Name: 1515-75-9|Methyl penta-2,4-dienoate|97%
Brand: Ambeed
SKU: A354891
Rating: 95 (30 reviews)

1
[ 1515-75-9 ]
[ 18424-76-5 ]
pent-3-ene-1,1,5-tricarboxylic acid trimethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With diethyl ether

Reference： [1]Kohler, Butler [Journal of the American Chemical Society, 1926, vol. 48, p. 1045]

2
[ 1515-75-9 ]
[ 89464-51-7 ]

Yield	Reaction Conditions	Operation in experiment
	With 1-chloro-1-nitrosocyclohexane In diethyl ether; ethanol at 0℃;

Reference： [1]Kresze,G.; Firl,J. [Tetrahedron, 1968, vol. 24, p. 1043 - 1050]

3
[ 1515-75-9 ]
[ 1193-63-1 ]
[ 98452-97-2 ]

Yield	Reaction Conditions	Operation in experiment
33%	With sodium hydride; dimethyl sulfoxide at 75 - 80℃; for 72h;
	In dimethyl sulfoxide

Reference： [1]Fuchs, Benzion; Zizuashvili, Jakob; Abramson, Sarah [Journal of Organic Chemistry, 1982, vol. 47, # 18, p. 3474 - 3477]
[2]Danishefsky,S. et al. [Tetrahedron Letters, 1969, p. 4333 - 4334]

4
[ 123-33-1 ]
[ 1515-75-9 ]
[ 79024-75-2 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1984,p. 155 - 164

5
[ 78-85-3 ]
[ 1515-75-9 ]
1-methyl-2-(methoxycarbonyl)-3-cyclohexen-1-carboxaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%	With hydroquinone In benzene at 120℃; for 72h;

Reference： [1]Wu, Pei-Lin; Chu, Min; Fowler, Frank W. [Journal of Organic Chemistry, 1988, vol. 53, # 5, p. 963 - 972]

6
[ 1515-75-9 ]
[ 78209-93-5 ]
<1R*,2R*>-1-Acetyl-2-(methoxycarbonyl)-3-cyclohexen-1-yl p-nitrobenzoate [ No CAS ]
<1R*,2S*>-1-Acetyl-2-(methoxycarbonyl)-3-cyclohexen-1-yl p-nitrobenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane at 40℃; for 15h;

Reference： [1]Reyes, Alicia; Aguilar, Raul; Munoz, Alfredo H.; Zwick, Jean-Christophe; Rubio, Manuel; et al. [Journal of Organic Chemistry, 1990, vol. 55, # 3, p. 1024 - 1034]

7
[ 1515-75-9 ]
[ 122835-08-9 ]
[ 125160-77-2 ]
[ 125160-73-8 ]

Yield	Reaction Conditions	Operation in experiment
1: 36% 2: 33%	In chlorobenzene at 150℃; for 6h;

Reference： [1]Palmisano, Giovanni; Danieli, Bruno; Lesma, Giordano; Passarella, Daniele [Tetrahedron, 1989, vol. 45, # 11, p. 3583 - 3596]

8
[ 1515-75-9 ]
[ 142103-97-7 ]
[ 142103-98-8 ]

Yield	Reaction Conditions	Operation in experiment
66%	With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine In acetonitrile at 75℃; for 20h;

Reference： [1]Meanwell; Pearce; Roth; Smith; Wedding; Wright; Buchanan; Baryla; Gamberdella; Gillespie; Hayes; Seiler; Stanton; Zavoico; Fleming [Journal of Medicinal Chemistry, 1992, vol. 35, # 14, p. 2672 - 2687]

9
[ 1515-75-9 ]
[ 78129-68-7 ]
methyl 2,8-di-tert-butyl-1,7-diphosphatricyclo<3.2.1.0^2,7>oct-3-ene-3-carboxylate [ No CAS ]
methyl 2,8-di-tert-butyl-1,7-diphosphatricyclo<3.2.1.0^2,7>oct-3-ene-6-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 85 % Spectr. 2: 15 % Spectr.	In benzene at 120℃; for 48h;

Reference： [1]Heydt, Heinrich; Bergstraesser, Uwe; Faessler, Rainer; Fuchs, Eberbard; Kamel, Nasr; et al. [Bulletin de la Societe Chimique de France, 1995, vol. 132, # 7, p. 652 - 668]

10
[ 1515-75-9 ]
[ 106-99-0 ]
[ 124939-60-2 ]
3-methylcarboxylate-4-(methylcarboxylate)vinylcyclohexene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; (R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthalene In toluene at 80℃; for 48h; Yield given. Yields of byproduct given;

Reference： [1]El Amrani, Med Amin; Suisse, Isabelle; Knouzi; Mortreux [Tetrahedron Letters, 1995, vol. 36, # 28, p. 5011 - 5014]

11
[ 1515-75-9 ]
[ 930-60-9 ]
(3aS,7aS)-1-Hydroxy-3-oxo-3a,4,7,7a-tetrahydro-3H-indene-4-carboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 2,5-bis(1,1-dimethylethyl)-1,4-benzenediol In benzene

Reference： [1]Buckle,D.R. et al. [Journal of Medicinal Chemistry, 1975, vol. 18, p. 203 - 206]

12
[ 1515-75-9 ]
[ 58512-80-4 ]
(5aS,9R,9aR)-5a,6,9,9a-Tetrahydro-5-oxa-10-thia-indeno[2,1-a]indene-9-carboxylic acid methyl ester [ No CAS ]
(5aS,9aR)-5a,6,7,9a-Tetrahydro-5-oxa-10-thia-indeno[2,1-a]indene-9-carboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 38% 2: 3%	With 4-(tert-octyl)catechol at 180℃; for 20h;

Reference： [1]Pihera, Pavel; Palecek, Jaroslav; Svoboda, Jiri [Collection of Czechoslovak Chemical Communications, 1998, vol. 63, # 5, p. 681 - 697]

13
[ 1515-75-9 ]
[ 612065-04-0 ]
[ 880764-64-7 ]
methyl (2E,4E)-5-(5-oxo-1,2,3,5-tetrahydroindolizin-6-yl)penta-2,4-dieonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide at 110℃; Title compound not separated from byproducts;

Reference： [1]Babjak, Matej; Kanazawa, Alice; Anderson, Regan J.; Greene, Andrew E. [Organic and Biomolecular Chemistry, 2006, vol. 4, # 3, p. 407 - 409]

