Name: 28286-88-6|2-(2,6-Dimethyl-4H-pyran-4-ylidene)malononitrile|98%
Brand: Ambeed
SKU: A556764
Price: 21.0 USD
Availability: InStock
Rating: 98 (27 reviews)

1
[ 1004-36-0 ]
[ 109-77-3 ]
[ 28286-88-6 ]

Yield	Reaction Conditions	Operation in experiment
72.5%	With acetic anhydride; for 2h;Reflux;	Preparation of compounds of formula (1) (R1, R2 are both H)2,6-dimethyl-4-pyrone (25 mmol, 3.1 g)withMalononitrile (250 mmol, 16.5 g)Added to 15mL of anhydrous acetic anhydride,The reaction mixture was stirred at reflux for 2h.After the reaction was completed, the reaction system was cooled to room temperature, 50 mL of boiling water was added thereto, a large amount of solid was precipitated, suction filtered, and the brown crude product was collected.The crude product was purified by silica gel column chromatography using petroleum ether / ethyl acetate (volume ratio of both: 10: 1) as eluent,The compound of formula (1) was obtained as a yellow solid,Yield 72.5%.
60%	In acetic anhydride; for 5h;Reflux; Inert atmosphere;	2,6-dimethyl-gamma-pyrone (12.50 g, 0.100 mol) and malononitrile (6.90 g, 0.104 mol) were dissolved in 50 mL of acetic anhydride; the solution was refluxed, under nitrogen flux, for 5 h. The system was then slowly cooled down to room temperature and the crystallization of a brown compound occurred. This compound was recovered by suction filtration and recrystallized by chloroform-hexane. Light brown needle-shape crystals were obtained. The yield was 60%. 1H NMR (CDCl3, 200 MHz); delta = 2.31 (s, 6H, -CH3); 6.53 (s, 2H, pyran CH). Mp: 192 C.
60%	With acetic anhydride;Reflux; Inert atmosphere;	2,6-dimethyl-g-pyrone (12.50 g, 0.100 mol) and malononitrile(6.90 g, 0.104 mol) were dissolved in 50 mL of acetic anhydride; thesolution was refluxed, under nitrogen flowing, for 5 h. The systemwas then slowly cooled down to room temperature and the crystallizationof a brown compound occurred. The compound wasrecovered by suction filtration and recrystallized by chloroformhexane.Light brown needle-shape crystals were obtained. Theyield was 60%.1H NMR (CDCl3, 200 MHz); delta 2.31 (s, 6H, -CH3); 6.53 (s, 2H,pyran CH).Mp: 192 C.

57%

With acetic anhydride; for 1.5h;Reflux;

Example 8; Preparation of a compound having the formula:; (a) A 10.00 g sample of 2,6-dimethyl-gamma-pyrone was dissolved in 40 niL of acetic anhydride. To this solution was added 5.3 rnL of malononitrile and the mixture was heated in an oil bath for 90 min at reflux temperature. Using a distillation apparatus, the volume was reduced by one half. The brown solution was added to 600 mL warm H2O, resulting in a dark brown crystalline solid, which was collected by vacuum filtration to yield 7.901 g (57%) (NMR (CDCl3) delta 6.57 (s, 2, pyrone), 2.32 (s, 6, CH3.)) of a compound having the formula:.

Reference： [1]Macromolecules,2005,vol. 38,p. 6336 - 6345
[2]RSC Advances,2015,vol. 5,p. 20712 - 20715
[3]Advanced Functional Materials,2012,vol. 22,p. 771 - 779
[4]Patent: CN104356055,2016,B .Location in patent: Paragraph 0057-0059
[5]Journal of Physical Chemistry A,2011,vol. 115,p. 2830 - 2836
[6]Chinese Journal of Chemistry,2011,vol. 29,p. 1951 - 1954
[7]New Journal of Chemistry,2017,vol. 41,p. 3790 - 3797
[8]Journal of Photochemistry and Photobiology A: Chemistry,2016,vol. 321,p. 79 - 89
[9]Dyes and Pigments,2016,vol. 133,p. 395 - 405
[10]Patent: WO2010/54183,2010,A2 .Location in patent: Page/Page column 49-50
[11]Chemistry - An Asian Journal,2017,vol. 12,p. 1374 - 1380
[12]Journal of the American Chemical Society,1958,vol. 80,p. 1440
[13]Tetrahedron,2008,vol. 64,p. 3772 - 3781
[14]Journal of Materials Chemistry,2011,vol. 21,p. 3768 - 3774
[15]Dyes and Pigments,2016,vol. 133,p. 261 - 272
[16]Journal of Materials Chemistry B,2016,vol. 4,p. 4683 - 4689
[17]Dyes and Pigments,2017,vol. 141,p. 428 - 440
[18]Journal of Organometallic Chemistry,2017,vol. 846,p. 397 - 406
[19]Journal of Materials Chemistry C,2017,vol. 5,p. 5183 - 5192
[20]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2019,vol. 214,p. 469 - 475

2
[ 28286-88-6 ]
[ 27913-86-6 ]
[ 119438-04-9 ]

Yield	Reaction Conditions	Operation in experiment
8.5%	With piperidine In ethanol at 100℃; for 48h;

Reference： [1]Bourson, Jean; Valeur, Bernard [Journal of Physical Chemistry, 1989, vol. 93, # 9, p. 3871 - 3876]

3
[ 28286-88-6 ]
[ 100-10-7 ]
[ 51325-91-8 ]

Yield	Reaction Conditions	Operation in experiment
57%	With piperidine In propan-1-ol for 10h; Reflux;	1 Synthesis of PAD-1: 2,6-Dimethyl-4-pyranylidenemalononitrile (86.0 mg, 0.50 mmol) and p-dimethylaminobenzaldehyde (75.0 mg, 0.50 mmol) were weighed and dissolved in 10 mL of n-propanol,Then add 200 μL piperidine,Under reflux for 10 hours with stirring;The n-propanol was distilled off, the residue was washed with water, extracted with ethyl acetate and dried over anhydrous magnesium sulfate overnight. The ethyl acetate layer was swirled to obtain the crude product.The crude product was separated by column chromatography (eluent, ethyl acetate: n-hexane = 2: 1) to give 86.1 mg of PAD-1. The structure was as follows. The yield was 57.0%.
35%	With piperidine; acetic acid In toluene
11%	With piperidine In ethanol at 100℃; for 48h;

Reference： [1]Current Patent Assignee: SICHUAN UNIVERSITY - CN104178132, 2017, B Location in patent: Paragraph 0057-0058
[2]Yang, Jinfeng; Li, Meng; Kang, Lihua; Zhu, Weihong [Science China Chemistry, 2017, vol. 60, # 5, p. 607 - 613]
[3]Bourson, Jean; Valeur, Bernard [Journal of Physical Chemistry, 1989, vol. 93, # 9, p. 3871 - 3876]

4
[ 28286-88-6 ]
[ 100-10-7 ]
2-(2,6-bis((E)-4-(dimethylamino)-styryl)-4H-pyran-4-ylidene)malononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
20.5%	With piperidine In acetonitrile for 12h; Reflux;	General procedure A General procedure: To a solution of (2,6-dimethyl-4H-pyran-4-ylidene)malononitrile(1 mmol) and substituted aromatic aldehydes (1-2 mmol) in acetonitrile (10 mL) was added piperidine (200 μL). The reaction mixture was stirred under reflux for 12 h. The precipitate was collected by filtration and recrystallized from ethanol or purified by silica gel chromatography to afford the final products.
	With potassium etoxide In propyl alcohol for 12h; Heating;
	With piperidine; glacial acetic acid In toluene diastereoselective reaction;

With piperidine In acetonitrile

Reference： [1]Zhu, Bi-Yue; Cheng, Yan; Li, Guo-Bo; Yang, Sheng-Yong; Zhang, Zhi-Rong [Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 4, p. 827 - 834]
[2]Yi, Ki-Wook; Jung, Kyoung-Hoon; Lim, Sung-Taek; Ryu, Gweon-Young; Shin, Dong-Myung [Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 2002, vol. 377, p. 97 - 100]
[3]Wang, Xiaohang; Guo, Zhiqian; Zhu, Shiqin; Liu, Yajing; Shi, Ping; Tian, He; Zhu, Wei-Hong [Journal of Materials Chemistry B, 2016, vol. 4, # 27, p. 4683 - 4689]
[4]Han, Xiangdong; Liu, Xiaoqing; Liu, Nannan; Gao, Wenxia; Lei, Yunxiang; Zhou, Yunbing; Liu, Miaochang; Wu, Huayue; Huang, Xiaobo [Journal of Materials Chemistry C, 2022, vol. 10, # 26, p. 9875 - 9881]

5
[ 28286-88-6 ]
[ 7770-45-8 ]
2-{2-[2-(4-hydroxynaphthalen-1-yl)vinyl]-6-methylpyran-4-ylidene}malononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48.2%	In ethanol; for 6h;Inert atmosphere; Reflux;	(Comparative Example 2) Synthesis of Compound 3 ((E)-2-(2-(4-hydroxynaphthalene-1-yl)vinyl)-6-methyl-4H-pyrane-4-ylidene)malononitrile) 4-hydroxy-1-naphtaldehyde (0.70 g (5.81 mmol)), 4-(dicyanomethylene)-2,6-dimethyl-4H-pyrane (1.0 g (5.81 mmol)), piperidine (0.50 g (5.81 mmol)), and ethanol (50 mL) were added to a 50-mL three-neck flask. The resultant was heated and refluxed under an argon atmosphere for 6 hours and then the solvent was removed under reduced pressure, followed by purification by column chromatography (SiO2, CHCl3:MeOH=10:1 (v/v)). Thus a desired compound was obtained (yield: 48.2%). ESI-MS(+): [M+Na]+=349.1 1H-NMR (400 MHz, CDCl3, r.t., TMS, delta/ppm) 1.71 (s, 3H), 5.27 (s, 1H), 5.51 (s, 1H), 6.65 (d, 1H), 6.85 (d, 1H), 6.59 (d, 1H), 7.21 (d, 1H), 7.35 (t, 1H), 7.38 (t, 1H), 8.08 (d, 1H).

Reference： [1]Journal of the American Chemical Society,2005,vol. 127,p. 17799 - 17802
[2]Patent: US8263791,2012,B2 .Location in patent: Page/Page column 8-9

6
[ 28286-88-6 ]
[ 25069-38-9 ]
C₂₉H₁₉Br₂N₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	With piperidine In acetonitrile for 24h; Heating;

Reference： [1]Cheon, Cheol Hong; Joo, Sung-Hoon; Kim, Kyungkon; Jin, Jung-Il; Shin, Hee-Won; Kim, Yong-Rok [Macromolecules, 2005, vol. 38, # 15, p. 6336 - 6345]

7
[ 28286-88-6 ]
[ 596107-37-8 ]
DCJP [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With piperidine In acetonitrile at 45℃; for 5h;	1 Synthesis of Compound 4a; [0088] A solution containing 18 g of compound 3, 0.1 g of piperidine, 11.4 g of 2-(2,6-dimethyl-4H-4-pyranyliden) malononitrile (the synthesis procedure was reported by Chen et al., Macromol. Symp. 125, 49, 1997) and 250 mL of acetonitrile was stirred at 45[deg.] C. for 5 hours. The mixture was diluted with water and then extracted with diethyl ether. The organic layer obtained was dried over MgSO4, concentrated and purified by chromatography using ethyl acetate/hexane (1/8) as the eluent to give 23.1 g of red solid. Yield: 82%. Mp: 250[deg.] C.

Reference： [1]Current Patent Assignee: E-RAY OPTOELECTRONICS TECHNOLOGY CO., LTD.; YUIRAI KODEN KAGI KOFUN YUGENK - US2003/193043, 2003, A1 Location in patent: Page/Page column 14

8
[ 110-89-4 ]
[ 28286-88-6 ]
[ 7770-45-8 ]
((E)-2-(2-(4-hydroxynaphthalene-1-yl)vinyl)-6-methyl-4H-pyrane-4-ylidene)malononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48.2%	In ethanol;	Comparative Example 2 Synthesis of compound 3 ((E)-2-(2-(4-hydroxynaphthalene-1-yl)vinyl)-6-methyl-4H-pyrane-4-ylidene)malononitrile) 4-hydroxy-1-naphtaldehyde (0.70 g (5.81 mmol)), 4-(dicyanomethylene)-2,6-dimethyl-4H-pyrane (1.0 g (5.81 mmol)), piperidine (0.50 g (5.81 mmol)), and ethanol (50 mL) were added to a 50-mL three-neck flask. The resultant was heated and refluxed under an argon atmosphere for 6 hours and then the solvent was removed under reduced pressure, followed by purification by column chromatography (SiO2, CHCl3:MeOH=10:1 (v/v)). Thus a desired compound was obtained (yield: 48.2%). ESI-MS(+): [M+Na]+=349.1 1H-NMR (400 MHz, CDCl3, r.t., TMS, δ/ppm) 1.71 (s, 3H), 5.27 (s, 1H), 5.51 (s, 1H), 6.65 (d, 1H), 6.85 (d, 1H), 6.59 (d, 1H), 7.21 (d, 1H), 7.35 (t, 1H), 7.38 (t, 1H), 8.08 (d, 1H).

