120870-47-5 ]
[ 120870-48-6 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1988,vol. 27,p. 380.

2
[ 120870-47-5 ]
[ 120870-49-7 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1988,vol. 27,p. 380.
[2]Chemical Science,2018,vol. 9,p. 6041 - 6052.

3
[ 120870-47-5 ]
[ 120870-50-0 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1988,vol. 27,p. 380.

4
[ 120870-47-5 ]
[ 205250-14-2 ]

References: [1]Journal of Heterocyclic Chemistry,1998,vol. 35,p. 165 - 167.
[2]Synlett,2008,p. 1817 - 1820.
[3]Journal of Organic Chemistry,2015,vol. 80,p. 5320 - 5328.

5
[ 120870-47-5 ]
[ 30531-69-2 ]

Yield	Reaction Conditions	Operation in experiment
78%	With oxone; tetrabutylammomium bromide; In water; at 80℃; for 8h;	General procedure: 2-alkynylbenzoic acid 1 (0.2 mmol), TBAB (0.1 equiv), and Oxone(2.0 equiv) were added to a test tube, and then H2O (2.0 mL) wasadded. The mixture was stirred at 80 C for 8 h, under air. After thedisappearance of the substrate as indicated by TLC, the mixture wasfiltered and the resulting filtrate was extracted with DCM (3*2 mL).The organic layers were combined and dried over Na2SO4. Filtration,evaporation of the solvent and purification by flash column chromatography provided the desired product 2.
77%	With rhenium(I) pentacarbonyl chloride; In hexane; at 80℃; for 10h;Inert atmosphere;	General procedure: A hexane (2.0 mL)solution of 2-ethynylbenzoic acid (0.3 mmol) and ReCl(CO)5 (5 mol%) was stirred under an atmosphereof nitrogen at 80 C for 10 h. After the reaction was complete, H2O was added to the reaction mixture andextracted with EtOAc. The organic layer was dried with MgSO4. The resulting mixture was filtered, andthe filtrate was concentrated. Purification of the residue by silica gel column chromatography affordedisocoumarins. The structures of the products were assigned by their 1H and 13C-NMR, and mass spectra.The products were characterized by comparing its spectral data with those of authentic samples orprevious reports 2a,3e 2b,3e 2c,3e 2d,3e 2e,10 2f,3e 2g,7b 2h,3e 2i,7b,11 2j,3e 2k,12 2l,13 3a,14 3b,14 3d,15 and3g.7b The structures of the products (3e and 3f) were assigned by their 1H and 13C NMR, IR and massspectrum.

References: [1]Journal of Organic Chemistry,2018,vol. 83,p. 6673 - 6680.
[2]Tetrahedron,2019,vol. 75,p. 3850 - 3855.
[3]Heterocycles,2015,vol. 91,p. 2172 - 2179.
[4]Synthesis,1999,p. 1145 - 1148.
[5]Angewandte Chemie - International Edition,2018,vol. 57,p. 1688 - 1691.
Angew. Chem.,2018,vol. 130,p. 1704 - 1707,4.
[6]Advanced Synthesis and Catalysis,2012,vol. 354,p. 133 - 147.
[7]Chemistry - A European Journal,2015,vol. 21,p. 8771 - 8780.
[8]Chemistry - A European Journal,2015,vol. 21,p. 8771 - 8780.
[9]Chemistry - A European Journal,2015,vol. 21,p. 8771 - 8780.
[10]ChemCatChem,2019,vol. 11,p. 1458 - 1464.
[11]Organic and Biomolecular Chemistry,2019,vol. 17,p. 8522 - 8526.

6
2,3,4,6-Tetra-O-benzyl-D-glucopyranose [ No CAS ]
[ 120870-47-5 ]
C₄₇H₄₈O₇ [ No CAS ]

References: [1]Tetrahedron Letters,2008,vol. 49,p. 3604 - 3608.

7
2,3,4-tri-O-acetyl-L-rhamnopyranose [ No CAS ]
[ 120870-47-5 ]
[ 1230076-22-8 ]

References: [1]Tetrahedron Letters,2008,vol. 49,p. 3604 - 3608.

8
[ 627466-64-2 ]
[ 120870-47-5 ]
[ 1038411-44-7 ]
[ 1038411-36-7 ]

References: [1]Tetrahedron Letters,2008,vol. 49,p. 3604 - 3608.
[2]Chemistry - A European Journal,2010,vol. 16,p. 1871 - 1882.
[3]Chemistry - A European Journal,2010,vol. 16,p. 1871 - 1882.