14
[ 1515-75-9 ]
[ 93264-56-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: chlorobenzene / 110 °C 2: 1.) LDA, HMPA / 1.) THF, -78 deg C, 2.) THF, -40 deg C 3: 96 percent / tetrahydrofuran; dimethylsulfoxide 4: 17 percent / TsOH / tetrahydrofuran / 0.08 h / Heating 5: 83 percent / H₂ / Raney-Ni / cyclohexene; acetone / Heating 6: 70 percent / sodium cyanoborohydride / pH <7
	Multi-step reaction with 6 steps 1: chlorobenzene / 110 °C 2: 1.) LDA, HMPA / 1.) THF, -78 deg C, 2.) THF, -40 deg C 3: 96 percent / tetrahydrofuran; dimethylsulfoxide 4: 14 percent / TsOH / tetrahydrofuran / 0.08 h / Heating 5: 90 percent / H₂ / Raney-Ni / cyclohexene; acetone / Heating 6: 70 percent / sodium cyanoborohydride / pH <7

Reference： [1]Genin, Denis; Andriamialisoa, R. Zo; Langlois, Nicole; Langlois, Yves [Heterocycles, 1987, vol. 26, # 2, p. 377 - 383]
[2]Genin, Denis; Andriamialisoa, R. Zo; Langlois, Nicole; Langlois, Yves [Heterocycles, 1987, vol. 26, # 2, p. 377 - 383]

15
[ 1515-75-9 ]
[ 111675-09-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: chlorobenzene / 110 °C 2: 1.) LDA, HMPA / 1.) THF, -78 deg C, 2.) THF, -40 deg C 3: 96 percent / tetrahydrofuran; dimethylsulfoxide 4: 17 percent / TsOH / tetrahydrofuran / 0.08 h / Heating 5: 83 percent / H₂ / Raney-Ni / cyclohexene; acetone / Heating

Reference： [1]Genin, Denis; Andriamialisoa, R. Zo; Langlois, Nicole; Langlois, Yves [Heterocycles, 1987, vol. 26, # 2, p. 377 - 383]

16
[ 1515-75-9 ]
[ 111675-08-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: chlorobenzene / 110 °C 2: 1.) LDA, HMPA / 1.) THF, -78 deg C, 2.) THF, -40 deg C 3: 96 percent / tetrahydrofuran; dimethylsulfoxide 4: 14 percent / TsOH / tetrahydrofuran / 0.08 h / Heating 5: 90 percent / H₂ / Raney-Ni / cyclohexene; acetone / Heating

Reference： [1]Genin, Denis; Andriamialisoa, R. Zo; Langlois, Nicole; Langlois, Yves [Heterocycles, 1987, vol. 26, # 2, p. 377 - 383]

17
[ 1515-75-9 ]
15-oxo-14,15-dihydroeburnamenine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: chlorobenzene / 110 °C 2: 1.) LDA, HMPA / 1.) THF, -78 deg C, 2.) THF, -40 deg C 3: 96 percent / tetrahydrofuran; dimethylsulfoxide 4: TsOH / tetrahydrofuran / 0.08 h / Heating 5: H₂ / Raney-Ni / acetone / Heating

Reference： [1]Genin, Denis; Andriamialisoa, R. Zo; Langlois, Nicole; Langlois, Yves [Heterocycles, 1987, vol. 26, # 2, p. 377 - 383]

18
[ 1515-75-9 ]
[ 142104-09-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 66 percent / Pd(OAc)2, tri-o-tolylphosphine, Et₃N / acetonitrile / 20 h / 75 °C 2: H₂ / 10 percent Pd/C / ethyl acetate / 2585.7 Torr 3: LiAlH₄ / tetrahydrofuran / 1 h 4: 86 percent / TsOH / methanol / 0.5 h / Heating

Reference： [1]Meanwell; Pearce; Roth; Smith; Wedding; Wright; Buchanan; Baryla; Gamberdella; Gillespie; Hayes; Seiler; Stanton; Zavoico; Fleming [Journal of Medicinal Chemistry, 1992, vol. 35, # 14, p. 2672 - 2687]

19
[ 1515-75-9 ]
[ 142104-03-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 66 percent / Pd(OAc)2, tri-o-tolylphosphine, Et₃N / acetonitrile / 20 h / 75 °C 2: H₂ / 10 percent Pd/C / ethyl acetate / 2585.7 Torr 3: p-TsOH / methanol / 0.5 h / Heating 4: 74 percent / 1 N KOH / methanol / 18 h / Ambient temperature

Reference： [1]Meanwell; Pearce; Roth; Smith; Wedding; Wright; Buchanan; Baryla; Gamberdella; Gillespie; Hayes; Seiler; Stanton; Zavoico; Fleming [Journal of Medicinal Chemistry, 1992, vol. 35, # 14, p. 2672 - 2687]

20
[ 1515-75-9 ]
[ 142103-99-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 66 percent / Pd(OAc)2, tri-o-tolylphosphine, Et₃N / acetonitrile / 20 h / 75 °C 2: 100 percent / p-TsOH / methanol / 0.5 h / Heating

Reference： [1]Meanwell; Pearce; Roth; Smith; Wedding; Wright; Buchanan; Baryla; Gamberdella; Gillespie; Hayes; Seiler; Stanton; Zavoico; Fleming [Journal of Medicinal Chemistry, 1992, vol. 35, # 14, p. 2672 - 2687]

21
[ 1515-75-9 ]
[ 142104-02-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 66 percent / Pd(OAc)2, tri-o-tolylphosphine, Et₃N / acetonitrile / 20 h / 75 °C 2: H₂ / 10 percent Pd/C / ethyl acetate / 2585.7 Torr 3: p-TsOH / methanol / 0.5 h / Heating

Reference： [1]Meanwell; Pearce; Roth; Smith; Wedding; Wright; Buchanan; Baryla; Gamberdella; Gillespie; Hayes; Seiler; Stanton; Zavoico; Fleming [Journal of Medicinal Chemistry, 1992, vol. 35, # 14, p. 2672 - 2687]

22
[ 1515-75-9 ]
[ 142104-07-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 66 percent / Pd(OAc)2, tri-o-tolylphosphine, Et₃N / acetonitrile / 20 h / 75 °C 2: H₂ / 10 percent Pd/C / ethyl acetate / 2585.7 Torr 3: p-TsOH / methanol / 0.5 h / Heating 4: 74 percent / 1 N KOH / methanol / 18 h / Ambient temperature 5: Et₃N, DPPA / dimethylformamide / 18 h / Ambient temperature

Reference： [1]Meanwell; Pearce; Roth; Smith; Wedding; Wright; Buchanan; Baryla; Gamberdella; Gillespie; Hayes; Seiler; Stanton; Zavoico; Fleming [Journal of Medicinal Chemistry, 1992, vol. 35, # 14, p. 2672 - 2687]

23
[ 1515-75-9 ]
[ 142104-05-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 66 percent / Pd(OAc)2, tri-o-tolylphosphine, Et₃N / acetonitrile / 20 h / 75 °C 2: H₂ / 10 percent Pd/C / ethyl acetate / 2585.7 Torr 3: p-TsOH / methanol / 0.5 h / Heating 4: 74 percent / 1 N KOH / methanol / 18 h / Ambient temperature 5: 68 percent / Et₃N, DPPA / dimethylformamide / 18 h / Ambient temperature