Reference： [1]Patent: US2010/865,2010,A1

9
[ 28286-88-6 ]
[ 1201-91-8 ]
[ 1128210-84-3 ]

Yield	Reaction Conditions	Operation in experiment
54%	With piperidine In ethanol for 12h; Reflux;

Reference： [1]Park, Sanghyuk; Ji, Eon Kwon; Se, Hun Kim; Seo, Jangwon; Chung, Kyeongwoon; Park, Sun-Young; Jang, Du-Jeon; Medina, Begona Milian; Gierschner, Johannes; Soo, Young Park [Journal of the American Chemical Society, 2009, vol. 131, # 39, p. 14043 - 14049]

10
[ 28286-88-6 ]
[ 556-18-3 ]
[ 1193501-31-3 ]

Yield	Reaction Conditions	Operation in experiment
80%	With piperidine In propan-1-ol for 48h; Reflux;	A mixture of 2,6-dimethylpyran-4-ylidene-malononitrile (1.2 g, 6.8 mmol), 4-aminobenzaldehyde (1.0 g, 8.2 mmol) and piperidine (0.68 ml, 6.9 mmol) was dissolved in 150 ml 1-propanol and refluxed for 48 h. The reaction mixture was cooled, poured into water, stirred for 5 h and the precipitate was filtered and air-dried. The crude product was further purified by silica gel column chromatography using hexane/EAC 30-50% as eluent. The product was finally recrystallized from dichloromethane/1-propanol. Yield: 1.50 g (80%); mp: 249° C.; λmax=436 nm; 1H NMR (400 MHz, DMSO) δ 7.36 (d, J=8.4 Hz, 2H), 7.31 (s, 1H), 6.91 (d, J=16 Hz, 1H), 6.69 (s, 1H), 6.57 (d, J=16 Hz, 1H), 6.55 (d, J=8.4 Hz, 2H), 5.86 (s, 2H), 2.40 (s, 3H); 13C NMR (DMSO) δ 163.12, 160.71, 156.05, 151.12, 138.47, 129.61, 121.57, 115.31, 113.18, 111.53, 104.88, 104.22, 18.80. IR (neat, cm-1) 3478, 2957, 2200, 1647.
80%	With piperidine In propan-1-ol for 48h; Reflux;
20%	With piperidine In propan-1-ol for 3h; Reflux;	1 Synthesis of PAD-3: 2,6-Dimethyl-4-pyranylidenemalononitrile (86.0 mg, 0.50 mmol) and p-aminobenzaldehyde(61.0 mg, 0.50 mmol), dissolved in 10 mL of n-propanol, added with 200 μL of piperidine and refluxed with stirring for 3 hours;The n-propanol was distilled off, the residue was washed with water, extracted with ethyl acetate and dried over anhydrous magnesium sulfate overnight. The ethyl acetate layer was swirled to obtain the crude product.The crude product was separated by column chromatography (eluent: ethyl acetate: n-hexane = 4: 1) to give 27.5 mg of PAD-3. The structure was as follows. The yield was 20.0%.

Reference： [1]Current Patent Assignee: STANFORD UNIVERSITY; UNIVERSITY SYSTEM OF OHIO - US2010/29952, 2010, A1 Location in patent: Page/Page column 20
[2]Location in patent: experimental part Lord, Samuel J.; Lee, Hsiao-Lu D.; Samuel, Reichel; Weber, Ryan; Liu, Na; Conley, Nicholas R.; Thompson, Michael A.; Twieg, Robert J.; Moerner [Journal of Physical Chemistry B, 2010, vol. 114, # 45, p. 14157 - 14167]
[3]Current Patent Assignee: SICHUAN UNIVERSITY - CN104178132, 2017, B Location in patent: Paragraph 0054-0056; 0063-0064

11
[ 28286-88-6 ]
[ 100-10-7 ]
[ 70503-00-3 ]

Yield	Reaction Conditions	Operation in experiment
60%	With piperidine In acetonitrile at 40℃;
56%	With piperidine In acetonitrile at 76℃; for 24h; Inert atmosphere;	1 The PS2 synthesis method includes the following steps: Weigh 0.17g (1mmoL) of 2,6-dimethyl-4-pyranylidene malononitrile, 0.21g (2mmoL) of N,N-dimethyl-4-aminobenzaldehyde, and dissolve in 10mL of freshly steamed acetonitrile Then add 2-3 drops of piperidine and stir the reaction at 76°C for 24 hours under the protection of argon. After the substrate reaction is complete, cool to room temperature, filter the above reaction solution and recrystallize it with acetonitrile to obtain dark red crystals ( 0.2439g), yield: 56%.
23%	With piperidine In acetonitrile for 8h; Reflux;

Reference： [1]Gao, Zheng; Chen, Yi [RSC Advances, 2015, vol. 5, # 27, p. 20712 - 20715]
[2]Current Patent Assignee: ZUNYI MEDICAL UNIVERSITY - CN111484469, 2020, A Location in patent: Paragraph 0046-0048
[3]Location in patent: experimental part Park, Sung Soo; Won, Yong Sun; Lee, Woojin; Kim, Jae Hong [Journal of Physical Chemistry A, 2011, vol. 115, # 13, p. 2830 - 2836]

12
[ 28286-88-6 ]
[ 1201-91-8 ]
[ 678193-55-0 ]

Yield	Reaction Conditions	Operation in experiment
73%	With piperidine In butan-1-ol at 120℃; for 24h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Zhang, Jinfeng; Wu, Jincai [Chinese Journal of Chemistry, 2011, vol. 29, # 9, p. 1951 - 1954]

13
[ 28286-88-6 ]
[ 1008-72-6 ]
2,2'-(1E,1'E)-2,2'-(4-(dicyanomethylene)-4H-pyrane-2,6-diyl)bis(ethene-2,1-diyl)bis(sodium benzenesulfonate)salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44.5%	In methanol; ethanol; for 12h;Inert atmosphere; Reflux;	(Example 1) Synthesis of Compound 1 (2,2'-(1E,1'E)-2,2'-(4-(dicyanomethylene)-4H-pyrane-2,6-diyl)bis(ethene-2,1-diyl)bis(sodium benzenesulfonate)salt) Sodium 2-sulfo benzaldehyde (2.42 g (11.6 mmol)) was added to a 50-mL three-neck flask and then suspended in 30 mL of ethanol:methanol=1:1 (v/v). 4-(dicyanomethylene)-2,6-dimethyl-4H-pyrane (1.0 g (5.81 mmol)) and piperidine (495 mg (5.81 mmol)) were added and then the resultant was refluxed under an argon atmosphere for 12 hours. The precipitate was collected by filtration. The thus obtained yellow powder was washed with water and then subjected to drying under reduced pressure, so that 1.43 g of a desired compound was obtained (yield: 44.5%). ESI-MS (+): [M+Na-H]+=574.6 1H-NMR (400 MHz, DMSO-d6) ? 6.92 (2H, s), 7.20 (2H, d, J=16 Hz), 7.37-7.46 (4H, m), 7.77-7.88 (4H, m), 8.62 (2H, d, J=16 Hz). 13C-NMR (100.53 MHz, DMSO-d6) ? 56.6, 106.5, 115.5, 120.3, 127.2, 127.4, 129.0, 129.3, 132.5, 138.1, 146.4, 156.1, 159.7.

Reference： [1]Patent: US8263791,2012,B2 .Location in patent: Page/Page column 7

14
[ 28286-88-6 ]
[ 1008-72-6 ]
[ 1204141-25-2 ]

Yield	Reaction Conditions	Operation in experiment
42.8%	With piperidine; In methanol; ethanol; for 3h;Reflux; Inert atmosphere;	(Comparative Example 1) Synthesis of Compound 2 ((E)-2-(2-(4-(dicyanomethylene)-6-methyl-4H-pyrane-2-yl)vinyl)sodium Benzenesulfonate Sodium 2-sulfo benzaldehyde (2.0 g (9.61 mmol)) was added to a 200-mL three-neck flask and then suspended in 120 mL of ethanol:methanol=1:1 (v/v). 4-(dicyanomethylene)-2,6-dimethyl-4H-pyrane (5.0 g (29.0 mmol)) and piperidine (818 mg (9.61 mmol)) were added and then the resultant was refluxed under an argon atmosphere for 3 hours. The precipitate was resolved by filtration and then the mother liquor was concentrated. The thus obtained precipitate was washed with ethyl acetate and then the resultant was dried under reduced pressure, so that 1.49 g of a desired compound was obtained (yield: 42.8%). ESI-MS(+): [M+Na-H]+=384.8 1H-NMR (400 MHz, DMSO-d6) ? 2.45 (3H, s), 6.72 (1H, dd, J=0.91, 2.3 Hz), 6.94 (1H, d, J=2.3 Hz), 7.23 (1H, d, J=16 Hz), 7.34-7.42 (2H, m), 7.79-7.84 (2H, m), 8.63 (1H, d, J=16 Hz). 13C-NMR (100.53 MHz, DMSO-d6) ? 19.5, 55.8, 106.0, 107.3, 115.4, 119.3, 126.4, 127.1, 129.0, 129.1, 132.1, 137.3, 147.0, 156.8, 160.2, 164.1.

Reference： [1]Patent: US8263791,2012,B2 .Location in patent: Page/Page column 8

15
[ 28286-88-6 ]
[ 1201-91-8 ]
[ 340142-53-2 ]

Yield	Reaction Conditions	Operation in experiment
53%	With piperidine In propan-1-ol for 24h; Reflux;

Reference： [1]Zhang, You-Hao; Gu, Pei-Yang; Zhou, Jie-Bo; Xu, Yu-Jie; Liu, Wu; Gu, Qian-Feng; Chen, Dong-Yun; Li, Na-Jun; Xu, Qing-Feng; Lu, Jian-Mei [Journal of Materials Chemistry C, 2014, vol. 2, # 11, p. 2082 - 2088]

16
[ 28286-88-6 ]
[ 144072-30-0 ]
C₂₂H₂₁N₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
39%	With piperidine; In ethanol; at 65 - 80℃; for 5h;	A mixture of 2-(2,6-dimethyl-4H-pyran-4-ylidene)malononitrile (1, 190 mg, 1.1 mmol) and aldehyde 2a (200 mg, 0.9 mmol) were dissolved in anhydrous EtOH (5 ml) at 65 C. Piperidine (5 mul) was added and the mixture was stirred at 80 C. for 5 hours. The solvent was removed with a stream of N2, the crude mixture was dissolved in EtOAc at 5 mg/ml and purified by normal phase preparative HPLC using hexanes/ethyl acetate as eluent. Yield: 132 mg (39%). A portion of this compound (68.4 mg, 0.18 mmol) was treated with a 4N HCl solution in dioxane (4N, 9 ml) for 3 hours. The mixture was diluted with hexanes, the precipitate centrifuged, re-suspended and washed with hexanes, then dried under vacuum to give the title dye as hydrochloride (50.4 mg, 90%). LCMS ESI+ m/z: 276 (M+H+). H-NMR (400 MHz, DMSO) 7.52 (1H, dd, J=16 Hz, J=2 Hz) 7.4 (2H, m) 6.96 (1H, m) 6.58-6.72 (4H, m) 2.42 (3H, s). C-NMR (400 MHz, DMSO) 164.16, 161.71, 160.47, 157.07, 139.47, 130.61, 122.72, 116.82, 114.31, 112.62, 105.89, 105.25, 54.39, 19.81.

