Name: 28010-12-0|(2E,4E)-5-Phenylpenta-2,4-dienoic acid|96%
Brand: Ambeed
SKU: A213392
Price: 5.0 USD
Availability: InStock
Rating: 92 (35 reviews)

1
[ 14371-10-9 ]
[ 463-51-4 ]
[ 28010-12-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium acetate
	With diethyl ether; boron trifluoride

Reference： [1]Hurd; Williams [Journal of the American Chemical Society, 1936, vol. 58, p. 962,967]
[2]Current Patent Assignee: DOW INC - US2484067, 1949, A

2
[ 14371-10-9 ]
[ 141-82-2 ]
[ 28010-12-0 ]

Yield	Reaction Conditions	Operation in experiment
91%	Stage #1: malonic acid With pyridine at 45℃; Stage #2: (E)-3-phenylpropenal at 60 - 80℃; for 14.1667h;
85%	With piperidine; pyridine at 80 - 100℃; for 3h;
70%	With piperidine; pyridine at 90 - 95℃; for 2.08333h;	3.3. General synthesis of (E)-3-(5-methylfuran-2-yl)acrylic acid (3a), (2E,4E)-5-phenylpenta-2,4-dienoic acid (3b), and (E)-3-(thiophen-2-yl)acrylic acid (3c) General procedure: Malonic acid (20 g, 0.2 mol), the corresponding aldehyde (0.1 mol), (5-methylfuran-2-carbaldehyde for 3a, cinnamaldehyde for 3b, and thiophene-2-carbaldehyde for 3c), 50 mL of freshly distilled pyridine, and 1 mL of piperidine were put into a two-necked reaction flask. The mixture was heated for 2 h to a temperature not exceeding 90-95 ° C and boiled for 5 min after that. The mixture was left to cool and diluted with water. After cooling, concentrated HCl was added dropwise. Formed precipitates were filtered and crystallized in EtOH-water.

	Stage #1: (E)-3-phenylpropenal; malonic acid With 4-methyl-morpholine at 80℃; for 8h; Stage #2: With sulfuric acid In water at 20℃; for 0.5h; regioselective reaction;
	With pyridine
	With [Hf₆O₄(OH)₄(2,2’-diamino-[1,1’-biphenyl]-4,4’-dicarboxylic acid)₆]10H₂O5DMF In N,N-dimethyl-formamide; toluene at 80℃; for 24h; Schlenk technique;

Reference： [1]Wang, Zhihan; Randazzo, Katelyn; Hou, Xiaodong; Simpson, Jeffrey; Struppe, Jochem; Ugrinov, Angel; Kastern, Brent; Wysocki, Erin; Chu, Qianli R. [Macromolecules, 2015, vol. 48, # 9, p. 2894 - 2900]
[2]Banerji, Avijit; Banerjee, Tapasri; Sengupta, Ratna; Sengupta, Piyali; Das, Chittaranjan; Sahu, Anita [Journal of the Indian Chemical Society, 2002, vol. 79, # 11, p. 876 - 883]
[3]Sari, Sait; Ünalan, Seda; Yilmaz, Mehmet [Turkish Journal of Chemistry, 2019, vol. 43, # 6, p. 1656 - 1671]
[4]Farmer; Hose [Journal of the Chemical Society, 1933, p. 962,965]
[5]Location in patent: experimental part Zhang, Shi-Jie; Hu, Wei-Xiao [Synthetic Communications, 2010, vol. 40, # 20, p. 3093 - 3100]
[6]Zhang, Ming; Kumagai, Naoya; Shibasaki, Masakatsu [Chemistry - A European Journal, 2016, vol. 22, # 16, p. 5525 - 5529]
[7]Gucma, Mirosław; Gołębiewski, W. Marek; Michalczyk, Alicja Katarzyna [Monatshefte fur Chemie, 2016, vol. 147, # 10, p. 1809 - 1818]
[8]Das, Aniruddha; Anbu, Nagaraj; Gogoi, Chiranjib; Dhakshinamoorthy, Amarajothi; Biswas, Shyam [European Journal of Inorganic Chemistry, 2021, vol. 2021, # 33, p. 3396 - 3403]

3
[ 67-56-1 ]
[ 28010-12-0 ]
(2E,4E)-methyl 5-phenylpenta-2,4-dienoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With hydrogenchloride at 20℃; for 16h; Inert atmosphere;
96%	With hydrogenchloride In methanol for 20h; Ambient temperature;
85%	With hydrogenchloride In diethyl ether for 20h;

35%	Acidic conditions;
	With hydrogenchloride
	With sulfuric acid
	With hydrogenchloride
	With thionyl chloride
	With sulfuric acid for 18h; Reflux;

Reference： [1]Huang, Yange; Fananas-Mastral, Martin; Minnaard, Adriaan J.; Feringa, Ben L. [Chemical Communications, 2013, vol. 49, # 32, p. 3309 - 3311]
[2]Drew; Letellier; Morand; Szabo [Journal of Organic Chemistry, 1987, vol. 52, # 18, p. 4047 - 4052]
[3]Kim, Dwight D.; Lee, Suk Joong; Beak, Peter [Journal of Organic Chemistry, 2005, vol. 70, # 14, p. 5376 - 5386]
[4]Gucma, Mirosław; Gołębiewski, W. Marek; Michalczyk, Alicja Katarzyna [Monatshefte fur Chemie, 2016, vol. 147, # 10, p. 1809 - 1818]
[5]Hinrichsen; Triepel [Justus Liebigs Annalen der Chemie, 1904, vol. 336, p. 197]
[6]Vorlaender; Groebel [Justus Liebigs Annalen der Chemie, 1906, vol. 345, p. 208] Posner; Rohde [Chemische Berichte, 1909, vol. 42, p. 2792][Chemische Berichte, 1910, vol. 43, p. 2665]
[7]Green,B.S. et al. [Journal of the Chemical Society B: Physical Organic, 1971, p. 1552 - 1564]
[8]Lewis, Frederick D.; Howard, Daniel K.; Barancyk, Steven V.; Oxman, Joe D. [Journal of the American Chemical Society, 1986, vol. 108, # 11, p. 3016 - 3023]
[9]Bao, Xia-Zhen; Dai, Fang; Wang, Qi; Jin, Xiao-Ling; Zhou, Bo [Free Radical Biology and Medicine, 2019, vol. 134, p. 406 - 418]

4
[ 64-17-5 ]
[ 28010-12-0 ]
[ 39806-16-1 ]

Yield	Reaction Conditions	Operation in experiment
98%	With sulfuric acid for 12h; Reflux; Inert atmosphere;
	With sulfuric acid

Reference： [1]Cho, Hyunkyung; Jeon, Hongjun; Shin, Jae Eui; Lee, Seokwoo; Park, Soojun; Kim, Sanghee [Chemistry - A European Journal, 2019, vol. 25, # 10, p. 2447 - 2451]
[2]Vorlaender; Groebel [Justus Liebigs Annalen der Chemie, 1906, vol. 345, p. 208]

5
[ 28010-12-0 ]
[ 2270-20-4 ]

Yield	Reaction Conditions	Operation in experiment
96%	With zinc copper In methanol; water for 6h; Heating;
	With acetic acid; platinum Hydrogenation;
	With sodium hydroxide; nickel

	With ethanol; nickel Hydrogenation;
	With potassium carbonate; palladium Hydrogenation;
	Multi-step reaction with 3 steps 1: water; sodium amalgam / 20 °C / durch Neutralisieren der gebildeten Natronlauge mit verd. Schwefelsaeure 2: aqueous hydrobromic acid 3: zinc dust; glacial acetic acid; alcohol

Reference： [1]Sondengam, B. Lucas; Fomum, Z. Tanee; Charles, Georges; Akam, T. Mac [Journal of the Chemical Society. Perkin transactions I, 1983, p. 1219 - 1222]
[2]Baker; Dodson [Journal of the American Chemical Society, 1946, vol. 68, p. 1283]
[3]Anderson; Wang [Journal of Organic Chemistry, 1954, vol. 19, p. 277,281]
[4]Kotschetkow; Dudykina [Zhurnal Obshchei Khimii, 1958, vol. 28, p. 2399,2401; engl. Ausg. S. 2437, 2439]
[5]Borsche [Chemische Berichte, 1912, vol. 45, p. 622]
[6]Rupe [Justus Liebigs Annalen der Chemie, 1909, vol. 369, p. 338]

6
[ 28010-12-0 ]
(2E,4E)-5-phenylpenta-2,4-dienoic anhydride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine In 1,4-dioxane at 25℃; for 15h;	General procedure for the synthesis of anhydride derivatives General procedure: To a round-bottom flask, cinnamic acid substrates (3.0 mmol) and CDMT (3.0 mmol) in dioxane (10 mL) were added, followed by that, NMM (3.0 mmol) was added to the reaction mixture. The resulted solution was stirred at room temperature for 15 h. The resulting mixture was cooled and then filtered using a syringe filter. Then the mass concentrated and further diluted with diethyl ether. The organic layer was washed with 5% citric acid and followed by 5% sodium bicarbonate. The organic layer was dried over sodium sulfate. The solvent was removed under reduced pressure, and the resulting crude product was purified by simple column chromatography (eluant hexane/ethyl acetate).
	With quinoline

Reference： [1]Raja, Gabriel Charles Edwin; Son, Yujeong; Kim, Myungjin; Lee, Sunwoo; Oh, Jonghoon [Synthetic Communications, 2017, vol. 47, # 24, p. 2449 - 2455]
[2]Doebner; Staudinger [Chemische Berichte, 1903, vol. 36, p. 4324 Anm. 1]

7
[ 676551-01-2 ]
[ 28010-12-0 ]

Yield	Reaction Conditions	Operation in experiment
	With quinoline at 160 - 170℃; Allocinnamalessigsaeure;
	at 210℃;
	durch Destillation;

	Reaktion ueber mehrere Stufen;
	With quinoline
	With pyridine

Reference： [1]Liebermann; Riiber [Chemische Berichte, 1902, vol. 35, p. 2697] Riiber [Chemische Berichte, 1904, vol. 37, p. 2274] Liebermann [Chemische Berichte, 1895, vol. 28, p. 1439]
[2]Stuart [Journal of the Chemical Society, 1886, vol. 49, p. 366]
[3]Riiber [Chemische Berichte, 1905, vol. 38, p. 2743]
[4]Bougault [Annales de Chimie (Cachan, France), 1908, vol. <8> 14, p. 157,167]
[5]Reynolds [American Chemical Journal, 1911, vol. 46, p. 207]
[6]Staudinger; Schneider [Chemische Berichte, 1923, vol. 56, p. 706] Dutt [Journal of the Indian Chemical Society, 1923, vol. 1, p. 301][Chemisches Zentralblatt, 1925, vol. 96, # II, p. 1852]

8
[ 4173-44-8 ]
[ 28010-12-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hypochlorite

Reference： [1]Plati; Strain; Warren [Journal of the American Chemical Society, 1943, vol. 65, p. 1273,1274]

9
[ 141-82-2 ]
[ 104-55-2 ]
[ 28010-12-0 ]

Yield	Reaction Conditions	Operation in experiment
67%	With piperidine; pyridine for 10h; Reflux;
56.2%	With pyridine Heating;
	With pyridine