Reference： [1]Meanwell; Pearce; Roth; Smith; Wedding; Wright; Buchanan; Baryla; Gamberdella; Gillespie; Hayes; Seiler; Stanton; Zavoico; Fleming [Journal of Medicinal Chemistry, 1992, vol. 35, # 14, p. 2672 - 2687]

24
[ 1515-75-9 ]
[ 142104-04-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 66 percent / Pd(OAc)2, tri-o-tolylphosphine, Et₃N / acetonitrile / 20 h / 75 °C 2: H₂ / 10 percent Pd/C / ethyl acetate / 2585.7 Torr 3: p-TsOH / methanol / 0.5 h / Heating 4: 74 percent / 1 N KOH / methanol / 18 h / Ambient temperature 5: Et₃N, DPPA / dimethylformamide / 18 h / Ambient temperature

Reference： [1]Meanwell; Pearce; Roth; Smith; Wedding; Wright; Buchanan; Baryla; Gamberdella; Gillespie; Hayes; Seiler; Stanton; Zavoico; Fleming [Journal of Medicinal Chemistry, 1992, vol. 35, # 14, p. 2672 - 2687]

25
[ 1515-75-9 ]
[ 142104-06-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 66 percent / Pd(OAc)2, tri-o-tolylphosphine, Et₃N / acetonitrile / 20 h / 75 °C 2: H₂ / 10 percent Pd/C / ethyl acetate / 2585.7 Torr 3: p-TsOH / methanol / 0.5 h / Heating 4: 74 percent / 1 N KOH / methanol / 18 h / Ambient temperature 5: Et₃N, DPPA / dimethylformamide / 18 h / Ambient temperature

Reference： [1]Meanwell; Pearce; Roth; Smith; Wedding; Wright; Buchanan; Baryla; Gamberdella; Gillespie; Hayes; Seiler; Stanton; Zavoico; Fleming [Journal of Medicinal Chemistry, 1992, vol. 35, # 14, p. 2672 - 2687]

26
[ 1515-75-9 ]
1,3-Bis-(tert-butyl-dimethyl-silanyl)-7-(5-hydroxy-pentyl)-1,3-dihydro-imidazo[4,5-b]quinolin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 66 percent / Pd(OAc)2, tri-o-tolylphosphine, Et₃N / acetonitrile / 20 h / 75 °C 2: H₂ / 10 percent Pd/C / ethyl acetate / 2585.7 Torr 3: LiAlH₄ / tetrahydrofuran / 1 h

Reference： [1]Meanwell; Pearce; Roth; Smith; Wedding; Wright; Buchanan; Baryla; Gamberdella; Gillespie; Hayes; Seiler; Stanton; Zavoico; Fleming [Journal of Medicinal Chemistry, 1992, vol. 35, # 14, p. 2672 - 2687]

27
[ 1515-75-9 ]
5-[1,3-Bis-(tert-butyl-dimethyl-silanyl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]quinolin-7-yl]-pentanoic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 66 percent / Pd(OAc)2, tri-o-tolylphosphine, Et₃N / acetonitrile / 20 h / 75 °C 2: H₂ / 10 percent Pd/C / ethyl acetate / 2585.7 Torr

Reference： [1]Meanwell; Pearce; Roth; Smith; Wedding; Wright; Buchanan; Baryla; Gamberdella; Gillespie; Hayes; Seiler; Stanton; Zavoico; Fleming [Journal of Medicinal Chemistry, 1992, vol. 35, # 14, p. 2672 - 2687]

28
[ 1515-75-9 ]
(1S,6R)-6-Hydroxyaminomethyl-6-methyl-cyclohex-2-enecarboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 44 percent / hydroquinone / benzene / 72 h / 120 °C 2: 86 percent / NH₂OH*HCl, Na₂CO₃ / H₂O; ethanol / 3 h / Ambient temperature 3: BH₃-pyridine, 10percent HCl / ethanol / 0.33 h / Ambient temperature

Reference： [1]Wu, Pei-Lin; Chu, Min; Fowler, Frank W. [Journal of Organic Chemistry, 1988, vol. 53, # 5, p. 963 - 972]

29
[ 1515-75-9 ]
(1S,6R)-6-(Hydroxyimino-methyl)-6-methyl-cyclohex-2-enecarboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 44 percent / hydroquinone / benzene / 72 h / 120 °C 2: 86 percent / NH₂OH*HCl, Na₂CO₃ / H₂O; ethanol / 3 h / Ambient temperature

Reference： [1]Wu, Pei-Lin; Chu, Min; Fowler, Frank W. [Journal of Organic Chemistry, 1988, vol. 53, # 5, p. 963 - 972]

30
[ 1515-75-9 ]
[ 112621-99-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 44 percent / hydroquinone / benzene / 72 h / 120 °C 2: 86 percent / NH₂OH*HCl, Na₂CO₃ / H₂O; ethanol / 3 h / Ambient temperature 3: BH₃-pyridine, 10percent HCl / ethanol / 0.33 h / Ambient temperature 4: sodium bicarbonate / H₂O / 1 h / Ambient temperature

Reference： [1]Wu, Pei-Lin; Chu, Min; Fowler, Frank W. [Journal of Organic Chemistry, 1988, vol. 53, # 5, p. 963 - 972]

31
[ 1515-75-9 ]
[ 89563-34-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 7 percent / Pb(OAc)4 / CH₂Cl₂ / Ambient temperature 2: 98 percent / H₂ / platinum oxide / methanol / 20 h 3: 64 percent / NaOH / methanol; H₂O / 1.5 h / 20 °C

Reference： [1]Hassall, Cedric H.; Kroehn, Antonin; Moody, Cristopher J.; Thomas, W. Anthony [Journal of the Chemical Society. Perkin transactions I, 1984, # 2, p. 155 - 164]

32
[ 1515-75-9 ]
[ 89563-33-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 7 percent / Pb(OAc)4 / CH₂Cl₂ / Ambient temperature 2: 98 percent / H₂ / platinum oxide / methanol / 20 h

Reference： [1]Hassall, Cedric H.; Kroehn, Antonin; Moody, Cristopher J.; Thomas, W. Anthony [Journal of the Chemical Society. Perkin transactions I, 1984, # 2, p. 155 - 164]

33
[ 1515-75-9 ]
8-methylspiro<5.5>undecan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 33 percent / (CH₃)2SO, NaH / 72 h / 75 - 80 °C 2: 87 percent / p-toluenesulfonic acid / benzene / 2 h / Heating 3: 90 percent / LiAlH₄ / diethyl ether / 2 h / Ambient temperature 4: 50 percent / (C₆H₅)3P, Br₂, pyridine / acetonitrile / 0.25 h / 0 °C 5: 90 percent / LiAlH₄ / tetrahydrofuran / 1 h / Ambient temperature 6: 81 percent / silica gel, 1percent aq. H₂SO₄ / CH₂Cl₂ / 12 h 7: H₂ / 10percent Pd/C / cyclohexane