Reference： [1]Patent: US2014/154178,2014,A1 .Location in patent: Paragraph 0104

17
[ 28286-88-6 ]
[ 1612184-53-8 ]
[ 1612184-59-4 ]

Yield	Reaction Conditions	Operation in experiment
26%	With piperidine In ethanol at 65 - 80℃; for 7h;	11 A mixture of 2-(2,6-dimethyl-4H-pyran-4-ylidene)malononitrile (1, 20.7 mg, 0.12 mmol) and aldehyde 2c (25.1 mg, 0.1 mmol) were dissolved in anhydrous EtOH (0.67 ml) at 65° C. Piperidine (0.5 μl) was added and the mixture was stirred at 80° C. for 7 hours. The solvent was removed with a stream of N2, the crude mixture was dissolved in EtOAc at 5 mg/ml and purified by normal phase preparative HPLC using hexanes/ethyl acetate as eluent. Yield: 10.6 mg (26%). LCMS ESI+m/z 406 (M+H+) H-NMR (400 MHz, CD2Cl2): 8.16 (1H, d, J=8 Hz) 7.47 (1H, d, J=16 Hz) 7.29 (1H, s) 7.19 (1h, dd, J=8 Hz, 0.4 Hz) 7.1 (1H, d, J=0.4 Hz) 6.67-6.74 (2H, m) 6.56 (1H, m) 3.97 (3H, s) 2.43 (3H, s) 1.55 (9H, s). C-NMR (400 MHz, CD2Cl2) 163.02, 160.11, 157.01, 152.81, 148.32, 138.31, 131.33, 129.29, 122.99, 118.01, 116.81, 115.74, 108.45, 107.26, 106.77, 81.27, 56.35, 28.56, 20.31. This compound was treated with a 4N HCl solution in dioxane (4 N, 1.3 ml) for 3 hrs. The mixture was diluted with hexanes, the precipitate centrifuged, re-suspended and washed with hexanes, then dried under vacuum. LCMS ESI+ m/z: 306 (M+H+). H-NMR (400 MHz, CD2Cl2) 7.37 (1H, d, J=16 hz) 7.12 (1H, dd, J=16 Hz, 0.4 Hz) 7.02 (1H, d, J=0.4 Hz) 6.56-6.63 (3H, m) 6.12 (1H, m) 3.97 (3H, s) 2.42 (3H, s). C-NMR (400 MHz, CD2Cl2) 164.58, 156.12, 151.52, 140.90, 139.05, 129.73, 127.19, 121.74, 115.48, 110.73, 109.95, 102.81, 101.68, 100.79, 90.2, 55.89, 21.02.

Reference： [1]Current Patent Assignee: GENERAL ELECTRIC CO - US2014/154178, 2014, A1 Location in patent: Paragraph 0102

18
[ 28286-88-6 ]
[ 1612184-54-9 ]
[ 1612184-60-7 ]

Yield	Reaction Conditions	Operation in experiment
17.4%	With piperidine In ethanol at 65 - 80℃; for 6h;	10 A mixture of 2-(2,6-dimethyl-4H-pyran-4-ylidene) malononitrile (1, 16.5 mg, 96 μmol) and aldehyde 2d (34.9 mg, 76.5 μmol) were dissolved in anhydrous EtOH (0.5 ml) at 65 C. Piperidine (1 μl) was added and the mixture was stirred at 80° C. for 6 hrs. The solvent was removed with a stream of N2 and the crude mixture was purified by reverse phase HPLC using water/acetonitrile 40-100% gradient. Yield: 8.1 mg (17.4%). LCMS: m/z 611 (M+H+), 623 (M+Na+). H-NMR (400 MHz, CD2Cl2): 7.45 (1H, d, J=16 Hz) 7.29 (2H, d, J=12 Hz) 7.17 (2H, d, J=8 Hz) 7.03-7.12 (2H, m) 6.69-6.79 (2H, m) 6.52-6.61 (2H, m) 4.76 (2H, brs) 3.89 (3H, s) 2.43 (3H, s) 1.52, (9H, s) 1.41 (9H, brs). C-NMR (400 MHz, CD2Cl2): 162.54, 159.01, 156.35, 152.56, 137.61, 137.21, 134.39, 133.06, 132.89, 128.82, 120.38, 118.39, 117.99, 115.03, 114.99, 107.37, 106.31, 80.21, 58.97, 55.49, 29.68, 28.00, 27.93, 19.75. The purified product (8.1 mg) was treated with a 4N HCl solution in dioxane (4 N, 0.65 ml) for 3 hrs. The mixture was diluted with hexanes, the precipitate centrifuged, re-suspended and washed with hexanes, then dried under vacuum. LCMS ESI+ m/z: 411 (M+H+). H-NMR (400 MHz, DMSO-D6) 7.22-7.28 (5H, m) 6.83-6.89 (2H, m) 6.65 (1H, d, J=16 Hz) 6.54 (1H, d, J=16 Hz) 5.54 91H, s) 5.32 (1H, s) 4.22-4.38 (2H, brs) 3.92 (3H, s) 2.39 (3H, s).

Reference： [1]Current Patent Assignee: GENERAL ELECTRIC CO - US2014/154178, 2014, A1 Location in patent: Paragraph 0101

19
4-[N-(2-hydroxyethyl)]aminobenzaldehyde [ No CAS ]
[ 28286-88-6 ]
[ 1612184-50-5 ]

Yield	Reaction Conditions	Operation in experiment
43%	With piperidine In ethanol at 65 - 80℃; for 4h;	12 Synthesis of (E)-2-(2-(4-(2-hydroxyethylamino) styryl)-6-methyl-4H-pyran-4-ylidene)malononitrile (3b) A mixture of 2-(2,6-dimethyl-4H-pyran-4-ylidene)malononitrile (1, 190 mg, 1.1 mmol) and aldehyde 2b (156.5 mg, 95%, 0.9 mmol) were dissolved in anhydrous EtOH (5 ml) at 65 C. Piperidine (5 μl) was added and the mixture was stirred at 80 C for 4 hrs. The solvent was removed with a stream of N2, the crude mixture was dissolved in CH3CN and purified by reverse phase preparative HPLC using water/acetonitrile gradient. Yield: 123 mg (43%). LCMS ESI+ m/z 320 (M+H+) H-NMR (400 MHz, acetone-D6) 7.54, (1H, s) 7.52 (2H, d, J=8 Hz) 6.91 (1H, d, J=16 Hz) 6.72 (2H, d, J=8 Hz) 6.65 (1H, d, J=0.4 Hz) 6.55 (1H, s) 5.67 91H, brs) 3.90 (1H, brs) 3.75 (2H, t, J=8 Hz) 3.31 (2H, q, J=8 Hz) 2.49 (3H, s). C-NMR (400 MHz, acetone-D6): 163.20, 161.24, 156.66, 151.42, 139.01, 131.73, 129.96, 123.09, 115.24, 112.39, 105.37, 104.77, 60.15, 55.81, 45.55, 18.82.

Reference： [1]Current Patent Assignee: GENERAL ELECTRIC CO - US2014/154178, 2014, A1 Location in patent: Paragraph 0103

20
[ 28286-88-6 ]
[ 556-21-8 ]
[ 1620563-09-8 ]
[ 1620563-10-1 ]

Yield	Reaction Conditions	Operation in experiment
1: 73% 2: 26%	With piperidine In acetonitrile Reflux; Inert atmosphere;	Compounds (2) and (3) A mixture of 2,6-dimethyl-4H-pyran-4-ylidene)malononitrile(1.98 g, 11.4 mmol), 4-(methylamino)benzaldehyde (1) (1.25 g,9.12 mmol), and piperidine (1 mL) in acetonitrile (50 mL) washeated to reflux under argon overnight. The reaction was thencooled and the insoluble material was filtered off to give dialkylationcompound 2 (1.92 g, 73%). The filtrate was then evaporated todryness under reduced pressure. Dichloromethane was added todilute the residue and filtered to give monoalkylation compound3 (0.99 g, 26%). Dialkylation (2) 1H NMR (500 MHz, DMSO-d6) d7.61 (d, 2H, J = 16 Hz), 7.57 (d, 4H, J = 8 Hz), 6.98 (d, 2H,J = 16 Hz), 6.64 (s, 2H), 6.58 (d, 4H, J = 8.5 Hz), 6.47 (dd, 2H,J = 4.5, 5 Hz), 2.74 (d, 6H, J = 5 Hz), 13C NMR (125 MHz, DMSO-d6)d 159.68, 155.56, 151.65, 138.49, 129.95, 122.04, 116.16, 112.09,111.31, 104.30, 52.64, 29.00, ESI-MS (positive ion) m/z: 407.2[M+H]+, HRMS (ESI) 407.1872 (407.1866 calcd for C26H23N4O).Monoalkylation (3) 1H NMR (500 MHz, DMSO-d6) d 7.45 (d, 2H,J = 9 Hz), 7.40 (d, 1H, J = 16 Hz), 6.95 (d, 1H, J = 16 Hz), 6.70(d, 1H, J = 2.5H), 6.60 (d, 1H, J = 1 Hz), 6.55 (d, 2H, J = 8.5 Hz),6.47 (q, 1H, J = 5 Hz), 2.72 (d, 3H, J = 5 Hz), 2.41 (s, 3H), 13C NMR(125 MHz, DMSO-d6) d 163.81, 161.43, 156.75, 152.21, 139.16,130.27, 122.22, 116.05, 112.23, 111.83, 105.59, 104.93, 54.07,29.43, 19.54, ESI-MS (positive ion) m/z: 290.2 [M+H]+, HRMS(ESI) 290.1284 (290.1288 calcd for C18H16N3O).

Reference： [1]Chang, May-Hua; Chang, Chia-Ni [Tetrahedron Letters, 2014, vol. 55, # 32, p. 4437 - 4441]

21
[ 291535-21-2 ]
[ 28286-88-6 ]
2-(2,6-bis(2-(4-bromo-3-hexylthienyl)vinyl)pyran-4-ylidene)malononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55.56%	With piperidine In acetonitrile at 80℃; for 24h; Inert atmosphere;

Reference： [1]Zhang, Jing; Wu, Guanglong; He, Chang; Deng, Dan; Li, Yongfang [Journal of Materials Chemistry, 2011, vol. 21, # 11, p. 3768 - 3774]

22
[ 28286-88-6 ]
[ 93730-39-3 ]
(2,6-bis(4-((4-(ethyl(2-hydroxyethyl)amino)phenyl)diazenyl)styryl)-pyran-4-ylidene)propanedinitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With piperidine In butan-1-ol at 120℃; for 16h; Inert atmosphere;	2.4. General procedure for preparation of chromophores 4 and 5 General procedure: (2,6-Dimethyl-pyran-4-ylidene)propanedinitrile (0.5 g, 3 mmol) and the appropriate azo aldehyde (6 mmol) were dissolved in butanol (50 mL). Piperidene (0.5 g, 6 mmol) was added and the reaction heated at 120 °C under argon for 16 h. The reaction was then cooled to room temperature and the product collected by filtration. The product was the purified on a silica column using an appropriate mixture of ethyl acetate and dichloromethane as eluent as determined by TLC.

Reference： [1]Breukers; Janssens; Raymond; Bhuiyan; Kay [Dyes and Pigments, 2015, vol. 112, p. 17 - 23]

23
[ 28286-88-6 ]
4-((4-(bis(2-hydroxyethyl)amino)phenyl)diazenyl)benzaldehyde [ No CAS ]
(2,6-bis(4-((4-(bis(2-hydroxyethyl)amino)phenyl)diazenyl)styryl)pyran-4-ylidene)propanedinitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With piperidine In butan-1-ol at 120℃; for 16h; Inert atmosphere;	2.4. General procedure for preparation of chromophores 4 and 5 General procedure: (2,6-Dimethyl-pyran-4-ylidene)propanedinitrile (0.5 g, 3 mmol) and the appropriate azo aldehyde (6 mmol) were dissolved in butanol (50 mL). Piperidene (0.5 g, 6 mmol) was added and the reaction heated at 120 °C under argon for 16 h. The reaction was then cooled to room temperature and the product collected by filtration. The product was the purified on a silica column using an appropriate mixture of ethyl acetate and dichloromethane as eluent as determined by TLC.