With piperidine; pyridine

Reference： [1]Huang, Xiaobo; Zhang, Bingchuan; Xu, Hui [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 18, p. 4336 - 4340]
[2]Venkatasamy, Radhakrishnan; Faas, Laura; Young, Antony R.; Raman, Amala; Hider, Robert C. [Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 8, p. 1905 - 1920]
[3]Doebner [Chemische Berichte, 1902, vol. 35, p. 2137] Riedel [Justus Liebigs Annalen der Chemie, 1908, vol. 361, p. 94] Hinrichsen; Triepel [Justus Liebigs Annalen der Chemie, 1904, vol. 336, p. 197]
[4]Dutt [Journal of the Indian Chemical Society, 1923, vol. 1, p. 301][Chemisches Zentralblatt, 1925, vol. 96, # II, p. 1852]

10
[ 28010-12-0 ]
[ 17142-81-3 ]
[ 108774-61-4 ]

Yield	Reaction Conditions	Operation in experiment
	Reaktion ueber mehrere Stufen;

Reference： [1]Al'perowitsch et al. [Zhurnal Obshchei Khimii, 1959, vol. 29, p. 3376,3381; engl. Ausg. S. 3338, 3343]

11
[ 908094-01-9 ]
[ 28010-12-0 ]
(2E,4E)-methyl 5-phenylpenta-2,4-dienoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	In methanol; diethyl ether at 0 - 5℃;

Reference： [1]Banerji, Avijit; Banerjee, Tapasri; Sengupta, Ratna; Sengupta, Piyali; Das, Chittaranjan; Sahu, Anita [Journal of the Indian Chemical Society, 2002, vol. 79, # 11, p. 876 - 883]
[2]Banerji, Avijit; Ghosal, Tapasree; Acharyya, Aditi K. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1984, vol. 23, # 6, p. 546 - 549]

12
[ 109-79-5 ]
[ 28010-12-0 ]
[ 75839-78-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	With pyridine; O-phenyl phosphorodichloridate In 1,2-dimethoxyethane for 16h; Ambient temperature;

Reference： [1]Liu, Hsing-Jang; Sabesan, Subramaniam Iyer [Canadian Journal of Chemistry, 1980, vol. 58, p. 2645 - 2648]

13
[ 28010-12-0 ]
[ 100636-30-4 ]

Yield	Reaction Conditions	Operation in experiment
	With oxalyl dichloride In benzene
	With thionyl chloride
	With pyridine; thionyl chloride at 40℃;

	With thionyl chloride at 65℃; for 3h;
	With oxalyl dichloride In benzene Heating;
	With thionyl chloride In dichloromethane at 50℃; for 1h;
	With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 3h; Inert atmosphere;
	With thionyl chloride In chloroform at 20℃; for 12h;	3.2. General synthesis of unsaturated acyl chlorides (2b-2j) General procedure: Thionyl chloride (22 mL, 0.3 mol, freshly distilled) was added to a solution of suitable carboxylic acid (3a-3g) (0.1 mol) in 100 mL of chloroform at room temperature. The mixture was allowed to stand for 12 h. Then the solvent and excess SOCl2 were distilled in vacuo. The residue was pure enough to be used as an acylating reagent without further purification.
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 23℃; Inert atmosphere;

Reference： [1]Banerji, Avijit; Ghosal, Tapasree; Acharyya, Aditi K. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1984, vol. 23, # 6, p. 546 - 549]
[2]Bogat-skii, A. V.; Galantina, A. I.; Derkach, L. G.; Taubert D. [Journal of Organic Chemistry USSR (English Translation), 1981, vol. 17, # 11, p. 2072 - 2075][Zhurnal Organicheskoi Khimii, 1981, vol. 17, # 11, p. 2320 - 2323]
[3]Rideout, Janet L.; Krenitsky, Thomas A.; Chao, Esther Y.; Elion, Gertrude B.; Williams, Raymond B.; Latter, Victoria S. [Journal of Medicinal Chemistry, 1983, vol. 26, # 10, p. 1489 - 1494]
[4]Zhang, Chen; Maeda, Yasuhiro; Sato, Yoshiro [Chemical and Pharmaceutical Bulletin, 1998, vol. 46, # 4, p. 572 - 576]
[5]Banerji, Avijit; Banerjee, Tapasri; Sengupta, Ratna; Sengupta, Piyali; Das, Chittaranjan; Sahu, Anita [Journal of the Indian Chemical Society, 2002, vol. 79, # 11, p. 876 - 883]
[6]Dockendorff, Chris; Sahli, Stefan; Olsen, Madeline; Milhau, Ludovic; Lautens, Mark [Journal of the American Chemical Society, 2005, vol. 127, # 43, p. 15028 - 15029]
[7]Zhao, Tingxing; Qin, Dekun; Han, Weiguo; Yang, Shiping; Feng, Boya; Gao, Ge; You, Jingsong [Chemical Communications, 2019, vol. 55, # 43, p. 6118 - 6121]
[8]Sari, Sait; Ünalan, Seda; Yilmaz, Mehmet [Turkish Journal of Chemistry, 2019, vol. 43, # 6, p. 1656 - 1671]
[9]Chaheine, Christian M.; Gladen, Paul T.; Romo, Daniel; Song, Conner J. [Organic Syntheses, 2021, vol. 98, p. 194 - 226]

14
[ 100-52-7 ]
[ 138193-51-8 ]
[ 28010-12-0 ]

Yield	Reaction Conditions	Operation in experiment
67%	With boron trifluoride diethyl etherate In dichloromethane 1= -60 deg C, 1 h, 2) reflux (55 deg C);

Reference： [1]Bellassoued, Moncef; Ennigrou, Rached [Bulletin des Societes Chimiques Belges, 1991, vol. 100, # 10, p. 767 - 768]

15
[ 28010-12-0 ]
[ 185038-94-2 ]

Yield	Reaction Conditions	Operation in experiment
60%	With N-Bromosuccinimide; lithium acetate In water; acetonitrile

Reference： [1]Chowdhury, Shantanu; Roy, Sujit [Journal of Organic Chemistry, 1997, vol. 62, # 1, p. 199 - 200]

16
[ 14371-10-9 ]
[ 75-36-5 ]
[ 28010-12-0 ]

Yield	Reaction Conditions	Operation in experiment
26%	With lithium perchlorate; triethylamine In diethyl ether for 6h; Ambient temperature;

Reference： [1]Arrastia, Iosune; Cossio, Fernando P. [Tetrahedron Letters, 1996, vol. 37, # 39, p. 7143 - 7146]

17
[ 28010-12-0 ]
[ 188802-38-2 ]

Yield	Reaction Conditions	Operation in experiment
91%	With N-Bromosuccinimide; tetrabutylammonium trifluoroacetate In 1,2-dichloro-ethane Ambient temperature;
91%	With N-Bromosuccinimide; tetrabutylammonium trifluoroacetate In 1,2-dichloro-ethane at 20℃; for 18h;
59%	With Oxone; sodium carbonate; sodium bromide In acetonitrile at 20℃; for 24h;

With N-Bromosuccinimide; lithium acetate In 1,2-dimethoxyethane; water at 100℃; for 0.0166667h; microwave irradiation;

Reference： [1]Naskar, Dinabandhu; Chowdhury, Shantanu; Roy, Sujit [Tetrahedron Letters, 1998, vol. 39, # 7, p. 699 - 702]
[2]Naskar, Dinabandhu; Roy, Sujit [Tetrahedron, 2000, vol. 56, # 10, p. 1369 - 1377]
[3]You; Lee [Synlett, 2001, # 1, p. 105 - 107]
[4]Bazin, Marc-Antoine; Kihel, Laïla El; Lancelot, Jean-Charles; Rault, Sylvain [Tetrahedron Letters, 2007, vol. 48, # 25, p. 4347 - 4351]

18
[ 14371-10-9 ]
[ 65946-59-0 ]
[ 28010-12-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	With cesium fluoride In dimethyl sulfoxide for 3h;

Reference： [1]Bellassoued, Moncef; Lensen, Nathalie; Bakasse, Mina; Mouelhi, Sinda [Journal of Organic Chemistry, 1998, vol. 63, # 24, p. 8785 - 8789]

19
[ 28010-12-0 ]
[ 21210-43-5 ]
methoxycarbonyl(phenyl)methyl 5-phenylpenta-2,4-dienoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃;

Reference： [1]Ripoche, Isabelle; Canet, Jean-Louis; Gelas, Jacques; Troin, Yves [European Journal of Organic Chemistry, 1999, # 7, p. 1517 - 1521]

20
[ 110-89-4 ]
[ 28010-12-0 ]
[ 66110-13-2 ]

Yield	Reaction Conditions	Operation in experiment
87%	Stage #1: 5-phenylpenta-2,4-dienoic acid With thionyl chloride In dichloromethane at 20℃; Schlenk technique; Stage #2: piperidine In dichloromethane at 20℃; for 1h; Schlenk technique; Inert atmosphere; stereoselective reaction;	General procedure: In a flame-dried Schlenk tube the carboxylic acid 4 (0,20 mmol,1.0 equiv.) was dissolved in anhydrous DCM (1 mL), followed bythe addition of thionyl chloride (0.40 mmol, 2.0 equiv.). Thereaction was stirred at room temperature until the solid dissolvedcompletely. Heating to reflux can be applied for a faster conversion. Thereafter, volatiles were removed under reducedpressure, and the flask was flushed with argon again (an argonfilledballoon was attached to the rotary evaporator). To theresulting residue anhydrous DCM was added (1 mL), and theamine was added dropwise (0.40 mmol, 2.0 equiv.). Afterwards,the solution was stirred for 1 h at room temperature. Finally, thereaction mixture was quenched and washed with saturatedaqueous NaHCO3 solution, and the aqueous layer was extracted3 times with DCM. The combined organic layer was dried overNa2SO4, filtered, and volatiles were removed under reducedpressure to yield the pure amide. Further purification via flashchromatography gave the desired amide. (Gradient: EtOAc/heptane10:90 to EtOAc/heptane 60:40).
36%	Stage #1: 5-phenylpenta-2,4-dienoic acid With methanesulfonyl chloride; triethylamine In dichloromethane at 0℃; for 0.5h; Stage #2: piperidine In dichloromethane at 0 - 20℃; for 2h;

Reference： [1]Bauer, Adriano; Nam, Jun-Hyun; Maulide, Nuno [Synlett, 2019, vol. 30, # 4, p. 413 - 416]
[2]Venkatasamy, Radhakrishnan; Faas, Laura; Young, Antony R.; Raman, Amala; Hider, Robert C. [Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 8, p. 1905 - 1920]

21
[ 120823-67-8 ]
[ 28010-12-0 ]

Yield	Reaction Conditions	Operation in experiment
	With gold(III) chloride In dichloromethane at 80℃; for 36h;

Reference： [1]Kang, Ji-Eun; Lee, Eun-Sun; Park, Sang-Il; Shin, Seunghoon [Tetrahedron Letters, 2005, vol. 46, # 43, p. 7431 - 7433]

22
[ 39806-16-1 ]
[ 28010-12-0 ]