Reference： [1]Fuchs, Benzion; Zizuashvili, Jakob; Abramson, Sarah [Journal of Organic Chemistry, 1982, vol. 47, # 18, p. 3474 - 3477]

34
[ 1515-75-9 ]
[ 82390-28-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 33 percent / (CH₃)2SO, NaH / 72 h / 75 - 80 °C 2: 87 percent / p-toluenesulfonic acid / benzene / 2 h / Heating 3: 90 percent / LiAlH₄ / diethyl ether / 2 h / Ambient temperature 4: 50 percent / (C₆H₅)3P, Br₂, pyridine / acetonitrile / 0.25 h / 0 °C 5: 90 percent / LiAlH₄ / tetrahydrofuran / 1 h / Ambient temperature 6: silica gel, 1percent aq. H₂SO₄ / CH₂Cl₂ / 12 h
	Multi-step reaction with 7 steps 1: 33 percent / (CH₃)2SO, NaH / 72 h / 75 - 80 °C 2: 87 percent / p-toluenesulfonic acid / benzene / 2 h / Heating 3: 90 percent / LiAlH₄ / diethyl ether / 2 h / Ambient temperature 4: 50 percent / (C₆H₅)3P, Br₂, pyridine / acetonitrile / 0.25 h / 0 °C 5: 90 percent / LiAlH₄ / tetrahydrofuran / 1 h / Ambient temperature 6: 81 percent / silica gel, 1percent aq. H₂SO₄ / CH₂Cl₂ / 12 h 7: trifluoroacetic acid (TFA) / CCl₄ / 48 h / Ambient temperature

Reference： [1]Fuchs, Benzion; Zizuashvili, Jakob; Abramson, Sarah [Journal of Organic Chemistry, 1982, vol. 47, # 18, p. 3474 - 3477]
[2]Fuchs, Benzion; Zizuashvili, Jakob; Abramson, Sarah [Journal of Organic Chemistry, 1982, vol. 47, # 18, p. 3474 - 3477]

35
[ 1515-75-9 ]
[ 82390-25-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 33 percent / (CH₃)2SO, NaH / 72 h / 75 - 80 °C 2: 87 percent / p-toluenesulfonic acid / benzene / 2 h / Heating 3: 90 percent / LiAlH₄ / diethyl ether / 2 h / Ambient temperature 4: 50 percent / (C₆H₅)3P, Br₂, pyridine / acetonitrile / 0.25 h / 0 °C 5: 90 percent / LiAlH₄ / tetrahydrofuran / 1 h / Ambient temperature 6: 81 percent / silica gel, 1percent aq. H₂SO₄ / CH₂Cl₂ / 12 h

Reference： [1]Fuchs, Benzion; Zizuashvili, Jakob; Abramson, Sarah [Journal of Organic Chemistry, 1982, vol. 47, # 18, p. 3474 - 3477]

36
[ 1515-75-9 ]
[ 82390-27-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 33 percent / (CH₃)2SO, NaH / 72 h / 75 - 80 °C 2: 87 percent / p-toluenesulfonic acid / benzene / 2 h / Heating 3: 90 percent / LiAlH₄ / diethyl ether / 2 h / Ambient temperature 4: 50 percent / (C₆H₅)3P, Br₂, pyridine / acetonitrile / 0.25 h / 0 °C 5: 90 percent / LiAlH₄ / tetrahydrofuran / 1 h / Ambient temperature 6: 81 percent / silica gel, 1percent aq. H₂SO₄ / CH₂Cl₂ / 12 h 7: 30 percent / trifluoroacetic acid (TFA) / CCl₄ / 48 h / Ambient temperature

Reference： [1]Fuchs, Benzion; Zizuashvili, Jakob; Abramson, Sarah [Journal of Organic Chemistry, 1982, vol. 47, # 18, p. 3474 - 3477]

37
[ 1515-75-9 ]
[ 82390-24-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 33 percent / (CH₃)2SO, NaH / 72 h / 75 - 80 °C 2: 87 percent / p-toluenesulfonic acid / benzene / 2 h / Heating 3: 90 percent / LiAlH₄ / diethyl ether / 2 h / Ambient temperature 4: 50 percent / (C₆H₅)3P, Br₂, pyridine / acetonitrile / 0.25 h / 0 °C 5: 90 percent / LiAlH₄ / tetrahydrofuran / 1 h / Ambient temperature

Reference： [1]Fuchs, Benzion; Zizuashvili, Jakob; Abramson, Sarah [Journal of Organic Chemistry, 1982, vol. 47, # 18, p. 3474 - 3477]

38
[ 1515-75-9 ]
[ 82390-22-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 33 percent / (CH₃)2SO, NaH / 72 h / 75 - 80 °C 2: 87 percent / p-toluenesulfonic acid / benzene / 2 h / Heating 3: 90 percent / LiAlH₄ / diethyl ether / 2 h / Ambient temperature

Reference： [1]Fuchs, Benzion; Zizuashvili, Jakob; Abramson, Sarah [Journal of Organic Chemistry, 1982, vol. 47, # 18, p. 3474 - 3477]

39
[ 1515-75-9 ]
[ 82390-23-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 33 percent / (CH₃)2SO, NaH / 72 h / 75 - 80 °C 2: 87 percent / p-toluenesulfonic acid / benzene / 2 h / Heating 3: 90 percent / LiAlH₄ / diethyl ether / 2 h / Ambient temperature 4: 50 percent / (C₆H₅)3P, Br₂, pyridine / acetonitrile / 0.25 h / 0 °C

Reference： [1]Fuchs, Benzion; Zizuashvili, Jakob; Abramson, Sarah [Journal of Organic Chemistry, 1982, vol. 47, # 18, p. 3474 - 3477]

40
[ 1515-75-9 ]
[ 82390-21-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 33 percent / (CH₃)2SO, NaH / 72 h / 75 - 80 °C 2: 87 percent / p-toluenesulfonic acid / benzene / 2 h / Heating

Reference： [1]Fuchs, Benzion; Zizuashvili, Jakob; Abramson, Sarah [Journal of Organic Chemistry, 1982, vol. 47, # 18, p. 3474 - 3477]

41
[ 1515-75-9 ]
(3aR,7aR)-1-Hydroxy-2-nitro-3-oxo-3a,4,7,7a-tetrahydro-3H-indene-4-carboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 2,5-di-tert-butyl-benzene-1,4-diol / benzene 2: NO₂/HNO₃ / diethyl ether

Reference： [1]Buckle,D.R. et al. [Journal of Medicinal Chemistry, 1975, vol. 18, p. 203 - 206]

42
[ 1515-75-9 ]
[ 54-42-2 ]
[ 157085-09-1 ]