Reference： [1]Breukers; Janssens; Raymond; Bhuiyan; Kay [Dyes and Pigments, 2015, vol. 112, p. 17 - 23]

24
[ 28286-88-6 ]
[ 24372-46-1 ]
(E)-2-(2-(2-(5-(dimethylamino)thiophen-2-yl)vinyl)-6-methyl-4H-pyran-4-ylidene)malononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
22%	With piperidine; In acetonitrile; for 16.0h;Reflux;	<strong>[24372-46-1]5-(dimethylamino)thiophene-2-carbaldehyde</strong>(310.0 mg, 2.0 mmol) was added to (2,6-dimethyl-4H-pyran-4-ylidene) malononitrile (310.0 mg, 1.8 mmol) in acetonitrile (30.0mL) followed by piperidine (200 muL). The solution was heated to reflux for 16 h and then cooled to room temperature. After extraction with ethylacetate, the organic phase was dried over Na2SO4 andfiltered. The filtrate was concentrated, and the residue was purified by silicagel chromatography (hexane : ethyl acetate 2 :1) to give 123.1 mg of PT-1 (22%).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 4472 - 4476

25
[ 28286-88-6 ]
(E)-3-(9-(2-ethylhexyl)-6-formyl-9H-carbazol-3-yl)acrylic acid [ No CAS ]
(2E,2'E)-3,3'-(((1E,1'E)-(4-(dicyanomethylene)-4H-pyran-2,6-diyl)bis(ethene-2,1-diyl))bis(9-(2-ethylhexyl)-9H-carbazole-6,3-diyl))diacrylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With piperidine; pyridine In acetonitrile Inert atmosphere; Reflux;	10 2.10. (2E,2'E)-3,3'-(((1E,1'E)-(4-(dicyanomethylene)-4H-pyran-2,6-diyl)bis(ethene-2,1-diyl))bis(9-(2-ethylhexyl)-9H-carbazole-6,3-diyl))diacrylic acid (C₁) Compound A1 (0.151 g, 0.88 mmol) and D (0.730 g, 1.93 mmol), were dissolved in a solution constituted by 9 mL of CH3CN and 1 mL of pyridine. The solution, stirred in nitrogen atmosphere, was taken at reflux temperature and then, five drops of piperidine were added. The solution was refluxed overnight and then poured in 50 mL of MeOH. The precipitation of a compound occurred, that was then recovered by filtration and recrystallized by THF-hexane. An amorphous orange solid was obtained. Yield was 62%. 1H NMR (DMSO, 500 MHz); δ = 0.74 (t, 6H, J = 7.0 Hz, -CH3); 0.81 (t, 6H, J = 7.0 Hz, -CH3); 1.10-1.29 (m, 16H, -CH2); 1.92 (m, 2H, -CH); 4.19 (d, 4H, J = 6.0 Hz); 6.51 (d, 2H, J = 15.0 Hz, CH=CH); 6.64 (s, 2H, pyran CH); 7.25 (d, 2H, J = 15.0 Hz, CH=CH); 7.54 (m, 4H, Ar-H); 7.74 (d, 2H, J = 15.0 Hz, CH=CH); 7.78-7.80 (m, 6H, Ar-H), 8.42 (s, 2H); 8.59 (s, 2H); 12.23 (s broad, 1H). 13C NMR (DMSO, 75 MHz): δ = 167.9; 158.7; 155.4; 144.8; 142.0; 141.9; 138.2; 127.2; 126.5; 125.8; 122.6; 122.5; 120.7; 120.4; 116.1; 116.0; 115.7; 110.1; 109.8; 105.6; 55.4; 46.8; 30.1; 28.0; 23.7; 22.4; 13.7; 10.6. Tg: 192 °C. MALDI-TOF-MS: Found: 890.46; 'Molecular formula C58H58N4O5 requires': 890.44. CHN elemental analysis: Found: C 78.24 H 6.63 N 6.21%; 'Molecular Formula C58H58N4O5 requires': C 78.18; H 6.56; N 6.29%.

Reference： [1]Maglione; Carella; Centore; Fusco; Velardo; Peluso; Colonna; Di Carlo [Journal of Photochemistry and Photobiology A: Chemistry, 2016, vol. 321, p. 79 - 89]

26
[ 12093-10-6 ]
[ 28286-88-6 ]
2-(2-ferrocenylvinyl-6-methyl-4H-pyran-4-ylidine)malononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With piperidine In acetonitrile for 24h; Inert atmosphere; Reflux;	4.3. Synthesis of Fc-DCM Both ferrocenecarboxaldehyde [18] and 2-(2,6-methyl-4H-pyran-4-ylidene) malononitrile [30] were prepared according to the reference method. A solution of 2-(2,6-methyl-4H-pyran-4-ylidine)malononitrile (1) (0.14 g, 1.40 mmol), ferrocenecarboxaldehyde (2) (0.20 g,1.40 mmol) and piperidine (1 mL) in dry acetonitrile (10 mL) was refluxed for 24 h under argon atmosphere. A red fluorescent colour was observed all along the reaction. The reaction was controlled with TLC method by monitoring the compound 1 in the solution of reaction. After the completion of the reaction, the solution was cooled to room temperature and the product was purified using liquid column chromatography over silica gel and hexane: EtOAc (8:2) as eluent. 0.24 g dark red solid was obtained (63% yield), FT-IR (KBr, cm-1): 3115 (Cp-H), 2205 (C≡N), 1690, 1509(C=C), 1048(Cp); 1H NMR (CDCl3, 400 MHz) δ: 7.31 (d, 3J = 15.80 Hz, 1H, =CH), 6.52 and 6.56 (s, 2H, pyran), 6.29 (d, 3J = 15.80 Hz, 1H, =CH), 4.53 (t, 2H, C5H4), 4.50 (t, 2H, C5H4), 4.19 (s, 5H, C5H5), 2.39 (s, 3H, CH3); 13C NMR (CDCl3, 100 MHz) δ: 160.74, 158.45, 155.51, 138.64, 138.17, 105.21, 104.15, 78.32, 70.39, 69.21, 68.75, 67.30, 18.91; Anal. Found: C, 68.42; H, 4.32; Fe, 15.13; N, 7.56. Calc. for: C21H16FeN2O: C, 68.50; H, 4.38; Fe, 15.17; N, 7.61%.

Reference： [1]Teimuri-Mofrad, Reza; Rahimpour, Keshvar; Ghadari, Rahim [Journal of Organometallic Chemistry, 2016, vol. 811, p. 14 - 19]

27
[ 28286-88-6 ]
[ 111-86-4 ]
2-(2,6-dimethyl-1-octylpyridin-4(1H)-ylidene)malononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	In acetonitrile at 80℃; for 24h; Inert atmosphere;	2.2 Synthesis of compounds 6a-c General procedure: A mixture of compound 5a/5b/5c (5mmol) and 1-octylamine (10mL) in acetonitrile (15mL) was heated under argon at 80°C for 24h. The reaction mixture was allowed to reach room temperature and then poured into ice methanol, a large amount of solids separated out in the mixture. After filtration, the crude product was washed with methanol three times, and then dried to afford pure compounds 6a-c. 2-(2,6-Dimethyl-1-octylpyridin-4(1H)-ylidene)malononitrile (6a). White solids (1.06g), 75% yield; m. p. 154-155°C. 1H NMR (CDCl3, 500MHz): δ 6.58 (s, 2H), 3.90 (t, J=8.5Hz, 2H), 2.46 (s, 6H), 1.71-1.65 (m, 2H), 1.39-1.26 (m, 10H), 0.87 (t, J=7.0Hz, 3H). 13C NMR (CDCl3, 125MHz): δ 155.7, 147.5, 147.4, 118.7, 113.8, 49.1, 44.7, 44.6, 31.6, 29.6, 29.0, 28.9, 26.6, 22.5, 20.5, 13.9. MS (ESI, m/z): 284.10 (M++H). FT-IR (KBr, cm-1): 2926, 2192, 2171, 1625, 1550, 1506, 1483, 1352, 1317, 1185, 1062, 874, 725.
	In acetonitrile

Reference： [1]Lei, Yunxiang; Yang, Dongliang; Hua, Huaijie; Dai, Chunhui; Wang, Lianhui; Liu, Miaochang; Huang, Xiaobo; Guo, Yang; Cheng, Yixiang; Wu, Huayue [Dyes and Pigments, 2016, vol. 133, p. 261 - 272]
[2]Lei, Yunxiang; Zhou, Yibin; Qian, Lebin; Wang, Yuxiang; Liu, Miaochang; Huang, Xiaobo; Wu, Ge; Wu, Huayue; Ding, Jinchang; Cheng, Yixiang [Journal of Materials Chemistry C, 2017, vol. 5, # 21, p. 5183 - 5192]

28
[ 28286-88-6 ]
1-(7-bromo-9,9-dihexyl-9H-fluoren-2-yl)-1,2,3,4-tetrahydroquinoline-6-carbaldehyde [ No CAS ]
2-[2,6-bis({2-[1-(7-bromo-9,9-dihexyl-9H-fluoren-3-yl)-1,2,3,4-tetrahydroquinolin-6-yl]ethenyl})-4H-pyran-4-ylidene]propanedinitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With piperidine In butan-1-ol for 24h; Heating;	3 Example 3: 2- (2,6-bis- {2- [1- (7-bromo-9,9-dihexyl -9H- fluorene-2-yl) -1,2,3,4- tetrahydro-quinolin-6-yl] -vinyl} - rayidin blue-4-yl) - Preparation of words no nitrile Synthesized in Example 2 1- (7-bromo-9,9-dihexyl -9H- fluoren-2-yl) -1,2,3,4-tetrahydro-carbazole-6-aldehyde (6.87 g , 12 mmol), (2,6-dimethyl-4H-pyran-4 - yl rayidin) words no-nitrile (0.94 g, 5.5 mmol), piperidine (0.6 mL) and n-butanol in 30mL of solution consisting of 120 the reaction was carried out for 24 hours at . After completion of the reaction, it cool to room temperature to give a red solid by the addition of excess methanol. After drying the resulting red solid was filtered, dissolved in methylene chloride then recrystallized dropped in methanol to give a red solid material (5.73 g, 77%)

Reference： [1]Current Patent Assignee: KAIST; DONGJIN SEMICHEM CO.,LTD. - KR101544415, 2015, B1 Location in patent: Paragraph 0052-0053; 0068-0069

29
[ 28286-88-6 ]
(E)-3-(10-(2-ethylhexyl)-7-formyl-10H-phenothiazine-3-yl)acrylic acid [ No CAS ]
(2E,2'E)-3,3'-(((1E,1'E)-(4-(dicyanomethylene)-4H-pyran-2,6-diyl)bis(ethene-2,1-diyl))bis(10-(2-ethylhexyl)-10H-phenothiazine-7,3-diyl))diacrylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With piperidine; pyridine In acetonitrile Inert atmosphere; Reflux;	2.1.8. (2E,20E)-3,30-(((1E,10E)-(4-(dicyanomethylene)-4H-pyran-2,6-diyl)bis(ethene-2,1-diyl))bis(10-(2-ethylhexyl)-10Hphenothiazine-7,3-diyl))diacrylic acid (P1) Compound A1 (0.151 g, 0.88 mmol) and D (0.730 g, 1.93 mmol),were dissolved in a solution constituted by 9mL of CH3CN and 1mLof pyridine. The solution, stirred in nitrogen atmosphere, washeated at reflux temperature and then, five drops of piperidinewere added. The solution was refluxed overnight and then pouredin 50 mL of MeOH. The precipitation of a compound occurred, thatwas recovered by filtration and recrystallized by THF-hexane. Anamorphous orange solid was obtained. Yield was 62%.1H NMR (DMSO, 400 MHz): δ 0.77-0.83 (m, 12H); 1.19-1.39(m,16H); 1.78 (m, 2H); 3.85 (s, 4H); 6.42 (d, 2H, J 16.0 Hz); 6.77 (s,2H); 7.08-7.13 (m, 4H); 7.26 (d, 2H, J 16.0 Hz); 7.47 (d, 2H,J 16 Hz); 7.53 (m, 4H); 7.62-7.65 (m, 6H).13C NMR (DMSO, 75 MHz): δ 169.0; 159.2; 156.2; 146.4; 145.6;140.6; 136.7; 130.3; 130.0; 130.2; 128.5; 128.1; 127.0; 126.7; 124.5;124.3; 121.05; 117.1; 116.8; 116.0; 106.9; 50.4; 36.0; 30.0; 28.1; 23.5;22.8; 14.1; 10.6.Tg:193 °C.MALDI-TOF-MS: Found: 954.46; ‘Molecular formulaC58H58N4O5S2 requires’: 954.38.CHN elemental analysis: Found: C 73.05 H 6.38 N 5.98%; ‘MolecularFormula C58H58N4O5S2 requires’: C 72.93; H 6.12; N 5.87%.

Reference： [1]Maglione; Carella; Carbonara; Centore; Fusco; Velardo; Peluso; Colonna; Lanuti; Di Carlo [Dyes and Pigments, 2016, vol. 133, p. 395 - 405]

30
[ 28286-88-6 ]
4-(bis-(4'-(1,2,2-triphenylvinyl)-[1,1'-biphenyl]-4-yl)amino)benzaldehyde [ No CAS ]
2-(2,6-bis-((E)-4-(bis(4'-(1,2,2-triphenylvinyl)-[1,1'-biphenyl]-4-yl)amino)styryl)-4H-pyran-4-ylidene)malononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With piperidine In acetonitrile at 100℃; for 72h;	Synthesis of compound 7[0366]Subsequently, piperidine (0.3 mL) was added into a stirred mixture of 198 mg (0.2 mmol) of CHO-TPA-2TPE and 14.5 mg (0.1mmol) of DCM in 5 mL of acetonitrile. The mixture was heated to 100 for 72 h. After cooling to room temperature, the solution was extracted with dichloromethane (DCM 100 mL) twice, washed with water, and dried over Na2SO4. After filtration and solvent evaporation under reduced pressure, the product was purified by silica-gel column chromatography using hexane/DCM as the eluent. TPE-TETRAD (compound 7) was obtained in 40yield (200 mg) as red powder. All the compounds were characterized by1H NMR,13C NMR and high resolution mass spectrometry, which confirmed the structures.