Yield	Reaction Conditions	Operation in experiment
98%	With potassium hydroxide In methanol at 75℃; for 14h;
84%	With potassium hydroxide In tetrahydrofuran; methanol; water at 20℃; for 1h;	1 Referential Example 1 5-Phenylpenta-(2E,4E)-dienoic acid Added to a solution of 8.14 g (40.3 mmol) of ethyl 5-phenylpenta-(2E,4E)-dienoate synthesized by the above process in methanol-tetrahydrofuran (40 ml-80 ml) was 40 ml of a 5N aqueous solution of potassium hydroxide, and the mixture was stirred for 1 hour at room temperature. The reaction mixture was concentrated under reduced pressure, and the resultant residue was cooled in an ice bath. To it were added 20 ml of chloroform and concentrated hydrochloric acid with vigorous stirring. An aqueous layer and an organic layer were separated from each other, and the aqueous layer was further extracted with chloroform. The resultant organic layers were collected, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resultant crude oil was recrystallized from ethyl acetate-hexane to purify it, thereby obtaining 5.91 g (yield: 84%) of the title compound.
	With sodium hydroxide In 1,4-dioxane at 20℃; for 12h;

With water; sodium hydroxide In methanol at 80℃; for 2h; Inert atmosphere;

Reference： [1]Dockendorff, Chris; Sahli, Stefan; Olsen, Madeline; Milhau, Ludovic; Lautens, Mark [Journal of the American Chemical Society, 2005, vol. 127, # 43, p. 15028 - 15029]
[2]Current Patent Assignee: KOWA COMPANY, LTD. - US6340682, 2002, B1 Location in patent: Page column 6
[3]Location in patent: experimental part Kokotos, George; Hsu, Yuan-Hao; Burke, John E.; Baskakis, Constantinos; Kokotos, Christoforos G.; Magrioti, Victoria; Dennis, Edward A. [Journal of Medicinal Chemistry, 2010, vol. 53, # 9, p. 3602 - 3610]
[4]Guo, Yafei; Kootstra, Johanan; Harutyunyan, Syuzanna R. [Angewandte Chemie - International Edition, 2018, vol. 57, # 41, p. 13547 - 13550][Angew. Chem., 2018, vol. 130, # 41, p. 13735 - 13738,4]

23
N,N-diisopropylethylamine (DIPEA) [ No CAS ]
2-(1H-benzotriazole-1-yl)-1,1,3,3-teramethyluronium tetrafluoroborate (TBTU) [ No CAS ]
[ 28010-12-0 ]
[ 2797-51-5 ]
[ 2592-95-2 ]
5-Phenyl-penta-2,4-dienoic acid (2-hydroxycarbonyl-ethyl)amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
12%	With hydroxylamine In 1-Methylpyrrolidine; 1,4-dioxane; methanol; dichloromethane; water	2 5-Phenyl-penta-2,4-dienoic acid (2-hydroxycarbonyl-ethyl)amide (PX083448) The resin (500 mg, 0.245 mmol) obtained from the second step was placed in a reaction vessel and was swollen by the addition of 1-methylpyrrolidine (2 ml). A solution of 5-phenylpenta-2,4-dienoic acid (171 mg, 0.98 mmol) (see Villieras J., Rambaud M., 1983, Synthesis, pp. 300-303; and Vig B., Kanwar R., Singh V., 1977, Indian J. Chem. Soc., Vol. 15B, pp. 1048-1049), 1-hydroxybenzotriazole (HOBT) (66 mg, 0.49 mmol), 2-(1H-benzotriazole-1-yl)-1,1,3,3-teramethyluronium tetrafluoroborate (TBTU) (315 mg, 0.98 mmol), N,N-diisopropylethylamine (DIPEA) (0.38 ml, 2.205 mmol) in 1-methylpyrrolidine (2 ml) was added and the resultant suspension was agitated at ambient temperature for sixteen hours. The resin was filtered and was washed with 1-methylpyrrolidine (5 ml) and alternately with methanol (45 ml) and dichloromethane (45 ml). The resin (500 mg, 0.245 mmol) obtained from the third step was placed in a reaction vessel and was swollen by the addition of dioxane (4 ml). A 50% wt solution of hydroxylamine in water (0.4 ml, 6.125 mmol) was added and the resultant suspension was agitated at ambient temperature for forty-eight hours. The resin was filtered and washed with a mixture of dioxane and water (1:1) (5 ml). The filtrates were combined and the solvent was removed under reduced pressure. The crude product obtained was purified by preparative hplc using a 150*21.2 mm 5 μm Hypersil7 Elite C18 column eluding with a gradient of 5% ACN/95% H2O+0.2% TFA to 95% ACN/5% H2O+0.2% TFA over 10 minutes. The flow rate was 25 mlmin-1 and the detector was set at 254 nm. The fractions that contained the desired product were concentrated under reduced pressure and the resultant residue was lyophilised from a mixture of dioxane and water to afford the desired compound as a yellow oil (7.8 mg, 12%), tR 1.35 (254 nm, 1.5 mlmin-1, 30% ACN/70% H2O+0.2% TFA), m/z [ES] 261 [M+H]+.

Reference： [1]Current Patent Assignee: ONXEO - US2004/92598, 2004, A1

24
(E)-phenylethenyl(phenyl)iodonium tetrafluoroborate [ No CAS ]
[ 79-10-7 ]
[ 28010-12-0 ]

Yield	Reaction Conditions	Operation in experiment
78%	In water for 0.00555556h; microwave irradiation;

Reference： [1]Zhu, Min; Song, Yunlong; Cao, Yan [Synthesis, 2007, # 6, p. 853 - 856]

25
[ 28010-12-0 ]
[ 34271-65-3 ]

Yield	Reaction Conditions	Operation in experiment
71%	Stage #1: 5-phenylpenta-2,4-dienoic acid With thionyl chloride In chloroform at 20℃; for 12h; Stage #2: With sodium hydroxide; ammonia In chloroform cooling; Further stages.;
60%	Stage #1: 5-phenylpenta-2,4-dienoic acid With thionyl chloride In tetrahydrofuran at 50℃; for 1h; Stage #2: With ammonium hydroxide In tetrahydrofuran at 0℃; for 0.0833333h;

Reference： [1]Burgaz, E. Vildan; Yilmaz, Mehmet; Pekel, A. Tarik; Öktemer, Atilla [Tetrahedron, 2007, vol. 63, # 30, p. 7229 - 7239]
[2]Al-Huniti, Mohammed H.; Rivera-Chávez, José; Colón, Katsuya L.; Stanley, Jarrod L.; Burdette, Joanna E.; Pearce, Cedric J.; Oberlies, Nicholas H.; Croatt, Mitchell P. [Organic Letters, 2018, vol. 20, # 19, p. 6046 - 6050]

26
[ 14371-10-9 ]
[ 3095-95-2 ]
[ 28010-12-0 ]

Yield	Reaction Conditions	Operation in experiment
72%	With N,N,N,N,-tetramethylethylenediamine; zinc trifluoromethanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 25℃; for 12h;

Reference： [1]Schauer, Douglas J.; Helquist, Paul [Synthesis, 2006, # 21, p. 3654 - 3660]

27
[ 28010-12-0 ]
C₁₆H₁₃F [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: N-bromosuccinimide; LiOAc / 1,2-dimethoxy-ethane; H₂O / 0.02 h / 100 °C / microwave irradiation 2: K₂CO₃ / Pd(PPh₃)4 / 1,2-dimethoxy-ethane; H₂O / 0.17 h / 100 °C / microwave irradiation

Reference： [1]Bazin, Marc-Antoine; Kihel, Laïla El; Lancelot, Jean-Charles; Rault, Sylvain [Tetrahedron Letters, 2007, vol. 48, # 25, p. 4347 - 4351]

28
[ 28010-12-0 ]
[ 869732-36-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: thionyl chloride / CH₂Cl₂ / 1 h / 50 °C 2: CH₂Cl₂

Reference： [1]Dockendorff, Chris; Sahli, Stefan; Olsen, Madeline; Milhau, Ludovic; Lautens, Mark [Journal of the American Chemical Society, 2005, vol. 127, # 43, p. 15028 - 15029]

29
[ 28010-12-0 ]
(1S,4S)-4-Phenyl-1,4-dihydro-naphthalene-1-carboxylic acid diisopropylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: thionyl chloride / CH₂Cl₂ / 1 h / 50 °C 2: CH₂Cl₂ 3: 54 percent / 1,2-dichloro-ethane / 60 °C

Reference： [1]Dockendorff, Chris; Sahli, Stefan; Olsen, Madeline; Milhau, Ludovic; Lautens, Mark [Journal of the American Chemical Society, 2005, vol. 127, # 43, p. 15028 - 15029]

30
[ 28010-12-0 ]
[ 142039-50-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: thionyl chloride / CH₂Cl₂ / 1 h / 50 °C 2.1: NaH / toluene / 1 h 2.2: 1372 mg / toluene / 4 h

Reference： [1]Dockendorff, Chris; Sahli, Stefan; Olsen, Madeline; Milhau, Ludovic; Lautens, Mark [Journal of the American Chemical Society, 2005, vol. 127, # 43, p. 15028 - 15029]

31
[ 28010-12-0 ]
((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-((1S,4S)-4-phenyl-1,4-dihydro-naphthalen-1-yl)-methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: thionyl chloride / CH₂Cl₂ / 1 h / 50 °C 2.1: NaH / toluene / 1 h 2.2: 1372 mg / toluene / 4 h 3.1: 48 percent / CsF / acetonitrile / 14 h / 20 °C

Reference： [1]Dockendorff, Chris; Sahli, Stefan; Olsen, Madeline; Milhau, Ludovic; Lautens, Mark [Journal of the American Chemical Society, 2005, vol. 127, # 43, p. 15028 - 15029]

32
[ 100-52-7 ]
[ 28010-12-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: NaH / 1,2-dimethoxy-ethane 1.2: 43 percent / 1,2-dimethoxy-ethane / 2 h / 20 - 85 °C 2.1: 98 percent / KOH / methanol / 14 h / 75 °C

Reference： [1]Dockendorff, Chris; Sahli, Stefan; Olsen, Madeline; Milhau, Ludovic; Lautens, Mark [Journal of the American Chemical Society, 2005, vol. 127, # 43, p. 15028 - 15029]

33
[ 28010-12-0 ]
[ 58506-33-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 85 percent / HCl / diethyl ether / 20 h 2: 55 percent / DIBAL-H / toluene / 3 h / 45 °C
	Multi-step reaction with 2 steps 1: thionyl chloride, pyridine / 40 °C 2: sodium borohydride / dioxane / Ambient temperature
	Multi-step reaction with 2 steps 1: 96 percent / dry HCl / methanol / 20 h / Ambient temperature 2: 1.) diisobutylaluminum hydride, 2.) MeOH / 1.) benzene, toluene, 45 deg C, 3 h, 2.) benzene, toluene

	Multi-step reaction with 2 steps 1: hydrogenchloride / 16 h / 20 °C / Inert atmosphere 2: diisobutylaluminium hydride / dichloromethane / 4 h / -78 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: sulfuric acid / 12 h / Reflux; Inert atmosphere 2: diisobutylaluminium hydride / dichloromethane; pentane / 3 h / -78 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: sulfuric acid / 18 h / Reflux 2: diisobutylaluminium hydride / dichloromethane / 4 h / -78 - 0 °C