Yield	Reaction Conditions	Operation in experiment
22.6%	Stage #1: With triethylamine In 1,4-dioxane at 70℃; for 0.583333h; Stage #2: methyl 2,4-pentadienoate; 5-Iodo-2'-deoxyuridine In 1,4-dioxane for 15h; Heating / reflux;	10 EXAMPLE 10; 5-(4-Carbomethoxy-1,3-butadienyl)-2'-dexoyuridine (Va) A solution of triethylamine (3.9 mL, 28.2 mmol) in dioxane (12 mL) was deareated by bubbling nitrogen through for 15 min. Palladium acetate (0.60 g, 0.26 mmol) and triphenylphosphine (0.183 g, 0.70 mmol) were added and the solution was heated at 70° C. for 20 min to give a dark brown solution. 5-Iodo-3'-deoxyuridine (5.0 g, 14.1 mmol) and methyl 2,4-pentadienoate (2.5 g, 22.3 mmol) was added and the mixture was heated under reflux for 15 h. The solvent and volatile components were evaporated in vacuo and the residue was partitioned between water (15 mL) and EtOAc (15 mL). The phases were separated and the aqueous phase was extracted twice with EtOAc (10 mL each). The combined organic phase was washed with brine and concentrated. The residue was dissolved in MEOH (15 mL) and allowed to cool to room temperature. The solid formed was collected by filtration, washed with a small quantity of MeOH and dried in vacuo to give 0.38 g brown powder. [00223] 1H NMR (DMSO-d6): 2.17 (2H, t, J=6.4 Hz), 3.55-3.70 (2H, m), 3.66 (3H, s), 3.82 (1H, q, J=3.6 Hz), 4.27 (1H, m), 5.18 (1H, t, J=4.9 Hz), 5.26 (1H, d, J=4.5 Hz), 5.99 (1H, d, J=14.4 Hz), 6.14 (1H, d, J=6.4 Hz), 6.74 (1H, d, J=14.8 Hz), 7.20-7.35 (2H, m), 8.30 (1H, s), 11.56 (1H, s). [00224] The filtrate from above was concentrated and chromatographed on silica gel using 60-100% EtOAc/hexanes as eluent to give another 0.70 g of product as a brown foam. The combined yield was 1.08 g (22.6%).

Reference： [1]Current Patent Assignee: SANOFI - US6683061, 2004, B1 Location in patent: Page column 37-38

43
[ 1515-75-9 ]
[ 698362-77-5 ]
(2E,4E)-5-{3-[Cyclopropanecarbonyl-(8-methoxy-2,2-dimethyl-2H-chromen-7-ylmethyl)-amino]-phenyl}-penta-2,4-dienoic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With triethylamine In N,N-dimethyl-formamide at 90℃; for 24h;

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH - WO2004/46162, 2004, A2 Location in patent: Page 7; Sheet 6

44
[ 1515-75-9 ]
[ 4949-20-6 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium aluminium tetrahydride In diethyl ether at -15℃; for 2h;

Reference： [1]Lange, Heiko; Fröhlich, Roland; Hoppe, Dieter [Tetrahedron, 2008, vol. 64, # 38, p. 9123 - 9135]

45
[ 1515-75-9 ]
C₁₁₀H₁₂₄N₈Zn [ No CAS ]
C₁₂₂H₁₃₆N₈O₄Zn [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
21 mg	Stage #1: C₁₁₀H₁₂₄N₈Zn With 4,4'-dimethyl-2,2'-bipyridines; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; bis(pinacol)diborane In 1,4-dioxane for 48h; Inert atmosphere; Reflux; Stage #2: methyl 2,4-pentadienoate With [Rh(OH)(cod)]2 In 1,4-dioxane; water at 40℃; for 48h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Chen, Jinping; Aratani, Naoki; Shinokubo, Hiroshi; Osuka, Atsuhiro [Chemistry - An Asian Journal, 2009, vol. 4, # 7, p. 1126 - 1133]

46
[ 1515-75-9 ]
[ 1243143-57-8 ]
[ 1243143-61-4 ]

Yield	Reaction Conditions	Operation in experiment
	With [Rh(OH)(cod)]2 In 1,4-dioxane; water at 40℃; for 48h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Chen, Jinping; Aratani, Naoki; Shinokubo, Hiroshi; Osuka, Atsuhiro [Chemistry - An Asian Journal, 2009, vol. 4, # 7, p. 1126 - 1133]

47
[ 74-85-1 ]
[ 89123-62-6 ]
[ 1515-75-9 ]

Yield	Reaction Conditions	Operation in experiment
63%	With 10H-phenothiazine; bis(μ-chloro)bis{(2-(1-(hydroxyimino)methyl)phenyl-C1,N)palladium(II)}; potassium acetate In N,N-dimethyl acetamide at 105℃; for 24h; Inert atmosphere;

Reference： [1]Smith, Craig R.; RajanBabu [Tetrahedron, 2010, vol. 66, # 5, p. 1102 - 1110]

48
[ 38330-80-2 ]
[ 107-02-8 ]
[ 1515-75-9 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: monomethyl monopotassium malonate With pyridine; pyridine hydrochloride In N,N-dimethyl-formamide at 40 - 45℃; for 1.5h; Inert atmosphere; Stage #2: acrolein In N,N-dimethyl-formamide at 25 - 35℃; for 25.8333h;	2 EXAMPLE 2: EXAMPLE 2: PREPARATION OF 2,4-PENTADIENYLMETHYL ESTER USING PYRIDINE HCI. N,N-Dimethylformamide (600 mL), malonic acid monomethyl ester potassium salt (300 g), pyridine HCI (233.2 g), and pyridine (7.6 g) are placed in a round-bottom flask equipped with a mechanical stirrer, under a nitrogen atmosphere. The mass is heated to 40-45°C and stirred under a nitrogen atmosphere for about 90 minutes. The mixture is cooled to 25-35°C and acrolein (161.2 g) is added at this temperature over about 50 minutes. The mixture is stirred at 25-35°C for about 25 hours and then cooled to 20-25°C. Water (3 L) is added and stirring is continued for about 30 minutes. Dichloromethane (1.5 L) is added, stirred, and separated from the aqueous layer. Additional dichloromethane (600 mL) is added, stirred, and separated from the aqueous layer. The organic layers are combined and washed with a mixture of 75 mL of concentrated HCl and 1.5 L of water. The aqueous layer is separated and extracted with dichloromethane (150 mL). The total organic layer is washed with water (1.5 L) to obtain the title compound in a dichloromethane solution. Approximate yield: 142.2 g.