Reference： [1]Current Patent Assignee: HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY - WO2017/8743, 2017, A1 Location in patent: Paragraph 249-250

31
[ 28286-88-6 ]
[ 66-77-3 ]
2-(2,6-bis((E)-2-(naphthalen-1-yl)vinyl)-4H-pyran-4-ylidene)malononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69.7%	With piperidine In acetonitrile at 80℃; for 3h; Inert atmosphere;	2.2. Synthesis of compounds 5a-5d General procedure: A solution of compound 4a/4b (1.0 mmol), 1-naphthaldehyde/2-naphthaldehyde (937.2 mg, 6.0 mmol), piperidine (1.0 mL) andacetonitrile (6 mL) was heated at 80 °C under argon for 3 h (5a and5b) or 24 h (5c and 5d). After cooling down to room temperature, the mixture was poured in methanol (50 mL) to precipitate out the crude product. The crude product was successively washed with acetone and methanol five times and then dried to afford the pure target compound.Characterization data for 2-(2,6-bis((E)-2-(naphthalen-1-yl)vinyl)-4H-pyran-4-ylidene)- malononitrile (5a). Yellow solid (312.6 mg),69.7% yield, m. p. 270-271 °C. 1H NMR (500 MHz, CDCl3): δ 8.53(d, J=15.5Hz, 2H), 8.28(d, J=8.5 Hz, 2H), 7.97 (d, J=8.5 Hz, 2H), 7.95(d, J =8.0 Hz, 2H), 7.90 (d, J =7.0 Hz, 2H), 7.61-7.58 (m, 6H), 6.96 (d,J =15.5 Hz, 2H), 6.82 ppm(s, 2H). 13C NMR (125 MHz, CDCl3): δ 158.0,155.8, 134.7, 133.9, 131.6, 131.4, 131.0, 129.2, 127.2, 126.5, 125.7, 124.9,122.7, 120.7, 115.0, 107.6 ppm. MS (ESI, m/z): 449.15 (M++H). Anal.CalcdforC32H20N2O: C,85.69;H,4.49;N,6.25.Found:C,85.39;H, 4.45;N, 6.20.

Reference： [1]Zhou, Yibin; Liu, Yanze; Guo, Yang; Liu, Miaochang; Chen, Jiuxi; Huang, Xiaobo; Gao, Wenxia; Ding, Jinchang; Cheng, Yixiang; Wu, Huayue [Dyes and Pigments, 2017, vol. 141, p. 428 - 440]

32
[ 28286-88-6 ]
[ 66-99-9 ]
2-(2,6-bis((E)-2-(naphthalen-2-yl)vinyl)-4H-pyran-4-ylidene)malononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60.1%	With piperidine In acetonitrile at 80℃; for 3h; Inert atmosphere;	2.2. Synthesis of compounds 5a-5d General procedure: A solution of compound 4a/4b (1.0 mmol), 1-naphthaldehyde/2-naphthaldehyde (937.2 mg, 6.0 mmol), piperidine (1.0 mL) andacetonitrile (6 mL) was heated at 80 °C under argon for 3 h (5a and5b) or 24 h (5c and 5d). After cooling down to room temperature, the mixture was poured in methanol (50 mL) to precipitate out the crude product. The crude product was successively washed with acetone and methanol five times and then dried to afford the pure target compound.

Reference： [1]Zhou, Yibin; Liu, Yanze; Guo, Yang; Liu, Miaochang; Chen, Jiuxi; Huang, Xiaobo; Gao, Wenxia; Ding, Jinchang; Cheng, Yixiang; Wu, Huayue [Dyes and Pigments, 2017, vol. 141, p. 428 - 440]

33
[ 28286-88-6 ]
[ethoxycarbonylmethyl-(5-formyl-2-hydroxy-benzyl)-amino]-acetic acid ethyl ester [ No CAS ]
(E)-diethyl2,2'-(5-(2-(4-(dicyanomethylene)-6-methyl-4H-pyran-2-yl)vinyl)-2-hydroxybenzylazanediyl)diacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With piperidine In ethanol Reflux; Inert atmosphere;	1-2 (E)-diethyl2,2'-(5-(2-(4-(dicyanomethylene)-6-methyl-4H-pyran-2-yl)vinyl)-2-hydroxybenzyl azanediyl)diacetate synthesis To a 50 mL three-necked flask, the above 1-1. 0.5 g (1.6 mmol) of Diethyl 2,2 '- (5-formyl-2-hydroxybenzylazanediyl) diacetate synthesized in Example 1, 0.3 g (1.6 mmol) of 4- (Dicyanomethylene) -2,6-dimethyl-4H-pyran, Piperidine 0.2 G (1.7 mmol),40 mL of EtOH was added, and the mixture was refluxed under a nitrogen stream. After distilling off the solvent under reduced pressure,The residue was dissolved in CHCl 3 and washed with water.After drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure,After purification by column chromatography (SiO 2, n-hexane: ethyl acetate = 1.5: 1 v / v), further purification by column chromatography (SiO 2, chloroform)To obtain the target compound. The yield was 84%.

Reference： [1]Current Patent Assignee: NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY - JP2017/101118, 2017, A Location in patent: Paragraph 0032

34
[ 28286-88-6 ]
[ 1271-51-8 ]
2-{2,6-bis[4-(2-ferrocenylvinyl)styryl]-4H-pyran-4-ylidine}malononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With piperidine In acetonitrile for 1h; Reflux; Inert atmosphere;	Condensation of 4-(2-ferrocenylvinyl)benzaldehyde withpyran derivatives A solution of 4H-pyrane derivative (4, 7a and7b) (1 mmol), 4-(2-ferrocenylvinyl)benzaldehyde (2 mmol) andpiperidine (1 mL) in dry acetonitrile (10 mL) was refluxed for 1 hunder argon atmosphere. The reaction was controlled with TLCmethod by monitoring the 4-(2-ferrocenylvinyl) benzaldehyde inthe solution of reaction. After the completion of the reaction, thesolution was cooled to room temperature and the product waspurified using column chromatography over silica gel and hexane/EtOAC as eluent. Further purification was performed by recrystallizationfrom hexane and EtOAc to give corresponding compoundas a pure solid. Specific details for each compound are given belowand spectral data in each case is similar to reported one in above.2,6-Bis [4-(2-ferrocenylvinyl)styryl]-4H-pyran-4-one (6):from 0.1 g (0.32 mmol) 4-(2-Ferrocenylvinyl) benzaldehyde and0.02 g (0.11 mmol) 2, 6-Methyl-4H-pyran-4-one, 0.08 g (0.13 mmol)orange solid was obtained in 75% yield.

Reference： [1]Teimuri-Mofrad, Reza; Rahimpour, Keshvar; Ghadari, Rahim [Journal of Organometallic Chemistry, 2017, vol. 846, p. 397 - 406]

35
[ 28286-88-6 ]
C₂₅H₄₂O₄ [ No CAS ]
C₃₅H₄₈N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With piperidine In butan-1-ol at 70℃; for 5h;	1.2.2.5 synthesis of intermediate 1 In a dry three-necked flaskStarting material 2 (0.2 g, 0.49 mmol),Starting material 1 (0.08, 0.49 mmol),Piperidine (0.1 mL) and n-butanol (10 mL)After ventilation at room temperature for 2 h,Slowly warming to 70 ,Reflux 5h,Cooling crystallization,To obtain a yellow crystal,After filtration,Recrystallization from acetonitrile,Yellow needle crystals can be obtainedThe Yield 60%.

Reference： [1]Current Patent Assignee: SICHUAN AGRICULTURAL UNIVERSITY - CN107033130, 2017, A Location in patent: Paragraph 0078; 0079

36
[ 28286-88-6 ]
[ 433254-46-7 ]
2-(2,6-bis((E)-2-(1-isobutyl-1H-indol-3-yl)vinyl)-4H-pyran-4-ylidene)malononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88.6%	With piperidine In acetonitrile at 80℃; for 24h; Inert atmosphere;

Reference： [1]Qian, Lebin; Zhou, Yibin; Liu, Miaochang; Huang, Xiaobo; Wu, Ge; Gao, Wenxia; Ding, Jinchang; Wu, Huayue [RSC Advances, 2017, vol. 7, # 67, p. 42180 - 42191]

37
[ 12093-10-6 ]
[ 28286-88-6 ]
2-(2,6-diferrocenylvinyl-4H-pyran-4-ylidine)malononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With piperidine In acetonitrile for 24h; Reflux; Inert atmosphere;	2 General procedure for the synthesis of pyran derivatives General procedure: A solution of 4H-pyran derivative (1, 3a and 3b) (1.20 mmol),ferrocenecarboxaldehyde (2.40 mmol), and piperidine (1 mL) in dryacetonitrile (10 mL) was refluxed for 24 h under argon atmosphere.The reaction was controlled with TLC method by monitoring theferrocenecarboxaldehyde in the solution of reaction. After the completionof the reaction, the solution was cooled to room temperature andthe product purified using column chromatography over silica gel andEtOAc as eluent. Further purificationwas performed by recrystallizationfrom hexane: EtOAc (8:2) to give the corresponding compound as apure solid.

Reference： [1]Teimuri-Mofrad, Reza; Rahimpour, Keshvar; Ghadari, Rahim; Ahmadi-Kandjani, Sohrab [Journal of Molecular Liquids, 2017, vol. 244, p. 322 - 329]

38
[ 28286-88-6 ]
[ 123-08-0 ]
2-(2-(4-hydroxystyryl)-6-methyl-4H-pyran-4-ylidene)malononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With piperidine In acetonitrile for 12h; Reflux;	Preparation of P To a solution of p-hydroxybenzaldehyde(122 mg, 1.00 mmol) and piperidine (0.02 mL, 0.2 mmol) in 5 mL CH3CN, was added malonitrile condensed 2,6-dimethyl-[1,4]-pyrone (172 mg,1.00 mmol). The resulting solution was heated under reflux for 12 h and then evaporated under reduced pressure. Further purification was performed by column chromatography to afford the desired product as a reddish solid in 70% yield.
56%	With piperidine; acetic acid In toluene for 8h; Inert atmosphere; Reflux;
51%	With piperidine; acetic acid In toluene for 8h; Reflux; Inert atmosphere;

42.7%	With piperidine In acetonitrile for 6h; Reflux; Inert atmosphere;	2.2.1. The synthesis of 2-(2-(4-hydroxystyryl)-6-methyl-4H-pyran-4-ylidene)malononitrile fluorophore (P-OH) Compound 2 (516 mg, 3 mmol) [49] and 4-hydroxybenzaldehyde (185 mg, 1.5 mmol), piperidine (0.3 ml) was added in 10 ml acetonitrile. The mixture was refluxed for 6 h under N2 atmosphere. After the removal of the solvent, the residue was dissolved with dichloromethane,washed with brine and deionized water three times respectively, then the obtained organic phase was dried over Na2SO4. Subsequently, the solvent was evaporated under reduced pressure to get the crude product, and the crude product was purified by silica column chromatography (dichloromethane: ethyl acetate = 100:5, v/v) to give an orange solid (42.7%). 1H NMR (500 MHz, DMSO-d6) δ 10.05 (s, 1H), 7.55(d, J = 8.6 Hz, 2H), 7.46 (d, J = 16.1 Hz, 1H), 7.12 (d, J = 16.1 Hz,1H), 6.86-6.79 (m, 3H), 6.66 (d, J = 1.3 Hz, 1H), 2.45 (s, 3H). 13C NMR(DMSO-d6): δ 163.89, 160.46, 159.72, 156.69, 137.84, 129.96, 125.94,115.93, 115.54, 115.39, 105.88, 105.66, 55.00, 19.35. HRMS: calculatedfor [M-H]-: 275.0821; found: 275.0827.
31.2%	With piperidine In propan-1-ol for 3h; Reflux;	1 Synthesis of PAD-4: 2,6-Dimethyl-4-pyranylidenemalononitrile (86.0 mg, 0.50 mmol) and p-hydroxybenzaldehyde(61.0 mg, 0.50 mmol), dissolved in 10 mL of n-propanol, added with 200 μL of piperidine and refluxed with stirring for 3 hours;The n-propanol was distilled off, the residue was washed with water, extracted with ethyl acetate and dried over anhydrous magnesium sulfate overnight. The ethyl acetate layer was swirled to obtain the crude product.The crude product was separated by column chromatography (eluent ethyl acetate: n-hexane = 4: 1) to give 43.0 mg of PAD-4 with the following structure in 31.2% yield.
	In toluene

Reference： [1]Seo, Hyun-Seok; Kim, Hae-Jo [Bulletin of the Korean Chemical Society, 2017, vol. 38, # 10, p. 1134 - 1137]
[2]Tian, Zhaoyan; Mi, Li; Wu, Yafeng; Shao, Fengying; Zou, Mingqiang; Zhou, Zhenxian; Liu, Songqin [Analytical Chemistry, 2019, vol. 91, # 12, p. 7902 - 7910]
[3]Wang, Xiaojun; Li, Wen; Li, Wanru; Gu, Chang; Zheng, Hongzhi; Wang, Yuyang; Zhang, Yu-Mo; Li, Minjie; Xiao-An Zhang, Sean [Chemical Communications, 2017, vol. 53, # 81, p. 11209 - 11212]
[4]Qian, Ming; Zhang, Liuwei; Wang, Jingyun; Peng, Xiaojun [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2019, vol. 214, p. 469 - 475]
[5]Current Patent Assignee: SICHUAN UNIVERSITY - CN104178132, 2017, B Location in patent: Paragraph 0054-0056; 0066-0067
[6]Yan, Chenxu; Guo, Zhiqian; Shen, Yanyan; Chen, Yi; Tian, He; Zhu, Wei-Hong [Chemical Science, 2018, vol. 9, # 22, p. 4959 - 4969]

39
[ 28286-88-6 ]
4-(9,9-dimethyl-9,10-dihydroacridin-10-yl)benzaldehyde [ No CAS ]
C₅₆H₄₄N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48.6%	With pyridine In acetonitrile Inert atmosphere; Reflux;	1 Embodiment 1: compound 1 synthesis of First of all, of formula (II) compound of formula (0.058 µM, 10 g), 4 - (9, 9 - dimethyl-acridine -10 (9 H)) benzaldehyde (0.117 µM, 36.4 g) is placed in a round-bottom flask, after 100 ml piperidine, 30 ml acetonitrile, inject the nitrogen protection, overnight reflux reaction, after stopping the reaction. The product through the extraction, after drying, for purifying the column chromatography, to obtain 21.58 g product. Yield: 48.6%.