Reference： [1]Kim, Dwight D.; Lee, Suk Joong; Beak, Peter [Journal of Organic Chemistry, 2005, vol. 70, # 14, p. 5376 - 5386]
[2]Rideout, Janet L.; Krenitsky, Thomas A.; Chao, Esther Y.; Elion, Gertrude B.; Williams, Raymond B.; Latter, Victoria S. [Journal of Medicinal Chemistry, 1983, vol. 26, # 10, p. 1489 - 1494]
[3]Drew; Letellier; Morand; Szabo [Journal of Organic Chemistry, 1987, vol. 52, # 18, p. 4047 - 4052]
[4]Huang, Yange; Fananas-Mastral, Martin; Minnaard, Adriaan J.; Feringa, Ben L. [Chemical Communications, 2013, vol. 49, # 32, p. 3309 - 3311]
[5]Cho, Hyunkyung; Jeon, Hongjun; Shin, Jae Eui; Lee, Seokwoo; Park, Soojun; Kim, Sanghee [Chemistry - A European Journal, 2019, vol. 25, # 10, p. 2447 - 2451]
[6]Bao, Xia-Zhen; Dai, Fang; Wang, Qi; Jin, Xiao-Ling; Zhou, Bo [Free Radical Biology and Medicine, 2019, vol. 134, p. 406 - 418]

34
[ 28010-12-0 ]
[ 109529-98-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 85 percent / HCl / diethyl ether / 20 h 2: 55 percent / DIBAL-H / toluene / 3 h / 45 °C 3: 80 percent / PBr₃ / diethyl ether / 1.5 h / 0 °C
	Multi-step reaction with 3 steps 1: 96 percent / dry HCl / methanol / 20 h / Ambient temperature 2: 1.) diisobutylaluminum hydride, 2.) MeOH / 1.) benzene, toluene, 45 deg C, 3 h, 2.) benzene, toluene 3: 80 percent / phosphorus tribromide / diethyl ether / 1.5 h / 0 °C
	Multi-step reaction with 3 steps 1: hydrogenchloride / 16 h / 20 °C / Inert atmosphere 2: diisobutylaluminium hydride / dichloromethane / 4 h / -78 °C / Inert atmosphere 3: N-Bromosuccinimide; dimethylsulfide / dichloromethane / 0.17 h / Inert atmosphere

	Multi-step reaction with 3 steps 1: sulfuric acid / 12 h / Reflux; Inert atmosphere 2: diisobutylaluminium hydride / dichloromethane; pentane / 3 h / -78 °C / Inert atmosphere 3: phosphorus tribromide / diethyl ether / 0.5 h / 0 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1: sulfuric acid / 18 h / Reflux 2: diisobutylaluminium hydride / dichloromethane / 4 h / -78 - 0 °C 3: phosphorus tribromide / diethyl ether / 1 h / 0 - 20 °C

Reference： [1]Kim, Dwight D.; Lee, Suk Joong; Beak, Peter [Journal of Organic Chemistry, 2005, vol. 70, # 14, p. 5376 - 5386]
[2]Drew; Letellier; Morand; Szabo [Journal of Organic Chemistry, 1987, vol. 52, # 18, p. 4047 - 4052]
[3]Huang, Yange; Fananas-Mastral, Martin; Minnaard, Adriaan J.; Feringa, Ben L. [Chemical Communications, 2013, vol. 49, # 32, p. 3309 - 3311]
[4]Cho, Hyunkyung; Jeon, Hongjun; Shin, Jae Eui; Lee, Seokwoo; Park, Soojun; Kim, Sanghee [Chemistry - A European Journal, 2019, vol. 25, # 10, p. 2447 - 2451]
[5]Bao, Xia-Zhen; Dai, Fang; Wang, Qi; Jin, Xiao-Ling; Zhou, Bo [Free Radical Biology and Medicine, 2019, vol. 134, p. 406 - 418]

35
[ 28010-12-0 ]
[ 1794-46-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: thionyl chloride, pyridine / 40 °C 2: sodium borohydride / dioxane / Ambient temperature 3: thionyl chloride, pyridine / benzene / 84 h / Ambient temperature

Reference： [1]Rideout, Janet L.; Krenitsky, Thomas A.; Chao, Esther Y.; Elion, Gertrude B.; Williams, Raymond B.; Latter, Victoria S. [Journal of Medicinal Chemistry, 1983, vol. 26, # 10, p. 1489 - 1494]

36
[ 28010-12-0 ]
[ 86687-49-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: thionyl chloride, pyridine / 40 °C 2: sodium borohydride / dioxane / Ambient temperature 3: thionyl chloride, pyridine / benzene / 84 h / Ambient temperature 4: 1.) K₂CO₃ / 1.) DMF, 40 deg C, 0.5 h, 2.) DMF, 0.5 h

Reference： [1]Rideout, Janet L.; Krenitsky, Thomas A.; Chao, Esther Y.; Elion, Gertrude B.; Williams, Raymond B.; Latter, Victoria S. [Journal of Medicinal Chemistry, 1983, vol. 26, # 10, p. 1489 - 1494]

37
[ 28010-12-0 ]
[ 109529-99-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 96 percent / dry HCl / methanol / 20 h / Ambient temperature 2: 1.) diisobutylaluminum hydride, 2.) MeOH / 1.) benzene, toluene, 45 deg C, 3 h, 2.) benzene, toluene 3: 80 percent / phosphorus tribromide / diethyl ether / 1.5 h / 0 °C 4: 20 h / 160 °C
	Multi-step reaction with 4 steps 1: sulfuric acid / 18 h / Reflux 2: diisobutylaluminium hydride / dichloromethane / 4 h / -78 - 0 °C 3: phosphorus tribromide / diethyl ether / 1 h / 0 - 20 °C 4: 6 h / 140 °C

Reference： [1]Drew; Letellier; Morand; Szabo [Journal of Organic Chemistry, 1987, vol. 52, # 18, p. 4047 - 4052]
[2]Bao, Xia-Zhen; Dai, Fang; Wang, Qi; Jin, Xiao-Ling; Zhou, Bo [Free Radical Biology and Medicine, 2019, vol. 134, p. 406 - 418]

38
[ 14371-10-9 ]
[ 28010-12-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: aqueous NaOH 2: aqueous sodium hypochlorite solution
		43 (2E,4E)-5-phenyl-2,4-pentadienoic acid (9h) Example 43 (2E,4E)-5-phenyl-2,4-pentadienoic acid (9h) The title compound was synthesised by the procedures described in the literature (Villieras et al., 1983; Vig et al., 1977; Banerji et al., 1984), from cinnamaldehyde (Acros)
	Multi-step reaction with 2 steps 1: <i>L</i>-proline / 3 h / Irradiation; Inert atmosphere 2: ethanol / 0.33 h / 150 °C / Microwave irradiation; Inert atmosphere

Multi-step reaction with 2 steps 1: water / 2 h / 75 °C 2: iron(III) chloride hexahydrate; water / nitromethane / 0.75 h / 110 °C / Sealed tube

Reference： [1]Plati; Strain; Warren [Journal of the American Chemical Society, 1943, vol. 65, p. 1273,1274]
[2]Current Patent Assignee: ONXEO - US2004/92598, 2004, A1
[3]Prevost, Marie S.; Delarue-Cochin, Sandrine; Marteaux, Justine; Colas, Claire; Van Renterghem, Catherine; Blondel, Arnaud; Malliavin, Thérèse; Corringer, Pierre-Jean; Joseph, Delphine [Journal of Medicinal Chemistry, 2013, vol. 56, # 11, p. 4619 - 4630]
[4]Mohite, Amar R.; Bhat, Ramakrishna G. [Organic Letters, 2013, vol. 15, # 17, p. 4564 - 4567]

39
[ 28010-12-0 ]
[ 5442-54-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: acetic acid; platinum / Hydrogenation 2: ethanol; sulfuric acid 3: ethanol; Raney nickel / 210 °C / 88260.9 Torr / Hydrogenation 4: sodium ethylate; diethyl ether / Behandeln des Reaktionsprodukts mit Anilin-hydrochlorid in H₂O und Erhitzen des danach erhaltenen Reaktionsprodukts in Mineraloel auf 250-260grad 5: aq.-ethanolic NaOH 6: 220 - 225 °C

Reference： [1]Baker; Dodson [Journal of the American Chemical Society, 1946, vol. 68, p. 1283]

40
[ 28010-12-0 ]
[ 17734-38-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: acetic acid; platinum / Hydrogenation 2: ethanol; sulfuric acid

Reference： [1]Baker; Dodson [Journal of the American Chemical Society, 1946, vol. 68, p. 1283]

41
[ 28010-12-0 ]
[ 17851-39-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: acetic acid; platinum / Hydrogenation 2: ethanol; sulfuric acid 3: ethanol; Raney nickel / 210 °C / 88260.9 Torr / Hydrogenation

Reference： [1]Baker; Dodson [Journal of the American Chemical Society, 1946, vol. 68, p. 1283]

42
[ 28010-12-0 ]
[ 709022-34-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: acetic acid; platinum / Hydrogenation 2: ethanol; sulfuric acid 3: ethanol; Raney nickel / 210 °C / 88260.9 Torr / Hydrogenation 4: sodium ethylate; diethyl ether / Behandeln des Reaktionsprodukts mit Anilin-hydrochlorid in H₂O und Erhitzen des danach erhaltenen Reaktionsprodukts in Mineraloel auf 250-260grad 5: aq.-ethanolic NaOH

Reference： [1]Baker; Dodson [Journal of the American Chemical Society, 1946, vol. 68, p. 1283]

43
[ 28010-12-0 ]
[ 709022-83-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: acetic acid; platinum / Hydrogenation 2: ethanol; sulfuric acid 3: ethanol; Raney nickel / 210 °C / 88260.9 Torr / Hydrogenation 4: sodium ethylate; diethyl ether / Behandeln des Reaktionsprodukts mit Anilin-hydrochlorid in H₂O und Erhitzen des danach erhaltenen Reaktionsprodukts in Mineraloel auf 250-260grad

Reference： [1]Baker; Dodson [Journal of the American Chemical Society, 1946, vol. 68, p. 1283]

44
[ 100-52-7 ]
[ 28010-12-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: zinc; benzene; diethyl ether 2: aq. NaOH solution
	Multi-step reaction with 5 steps 1: pyridine; piperidine / 10 h / Reflux 2: sulfuric acid / 16 h / Reflux 3: aluminum (III) chloride; lithium aluminium tetrahydride / tetrahydrofuran / 0 °C 4: manganese(IV) oxide / tetrahydrofuran / Reflux 5: pyridine; piperidine / 10 h / Reflux
	Multi-step reaction with 2 steps 1: sodium hydride / mineral oil; 1,2-dimethoxyethane / 2 h / 20 - 85 °C / Inert atmosphere; Cooling with ice 2: sodium hydroxide; water / methanol / 2 h / 80 °C / Inert atmosphere

Reference： [1]English; Gregory [Journal of the American Chemical Society, 1947, vol. 69, p. 2123]
[2]Huang, Xiaobo; Zhang, Bingchuan; Xu, Hui [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 18, p. 4336 - 4340]
[3]Guo, Yafei; Kootstra, Johanan; Harutyunyan, Syuzanna R. [Angewandte Chemie - International Edition, 2018, vol. 57, # 41, p. 13547 - 13550][Angew. Chem., 2018, vol. 130, # 41, p. 13735 - 13738,4]

45
[ 505-66-8 ]
[ 28010-12-0 ]
1,4-bis[5-phenylpenta-(2E,4E)-dienoyl]hexahydro-1,4-diazepine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With diphenylphosphoranyl azide; triethylamine In DMF (N,N-dimethyl-formamide) for 1h; Cooling with ice;	1 Example 1 Preparation of 1,4-bis[5-phenylpenta-(2E, 4E)-dienoyl]hexahydro-1,4-diazepine After 2.49 g (14.3 mmol) of 5-phenylpenta-(2E,4E)-dienoic acid were added to a solution of 653 mg (6.51 mmol) of homopiperazine in anhydrous dimethylformamide (30 ml), a reaction vessel was transferred to an ice bath, and 2.7 ml (19 mmol) of triethylamine and 3.0 ml (14 mmol) of diphenylphosphorylazide were added and the resultant mixture was stirred for 1 hour.. Added to the reaction mixture was 40 ml of a 5% aqueous solution of sodium hydrogencarbonate to conduct extraction with chloroform.. An organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure.. The resultant crude oil (8.4 g) was purified by column chromatography on alumina and column chromatography on silica gel, and then recrystallized from ethyl acetate-hexane, thereby obtaining 2.18 g (yield: 81%) of the title compound as a colorless crystalline powder. Melting point: 155-156° C. 1H-NMR (DMSO-d6, 120° C.) δ: 1.81(tt,J=6.0,6.0 Hz,2H), 3.58(dd,J=6.0,6.0 Hz,4H), 3.70(s,4H), 6.63(d,J=14.6 Hz,2H), 6.90(d,J=15.6 Hz,2H), 7.02(dd,J=15.6,10.3 Hz,2H), 7.23(dd,J=14.6,10.3 Hz,2H), 7.23-7.37(m,6H), 7.44-7.49(m,4H).