Reference： [1]Current Patent Assignee: DR REDDY'S LABORATORIES LIMITED - EP2221299, 2010, A2 Location in patent: Page/Page column 8

49
[ 1445-69-8 ]
[ 1515-75-9 ]
[ 32692-31-2 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium hypochlorite In dichloromethane; water at 0℃;	3 EXAMPLE 3: EXAMPLE 3: PREPARATION OF 6,11-DIOXO-1,4,6,11-TETRAHYDRO-PYRIDAZINO[1,2-B]PHTHALAZINE-1-CARBOXYLIC ACID METHYL ESTER. Water (711 mL) and concentrated HCl (284 mL) are placed into a round-bottom flask. 2,3-Dihydrophthalazine-1,4-dione (288 g) is added at 25-35°C. The mass is cooled to -10 to 0°C and 2,4-pentadienylmethyl ester (142.2 g) in dichloromethane is added at the same temperature. Sodium hypochlorite solution (12% w/w, 1140 g) is added slowly over about 7 hours, below 0°C. The reaction is maintained for about 2 hours. A solution of 30 g of sodium bisulfite in 207 mL of water is added below 5°C, stirred for 15 minutes, and the organic layer is separated. The aqueous layer pH is adjusted to about 5 by adding a solution of 128 g of NaOH in 640 mL water at 0-5°C, and is stirred for 30 minutes. Undissolved solid is filtered and the solid is washed with dichloromethane (284 mL). The aqueous layer is separated from the filtrate and is washed with dichloromethane (284 mL). The combined organic layer is washed with water (711 mL) and the final organic layer is distilled. Acetone (426 mL) is added to the residue and the acetone is distilled. Acetone (284 mL) is charged to the reaction mixture and 142 mL is distilled. The residue is cooled to 0-5°C and stirred for about 2 hours. The formed solid is filtered and washed with chilled acetone (213 mL). The wet solid is dried under vacuum at 25-35°C for 30 minutes, and then at 50-55°C for 7 hours, to obtain the title compound. Approximate yield: 171 g. Purity by HPLC: 98.8%.

Reference： [1]Current Patent Assignee: DR REDDY'S LABORATORIES LIMITED - EP2221299, 2010, A2 Location in patent: Page/Page column 8

50
[ 1515-75-9 ]
[ 13909-34-7 ]
C₁₉H₁₉NO₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 3-quinuclidinol In N,N-dimethyl-formamide at 20℃; for 24h;

Reference： [1]Clary, Kristen N.; Back, Thomas G. [Synlett, 2010, # 18, p. 2802 - 2804]

51
[ 1515-75-9 ]
[ 93102-05-7 ]
C₁₅H₁₉NO₂ [ No CAS ]
(3,4-trans)-methyl 1-benzyl-4-vinylpyrrolidine-3-carboxylate [ No CAS ]
C₂₄H₃₀N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37%	With trifluoroacetic acid In dichloromethane; toluene at 0 - 22℃; for 16h; Inert atmosphere;	(3,4-trans)-methyl 1-benzyl-4-vinylpyrrolidine-3-carboxylate 1a To a solution of of the commercial (E)-methyl penta-2,4-dienoate (0.965 g, 8.61 mmol) in toluene (5.0 mL) at 0°C in a 25 mL three-neck round bottom flask dried under N2 was added N-(methoxymethyl)-N-(trimethylsilylmethyl)benzamine (2.64 mL, 10.3 mmol). The solution was stirred at 0°C for 10 minutes and then treated with trifluoroacetic acid (0.86 mL, 0.86 mmol, 1 M solution of in anhydrous CH2Cl2) dropwise. The reaction mixture was allowed to warm to 22 oC and stir for 15 hours. The mixture was diluted in water (25 mL) and adjusted to a pH of ~8 with saturated aqueous sodium bicarbonate. The product was extracted with dichloromethane (3 x 10 mL) and the combined organics were then washed with brine, and dried over magnesium sulfate. Solvent was removed under reduced pressure, yielding 3.08 g of a yellow oil. The crude product was analyzed by H-NMR and COSY [00701271-0005-002] in deuterated chloroform. A small amount of this NMR sample was then diluted in dichloromethane and analyzed by GC-MS. The desired product 1a (0.77 g, 37% yield) was isolated by column chromatography (silica gel, 20% ethyl acetate in n-heptane). dH (400 MHz; CDCl3) 2.42 (1H, dd, 9.6, 6.8 Hz), 2.76-2.88 (4 H, m), 3.08 (1 H, m), 3.56 (1 H, d, 12.8 Hz) 3.64 (1 H, d, 12.8 Hz), 3.67 (3 H, s), 4.98 (1 H, d, 10 Hz), 5.06 (1 H, d, 17.4 Hz), 5.83 (1 H, m), 7.20-7.32 (5 H, m). dC (100 MHz; CDCl3) 45.80, 48.81, 51.91, 56.56, 59.44, 59.86, 115.01, 126.98, 128.22, 128.65, 139.74, 174.59. HRMS formula C15H19 NO2 m/z 246.1488 [M + H]+calculated; 246.1493 [M + H]+ found.

Reference： [1]Blumberg, Laura C.; Costa, Brian; Goldstein, Rebecca [Tetrahedron Letters, 2011, vol. 52, # 8, p. 872 - 874]

52
[ 1515-75-9 ]
[ 19656-74-7 ]
1,3-di-<i>tert</i>-butyl-2-oxo-5-vinyl-imidazolidine-4-carboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In benzene-d6 at 65℃; Inert atmosphere;

Reference： [1]Location in patent: experimental part Du, Haifeng; Zhao, Baoguo; Shi, Yian; Buck, Eric E.; Wipf, Peter [Organic Syntheses, 2009, vol. 86, p. 315 - 324]

53
[ 1515-75-9 ]
[ 42028-73-9 ]
C₁₄H₂₆N₂O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With tributylphosphine; copper(l) chloride In chloroform at 20℃; for 48h; sealed vial; Inert atmosphere; regioselective reaction;

Reference： [1]Cornwall, Richard G.; Zhao, Baoguo; Shi, Yian [Organic Letters, 2011, vol. 13, # 3, p. 434 - 437]

54
[ 1515-75-9 ]
[ 6971-74-0 ]
C₂₀H₁₉NO₅S [ No CAS ]

Reference： [1]Organic Letters,2011,vol. 13,p. 1214 - 1217

55
[ 14468-80-5 ]
[ 1515-75-9 ]
[ 1357356-21-8 ]

Yield	Reaction Conditions	Operation in experiment
73%	Stage #1: N-benzyloxycarbonylpyrrolidin-2-one With diisobutylaluminium hydride In tetrahydrofuran; hexane at -40℃; for 0.5h; Stage #2: With methanol In tetrahydrofuran; hexane for 0.5h; Stage #3: methyl 2,4-pentadienoate With samarium diiodide; boron trifluoride diethyl etherate In tetrahydrofuran; hexane; <i>tert</i>-butyl alcohol at -40℃; for 0.166667h;

Reference： [1]Location in patent: experimental part Liu, Xue-Kui; Zheng, Xiao; Ruan, Yuan-Ping; Ma, Jie; Huang, Pei-Qiang [Organic and Biomolecular Chemistry, 2012, vol. 10, # 6, p. 1275 - 1284]