9
3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose [ No CAS ]
[ 120870-47-5 ]
[ 1038411-38-9 ]

References: [1]Tetrahedron Letters,2008,vol. 49,p. 3604 - 3608.
[2]Chemistry - A European Journal,2010,vol. 16,p. 1871 - 1882.

10
[ 60-12-8 ]
[ 120870-47-5 ]
[ 1093198-48-1 ]

References: [1]Tetrahedron Letters,2008,vol. 49,p. 7046 - 7049.

11
[ 91-01-0 ]
[ 120870-47-5 ]
[ 1082852-49-0 ]

References: [1]Organic Letters,2008,vol. 10,p. 5119 - 5122.

12
3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-α,β-D-glucopyranose [ No CAS ]
[ 120870-47-5 ]
[ 1185868-57-8 ]

References: [1]Journal of the American Chemical Society,2009,vol. 131,p. 12076 - 12077.

13
3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-glucopyranose [ No CAS ]
[ 120870-47-5 ]
[ 1185868-56-7 ]
[ 1219934-97-0 ]

References: [1]Journal of the American Chemical Society,2009,vol. 131,p. 12076 - 12077.
[2]Chemistry - A European Journal,2010,vol. 16,p. 1871 - 1882.

14
[ 120870-47-5 ]
4-O-(2'-azido-3',4',6'-tri-O-benzyl-2'-deoxy-β-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-D-glucopyranose [ No CAS ]
[ 1185868-73-8 ]

References: [1]Journal of the American Chemical Society,2009,vol. 131,p. 12076 - 12077.

15
[ 120870-47-5 ]
[ 106-95-6 ]
[ 1136117-64-0 ]

References: [1]Journal of the American Chemical Society,2009,vol. 131,p. 18022 - 18023.

16
[ 462637-40-7 ]
[ 120870-47-5 ]

Yield	Reaction Conditions	Operation in experiment
	With water;	General procedure: ReBr(CO)5, ReCl(CO)5, (C5H5)ReO3, Re2(CO)10, and ReCl5 were commercially available andwere used without further purification. 2-(Arylethynyl)benzoic acids were prepared by the hydoration ofcorresponding methyl esters, which were prepared by the Sonogashira coupling of methyl 2-iodobenzoateand arylethyny, 1-pentyne, 1-hexyne, ethynylcyclohexane or 3,3-dimethyl-1-butyne. Other chemicalagents were obtained commercially and were purified if necessary by distillation.

References: [1]Chemistry - A European Journal,2010,vol. 16,p. 1871 - 1882.
[2]Organic and Biomolecular Chemistry,2019,vol. 17,p. 8522 - 8526.
[3]Advanced Synthesis and Catalysis,2012,vol. 354,p. 133 - 147.
[4]Journal of Organic Chemistry,2021,vol. 86,p. 1281 - 1291.
[5]Organic and Biomolecular Chemistry,2018,vol. 16,p. 1837 - 1842.
[6]Journal of the American Chemical Society,2009,vol. 131,p. 18022 - 18023.
[7]Heterocycles,2015,vol. 91,p. 2172 - 2179.
[8]Organic and Biomolecular Chemistry,2017,vol. 15,p. 4831 - 4841.
[9]Journal of Organic Chemistry,2018,vol. 83,p. 6673 - 6680.
[10]Advanced Synthesis and Catalysis,2019.

17
[ 120870-47-5 ]
[ 148926-02-7 ]
[ 1219934-61-8 ]

References: [1]Chemistry - A European Journal,2010,vol. 16,p. 1871 - 1882.

18
C₃₅H₃₈N₄O₁₅ [ No CAS ]
[ 120870-47-5 ]
[ 1185868-61-4 ]

References: [1]Chemical Communications,2010,vol. 46,p. 6060 - 6062.

19
[ 627466-64-2 ]
[ 120870-47-5 ]
[ 1221151-98-9 ]

References: [1]Chemical Communications,2010,vol. 46,p. 6060 - 6062.
[2]Journal of Organic Chemistry,2010,vol. 75,p. 6879 - 6888.

20
3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-glucopyranose [ No CAS ]
[ 120870-47-5 ]
[ 1241376-04-4 ]

References: [1]Chemical Communications,2010,vol. 46,p. 6060 - 6062.