Reference： [1]Current Patent Assignee: KOWA COMPANY, LTD. - US6340682, 2002, B1 Location in patent: Page column 6-7

46
[ 79-37-8 ]
[ 28010-12-0 ]
[ 100636-30-4 ]
N-methyl-5-phenyl-2,4-pentadienoylhydroxamic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide In <i>N</i>-methyl-acetamide; dichloromethane; chloroform; water	15 Synthesis of N-methyl-5-phenyl-2,4-pentadienoylhydroxamic acid EXAMPLE 15 Synthesis of N-methyl-5-phenyl-2,4-pentadienoylhydroxamic acid 5-Phenyl-2,4-pentadienoic acid (6 g) and oxalyl chloride (6.1 mL) were dissolved in 50 mL of methylene chloride and 0.2 mL of dimethylformamide was added. The reaction was stirred for three hours, concentrated under vacuum and then co-evaporated with 100 mL of chloroform to remove oxalyl chloride. The crude 5-phenyl-2,4-pentadienoic acid chloride was used in the next step without further purification. 5-Phenyl-2,4-pentadienoic acid chloride was dissolved in 50 mL of methylene chloride and added to a solution of 13.8 mL of 40% sodium hydroxide in 50 mL of water at 0-5° C. The resulting solution was stirred for two hours and then acidified to a pH of 4 with concentrated hydrochloric acid. The precipitate was collected by filtration and dried under vacuum to afford 4.2 g of N-methyl-5-phenyl-2,4-pentadienoylhydroxamic acid. 1H NMR (DMSO-d6, 300 MHz), δ(ppm) 7.57 (d, 2H), 7.35 (m, 4H), 7.19 (m, 1H), 6.99 (d, 1H), 6.82 (d, 1H), 3.21 (s, 3H).

Reference： [1]Current Patent Assignee: ERRANT GENE THERAPEUTICS LLC - US2002/143037, 2002, A1

47
[ 28010-12-0 ]
[ 543-27-1 ]
5-phenyl-2,4-pentadienoylhydroxamic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethanolamine; hydroxylamine hydrochloride; triethylamine; citric acid In <i>N</i>-methyl-acetamide; acetonitrile	14 Synthesis of 5-phenyl-2,4-pentadienoylhydroxamic acid EXAMPLE 14 Synthesis of 5-phenyl-2,4-pentadienoylhydroxamic acid Triethylamine (TEA, 29 mL) was added to a cooled (0-5° C.) solution of 5-phenyl-2,4-pentadienoic acid (29.0 g) in 300 mL of anhydrous dimethylformamide. To this solution was added dropwise isobutyl chloroformate (27.0 mL). The reaction mixture was stirred for 15 minutes and hydroxylamine hydrochloride (28.92 g) was added followed by dropwise addition of 58 mL of TEA over a period of 60 minutes at 0-5° C. The reaction was allowed to warm to room temperature and stirred overnight. The reaction was then poured into 450 mL of a 1% (by weight) solution of citric acid and then extracted with 200 mL of methylene chloride twice and 500 mL of ether once. The solvents were removed under vacuum to give an oil. The crude oil was crystallized with 200 mL of hot acetonitrile to give a tan solid. The tan solid was recrystallized from 60 mL of hot acetonitrile to afford 12.5 g of the desired 5-phenyl-2,4-pentadienoylhydroxamic acid. 1H NMR (DMSO-d6, 300 MHz), δ(ppm) 7.56 (d, 2H), 7.31 (m, 4H), 7.03 (m, 2H), 6.05 (s, 1H).
	With triethanolamine; hydroxylamine hydrochloride; triethylamine; citric acid In <i>N</i>-methyl-acetamide; acetonitrile	2 Synthesis of 5-phenyl-2,4-pentadienoylhydroxamic acid EXAMPLE 2 Synthesis of 5-phenyl-2,4-pentadienoylhydroxamic acid Triethylamine (TEA, 29 mL) was added to a cooled (0-5° C.) solution of 5-phenyl-2,4-pentadienoic acid (29.0 g) in 300 mL of anhydrous dimethylformamide. To this solution was added dropwise isobutyl chloroformate (27.0 mL). The reaction mixture was stirred for 15 minutes and hydroxylamine hydrochloride (28.92 g) was added followed by dropwise addition of 58 mL of TEA over a period of 60 minutes at 0-5° C. The reaction was allowed to warm to room temperature and stirred overnight. The reaction was then poured into 450 mL of a 1% (by weight) solution of citric acid and then extracted with 200 mL of methylene chloride twice and 500 mL of ether once. The solvents were removed under vacuum to give an oil. The crude oil was crystallized with 200 mL of hot acetonitrile to give a tan solid. The tan solid was recrystallized from 60 mL of hot acetonitrile to afford 12.5 g of the desired 5-phenyl-2,4-pentadienoylhydroxamic acid. 1H NMR (DMSO-d6, 300 MHz), δ(ppm) 7.56 (d, 2H), 7.31 (m, 4H), 7.03 (m, 2H), 6.05 (s, 1H).

Reference： [1]Current Patent Assignee: ERRANT GENE THERAPEUTICS LLC - US2002/143037, 2002, A1
[2]Current Patent Assignee: ERRANT GENE THERAPEUTICS LLC - US2004/167184, 2004, A1

48
[ 28010-12-0 ]
[ 148546-78-5 ]
N-(4-methoxy-3-(4-methyl-1-piperazinyl)phenyl)-5-phenylpenta-2,4-dienamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With thionyl chloride; triethylamine In dichloromethane; toluene	6 N-(4-Methoxy-3-(4-methyl-1-piperazinyl)phenyl)-5-phenylpenta-2,4-dienamide EXAMPLE 6 N-(4-Methoxy-3-(4-methyl-1-piperazinyl)phenyl)-5-phenylpenta-2,4-dienamide 5-Phenylpenta-2,4-dienoic acid (270 mg, 1.55 mmol) was heated at reflux with thionyl chloride (3 ml) and toluene (40 ml) for 2 h, and then evaporated to dryness under reduced pressure. 4-Methoxy-3-(4-methyl-1-piperazinyl)phenylamine (340 mg, 1.55 mmol) in dry dichloromethane (40 ml) was added with triethylamine (1 ml) and the mixture stirred for 1 h. The solution was partitioned between dichloromethane (40 ml) and saturated aqueous potassium carbonate (40 ml), the organic solution dried (sodium sulphate) and evaporated to dryness under reduced pressure to afford an oil, which was purified by column chromatography (silica, chloroform/methanol 5%) to afford the title compound (595 mg, 100%) which was crystallized from methanol/diethyl ether as the oxalate salt. 1H nmr (d6-DMSO) δ 2.78 (3H, s), 3.24 (8H, bs), 3.79 (3H, s), 6.32 (1H, d), 7.06(3H, m), 7.35 (6H, m), 7.62 (2H, d), 10.05 (1H, s, NH). Mass Spectrum M+ found 377 C23 H27 N3 O2 requires 377 Elemental analysis C 62.17, H 6.05, N 8.69% C23 H27 N3 O2.1.3C2 H2 O4 requires C 62.18, H 6.03, N 8.50%

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - US5905080, 1999, A

49
1-benzhydryl-4-(5-phenyl-2,4-pentadienoyl)piperazine [ No CAS ]
[ 28010-12-0 ]
[ 841-77-0 ]
[ 79-03-8 ]
1-benzhydryl-4-(5-phenyl-2,4-pentadienyl)piperazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium bicarbonate; ammonium chloride; triethylamine In dichloromethane; chloroform; water	1 EXAMPLE 1 To 1.00 g (5.74 mmol) of 5-phenyl-2,4-pentadienoic acid were added 60 ml of dry dichloromethane and 0.80 ml (5.74 mmol) of triethylamine in the atmosphere of argon. The mixture was stirred at 0° C. followed by addition of 0.55 ml (5.74 mmol) of ethylcarbonyl chloride. The resulting mixture was stirred for 1 hour followed by addition of 1.74 g (6.89 mmol) of benzhydrylpiperazine. Temperature of the mixture was raised to room temperature followed by stirring for additional 30 min., addition of chloroform and successive extractions with aqueous hydrochloric acid solution (pH=1), saturated aqueous solution of sodium hydrogen carbonate and water. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. There was obtained 2.50 g of a residue. Column chromatography on silica gel and recrystallization from ethanol of the benzene-ethyl acetate (10: 1) fraction yielded 1.26 g (3.08 mmol) of 1-benzhydryl-4-(5-phenyl-2,4-pentadienoyl)piperazine. To 1.25 g (3.06 mmol) of said 1-benzhydryl-4-(5-phenyl-2,4-pentadienoyl)piperazine was added 50 ml of dry ether, and the mixture was stirred. After slow addition of 87 mg (2.29 mmol) of lithium aluminum hydride, the mixture was stirred for 30 min. under spontaneous reflux. To the reaction mixture were added saturated aqueous solution of ammonium chloride and water, and the mixture was extracted with chloroform. The organic layer was successively washed with aqueous hydrochloric acid solution (pH=1), saturated sodium hydrogen carbonate solution and water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. There was obtained 1.07 g of a residue. Column chromatography on silica gel and recrystallization from ethanol of the fraction eluted with benzene-ethyl acetate (10: 1) yielded 0.16 g (0.41 mmol) of 1-benzhydryl-4-(5-phenyl-2,4-pentadienyl)piperazine. Spectrophotometric data of the product support the structure (IV).