56
[ 1515-75-9 ]
(S)-tert-butyl 2-((tert-butyldiphenylsilyloxy)methyl)-5-oxopyrrolidine-1-carboxylate [ No CAS ]
[ 1357356-27-4 ]
(2S,5R)-1-(t-butyloxycarbonyl)-2-[(t-butyldiphenylsilyl)oxymethyl]-5-[(E)-4-(methyloxycarbonyl)but-2-enyl]pyrrolidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: (S)-tert-butyl 2-((tert-butyldiphenylsilyloxy)methyl)-5-oxopyrrolidine-1-carboxylate With diisobutylaluminium hydride In tetrahydrofuran; hexane at -40℃; for 0.5h; Stage #2: With methanol In tetrahydrofuran; hexane for 0.5h; Stage #3: methyl 2,4-pentadienoate With samarium diiodide; boron trifluoride diethyl etherate In tetrahydrofuran; hexane; <i>tert</i>-butyl alcohol at -40℃; for 0.166667h; optical yield given as %de; diastereoselective reaction;

Reference： [1]Location in patent: experimental part Liu, Xue-Kui; Zheng, Xiao; Ruan, Yuan-Ping; Ma, Jie; Huang, Pei-Qiang [Organic and Biomolecular Chemistry, 2012, vol. 10, # 6, p. 1275 - 1284]

57
[ 1515-75-9 ]
[ 101137-70-6 ]
[ 1357356-18-3 ]

Yield	Reaction Conditions	Operation in experiment
73%	Stage #1: tert-butyl acetyl(benzyl)carbamate With diisobutylaluminium hydride In tetrahydrofuran; hexane at -40℃; for 0.5h; Stage #2: With methanol In tetrahydrofuran; hexane for 0.5h; Stage #3: methyl 2,4-pentadienoate With samarium diiodide; boron trifluoride diethyl etherate In tetrahydrofuran; hexane; <i>tert</i>-butyl alcohol at -40℃; for 0.166667h; regioselective reaction;

Reference： [1]Location in patent: experimental part Liu, Xue-Kui; Zheng, Xiao; Ruan, Yuan-Ping; Ma, Jie; Huang, Pei-Qiang [Organic and Biomolecular Chemistry, 2012, vol. 10, # 6, p. 1275 - 1284]

58
[ 1515-75-9 ]
[ 245648-28-6 ]
[ 1357356-23-0 ]

Yield	Reaction Conditions	Operation in experiment
77%	Stage #1: (S)-benzyl 2-(((tert-butyldiphenylsilyl)oxy)methyl)-5-oxopyrrolidine-1-carboxylate With diisobutylaluminium hydride In tetrahydrofuran; hexane at -40℃; for 0.5h; Stage #2: With methanol In tetrahydrofuran; hexane for 0.5h; Stage #3: methyl 2,4-pentadienoate With samarium diiodide; boron trifluoride diethyl etherate In tetrahydrofuran; hexane; <i>tert</i>-butyl alcohol at -40℃; for 0.166667h; optical yield given as %de; diastereoselective reaction;

Reference： [1]Location in patent: experimental part Liu, Xue-Kui; Zheng, Xiao; Ruan, Yuan-Ping; Ma, Jie; Huang, Pei-Qiang [Organic and Biomolecular Chemistry, 2012, vol. 10, # 6, p. 1275 - 1284]

59
[ 1515-75-9 ]
[ 6746-94-7 ]
[ 148438-02-2 ]
[ 148438-01-1 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: methyl 2,4-pentadienoate; Cyclopropylacetylene With cobalt(II) bromide-[1,2-bis(diphenylphosphino)ethane]; zinc(II) iodide; zinc In dichloromethane at 20℃; Inert atmosphere; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In benzene at 20℃; for 1h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Arndt, Marion; Hilt, Gerhard; Khlebnikov, Alexander F.; Kozhushkov, Sergei I.; De Meijere, Armin [European Journal of Organic Chemistry, 2012, # 16, p. 3112 - 3121]

60
[ 40314-06-5 ]
[ 1515-75-9 ]
[ 1606159-91-4 ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 1630 - 1635
Angew. Chem.,2014,vol. 126,p. 1656 - 1661,6

61
[ 74-85-1 ]
[ 1515-75-9 ]
C₈H₁₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With [2-(benzyloxy)phenyl]diphenylphosphane; bi(allylnickel bromide); sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In dichloromethane at 25℃; for 43h; Schlenk technique;

Reference： [1]Biswas, Souvagya; Zhang, Aibin; Raya, Balaram; Rajanbabu [Advanced Synthesis and Catalysis, 2014, vol. 356, # 10, p. 2281 - 2292]

62
[ 1515-75-9 ]
[ 124-38-9 ]
sodium 6-methoxy-6-oxohexa-2,4-dienoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (R,R)-(-)-2,3-bis(tert-butylmethylphosphino)benzene; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; Sodium 2-fluorophenoxide; zinc In tetrahydrofuran at 25 - 100℃; for 20h; Autoclave; Glovebox; Inert atmosphere;

Reference： [1]Huguet, Nfflria; Jevtovikj, Ivana; Gordillo, Alvaro; Lejkowski, Michael L.; Lindner, Ronald; Bru, Miriam; Khalimon, Andrey Y.; Rominger, Frank; Schunk, Stephan A.; Hofmann, Peter; Limbach, Michael [Chemistry - A European Journal, 2014, vol. 20, # 51, p. 16858 - 16862]

63
[ 1295-35-8 ]
[ 1515-75-9 ]
[ 124-38-9 ]
[ 4141-59-7 ]
[(dtbpe)Ni(OC(=O)C₄H₆(COOMe))] [ No CAS ]

Reference： [1]Dalton Transactions,2015,vol. 44,p. 11083 - 11094

64
[ 1295-35-8 ]
[ 1515-75-9 ]
[ 4141-59-7 ]
[(dtbpe)Ni(Me-2,4-pentadienoate)] [ No CAS ]

Reference： [1]Dalton Transactions,2015,vol. 44,p. 11083 - 11094

65
[ 1295-35-8 ]
[ 1515-75-9 ]
[ 4141-59-7 ]
[(dcpe)Ni(Me-2,4-pentadienoate)] [ No CAS ]

Reference： [1]Dalton Transactions,2015,vol. 44,p. 11083 - 11094

66
[ 1515-75-9 ]
[ 124-38-9 ]
sodium 6-methoxy-6-oxohexa-2,4-dienoate [ No CAS ]
C₇H₇O₄^(1-)*Na⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; Sodium 2-fluorophenoxide; zinc In tetrahydrofuran at 100℃; for 20h;

Reference： [1]Jevtovikj, Ivana; Manzini, Simone; Hanauer, Matthias; Rominger, Frank; Schaub, Thomas [Dalton Transactions, 2015, vol. 44, # 24, p. 11083 - 11094]