21
[ 120870-47-5 ]
[ 148926-02-7 ]
2-O-benzoyl-3,4,6-tri-O-benzyl-D-glucopyranosyl ortho-(hex-1-ynyl)benzoate [ No CAS ]

References: [1]Chemical Communications,2010,vol. 46,p. 6060 - 6062.
[2]Journal of Organic Chemistry,2010,vol. 75,p. 6879 - 6888.

22
2,3,4,6-tetra-O-acetyl-α/β-D-galactopyranose [ No CAS ]
[ 120870-47-5 ]
[ 1311109-71-3 ]
[ 1311109-72-4 ]

References: [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 4933 - 4936.
[2]Chemical Communications,2011,vol. 47,p. 7515 - 7517.

23
[ 120870-47-5 ]
2,3,5-tri-O-benzoyl-α,β-L-arabinofuranose [ No CAS ]
[ 1311109-69-9 ]
[ 1311109-70-2 ]

References: [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 4933 - 4936.
[2]Journal of the American Chemical Society,2015,vol. 137,p. 15098 - 15101.

24
[ 120870-47-5 ]
[ 604-69-3 ]
[ 1219934-69-6 ]

References: [1]Chemical Communications,2011,vol. 47,p. 7515 - 7517.

25
3,4,6-tri-O-acetyl-2-deoxy-2-p-methoxybenzylideneamino-D-glucopyranose [ No CAS ]
[ 120870-47-5 ]
[ 1334371-19-5 ]

References: [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 8329 - 8332.

26
C₇₈H₇₅N₅O₁₈ [ No CAS ]
[ 120870-47-5 ]
3,4,6-tri-O-benzyl-2-azido-2-deoxy-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-acetylamino-2-deoxy-β-D-glucopyranosyl-(1->4)-3,6-O-benzyl-2-N-phthalimido-2-deoxy-β-D-glucopyranosyl o-hexynylbenzoate [ No CAS ]

References: [1]ChemBioChem,2011,vol. 12,p. 457 - 467.

27
[ 98-00-0 ]
[ 120870-47-5 ]
[ 1357469-19-2 ]

References: [1]Advanced Synthesis and Catalysis,2012,vol. 354,p. 133 - 147.

28
[ 610-97-9 ]
[ 120870-47-5 ]

References: [1]Advanced Synthesis and Catalysis,2012,vol. 354,p. 133 - 147.
[2]Heterocycles,2015,vol. 91,p. 2172 - 2179.
[3]Organic and Biomolecular Chemistry,2017,vol. 15,p. 4831 - 4841.
[4]Organic and Biomolecular Chemistry,2018,vol. 16,p. 1837 - 1842.
[5]Journal of Organic Chemistry,2018,vol. 83,p. 6673 - 6680.
[6]Advanced Synthesis and Catalysis,2019.
[7]Organic and Biomolecular Chemistry,2019,vol. 17,p. 8522 - 8526.
[8]Journal of Organic Chemistry,2021,vol. 86,p. 1281 - 1291.

29
[ 120870-47-5 ]
[ 4407-36-7 ]
[ 1357469-14-7 ]

References: [1]Advanced Synthesis and Catalysis,2012,vol. 354,p. 133 - 147.

30
[ 120870-47-5 ]
[ 100-51-6 ]
benzyl 2-hex-1-yn-1-ylbenzoate [ No CAS ]

References: [1]Advanced Synthesis and Catalysis,2012,vol. 354,p. 133 - 147.

31
2,3,4-tri-O-benzoyl-6-deoxy-L-talopyranose [ No CAS ]
[ 120870-47-5 ]
2,3,4-tri-O-benzoyl-6-deoxy-L-talopyranosyl ortho-hexynylbenzoate [ No CAS ]

References: [1]Organic Letters,2012,vol. 14,p. 4022 - 4025.

32
[ 120870-47-5 ]
[ 100-44-7 ]
benzyl 2-hex-1-yn-1-ylbenzoate [ No CAS ]

References: [1]Journal of the American Chemical Society,2013,vol. 135,p. 18396 - 18405.