Reference： [1]Current Patent Assignee: TERUMO CORPORATION - US4792553, 1988, A

50
[ 42516-28-9 ]
[ 39806-16-1 ]
[ 28010-12-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium hydroxide; ammonium chloride; benzaldehyde In tetrahydrofuran; methanol; water	1 EXAMPLE 1 EXAMPLE 1 To 2.71 g (56.5 mmol) of 50% sodium hydride, washed with anhydrous tetrahydrofuran in the atmosphere of argon, was added 150 ml of anhydrous tetrahydrofuran. To the mixture, cooled to 0° C., was added dropwise a solution of 14.15 g (56.5 mmol) of triethyl-4-phosphocrotonate dissolved in 25 ml of anhydrous tetrahydrofuran through a dropping funnel over 10 minutes. After 30 min., a solution of 4.00 g (37.7 mmol) of benzaldehyde dissolved in 25 ml of anhydrous tetrahydrofuran was added dropwise through a dropping funnel over 10 minutes. Temperature of the reaction mixture was raised from 0° C. to room temperature followed by stirring for 17 hours. To the resulting mixture were successively added saturated aqueous solution of ammonium chloride and water followed by extraction with benzene. The organic layer was washed three times with water, then dried over anhydrous sodium sulfate and concentrated under reduced pressure. There was obtained 10.10 g of a residue. It was subjected to column chromatography on silica, and from the benzene elude fraction was produced 3.72 g (18.4 mmol) of ethyl 5-phenyl-2,4-pentadienoate. To 3.72 g (18.4 mmol) of said ethyl 5-phenyl-2,4 -pentadienoate was added 40 ml of methanol to give a solution. To the solution was then added a solution of 7.40 g (184 mmol) of sodium hydroxide dissolved in 10 ml of water, and the mixture was stirred at room temperature for 1 hour. The resulting mixture was concentrated under reduced pressure followed by addition of water and a hydrochloric acid solution to adjust the pH to 1 and extraction with chloroform. The organic layer was washed with water and then dried over anhydrous sodium sulfate. Concentration under reduced pressure gave 3.10 g of a residue. Recrystallization from ethanol yielded 1.12 g (6.43 mmol) of 5-phenyl-2,4-pentadienoic acid.

Reference： [1]Current Patent Assignee: TERUMO CORPORATION - US4792553, 1988, A

51
[ 28010-12-0 ]
[ 541-41-3 ]
[ 58506-33-5 ]

Yield	Reaction Conditions	Operation in experiment
18.9 g (86.4%)	With sodium borohydrid; triethylamine In tetrahydrofuran; water	7 5-Phenyl-2,4-Pentadienol EXAMPLE 7 5-Phenyl-2,4-Pentadienol The procedure of Example 1 was substantially followed using 5-phenyl-2,4-pentadienoic acid (22.65 g, 0.13 mole), THF (195 mL), triethylamine (18.2 mL, 13.21 g, 0.13 mole) and ethyl chloroformate (14.1 g, 0.13 mole) dissolved in THF (39 mL). The ethyl chloroformate solution was added at a temperature in the range 0° to 10° C. The resulting mixed anhydride was reduced with sodium borohydride (12.28 g, 0.13 mole) in water (130 mL). Work-up and removal of the organic solvent at reduced pressure in a rotary evaporator yielded 19.4 g of an off-white solid. Trituration of this material gave 18.9 g (86.4%) of a white powder, m.p. 79.5°-81.5° C. TLC (silica gel, 96:4 v/v methylene chloride-isopropanol) showed one major spot of Rf 0.61 corresponding to 5-phenyl-2,4-pentadienol, with little or no trace of starting material. 80 MHz 'H NMR: δ3.05 (br s, 0.375 H, exchangeable with D2 O), 3.97 (br doublet, J=5.3 Hz, 0.625 H, exchangeable with D2 O), 4.17 (d, J=5.3 Hz, 2H, C=C--CH2 --O), 5.80-7.50 (complex m, 9H Ar-H and CH=C).

Reference： [1]Current Patent Assignee: DUPONT DE NEMOURS INC - US4526993, 1985, A

52
[ 79-37-8 ]
[ 28010-12-0 ]
[ 100636-30-4 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane	R.7 N-cyclopropylmethyl-7α-(5-phenyl-2,4-pentadienoylamino)-3-O-(5-phenyl-2,4-pentadienoyl)-6,14-endoethenotetrahydronorolipabin 50 Reference Example 7 N-cyclopropylmethyl-7α-(5-phenyl-2,4-pentadienoylamino)-3-O-(5-phenyl-2,4-pentadienoyl)-6,14-endoethenotetrahydronorolipabin 50 In 5 ml of dichloromethane, 0.42 g of 5-phenyl-2,4-pentadienoic acid was suspended. While cooling the suspension in an ice bath, 0.6 ml of oxalyl chloride was added dropwise and the mixture was stirred at room temperature for 1 hour, followed by concentrating the mixture. The remaining solvent and oxalyl chloride were evaporated by using a vacuum pump to prepare 5-phenyl-2,4-pentadienoyl chloride.

Reference： [1]Current Patent Assignee: TORAY INDUSTRIES INC - US6187782, 2001, B1

53
[ 28010-12-0 ]
[ 1926-80-3 ]
[ 406725-12-0 ]

Yield	Reaction Conditions	Operation in experiment
60%	With triethylamine In tetrahydrofuran; water	118 (2E)(4E)-6-(5-Phenylpenta-2,4-dienoylamino)hexanoic acid methyl ester (3/1) Example 118 (2E)(4E)-6-(5-Phenylpenta-2,4-dienoylamino)hexanoic acid methyl ester (3/1) (Method J1A) 1,1'-Carbonyidiimidazole (0.36 g, 2.2 mmol) was added to a solution of 5-phenyl-penta-2E,4E-dienoic acid (1/1) (0.35 g, 2 mmol) in dry tetrahydrofuran (10 ml) and the obtained mixture was stirred for 1 hour at ambient temperature. To the mixture triethylamine (0.30 g 3.0 mmol) and methyl 6-aminohexanoate hydrochloride (2c) (0.40 g, 2.2 mmol) were added and the resultant suspension was stirred for 6 hours at ambient temperature. The solvent was removed under reduced pressure, to the residue water (15 ml) was added and the precipitate was filtered off, washed with water and dried. The title compound (0.36 g, 60%) was obtained as a white solid. M. p. 125-127° C. 1H NMR (DMSO-d6, HMDSO), δ: 1.05-1.72 (6H, m, CH2); 2.29 (2H, t, J=7.3 Hz, CH2); 3.12 (2H, q, J=6.0 Hz, CH2N); 3.58 (3H, s, CH3); 6.12 (1H, d, J=14.8 Hz, CH); 6.91-7.16 (2H, m, CH-CH); 7.23-7.66 (6H, m, C6H5, CH); 8.05 (1H, t, J=5.8 Hz, NH).
60%	Stage #1: 5-phenylpenta-2,4-dienoic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃; for 1h; Stage #2: methyl 6-aminocaproate hydrochloride With triethylamine In tetrahydrofuran at 20℃; for 6h;

Reference： [1]Current Patent Assignee: ONXEO - US2004/92598, 2004, A1
[2]Location in patent: experimental part Andrianov, Victor; Gailite, Vija; Lola, Daina; Loza, Einars; Semenikhina, Valentina; Kalvinsh, Ivars; Finn, Paul; Petersen, Kamille Dumong; Ritchie, James W.A.; Khan, Nagma; Tumber, Anthony; Collins, Laura S.; Vadlamudi, Sree M.; Bjoerkling, Fredrik; Sehested, Maxwell [European Journal of Medicinal Chemistry, 2009, vol. 44, # 3, p. 1067 - 1085]

54
N,N-diisopropylethylamine (DIPEA) [ No CAS ]
2-(1H-benzotriazole-1-yl)-1,1,3,3-teramethyluronium tetrafluoroborate (TBTU) [ No CAS ]
[ 28010-12-0 ]
[ 2797-51-5 ]
[ 2592-95-2 ]
5-Phenyl-penta-2,4-dienoic acid (2-hydroxycarbamoyl-propyl)amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
10%	With hydroxylamine In 1-Methylpyrrolidine; 1,4-dioxane; methanol; dichloromethane; water	7 5-Phenyl-penta-2,4-dienoic acid (2-hydroxycarbamoyl-propyl)amide (PX083808) The resin (500 mg, 0.245 mmol) obtained from the second step was placed in a reaction vessel and was swollen by the addition of 1-methylpyrrolidine (2 ml). A solution of 5-phenylpenta-2,4-dienoic acid (171 mg, 0.98 mmol) (see Villieras J., Rambaud M., 1983, Synthesis, pp. 300-303; and Vig B., Kanwar R., Singh V., 1977, Indian J. Chem. Soc., Vol. 15B, pp. 1048-1049), 1-hydroxybenzotriazole (HOBT) (66 mg, 0.49 mmol), 2-(1H-benzotriazole-1-yl)-1,1,3,3-teramethyluronium tetrafluoroborate (TBTU) (315 mg, 0.98 mmol), N,N-diisopropylethylamine (DIPEA) (0.38 ml, 2.205 mmol) in 1-methylpyrrolidine (2 ml) was added and the resultant suspension was agitated at ambient temperature for sixteen hours. The resin was filtered and was washed with 1-methylpyrrolidine (5 ml) and alternately with methanol (45 ml) and dichloromethane (45 ml). The resin (500 mg, 0.245 mmol) obtained from the third step was placed in a reaction vessel and was swollen by the addition of dioxane (4 ml). A 50% wt solution of hydroxylamine in water (0.4 ml, 6.125 mmol) was added and the resultant suspension was agitated at ambient temperature for forty-eight hours. The resin was filtered and washed with a mixture of dioxane and water (1:1) (5 ml). The filtrates were combined and the solvent was removed under reduced pressure. The crude product obtained was purified by preparative hplc using a 150*21.2 mm 5 μm Hypersil7 Elite C18 column eluding with a gradient of 5% ACN/95% H2O+0.2% TFA to 95% ACN/5% H2O+0.2% TFA over 10 minutes. The flow rate was 25 mlmin-1 and the detector was set at 254 nm. The fractions that contained the desired product were concentrated under reduced pressure and the resultant residue was lyophilised from a mixture of dioxane and water to afford the desired product as a yellow oil (6.4 mg, 10%), tR 3.99 (254 nm, 3.0 mlmin-1, 5% ACN/95% H2O+0.2% TFA to 95% ACN/5% H2O+0.2% TFA over 3.5 min then 2.5 min at 95% ACN/5% H2O+0.2% TFA), m/z [ES] 275 [M+H]+.

Reference： [1]Current Patent Assignee: ONXEO - US2004/92598, 2004, A1

55
[ 28010-12-0 ]
[ 13031-60-2 ]
[ 530-62-1 ]
[ 406725-10-8 ]
5-Phenyl-penta-2,4-dienoic acid (2-hydroxycarbamoyl-propyl)amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In tetrahydrofuran	9 5-Phenyl-penta-2,4-dienoic acid (2-hydroxycarbamoyl-propyl)amide (PX083808) Example 9 5-Phenyl-penta-2,4-dienoic acid (2-hydroxycarbamoyl-propyl)amide (PX083808) 1,1'-Carbonyldiimidazole (0.81 g, 5 mmol) was added to a solution of 5-phenylpenta-2,4-dienoic acid (0.87 g, 5 mmol) in dry tetrahydrofuran (10 ml) and the obtained mixture was stirred for one hour at ambient temperature. Triethylamine (0.76 g 7.5 mmol) and methyl 4-aminobutyrate hydrochloride (0.84 g, 0.55 mmol) were added and the resultant mixture was stirred for six hours at ambient temperature. The residue was filtered off, washed with water and dried. The intermediate product, 4-((2E)(4E)-5-phenylpenta-2,4-dienoylamino)butyric acid methyl ester, (0.93 g, 68%) was obtained as a white solid, m.p. 153-155° C. 1H NMR (DMSO-d6, HMDSO), δ: 1.47-1.89 (2H, m, CH2); 2.34 (2H, t, J=7.5 Hz, CH2); 3.16 (2H, q, J=6.5 Hz, CH2); 3.58 (3H, s, CH3); 6.12 (1H, d, J=14.8 Hz, CH); 6.83-7.65 (8H, m, C6H5, CH=CH-CH); 8.07 (1H, unresolv. t, NH).