67
[ 1515-75-9 ]
C₇₄H₆₆Br₂N₄O₂ [ No CAS ]
C₈₆H₇₈N₄O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	Stage #1: methyl 2,4-pentadienoate; C₇₄H₆₆Br₂N₄O₂ With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; bis(tri-t-butylphosphine)palladium⁽⁰⁾; N,N-dicyclohexylmethylamine In tetrahydrofuran at 45℃; Schlenk technique; Inert atmosphere; Sealed tube; Stage #2: With chloranil In toluene for 12h; Reflux; Inert atmosphere;

Reference： [1]Hu, Yi; Yellappa, Shivaraj; Thomas, Michael B.; Jinadasa, R. G. Waruna; Matus, Alex; Shulman, Max; D'Souza, Francis; Wang, Hong [Chemistry - An Asian Journal, 2017, vol. 12, # 20, p. 2749 - 2762]

68
[ 1515-75-9 ]
[ 121-69-7 ]
methyl 6-(methyl(phenyl)amino)hex-3-enoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; 1,3-bis-(diphenylphosphino)propane; cesium pivalate; cobalt(II) bromide In acetonitrile at 20℃; for 12h; Inert atmosphere; Irradiation;

Reference： [1]Thullen, Scott M.; Rovis, Tomislav [Journal of the American Chemical Society, 2017, vol. 139, # 43, p. 15504 - 15508]

69
[ 1515-75-9 ]
[ 1360651-27-9 ]
methyl (S,E)-3-(2-methoxy-5-methyl-1-oxo-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-3-yl)acrylate [ No CAS ]
methyl (E)-3-(2-methoxy-5-methyl-1-oxo-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-3-yl)acrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86 % ee	With (S)-4-(tert-butyl)-2-(5-methoxypyridin-2-yl)-5,5-dimethyl-4,5-dihydrooxazole; oxygen; palladium diacetate In methanol at 90℃; for 24h; Inert atmosphere; Schlenk technique; Molecular sieve; Overall yield = 82 %; Overall yield = 25.7 mg; enantioselective reaction;

Reference： [1]Zhang, Tao; Shen, Hong-Cheng; Xu, Jia-Cheng; Fan, Tao; Han, Zhi-Yong; Gong, Liu-Zhu [Organic Letters, 2019, vol. 21, # 7, p. 2048 - 2051]

70
[ 1515-75-9 ]
[ 2446-51-7 ]
methyl (S,E)-3-(2-methoxy-1-oxo-1,2,3,4-tetrahydroisoquinolin-3-yl)acrylate [ No CAS ]
methyl (E)-3-(2-methoxy-1-oxo-1,2,3,4-tetrahydroisoquinolin-3-yl)acrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77 % ee	With (S)-4-(tert-butyl)-2-(5-methoxypyridin-2-yl)-5,5-dimethyl-4,5-dihydrooxazole; oxygen; palladium diacetate In methanol at 90℃; for 24h; Schlenk technique; Inert atmosphere; Molecular sieve; Overall yield = 42 %; Overall yield = 11 mg; enantioselective reaction;

Reference： [1]Zhang, Tao; Shen, Hong-Cheng; Xu, Jia-Cheng; Fan, Tao; Han, Zhi-Yong; Gong, Liu-Zhu [Organic Letters, 2019, vol. 21, # 7, p. 2048 - 2051]

71
[ 1515-75-9 ]
C₇₆H₉₂Br₂N₄ [ No CAS ]
C₈₈H₁₀₆N₄O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; bis(tri-t-butylphosphine)palladium⁽⁰⁾; N-Methyldicyclohexylamine In tetrahydrofuran at 45℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube;

Reference： [1]Hu, Yi; Webre, Whitney A.; Thomas, Michael B.; Moss, Austen; Hancock, Sarah N.; Schaffner, Jacob; D'Souza, Francis; Wang, Hong [Journal of Materials Chemistry A, 2019, vol. 7, # 17, p. 10712 - 10722]

72
[ 1515-75-9 ]
C₅₆H₅₀Br₄N₄ [ No CAS ]
C₈₀H₇₈N₄O₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; bis(tri-t-butylphosphine)palladium⁽⁰⁾; N-Methyldicyclohexylamine In tetrahydrofuran at 50℃; for 36h; Schlenk technique; Inert atmosphere; Sealed tube;

Reference： [1]Kumar, Siddhartha; Webre, Whitney; Schaffner, Jacob; Islam, Sheikh M. S.; D'souza, Francis; Wang, Hong [Journal of Porphyrins and Phthalocyanines, 2019, vol. 23, # 4-5, p. 599 - 610]

73
[ 1515-75-9 ]
C₈₈H₆₈Br₄N₄Zn [ No CAS ]
C₁₁₂H₉₆N₄O₈Zn [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; bis(tri-t-butylphosphine)palladium⁽⁰⁾; N-Methyldicyclohexylamine In tetrahydrofuran at 50℃; for 48h; Schlenk technique; Inert atmosphere; Sealed tube;

Reference： [1]Kumar, Siddhartha; Webre, Whitney; Schaffner, Jacob; Islam, Sheikh M. S.; D'souza, Francis; Wang, Hong [Journal of Porphyrins and Phthalocyanines, 2019, vol. 23, # 4-5, p. 599 - 610]

74
[ 1515-75-9 ]
[ 129748-56-7 ]
(E)-methyl 6-(1-tosylpyrrolidin-3-yl)hex-3-enoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%	With vitamin B₁₂; ammonium chloride; zinc In methanol at 20℃; for 0.25h; Inert atmosphere; Sealed tube; Irradiation;	Pyrrolidine Derivatives; General Procedure B General procedure: A glass reaction tube (inner diameter = 18 mm) equipped with a magneticbar was charged with NH4Cl (47 mg, 0.87 mmol, 3.5 equiv), vitaminB12 (21 mg, 0.016 mmol, 6.0 mol%), and activated Zn (98 mg, 1.5mmol, 6.0 equiv), then MeOH (2.5 mL, HPLC grade) was added. Thetubewas sealed with a septum and the resulting mixture was degassed bypurging the solution with argon for 20 min with simultaneous sonicationin ultrasonic bath (the solution turned from red to dark greenor brown). Subsequently, an electron-deficient olefin (0.25 mmol, 1.0equiv) and bromoalkene (0.5 mmol, 2.0 equiv) were added and the reactionvessel was placed in a photoreactor and irradiated with blueLED (10 W) for 15-20 min. The reaction mixture was quenched withEtOAc, filtered through a cotton pad, and concentrated in vacuo. Thecrude product was purified using column chromatography (SiO2, gradientfrom 0 to 30% EtOAc in hexane).

Reference： [1]Smoleń, Sabina; Wincenciuk, Aleksandra; Drapała, Olga; Gryko, Dorota [Synthesis, 2021, vol. 53, # 9, p. 1645 - 1653]

75
[ 1515-75-9 ]
[ 789-25-3 ]
methyl (E)-4-(triphenylsilyl)pent-2-enoate [ No CAS ]