Reference： [1]Current Patent Assignee: CHANGCHUN HAIPU RUNSI TECHNOLOGY CO LTD - CN107298676, 2017, A Location in patent: Paragraph 0049-0052

40
[ 28286-88-6 ]
[ 24372-46-1 ]
C₁₇H₁₅N₃OS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
21%	With piperidine; In acetonitrile; for 16.0h;Reflux;	2,6-dimethyl-4-pyranylenemalononitrile (172.0 mg, 1.00 mmol)And 5- (dimethylamino) -2-thiophenecarboxaldehyde (155.0 mg, 1.00 mmol),Dissolved in 10 mL acetonitrile, then add 200 muL piperidine, refluxed for 16 hours with stirring; evaporated to acetonitrile,The residue was washed with water, extracted with ethyl acetate, and dried over anhydrous magnesium sulfate overnight. The ethyl acetate layer was swirledCrude product. The crude product was separated by column chromatography (eluent ethyl acetate: n-hexane = 5: 1)64.9 mg PAD-1 was obtained with the following structure in a yield of 21.0%.

Reference： [1]Patent: CN104803993,2017,B .Location in patent: Paragraph 0044-0046; 0047; 0048

41
[ 28286-88-6 ]
[ 75-04-7 ]
2-(1-ethyl-2,6-dimethyl-pyridin-4(1H)-ylidene)malononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81.6%	In acetonitrile at 80℃; for 12h;	2 Preparation Example 2: Preparation of Formula (2) The compound of formula (1) (1.72 g, 10 mmol) obtained in Preparation Example 1 above,And 70% aqueous ethylamine (10 mmol in terms of ethylamine)Into 20mL of acetonitrile,The reaction solution was stirred at 80 for 12h.After the reaction,The reaction was cooled to room temperature and the solvent was removed under reduced pressure. The residue was chromatographed on silica gel eluting with petroleum ether-ethyl acetate (15: 1, v / v)The compound of formula (2) was obtained as a yellow solid,Where R is ethyl, the yield is 81.6%
	In acetonitrile

Reference： [1]Current Patent Assignee: WENZHOU UNIVERSITY - CN104356055, 2016, B Location in patent: Paragraph 0060-0062
[2]Lei, Yunxiang; Zhou, Yibin; Qian, Lebin; Wang, Yuxiang; Liu, Miaochang; Huang, Xiaobo; Wu, Ge; Wu, Huayue; Ding, Jinchang; Cheng, Yixiang [Journal of Materials Chemistry C, 2017, vol. 5, # 21, p. 5183 - 5192]

42
[ 28286-88-6 ]
[ 433254-46-7 ]
C₃₆H₃₄N₄O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With piperidine In acetonitrile at 80℃; for 24h; Inert atmosphere;	3.2.21; 3.2.22; 3.2.23 Further, step (2) comprises the following steps: (21) Piperidine and acetonitrile are mixed at a volume ratio of 1:50 to form an excess mixed solvent; (22) Intermediate 2, indole aldehyde with a different alkyl chain is added to the mixed solution to form a reaction solution, wherein: The molar ratio of intermediate 2 to indole aldehydes with different alkyl chains is 1: 5; (23) The reaction solution was heated at 80 ° C for 24 hours under the protection of nitrogen, and then cooled to room temperature to obtain dicyanomethylene-4H-pyran derivative.

Reference： [1]Current Patent Assignee: WENZHOU UNIVERSITY - CN107382982, 2017, A Location in patent: Paragraph 0115; 0116; 0117; 0118; 0119-0121; 0128-0131

43
[ 28286-88-6 ]
[ 6203-18-5 ]
C₂₁H₁₉N₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60.1%	With piperidine In propan-1-ol for 3h; Reflux;	1 Synthesis of PAD-2: 2,6-Dimethyl-4-pyranylidenemalononitrile (86.0 mg, 0.50 mmol) and p-dimethylaminocinnamaldehyde (88.0 mg, 0.50 mmol) were weighed out,Dissolved in 10 mL n-propanol, then add 200 μL piperidine,Under stirring Reflux for 3 hours;The n-propanol was distilled off, the residue was washed with water, extracted with ethyl acetate and dried over anhydrous magnesium sulfate overnight. The ethyl acetate layer was swirled to obtain the crude product.The crude product was separated by column chromatography (eluent: ethyl acetate: n-hexane = 7: 3) to give 99.1 mg of PAD-2. The structure was as follows. The yield was 60.1%.

Reference： [1]Current Patent Assignee: SICHUAN UNIVERSITY - CN104178132, 2017, B Location in patent: Paragraph 0054-0056; 0060-0061

44
[ 28286-88-6 ]
[ 123-11-5 ]
C₁₈H₁₄N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50.2%	With piperidine In propan-1-ol for 3h; Reflux;	1 Synthesis of PAD-5: 2,6-Dimethyl-4-pyranylidenemalononitrile (86.0 mg, 0.50 mmol) and 4-methoxybenzaldehyde (116.0 mg, 0.50 mmol) in 10 mL of n-propanol,Then add 200 μL piperidine,Under stirringReflux for 3 hours;The n-propanol was distilled off, the residue was washed with water, extracted with ethyl acetate and dried over anhydrous magnesium sulfate overnight. The ethyl acetate layer was swirled to obtain the crude product.The crude product was separated by column chromatography (eluent: ethyl acetate: n-hexane = 4: 1) to give 25.6 mg of PAD-5. The structure was as follows. The yield was 50.2%.

Reference： [1]Current Patent Assignee: SICHUAN UNIVERSITY - CN104178132, 2017, B Location in patent: Paragraph 0054-0056; 0069-0070

45
[ 28286-88-6 ]
[ 1122-91-4 ]
2‑[2‑(4‑bromostyryl)‑6‑methyl‑4H‑pyran‑4‑ylidene]propanedinitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With sodium methylate In methanol at 20℃; for 24h;	General procedure for the synthesisof bromine-substituted pyranilidene derivatives General procedure: To a magnetically stirred mixture of 1 mmol pyranilidenederivatives (1 or 3) in dry MeOH, the appropriate amount(1 or 2 mmol) of 4-bromobenzaldehyde and same amountof NaOMe were added. After 24 h in room temperature,the reaction mixture was filtrated and obtained precipitatewas purified with recrystallization in MeOH.
23.2%	With piperidine In propan-1-ol for 3h; Reflux;	1 Synthesis of PAD-7: 2,6-Dimethyl-4-pyranylidenemalononitrile (86.0 mg, 0.50 mmol) and 4-bromobenzaldehyde (93.0 mg, 0.50 mmol) in 10 mL of n-propanol and add 200 μL piperidine, reflux with stirring for 3 hours;The n-propanol was distilled off, the residue was washed with water, extracted with ethyl acetate and dried over anhydrous magnesium sulfate overnight. The ethyl acetate layer was swirled to obtain the crude product.The crude product was separated by column chromatography (eluent: ethyl acetate: n-hexane = 4: 1) to give 38.8 mg of PAD-7. The structure was as follows. The yield was 23.2%.

Reference： [1]Rahimpour, Keshvar; Zarenezhad, Hassan; Teimuri-Mofrad, Reza [Journal of the Iranian Chemical Society, 2020, vol. 17, # 10, p. 2627 - 2636]
[2]Current Patent Assignee: SICHUAN UNIVERSITY - CN104178132, 2017, B Location in patent: Paragraph 0054-0056; 0075-0076

46
[ 28286-88-6 ]
[ 556-21-8 ]
[ 1620563-10-1 ]

Yield	Reaction Conditions	Operation in experiment
56%	With piperidine In propan-1-ol for 10h; Reflux;	1 Synthesis of PAD-9: 2,6-Dimethyl-4-pyranylidenemalononitrile (86.0 mg, 0.50 mmol) and (68.0 mg, 0.50 mmol) in 10 mL of n-propanol and add 200 μL of piperidine, Under reflux for 10 hours with stirring;The n-propanol was distilled off, the residue was washed with water, extracted with ethyl acetate and dried over anhydrous magnesium sulfate overnight. The ethyl acetate layer was swirled to obtain the crude product.The crude product was separated by column chromatography (eluent: ethyl acetate: n-hexane = 3: 7) to give 81.0 mg of PAD-9. The structure was as follows. The yield was 56.0%.

Reference： [1]Current Patent Assignee: SICHUAN UNIVERSITY - CN104178132, 2017, B Location in patent: Paragraph 0054-0056; 0081-0082

47
[ 28286-88-6 ]
[ 22042-73-5 ]
C₁₉H₁₆N₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With piperidine In propan-1-ol for 10h; Reflux;	2 Radioactive fluorine-labeled compound PAD-8: 2,6-Dimethyl-4-pyranylidenemalononitrile (86.0 mg, 0.50 mmol) and (83.0 mg, 0.50 mmol) in 10 mL of n-propanol and add 200 μL of piperidine,The mixture was refluxed with stirring for 10 hours; the n-propanol was distilled off, the residue was washed with water, extracted with ethyl acetate and dried over anhydrous magnesium sulfateNight; the ethyl acetate layer was swirled to give the crude product. The crude product was separated by column chromatography (eluent ethyl acetate: n-hexane = 2: 1)Isolated, 96.0 mg of Intermediate 1 was obtained in a yield of 60.0%.

Reference： [1]Current Patent Assignee: SICHUAN UNIVERSITY - CN104178132, 2017, B Location in patent: Paragraph 0089-0091

48
[ 28286-88-6 ]
[ 42906-19-4 ]
2-(2,6-bis((E)-4-(di-p-tolylamino)styryl)-4H-pyran-4-ylidene)malononitrile [ No CAS ]

Reference： [1]ChemPlusChem,2019,vol. 84,p. 1630 - 1637

49
[ 28286-88-6 ]
[ 87199-17-5 ]
C₁₇H₁₃BN₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With piperidine In acetonitrile Inert atmosphere; Reflux; Darkness;	1 1) Under nitrogen protection, 3 mmol of 2,6-dimethyl-4-pyranylidene malononitrile,1.5 mmol of 4-formylphenylboronic acid and 0.3 mL of piperidine in 10 mL of acetonitrile, heat and reflux for 5-10 hours in the dark, and then cool to room temperature;2) The solvent was removed under reduced pressure on a rotary evaporator, and the solvent was dissolved in dichloromethane, washed with saturated brine, deionized water, and dried over anhydrous sodium sulfate to obtain a crude product.3) The solvent of the above crude product is evaporated to dryness, and then the silica gel column is used for separation and purification.That is the prepared 2- (2- (4-borate styryl) -6-methyl-4H-pyran-4-ylidene) malononitrile fluorescent probe,The yield is about 60%.