Reference： [1]Current Patent Assignee: ONXEO - US2004/92598, 2004, A1

56
methyl 6-N-methylaminohexanoate hydrochloride [ No CAS ]
[ 28010-12-0 ]
[ 406726-07-6 ]

Yield	Reaction Conditions	Operation in experiment
69%		168 6-{Methyl-[(2E)(4E)-5-phenylpenta-2,4-dienoyl]amino}hexanoic acid methyl ester (3/27) Example 168 6-{Methyl-[(2E)(4E)-5-phenylpenta-2,4-dienoyl]amino}hexanoic acid methyl ester (3/27) Using an analogous method (J1A), the title compound was obtained was prepared from 5-phenyl-penta-2E,4E-dienoic acid (1/1) and methyl 6-N-methylaminohexanoate hydrochloride (2d) by the method of example 1. Yield 69%, oil. 1H NMR (90 MHz, DMSO-d6): δ: 0.98-1.77 (6H, m, CH2); 2.29 (2H, t, J=6.5 Hz, CH2); 2.87 and 3.03 (3H, s,s, CH3); 3.38 (2H, unresolv. t, CH2N); 3.56 (3H, s, CH3); 6.78 (1H, d, J=15.5 Hz, CH); 6.85-7.75 (8H, m, C6H5, CH-CH=CH).

Reference： [1]Current Patent Assignee: ONXEO - US2004/92598, 2004, A1

57
[ 1046862-50-3 ]
[ 28010-12-0 ]

Yield	Reaction Conditions	Operation in experiment
88%	With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 22℃; for 1h;

Reference： [1]Lipshutz, Bruce H.; Ghorai, Subir; Bošković, Žarko V. [Tetrahedron, 2008, vol. 64, # 29, p. 6949 - 6954]

58
[ 28028-86-6 ]
[ 28010-12-0 ]

Yield	Reaction Conditions	Operation in experiment
32%	In ethanol at 150℃; for 0.333333h; Microwave irradiation; Inert atmosphere;
	Stage #1: (E)-2-(3-phenylallylidene)malonic acid With acetic anhydride; acetic acid for 1h; Heating; Stage #2: With iodine In chloroform for 5h; Irradiation; Further stages.;

Reference： [1]Prevost, Marie S.; Delarue-Cochin, Sandrine; Marteaux, Justine; Colas, Claire; Van Renterghem, Catherine; Blondel, Arnaud; Malliavin, Thérèse; Corringer, Pierre-Jean; Joseph, Delphine [Journal of Medicinal Chemistry, 2013, vol. 56, # 11, p. 4619 - 4630]
[2]Pretorius, Judey; Malan, Sarel F.; Castagnoli Jr., Neal; Bergh, Jacobus J.; Petzer, Jacobus P. [Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 18, p. 8676 - 8684]

59
[ 28010-12-0 ]
[ 6638-79-5 ]
[ 502470-95-3 ]

Yield	Reaction Conditions	Operation in experiment
67%	With 4-methyl-morpholine; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 18h;

Reference： [1]Location in patent: experimental part Kokotos, George; Hsu, Yuan-Hao; Burke, John E.; Baskakis, Constantinos; Kokotos, Christoforos G.; Magrioti, Victoria; Dennis, Edward A. [Journal of Medicinal Chemistry, 2010, vol. 53, # 9, p. 3602 - 3610]

60
[ 108-86-1 ]
[ 28010-12-0 ]
[ 538-81-8 ]

Yield	Reaction Conditions	Operation in experiment
52%	With lithium acetate; palladium diacetate; triphenylphosphine; lithium chloride In N,N-dimethyl-formamide at 120℃; Inert atmosphere;

Reference： [1]Location in patent: experimental part Yamashita, Mana; Hirano, Koji; Satoh, Tetsuya; Miura, Masahiro [Advanced Synthesis and Catalysis, 2011, vol. 353, # 4, p. 631 - 636]

61
[ 591-50-4 ]
[ 28010-12-0 ]
[ 538-81-8 ]

Yield	Reaction Conditions	Operation in experiment
73%	With lithium acetate; silver(I) acetate; palladium diacetate; lithium chloride In N,N-dimethyl-formamide at 120℃; for 6h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Yamashita, Mana; Hirano, Koji; Satoh, Tetsuya; Miura, Masahiro [Advanced Synthesis and Catalysis, 2011, vol. 353, # 4, p. 631 - 636]

62
[ 637-87-6 ]
[ 28010-12-0 ]
[ 37985-13-0 ]

Yield	Reaction Conditions	Operation in experiment
61%	With lithium acetate; silver(I) acetate; palladium diacetate; lithium chloride In N,N-dimethyl-formamide at 120℃; for 6h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Yamashita, Mana; Hirano, Koji; Satoh, Tetsuya; Miura, Masahiro [Advanced Synthesis and Catalysis, 2011, vol. 353, # 4, p. 631 - 636]

63
[ 28010-12-0 ]
[ 624-31-7 ]
[ 37985-11-8 ]

Yield	Reaction Conditions	Operation in experiment
76%	With lithium acetate; silver(I) acetate; palladium diacetate; lithium chloride In N,N-dimethyl-formamide at 120℃; for 6h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Yamashita, Mana; Hirano, Koji; Satoh, Tetsuya; Miura, Masahiro [Advanced Synthesis and Catalysis, 2011, vol. 353, # 4, p. 631 - 636]

64
[ 28010-12-0 ]
[ 696-62-8 ]
[ 22145-08-0 ]

Yield	Reaction Conditions	Operation in experiment
57%	With lithium acetate; silver(I) acetate; palladium diacetate; lithium chloride In N,N-dimethyl-formamide at 120℃; for 6h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Yamashita, Mana; Hirano, Koji; Satoh, Tetsuya; Miura, Masahiro [Advanced Synthesis and Catalysis, 2011, vol. 353, # 4, p. 631 - 636]

65
[ 28010-12-0 ]
[ 455-13-0 ]
[ 1292767-23-7 ]

Yield	Reaction Conditions	Operation in experiment
62%	With lithium acetate; silver(I) acetate; palladium diacetate; lithium chloride In N,N-dimethyl-formamide at 120℃; for 6h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Yamashita, Mana; Hirano, Koji; Satoh, Tetsuya; Miura, Masahiro [Advanced Synthesis and Catalysis, 2011, vol. 353, # 4, p. 631 - 636]

66
[ 14371-10-9 ]
[ 1067-74-9 ]
[ 28010-12-0 ]

Yield	Reaction Conditions	Operation in experiment
61%	Stage #1: Methyl diethylphosphonoacetate With sodium hydride In tetrahydrofuran at 0℃; for 0.25h; Stage #2: (E)-3-phenylpropenal In tetrahydrofuran at 0 - 20℃; for 18h; Stage #3: With hydrogenchloride; water In tetrahydrofuran	4.11. Preparation of (2E,4E)-5-phenylpenta-2,4-dienoic acid (21) A mixture of methyl chloroacetate (4.8 g, 44 mmol) and triethylphosphite (7.3 g, 44 mmol) was heated at 135 °C for 10 h. The mixture was allowed to cool to room temperature to afford the desired product, methyl 2-(diethylphosphoryl)acetate, in 98% yield (6.2 g) as a mixture of rotamers.To a suspension of sodium hydride (7.8 mmol) in dry THF (10 mL), methyl 2-(diethyl phosphoryl)acetate (420 mg) in 5 mL of THF was added dropwise at -60 °C. The reaction mixture was then stirred at 0 °C for 15 min and cooled to -60 °C again. Next cinnamaldehyde (18, 300 mg) in 2 mL of THF was added to the reaction solution and stirred for 90 min. The reaction mixture was stirred at 0 °C for 16 h, then at room temperature for 2 h. Next the reaction was acidified with 2 M hydrochloric acid and extracted with ethyl acetate. The organic fractions were collected, washed with brine, dried with anhydrous magnesium sulfate and filtered. The crude product was purified using a SiO2 column to afford 240 mg of (2E,4E)-5-phenylpenta-2,4-dienoic acid (21, 61% yield).(2E,4E)-5-Phenylpenta-2,4-dienoic acid (21): IR νmax (film) 3022, 1679 cm-1; 1H NMR (CD3OD, 500 MHz): δ 7.55-7.29 (5H, m; aromatic), 7.44 (1H, dd, J = 15.9, 10.6 Hz; H-3), 7.11 (1H, dd, J = 15.9, 10.6 Hz; H-4), 7.03 (1H, d, J = 15.9 Hz; H-5), 6.03 (1H, d, J = 15.9 Hz; H-2); EIMS m/z 174 [M]+, 129 (base).

Reference： [1]Location in patent: experimental part Aung, Hnin Thanda; Furukawa, Tadashi; Nikai, Toshiaki; Niwa, Masatake; Takaya, Yoshiaki [Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 7, p. 2392 - 2396]

67
[ 28010-12-0 ]
[ 62-53-3 ]
[ 34271-93-7 ]

Yield	Reaction Conditions	Operation in experiment
	With 1H-imidazole; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 4h;	4.2. Synthesis of the anilide derivatives 2a-l General procedure: The appropriately substituted aniline (5) (10 mmol), the carboxylic acid (6a-c) (10 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDAC, 15 mmol) were dissolved in a minimum amount of N,N-dimethylformamide (DMF). 4-Dimethylaminopyridine (DMAP, 0.5 mmol) and imidazole (0.5 mmol) were added as catalysts. The reaction was stirred for 4 h at room temperature and an excess amount of water was added to the mixture to precipitate the product. Except for 2f, which was isolated via extraction to ethyl acetate (50 mL), the products were collected by filtration and purified by recrystallization as indicated below. Compounds 2b-d were purified by silica gel column chromatography using ethyl acetate/petroleum ether (1:1) as mobile phase.

Reference： [1]Location in patent: experimental part Legoabe, Lesetja; Kruger, Johann; Petzer, Anél; Bergh, Jacobus J.; Petzer, Jacobus P. [European Journal of Medicinal Chemistry, 2011, vol. 46, # 10, p. 5162 - 5174]

68
[ 28010-12-0 ]
[ 108-42-9 ]
[ 1338963-69-1 ]

Yield	Reaction Conditions	Operation in experiment
42%	With 1H-imidazole; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 4h;	4.2. Synthesis of the anilide derivatives 2a-l General procedure: The appropriately substituted aniline (5) (10 mmol), the carboxylic acid (6a-c) (10 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDAC, 15 mmol) were dissolved in a minimum amount of N,N-dimethylformamide (DMF). 4-Dimethylaminopyridine (DMAP, 0.5 mmol) and imidazole (0.5 mmol) were added as catalysts. The reaction was stirred for 4 h at room temperature and an excess amount of water was added to the mixture to precipitate the product. Except for 2f, which was isolated via extraction to ethyl acetate (50 mL), the products were collected by filtration and purified by recrystallization as indicated below. Compounds 2b-d were purified by silica gel column chromatography using ethyl acetate/petroleum ether (1:1) as mobile phase.