33
[ 120870-47-5 ]
2,3-di-O-benzyl-4,6-O-benzylidene-α/β-D-mannopyranose [ No CAS ]
4,6-O-benzylidene-2,3-di-O-benzyl-1-(ortho-hexynylbenzoate)-D-mannopyranoside [ No CAS ]
4,6-O-benzylidene-2,3-di-O-benzyl-1-(ortho-hexynylbenzoate)-D-mannopyranoside [ No CAS ]

References: [1]Journal of Organic Chemistry,2015,vol. 80,p. 4164 - 4175.
[2]Chemistry - A European Journal,2015,vol. 21,p. 8771 - 8780.

34
C₃₁H₄₀O₆Si [ No CAS ]
[ 120870-47-5 ]
4,6-O-benzylidene-2-O-(diethylisopropylsilyl)-3-O-(2-methylnaphthyl)-1-(ortho-hexynylbenzoate)-D-mannopyranoside [ No CAS ]
4,6-O-benzylidene-2-O-(diethylisopropylsilyl)-3-O-(2-methylnaphthyl)-1-(ortho-hexynylbenzoate)-D-mannopyranoside [ No CAS ]

References: [1]Journal of Organic Chemistry,2015,vol. 80,p. 4164 - 4175.

35
2-O-benzyl-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-α/β-D-mannopyranoside [ No CAS ]
[ 120870-47-5 ]
2-O-benzyl-3-O-(tert-butyldimethylsilyl)-4,6-O-benzylidene-D-mannopyranosyl-ortho-hexynylbenzoate [ No CAS ]
2-O-benzyl-3-O-(tert-butyldimethylsilyl)-4,6-O-benzylidene-D-mannopyranosyl-ortho-hexynylbenzoate [ No CAS ]

References: [1]Chemistry - A European Journal,2015,vol. 21,p. 8771 - 8780.

36
[ 120870-47-5 ]
3-O-benzyl-4,6-O-benzylidene-2-O-(tert-butyldimethylsilyl)-D-mannopyranose [ No CAS ]
2-O-(tert-butyldimethylsilyl)-3-O-benzyl-4,6-O-benzylidene-D-mannopyranosyl-ortho-hexynylbenzoate [ No CAS ]
2-O-(tert-butyldimethylsilyl)-3-O-benzyl-4,6-O-benzylidene-D-mannopyranosyl-ortho-hexynylbenzoate [ No CAS ]

References: [1]Chemistry - A European Journal,2015,vol. 21,p. 8771 - 8780.

37
2,3-di-O-benzyl-4,6-di-O-benzoyl-D-mannopyranose [ No CAS ]
[ 120870-47-5 ]
2,3-di-O-benzyl-4,6-di-O-benzoyl-D-mannopyranosyl ortho-hexynylbenzoate [ No CAS ]
2,3-di-O-benzyl-4,6-di-O-benzoyl-D-mannopyranosyl ortho-hexynylbenzoate [ No CAS ]

References: [1]Chemistry - A European Journal,2015,vol. 21,p. 8771 - 8780.

38
2-azido-3-O-benzyl-4,6-di-O-benzoyl-2-deoxy-D-mannopyranose [ No CAS ]
[ 120870-47-5 ]
2-azido-3-O-benzyl-4,6-di-O-benzoyl-2-deoxy-D-mannopyranosyl ortho-hexynylbenzoate [ No CAS ]
2-azido-3-O-benzyl-4,6-di-O-benzoyl-2-deoxy-D-mannopyranosyl ortho-hexynylbenzoate [ No CAS ]

References: [1]Chemistry - A European Journal,2015,vol. 21,p. 8771 - 8780.

39
[ 693-02-7 ]
[ 120870-47-5 ]

References: [1]Heterocycles,2015,vol. 91,p. 2172 - 2179.
[2]Organic and Biomolecular Chemistry,2017,vol. 15,p. 4831 - 4841.
[3]Organic and Biomolecular Chemistry,2018,vol. 16,p. 1837 - 1842.
[4]Journal of Organic Chemistry,2018,vol. 83,p. 6673 - 6680.
[5]Organic and Biomolecular Chemistry,2019,vol. 17,p. 8522 - 8526.
[6]Journal of Organic Chemistry,2021,vol. 86,p. 1281 - 1291.

40
3,4-di-O-benzoyl-2-O-benzyl-L-rhamnopyranose [ No CAS ]
[ 120870-47-5 ]
3,4-di-O-benzoyl-2-O-benzyl-α-L-rhamnopyranosyl ortho-hexynylbenzoate [ No CAS ]
3,4-di-O-benzoyl-2-O-benzyl-β-L-rhamnopyranosyl ortho-hexynylbenzoate [ No CAS ]