Reference： [1]Current Patent Assignee: NANJING UNIVERSITY OF INFORMATION SCIENCE & TECHNOLOGY - CN110698503, 2020, A Location in patent: Paragraph 0022-0026

50
[ 28286-88-6 ]
[ 1122-91-4 ]
2‑[2,6‑bis(4‑bromostyryl)‑4H‑pyran‑4‑ylidene]propanedinitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With sodium methoxide In methanol at 20℃; for 24h;	General procedure for the synthesisof bromine-substituted pyranilidene derivatives General procedure: To a magnetically stirred mixture of 1 mmol pyranilidenederivatives (1 or 3) in dry MeOH, the appropriate amount(1 or 2 mmol) of 4-bromobenzaldehyde and same amountof NaOMe were added. After 24 h in room temperature,the reaction mixture was filtrated and obtained precipitatewas purified with recrystallization in MeOH.
	With piperidine In acetonitrile at 100℃; for 24h; Inert atmosphere;	2. Synthesis All the target compounds were synthesized according to the procedure as shown in Scheme 1. A mixture of 2,6-dimethyl-γ-pyrone (3.00 g, 24.17 mmol) and malononitrile (2.40 g, 36.25 mmol) in acetic anhydride (50 mL) was heated at 130°C for 3 h. After cooling, the reaction solution was poured into ice water (1000 mL). The precipitated solid was recrystallized in ethyl alcohol (100 mL). The obtained brownish-needle like crystal (0.50 g, 2.90 mmol) and related aldehyde (5.80 mmol) were dissolved in the solution of acetonitrile (50 mL) and piperidine (0.60 mL). The mixture was heated at 100°C under nitrogen atmosphere for 24 h. After cooling, the mixture was poured into cold methanol (50 mL) and then a large amount of solids separated out. After vacuum filtration, the crude product was washed with methanol (20 mL× 3). The residue was purified by column chromatography through silica gel with petroleum ether/dichloromethane (1/2, v/v) to afford the pure target compound.

Reference： [1]Rahimpour, Keshvar; Zarenezhad, Hassan; Teimuri-Mofrad, Reza [Journal of the Iranian Chemical Society, 2020, vol. 17, # 10, p. 2627 - 2636]
[2]Zhang, Jiayu; Lu, Jiayu; Wang, Wen; Zhang, Xinghong; Lan, Haichuang; Xiao, Shuzhang [Tetrahedron Letters, 2022, vol. 100]

51
[ 28286-88-6 ]
[ 51325-91-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium methylate / methanol / 24 h / 20 °C 2: potassium carbonate; copper(l) iodide; <i>L</i>-proline / dimethyl sulfoxide / 24 h / 100 °C / Inert atmosphere

Reference： [1]Rahimpour, Keshvar; Zarenezhad, Hassan; Teimuri-Mofrad, Reza [Journal of the Iranian Chemical Society, 2020, vol. 17, # 10, p. 2627 - 2636]

52
[ 28286-88-6 ]
[ 769971-95-1 ]
C₂₄H₁₅N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43.7%	With piperidine In acetonitrile for 8h; Reflux;	2.5. Synthesis of BPMOH 0.27 g (1.2 mmol) of 3′-formyl-4′-hydroxybiphenyl-4-carbonitrile[34] and 0.204 g (1.2 mmol) of 2-(2,6-dimethyl-4H-pyran-4-ylidene)malononitrile were poured into a 100 mL round-bottom flask with one drop of piperidine as a catalyst and 20 mL of acetonitrile as a solvent.The mixture was stirred at reflux temperature for 8 h. The precipitatedsolid was filtered and washed three times by using coldacetonitrile, and after drying, the product BPMOHwas obtained as a yellowsolid(43.7%). 1H NMR(600MHz, DMSO-d6) δ 10.66 (s, 1H), 8.10 (d,J=1.7 Hz, 1H), 7.90 (s, 4H), 7.78 (d, J=16.3 Hz, 1H), 7.68 (dd, J=8.5,2.0 Hz, 1H), 7.50 (d, J = 16.3 Hz, 1H), 7.06 (d, J = 8.5 Hz, 1H), 6.86 (d,J = 1.8 Hz, 1H), 6.70 (s, 1H), 2.48 (s, 3H)·13C NMR (150 MHz, DMSOd6)δ 164.67, 160.63, 157.65, 157.23, 144.41, 133.21, 129.86, 127.23,126.62, 119.36, 115.95, 109.67, 107.39, 106.32, 56.14, 19.92. HRMS(EI) m/z calcd for [C24H15N3O2+H]+: 378.1243, Found: 378.1234.

Reference： [1]Chen, Song; Hou, Peng; Liu, Lei; Sun, Jingwen; Wang, Haijun [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2020, vol. 241]

53
[ 28286-88-6 ]
[ 100-52-7 ]
C₂₄H₁₆N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32%	With piperidine In acetonitrile at 76℃; for 24h; Inert atmosphere;	1 1. Synthesis of the three pyranylidene malononitrile photosensitizer lead compounds of the present invention. The PS1 synthesis method includes the following steps: Weigh 0.17g (1mmoL) of 2,6-dimethyl-4-pyranylidene malononitrile and 0.21g (2mmoL) of benzaldehyde in 10mL of freshly steamed acetonitrile.Then add 2-3 drops of piperidine,The reaction was stirred at 76°C for 24h under the protection of argon,After the substrate reaction is complete, cool to room temperature,The above reaction solution was suction filtered and recrystallized with acetonitrile to obtain yellow crystals (0.1198 g), yield: 32%.
	With piperidine In acetonitrile for 24h; Inert atmosphere; Reflux;	The mixture of compound D1 (1.0 mmol), aldehyde (6.0 mmol), piperidine (1.0 mL) and acetonitrile (10 mL) was refluxed and reacted under N2 atmosphere for 24 hours.The reaction mixture was poured into 50 mL of methanol and cooled to room temperature to precipitate a crude product. The crude product was washed three times with acetone and methanol, and then dried to obtain the corresponding pure compound.
	With piperidine In acetonitrile at 100℃; for 24h; Inert atmosphere;	2. Synthesis All the target compounds were synthesized according to the procedure as shown in Scheme 1. A mixture of 2,6-dimethyl-γ-pyrone (3.00 g, 24.17 mmol) and malononitrile (2.40 g, 36.25 mmol) in acetic anhydride (50 mL) was heated at 130°C for 3 h. After cooling, the reaction solution was poured into ice water (1000 mL). The precipitated solid was recrystallized in ethyl alcohol (100 mL). The obtained brownish-needle like crystal (0.50 g, 2.90 mmol) and related aldehyde (5.80 mmol) were dissolved in the solution of acetonitrile (50 mL) and piperidine (0.60 mL). The mixture was heated at 100°C under nitrogen atmosphere for 24 h. After cooling, the mixture was poured into cold methanol (50 mL) and then a large amount of solids separated out. After vacuum filtration, the crude product was washed with methanol (20 mL× 3). The residue was purified by column chromatography through silica gel with petroleum ether/dichloromethane (1/2, v/v) to afford the pure target compound. SPM was obtained as a yellow solid (yield: 40.2%). 1H NMR (CDCl3, 400 MHz): δ 7.63-7.55 (m, 5H), 7.53 (s, 1H), 7.51-7.39 (m, 6H), 6.81 (s, 1H), 6.77 (s, 1H), 6.72 (s, 2H). 13C NMR (CDCl3, 100 MHz): δ 158.11, 155.71, 138.03, 134.47, 130.46, 129.15, 127.82, 118.19, 115.03, 107.25. HRMS: calcd for C24H17N2O [M+H]+ 349.1341, found 349.1334..

Reference： [1]Current Patent Assignee: ZUNYI MEDICAL UNIVERSITY - CN111484469, 2020, A Location in patent: Paragraph 0043-0045
[2]Current Patent Assignee: WENZHOU UNIVERSITY - CN112851582, 2021, A Location in patent: Paragraph 0065-0068
[3]Zhang, Jiayu; Lu, Jiayu; Wang, Wen; Zhang, Xinghong; Lan, Haichuang; Xiao, Shuzhang [Tetrahedron Letters, 2022, vol. 100]

54
[ 28286-88-6 ]
[ 120-21-8 ]
C₃₂H₃₄N₄O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With piperidine In acetonitrile at 76℃; for 24h; Inert atmosphere;	1 The PS3 synthesis method includes the following steps: Weigh 0.17g (1mmoL) of 2,6-dimethyl-4-pyranylidene malononitrile, 0.49g (2mmoL) of N,N-diethyl-4-aminobenzaldehyde, and dissolve in 10ml of freshly steamed acetonitrile Then add 2-3 drops of piperidine and stir the reaction at 76°C for 24 hours under the protection of argon. After the substrate reaction is complete, cool to room temperature, filter the above reaction solution and recrystallize it with acetonitrile to obtain brown crystals (0.3581 g), yield: 73%.

Reference： [1]Current Patent Assignee: ZUNYI MEDICAL UNIVERSITY - CN111484469, 2020, A Location in patent: Paragraph 0049-0051

55
[ 28286-88-6 ]
5-(N,N-diphenylamino)furan-2-carbaldehyde [ No CAS ]
2-(2,6-bis((E)-2-(5-(diphenylamino)furan-2-yl)vinyl)-4H-pyran-4-ylidene)malononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With piperidine In acetonitrile at 90℃; for 24h;	1.3 Synthesis of Alkyl near-infrared fluorescent probe 2-(2,6-bis((E)-2-(5-(diphenylamino)furan-2-yl)vinyl)-4H-pyran-4-ylidene)Malononitrile (I) Put 0.292g (1.108mmol) 5-(diphenylamino)furan-2-carboxaldehyde and 0.087g (0.504mmol) 2,6-dimethyl-4-pyranylidene malononitrile into a 50ml single-necked flask Add 21ml acetonitrile and 0.2ml piperidine, and react at 90°C for 24 hours; recrystallize in acetonitrile to obtain near-infrared fluorescent probe I with a yield of 80%.

Reference： [1]Current Patent Assignee: SHANDONG UNIVERSITY - CN111689950, 2020, A Location in patent: Paragraph 0058; 0067-0073

56
[ 28286-88-6 ]
[ 133878-94-1 ]
2-(2,6-bis((E)-2-(5-(diphenylamino)thiophen-2-yl)vinyl)-4H-pyran-4-ylidene)malononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With piperidine In acetonitrile at 90℃; for 24h;	2.3 Synthesis of Alkyl near-infrared fluorescent probe 2-(2,6-bis((E)-2-(5-(diphenylamino)thiophen-2-yl)vinyl)-4H-pyran-4-ylidene)Malononitrile (II) Put 0.296g (1.3074mmol) 5-(diphenylamino)thiophene-2-carboxaldehyde and 0.081g (0.568mmol) 2,6-dimethyl-4-pyranylidene malononitrile into a 50ml single-necked flask , Add 25ml acetonitrile and 0.3ml piperidine, react at 90°C for 24 hours. The near-infrared fluorescent probe II was obtained by recrystallization in acetonitrile with a yield of 76%.

Reference： [1]Current Patent Assignee: SHANDONG UNIVERSITY - CN111689950, 2020, A Location in patent: Paragraph 0074; 0081-0088

57
[ 28286-88-6 ]
[ 1387005-14-2 ]
2-(2,6-bis((E)-2-(5-(9H-carbazol-9-yl)thiophene-2-yl)vinyl)-4H-pyran-4-ylidene)propanedinitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With piperidine In acetonitrile at 88℃; for 24h;	2.3 (3) Near-infrared fluorescent probe 2-(2,6-bis((E)-2-(5-(9H-carbazol-9-yl)thiophen-2-yl)vinyl)-4H-pyran Synthesis of -4-alkylene)malononitrile Put 0.277g (1mmol) 5-(9H-carbazol-9-yl)thiophene-2-carbaldehyde and 0.086g (0.5mmol) 2,6-dimethyl-4-pyranylidene malononitrile into 50ml Add 20ml acetonitrile and 0.2ml piperidine to a single-necked flask, and react at 88°C for 24 hours. It was recrystallized in acetonitrile to obtain the near-infrared fluorescent probe II with a yield of 87%.

Reference： [1]Current Patent Assignee: SHANDONG UNIVERSITY - CN111961040, 2020, A Location in patent: Paragraph 0077; 0084-0090

58
[ 28286-88-6 ]
5-(9H-carbazol-9-yl)furan-2-carbaldehyde [ No CAS ]
2-(2,6-bis((E)-2-(5-(9H-carbazol-9-yl)furan-2-yl)vinyl)-4H-pyran-4-ylidene)propanedinitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With piperidine In acetonitrile at 80℃; for 24h;	1.3 (3) Near infrared fluorescent probe 2-(2,6-Bis((E)-2-(5-(9H-carbazol-9-yl)furan-2-yl)vinyl)-4H-pyran-4-alkylene)propane Dinitrile Synthesis of Put 0.261g (1mmol) 5-(9H-carbazol-9-yl)furan-2-carbaldehyde and 0.086g (0.5mmol) 2,6-dimethyl-4-pyranylidene malononitrile into 50ml Add 20ml acetonitrile and 0.2ml piperidine to a single-necked flask, and react at 88°C for 24 hours. The near-infrared fluorescent probe I was obtained by recrystallization in acetonitrile with a yield of 84%.