Reference： [1]Location in patent: experimental part Legoabe, Lesetja; Kruger, Johann; Petzer, Anél; Bergh, Jacobus J.; Petzer, Jacobus P. [European Journal of Medicinal Chemistry, 2011, vol. 46, # 10, p. 5162 - 5174]

69
[ 28010-12-0 ]
[ 108-44-1 ]
[ 1338963-68-0 ]

Yield	Reaction Conditions	Operation in experiment
22%	With 1H-imidazole; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 4h;	4.2. Synthesis of the anilide derivatives 2a-l General procedure: The appropriately substituted aniline (5) (10 mmol), the carboxylic acid (6a-c) (10 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDAC, 15 mmol) were dissolved in a minimum amount of N,N-dimethylformamide (DMF). 4-Dimethylaminopyridine (DMAP, 0.5 mmol) and imidazole (0.5 mmol) were added as catalysts. The reaction was stirred for 4 h at room temperature and an excess amount of water was added to the mixture to precipitate the product. Except for 2f, which was isolated via extraction to ethyl acetate (50 mL), the products were collected by filtration and purified by recrystallization as indicated below. Compounds 2b-d were purified by silica gel column chromatography using ethyl acetate/petroleum ether (1:1) as mobile phase.

Reference： [1]Location in patent: experimental part Legoabe, Lesetja; Kruger, Johann; Petzer, Anél; Bergh, Jacobus J.; Petzer, Jacobus P. [European Journal of Medicinal Chemistry, 2011, vol. 46, # 10, p. 5162 - 5174]

70
[ 28010-12-0 ]
[ 591-19-5 ]
[ 1338963-70-4 ]

Yield	Reaction Conditions	Operation in experiment
40%	With 1H-imidazole; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 4h;	4.2. Synthesis of the anilide derivatives 2a-l General procedure: The appropriately substituted aniline (5) (10 mmol), the carboxylic acid (6a-c) (10 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDAC, 15 mmol) were dissolved in a minimum amount of N,N-dimethylformamide (DMF). 4-Dimethylaminopyridine (DMAP, 0.5 mmol) and imidazole (0.5 mmol) were added as catalysts. The reaction was stirred for 4 h at room temperature and an excess amount of water was added to the mixture to precipitate the product. Except for 2f, which was isolated via extraction to ethyl acetate (50 mL), the products were collected by filtration and purified by recrystallization as indicated below. Compounds 2b-d were purified by silica gel column chromatography using ethyl acetate/petroleum ether (1:1) as mobile phase.

Reference： [1]Location in patent: experimental part Legoabe, Lesetja; Kruger, Johann; Petzer, Anél; Bergh, Jacobus J.; Petzer, Jacobus P. [European Journal of Medicinal Chemistry, 2011, vol. 46, # 10, p. 5162 - 5174]

71
[ 28010-12-0 ]
[ 108-95-2 ]
[ 1068657-34-0 ]

Yield	Reaction Conditions	Operation in experiment
63%	With dmap; dicyclohexyl-carbodiimide In dichloromethane Inert atmosphere; Reflux;

Reference： [1]Trost, Barry M.; Hirano, Keiichi [Organic Letters, 2012, vol. 14, # 10, p. 2446 - 2449]

72
[ 28010-12-0 ]
trans,trans-1-Trifluoromethyl-4-phenyl-1,3-butadiene [ No CAS ]
(Z)-[(1E)-5,5,5-trifluoropenta-1,3-dien-1-yl]benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82 % de	With tert.-butylhydroperoxide; copper(ll) sulfate pentahydrate; Langlois reagent In dichloromethane; water at 50℃; for 12h; Overall yield = 48%; stereospecific reaction;

Reference： [1]Li, Zejiang; Cui, Zili; Liu, Zhong-Quan [Organic Letters, 2013, vol. 15, # 2, p. 406 - 409]

73
[ 28010-12-0 ]
N-2'-hydroxyethyl-5-(α-hydroxy-α-2-pyridylbenzyl)-7-(α-2-pyridylbenzylidene)-5-norbornene-2,3-dicarboximide [ No CAS ]
5-(α-hydroxy-α-2-pyridylbenzyl)-N-[2'-(5''-phenyl-2''E,4''E-pentadienoyloxy)ethyl]-7-(α-2-pyridylbenzylidene)-5-norbornene-2,3-dicarboximide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
3%	Stage #1: 5-phenylpenta-2,4-dienoic acid With thionyl chloride for 2h; Reflux; Stage #2: N-2'-hydroxyethyl-5-(α-hydroxy-α-2-pyridylbenzyl)-7-(α-2-pyridylbenzylidene)-5-norbornene-2,3-dicarboximide With pyridine at 70℃; for 16h;	5-(-Hydroxy--2-pyridylbenzyl)-A^[2'-(5''-phenyl-2''£,4''£'-pentadienoyloxy)ethyl]-7-(-2- pyridylbenzylidene)-5-norbornene-2,3-dicarboximide (187) 5-(-Hydroxy--2-pyridylbenzyl)-A^[2'-(5''-phenyl-2''£,4''£'-pentadienoyloxy)ethyl]-7-(-2- pyridylbenzylidene)-5-norbornene-2,3-dicarboximide (187) A similar procedure (Lu, M. C. et a. J. Med. Chem. 1987, 30, 273-278 and Nagao, Y. et al. Tetrahedron Lett. 1988, 29, 6133-6136) to that described for the preparation of 117 was followed using S-phenyl^i^E-pentadienoic acid (125 mg, 0.72 mmol) and thionyl chloride (1 mL), under reflux for 2 h. A solution of 102 (200 mg, 0.36 mmol) and crude pentadienoyl chloride in pyridine (2 mL) was then stirred at 70 °C for 16 h. Purification by flash chromatography (hexane/ethyl acetate 1 : 1) afforded 187 as a colourless solid (8 mg, 0.004mmol, 3%). mp 99-104 °C; NMR (300 MHz, CDC13) 3.34-3.45 (0.7H, m, 0.3H W7H- 3 and 0.4H Y/H-4), 3.49-3.53 (0.3H, m, V/H-2), 3.58-3.73 (2.3H, m, 1H NCH2, 0.3H V/H-3, 0.6H W/H-2 and W/H-4, 0.4H Y/H-2), 3.82-3.96 (1.7H, m, 1H NCH2, 0.3H V/H-l and 0.4H Y H-4), 4.26-4.44 (3H, m, 2H CH20, 0.3H V/H-4, 0.3H W H-l and 0.4H Y H-l), 5.51-5.66 (1.7H, m, 0.3H V/H-6, 0.4H Y H-6 and 1H OH), 5.82-6.06 (0.9H, m, 0.6H =CH and 0.3H W H- 6), 6.32 (0.4H, d, J= 15.9 Hz, =CH), 6.73-7.67 (24H, m, 3H =CH and 21H Ar), 8.48-8.51 (1.3H, m, 0.6H 2V/Pyr, 0.3H W/aPyr and 0.4H Y/aPyr), 8.65-8.67 (0.7H, m, 0.3H W/c^yr and 0.4H Y/aPyr); vmax/cm (C-0 ester), (C=0 imide), (C=0 ester); m/z (FAB+) (Found: MH+, C45H38N306 requires), m/z (FAB+) 712 (MH+, 9%), 120 (100); (Found: MH+ 712.2811, C46H38N3O5 requires 712.2812).

Reference： [1]Current Patent Assignee: LANDCARE RESEARCH NEW ZEALAND - WO2013/133726, 2013, A1 Location in patent: Page/Page column 119

74
[ 548765-13-5 ]
[ 28010-12-0 ]

Yield	Reaction Conditions	Operation in experiment
87%	With iron(III) chloride hexahydrate; water In nitromethane at 110℃; for 0.75h; Sealed tube; stereoselective reaction;

Reference： [1]Mohite, Amar R.; Bhat, Ramakrishna G. [Organic Letters, 2013, vol. 15, # 17, p. 4564 - 4567]

75
[ 28010-12-0 ]
((1E,3E)-4-nitrobuta-1,3-dien-1-yl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
34%	With tert.-butylnitrite; copper(l) chloride In acetonitrile at 80℃;

Reference： [1]Rokade, Balaji V.; Prabhu, Kandikere Ramaiah [Organic and Biomolecular Chemistry, 2013, vol. 11, # 39, p. 6713 - 6716]

76
[ 28010-12-0 ]
[ 3867-92-3 ]
(2E,4E)-N-((2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3-yl)-5-phenylpenta-2,4-dienamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
27%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran; N,N-dimethyl-formamide at 20℃;	1 EXAMPLE ISynthesis of (2E,4E)-N-((2R,3R,4R,55,6R)-4,5-dihydroxy-6-(hyd roxymethyl )-2-methoxytetrahyd ro-2 H-rjyran-3-yl )-5-rhenyl renta-2 .4-dienamide EXAMPLE ISynthesis of (2E,4E)-N-((2R,3R,4R,55,6R)-4,5-dihydroxy-6-(hyd roxymethyl )-2-methoxytetrahyd ro-2 H-rjyran-3-yl )-5-rhenyl renta-2 .4-dienamideHO:Me + RT,Overni:htScheme 15-Phenyl-2,4-pentadienoic acid (0.1111 g, 0.63 mmol) was dissolved in a solvent mixture of DMF/THF (V/V = 1/2, 3 mL total). To this solution, 4-dimethylaminopyridine (DMAP; 0.071 g, 0.58 mmol), 1-(3- dimethylaminopropyl)-3-ethylcarbodiimide (EDO) HCI (0.112 g, 0.58mmol), and (2R,35,4R,5R,6R)-5-amino-2-(hydroxymethyl)-6- methoxytetrahydro-2H-pyran-3,4-diol (0.1 g, 0.53 mmol) were added and the reaction was stirred overnight at room temperature. The reaction is diagrammed in Scheme 1.The reaction mixture was pumped dry and washed with DI-H20 3times (1 mL each). The purified product was dried under vacuum andanalyzed with 1H NMR and LO-MS. 50 mg of product was obtained in ayield of 27% based on the amount of the amine.1H NMR (500 MHz, DMSO-D6): 67.95 (d, J= 11.3 Hz, 1H), 7.55 (d, J9.2 Hz, 2H), 7.37 (t, J= 9.2 Hz, 2H), 7.30-7.27 (m, 1H), 7.18-6.91 (m, 3H),6.14 (d, J= 18.6 Hz, 1H), 5.03-4.96 (m, 2H), 4.62-4.59 (m, 1H), 4.26 (d, J40= 10.5 Hz, 1 H), 3.73-3.69 (m, 1H), 3.56-3.46 (m, 3H), 3.32 (s, 3H), 3.12- 3.10 (m, 2H). LC-MS (ESI): m/z 350 [M-’-1].

Reference： [1]Current Patent Assignee: DUPONT DE NEMOURS INC - WO2014/138490, 2014, A1 Location in patent: Page/Page column 40; 41

77
[ 221044-05-9 ]
[ 28010-12-0 ]
(E)-2-(4-phenyl-buta-1,3-dienyl)-1-pyrimidin-2-yl-1H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; 2,2-dimethylpropanoic anhydride In toluene at 140℃; for 24h; Inert atmosphere; stereoselective reaction;

Reference： [1]Zhang, Lingjuan; Qiu, Ruiying; Xue, Xiao; Pan, Yixiao; Xu, Conghui; Wang, Doudou; Wang, Xinyu; Xu, Lijin; Li, Huanrong [Chemical Communications, 2014, vol. 50, # 82, p. 12385 - 12388]

78
[ 110-91-8 ]
[ 28010-12-0 ]
4-((2E,4E)-5-phenylpenta-2,4-dienyl)morpholine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With formaldehyd In water at 100℃; for 12h; Sealed tube;