Reference： [1]Current Patent Assignee: SHANDONG UNIVERSITY - CN111961040, 2020, A Location in patent: Paragraph 0059; 0069-0076

59
[ 28286-88-6 ]
[ 329025-44-7 ]
2-(2,6-bis((E)-2-(4-(4-(diphenylamino)phenyl)furyl-1-vinyl))-4H-pyran-4-ylidene)malononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%	With piperidine In acetonitrile at 80℃; for 24h; Inert atmosphere;	3.3 (3) Synthesis of 2-(2,6-bis((E)-2-(4-(4-(diphenylamino)phenyl)furyl-1-vinyl))-4H-pyran-4-ylidene)malononitrile (I-3) 5-(4-(Diphenylamino)phenyl)furan-2-carboxaldehyde (1.1mmol, 373.3mg) and 2,6-dimethyl-4-pyranylidene malononitrile (0.5mmol, 86.1mg) Dissolve in 50mL of acetonitrile, add 0.3mL of piperidine, and under N2, reflux for 24h at 80°C; after the reaction, cool to room temperature, let stand at -4 for 12h, filter under reduced pressure to obtain the crude product . The crude product obtained was purified by silica gel column chromatography (the eluent is a mixed solvent of ethyl acetate and petroleum ether, the volume ratio of ethyl acetate to petroleum ether is 1:20, and dichloromethane is used as the wash after the red product flows out. Removal) to obtain the target product near-infrared luminescent triphenylamine derivative fluorescent molecule I-3, with a yield of 46%.

Reference： [1]Current Patent Assignee: SHANDONG UNIVERSITY - CN112812088, 2021, A Location in patent: Paragraph 0096; 0104-0111

60
[ 291279-14-6 ]
[ 28286-88-6 ]
2-(2,6-bis((E)-2-(4-(4-(diphenylamino)phenyl)thienyl-1-vinyl))-4H-pyran-4-ylidene)malononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With piperidine; In acetonitrile; at 80℃; for 24h;Inert atmosphere;	5-(4-(Diphenylamino)phenyl)furan-2-carbaldehyde (1.1mmol, 390.5mg) and 2,6-dimethyl-4-pyranylidene malononitrile (0.5mmol, 86.1mg) Dissolve in 50mL of CH3CN, add 0.3mL of piperidine, and under N2, reflux for 24h at 80C; after the reaction, cool to room temperature, stand at -4 for 12h, and filter under reduced pressure to obtain the crude product ; Purify the obtained crude product using silica gel column chromatography (first eluent is a mixed solvent of ethyl acetate and petroleum ether, the volume ratio of ethyl acetate and petroleum ether is 1:20, after the red product flows out, use dichloromethane Is an eluent) to obtain the target product near-infrared luminescent triphenylamine derivative fluorescent molecule I-4 with a yield of 50%.

Reference： [1]Patent: CN112812088,2021,A .Location in patent: Paragraph 0096; 0104-0111

61
[ 28286-88-6 ]
[ 133878-93-0 ]
2-(2,6-bis((E)-2-(4-(4-(diphenylamino)-phenyl)phenyl-1-vinyl))-4H-pyran-4-ylidene)malononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With piperidine In acetonitrile at 80℃; for 24h; Inert atmosphere;	1.3 (3) Synthesis of 2-(2,6-bis((E)-2-(4-(4-(diphenylamino)phenyl)phenyl-1-vinyl))-4H-pyran-4-ylidene) malononitrile (I-1) 4'-(Diphenylamino)-[1,1'-biphenyl]-4-carbaldehyde (0.42mmol, 146.7mg) and 2,6-dimethyl-4-pyranylidene malononitrile (0.2 mmol, 34.4 mg) was dissolved in 15 mL of acetonitrile, 0.05 mL of piperidine was added, and the reaction was refluxed at 80°C for 24h under N2; after the reaction, cooled to room temperature, left standing at -4°C for 12h, and filtered under reduced pressure. , A crude product. The crude product obtained is purified by silica gel column chromatography (first eluent is a mixed solvent of ethyl acetate and petroleum ether, the volume ratio of ethyl acetate and petroleum ether is 1:20, when the red product flows out, use dichloromethane as Eluent) to obtain the target product near-infrared luminescent triphenylamine derivative fluorescent molecule I-1, dark red solid powder, and the yield is 67%.

Reference： [1]Current Patent Assignee: SHANDONG UNIVERSITY - CN112812088, 2021, A Location in patent: Paragraph 0062; 0072-0079

62
[ 28286-88-6 ]
[ 104-87-0 ]
C₂₆H₂₀N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With piperidine In acetonitrile for 24h; Inert atmosphere; Reflux;	General procedure: Compound D1(1.0mmol), a mixture of different aldehydes (6.0mmol), piperidine (1.0mL) and acetonitrile (10mL) in N2The reaction was refluxed under the atmosphere for 24h.The reaction mixture was poured into 50 mL of methanol and cooled to room temperature to precipitate a crude product.The crude product was washed three times with acetone and methanol, and then dried to obtain the corresponding pure compound.

Reference： [1]Current Patent Assignee: WENZHOU UNIVERSITY - CN112745299, 2021, A Location in patent: Paragraph 0055-0061

63
[ 28286-88-6 ]
4-[2-(1H-imidazole-1-yl)ethoxy]benzaldehyde [ No CAS ]
C₃₄H₂₈N₆O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79.3%	With piperidine In ethanol Reflux;	2.3. Synthesis of ImDCM-1 A mixture of 4-[2-(1H-imidazole-1-yl)ethoxy]benzaldehyde (0.432g,2 mmol), 2-(2,6-dimethyl-4H-pyran-4-ylidene)malononitrile (0.172g, 1 mmol) and piperidine (0.5 mL) in dry ethanol were heated underreflux till a large amount of precipitates appeared. After cooling down toroom temperature, the resulting solid was collected and washed by coldethanol for several times. The crude product was purified by recrystallizationfrom CH3CN/EtOH (v/v = 1 : 1) to give ImDCM-1 as yellowpowder (0.450 g, 79.3%). M. p.: >300 C. 1H NMR (400 MHz, DMSO-d6)δ 7.77-7.70 (m, 8H), 7.27-7.23 (m, 4H), 7.04 (d, J = 8.8 Hz, 4H), 6.90(s, 2H), 6.82 (s, 2H), 4.39 (t, J = 5.0 Hz, 4H), 4.32 (t, J = 4.8 Hz, 4H). 13C NMR (100 MHz, DMSO-d6) δ 159.70, 159.24, 156.16, 137.67, 129.96,128.32, 119.77, 117.00, 115.71, 115.05, 106.44, 67.36, 55.85, 45.54.HRMS (m/z) calcd for [M+H]+: 569.2301, found: 569.2393; calcd for[M+Na]+: 591.2121, found: 591.2121.

Reference： [1]Huang, Kun; Li, Qi; Qin, Dabin; Qiu, Qi; Zeng, Xianshun; Zhang, Xiangyu [Dyes and Pigments, 2021, vol. 193]

64
[ 28286-88-6 ]
[ 10040-98-9 ]
C₃₀H₂₀N₆O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71.2%	With piperidine In ethanol Reflux;	2.4. Synthesis of ImDCM-2 A mixture of 4-(1-imidazolyl)benzaldehyde (0.340 g, 2 mmol), 2-(2,6-dimethyl-4H-pyran-4-ylidene)malononitrile (0.172 g, 1 mmol) andpiperidine (0.5 mL) in dry ethanol were heated under reflux till a largeamount of precipitates appeared. After cooling down to ambient temperature,the resulting solid was collected and washed by cold ethanolfor twice. ImDCM-2 was purified by recrystallization from CH3CN/EtOH(v/v = 1 : 1) as faint yellow powder (0.341 g, 71.2%). M. p.: 214-216 C.1H NMR (400 MHz, DMSO-d6) δ 8.40 (s, 2H), 7.96 (d, J = 8.4 Hz, 4H),7.87-7.80 (m, 8H), 7.49 (d, J = 16.2 Hz, 2H), 7.15 (s, 2H), 6.93 (s, 2H).13 C NMR (100 MHz, DMSO-d6) δ 158.74, 156.05, 137.79, 136.45,135.52, 133.44, 130.13, 129.62, 120.27, 119.51, 117.70, 115.41,107.46, 57.14. HRMS (m/z) calcd for [M + H]+: 481.1777, found:481.1806.

Reference： [1]Huang, Kun; Li, Qi; Qin, Dabin; Qiu, Qi; Zeng, Xianshun; Zhang, Xiangyu [Dyes and Pigments, 2021, vol. 193]

65
[ 28286-88-6 ]
[ 39208-00-9 ]
2-{3-[4-(4-dimethylaminophenyldiazenyl)styryl]-6-methyl-4H-pyran-4-ylidene}malononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With piperidine In ethanol Reflux; Inert atmosphere;	Synthesis of chromophores 1 and 2 (general procedure) General procedure: A mixture of aldehyde 3a,b (0.4 mmol), either (2,6-dimethyl-4H-pyran-4-ylidene)malononitrile (0.10 g, 0.6 mmol) or (3,5,5-trimethylcyclohex-2-en-1-ylidene)malononitrile (0.11 g, 0.6 mmol),piperidine (0.1 mL, 1 mmol), and EtOH (20 mL) was refl uxedfor 24 h, cooled to room temperature and concentrated in vacuo.Products were purifi ed by silica gel column chromatographyusing dichloromethane-hexane (1 : 9, v/v) as an eluent.

Reference： [1]Abashev, G. G.; Lunegov, I. V.; Sklyaeva, E. V.; Slobodinyuk, D. G.; Vasyanin, A. N. [Russian Chemical Bulletin, 2022, vol. 71, # 2, p. 341 - 349][Izv. Akad. Nauk, Ser. Khim., 2022, # 2, p. 341 - 349]

66
[ 28286-88-6 ]
[ 92278-49-4 ]
2-{3-[4-(4-dimethylaminostyryl)styryl]-6-methyl-4H-pyran-4-ylidene}malononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With piperidine In ethanol Reflux; Inert atmosphere;	Synthesis of chromophores 1 and 2 (general procedure) General procedure: A mixture of aldehyde 3a,b (0.4 mmol), either (2,6-dimethyl-4H-pyran-4-ylidene)malononitrile (0.10 g, 0.6 mmol) or (3,5,5-trimethylcyclohex-2-en-1-ylidene)malononitrile (0.11 g, 0.6 mmol),piperidine (0.1 mL, 1 mmol), and EtOH (20 mL) was refl uxedfor 24 h, cooled to room temperature and concentrated in vacuo.Products were purifi ed by silica gel column chromatographyusing dichloromethane-hexane (1 : 9, v/v) as an eluent.

Reference： [1]Abashev, G. G.; Lunegov, I. V.; Sklyaeva, E. V.; Slobodinyuk, D. G.; Vasyanin, A. N. [Russian Chemical Bulletin, 2022, vol. 71, # 2, p. 341 - 349][Izv. Akad. Nauk, Ser. Khim., 2022, # 2, p. 341 - 349]

Type	HazMat fee for 500 gram (Estimated)
Excepted Quantity	USD 0.00
Limited Quantity	USD 15-60
Inaccessible (Haz class 6.1), Domestic	USD 80+
Inaccessible (Haz class 6.1), International	USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic	USD 100+
Accessible (Haz class 3, 4, 5 or 8), International	USD 200+

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

CAS No. :	28286-88-6	MDL No. :	MFCD00181519
Formula :	C₁₀H₈N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XYBUCJYJVULPHW-UHFFFAOYSA-N
M.W :	172.18	Pubchem ID :	119915
Synonyms :

Num. heavy atoms :	13
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.2
Num. rotatable bonds :	0
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	47.23
TPSA :	56.81 Å²

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.4 cm/s

[ CAS No. 28286-88-6 ] {[proInfo.proName]}

Quality Control of [ 28286-88-6 ]

Related Doc. of [ 28286-88-6 ]

Product Details of [ 28286-88-6 ]

Calculated chemistry of [ 28286-88-6 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 28286-88-6 ]

Application In Synthesis of [ 28286-88-6 ]

[ 28286-88-6 ] Synthesis Path-Downstream 1~66

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Log Po/w (iLOGP) :	2.02
Log Po/w (XLOGP3) :	1.34
Log Po/w (WLOGP) :	2.17
Log Po/w (MLOGP) :	0.12
Log Po/w (SILICOS-IT) :	1.55
Consensus Log Po/w :	1.44

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

Log S (ESOL) :	-1.75
Solubility :	3.05 mg/ml ; 0.0177 mol/l
Class :	Very soluble
Log S (Ali) :	-2.13
Solubility :	1.26 mg/ml ; 0.00733 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.48
Solubility :	5.66 mg/ml ; 0.0329 mol/l
Class :	Soluble

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.33

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P310+P330-P302+P352+P312+P361+P364-P304+P340+P311-P305+P351+P338+P337+P313-P403+P233-P405-P501	UN#:	3439
Hazard Statements:	H301+H311+H331-H315-H319	Packing Group:	Ⅲ
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling