[ CAS No. 919789-80-3 ] {[proInfo.proName]}

Name: 919789-80-3|4-(1,2,2-Triphenylvinyl)aniline|98%
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SKU: A1149517
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Quality Control of [ 919789-80-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 919789-80-3 ]

SDS Specification

Alternatived Products of [ 919789-80-3 ]

Product Details of [ 919789-80-3 ]

CAS No. :	919789-80-3	MDL No. :	MFCD31697689
Formula :	C₂₆H₂₁N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WCNQRPKNQRXHQJ-UHFFFAOYSA-N
M.W :	347.45	Pubchem ID :	15946553
Synonyms :

Calculated chemistry of [ 919789-80-3 ]

Physicochemical Properties

Num. heavy atoms :	27
Num. arom. heavy atoms :	24
Fraction Csp3 :	0.0
Num. rotatable bonds :	4
Num. H-bond acceptors :	0.0
Num. H-bond donors :	1.0
Molar Refractivity :	115.19
TPSA :	26.02 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-3.25 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.47
Log Po/w (XLOGP3) :	7.28
Log Po/w (WLOGP) :	6.28
Log Po/w (MLOGP) :	5.81
Log Po/w (SILICOS-IT) :	5.95
Consensus Log Po/w :	5.76

Druglikeness

Lipinski :	1.0
Ghose :	None
Veber :	0.0
Egan :	1.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-6.97
Solubility :	0.0000369 mg/ml ; 0.000000106 mol/l
Class :	Poorly soluble
Log S (Ali) :	-7.65
Solubility :	0.00000774 mg/ml ; 0.0000000223 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-9.64
Solubility :	0.0000000794 mg/ml ; 0.0000000002 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.49

Safety of [ 919789-80-3 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 919789-80-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 919789-80-3 ]

[ 919789-80-3 ] Synthesis Path-Downstream 1~4

1
[ 119-61-9 ]
[ 1137-41-3 ]
(2-(4-aminophenyl)ethene-1,1,2-triyl)tribenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With pyridine; titanium tetrachloride; zinc In tetrahydrofuran at 68℃; for 14h; Inert atmosphere;	Synthesis of 1 and 2 General procedure: Under an Ar atmosphere, a three-necked flask equipped with a magnetic stirrer was charged with zinc powder (1.6 g, 24 mmol) and 40 mL THF. The mixture was cooled to -5°C, and TiCl4 (1.3 mL, 12 mmol) was slowly added by a syringe with the temperature kept under 10°C. The suspending mixture was warmed to room temperature and stirred for 0.5 h, then heated at reflux for 2.5 h. The mixture was again cooled to -5 to 0°C, charged with pyridine (0.5 mL, 6 mmol) and stirred for 10 min. The solution of two carbonyl compounds (4-aminobenzophenone: benzophenone or 4, 4’-dimethoxybenzophenone: 4-aminobenzophenone) in 1:1.2 mole ratio in 15 mL THF was added slowly. After addition, the reaction mixture was heated to reflux until the carbonyl compounds were consumed (monitored by TLC) (about 14h). The reaction was quenched with 10% K2CO3 aqueous solution and taken up with CH2Cl2. The organic layer was collected and concentrated. The crude material was purified by flash chromatography to give the desired products.
82.3%	With pyridine; titanium tetrachloride; zinc In tetrahydrofuran Inert atmosphere; Cooling with ice; Reflux;	1.2 Step 2. Synthesis of Compound B: 5.8 g of zinc powder was added to a 250 mL three-necked flask, and vacuum was applied continuously for 2 to 4 times.Nitrogen gas is circulated to remove oxygen and water from the system. Under nitrogen protection, 60 mL of THF is added.Under ice salt bath conditions, 5 mL of TiCl4 was slowly added dropwise with a constant pressure dropping funnel, and stirred at room temperature for 2.5 h.Then change to ice salt bath, add 1.53mL pyridine and stir for 10min.2 g of benzophenone, 1.75 g of 4-aminobenzophenone and 40 mL of dry THF solution were added slowly.Heat to reflux overnight, stop the reaction, work up, cool to room temperature, and quench with 10% K2CO3 solution.Filtration through celite, DCM extraction (100 mL×3), combined organic phase drying and steaming.A yellow solid was obtained in a yield of 82.3%.
80%	With pyridine; titanium tetrachloride; zinc In tetrahydrofuran Heating;

80%	With pyridine; titanium tetrachloride; zinc In tetrahydrofuran
74%	With pyridine; titanium tetrachloride; zinc In tetrahydrofuran at 24℃; Inert atmosphere; Schlenk technique; Reflux;
72%	With titanium tetrachloride; zinc In tetrahydrofuran; pyridine Reflux;	TPE-NH2: TPE-NH2 was synthesized by the typical McMurry reaction according to the literature procedures [34]. Into a two-necked round-bound scosk (100mL) were added of zinc powder (Zn, 1.49 g, 22.8 mmol) and THF (60mL). The scosk was evacuated and flushed with dry nitrogen three times. After cooling to -5 °C, TiCl4 was slowly added. The mixture was stirred for 2.5 h at room temperature. After cooling to -5 °C again, pyridine (1.53 mL, 19.0 mmol) was added and the mixture was stirred for 10 min. Then the solution of BP (1.5 g, 7.6 mmol) and BP-NH2 (1.66 g, 9.1 mmol) in THF (40 mL) was added, the mixture was refluxed overnight. Afterwards, K2CO3 solution was added to quench the reaction. After cooling to room temperature, THF was removed by a rotatory evaporator. The solution was poured into water and extracted with DCM. The collected organic layer was dried over anhydrous Na2SO4. After filtration and solvent evaporation, the crude product was purified by silica-gel column chromatography using DCM/PE (1/2, v/v) as eluent. A pale yellow solid was obtained in 72 % yield. 1H NMR (400 MHz, CDCl3): δ 7.13-6.99 (m, 17H); 6.85-6.82 (d, 2H); 6.52-6.49 (d, 2H). 13C NMR (101 MHz, CDCl3): δ 144.69, 144.57, 144.52, 144.24, 141.25, 139.87, 135.04, 132.94, 131.89, 131.82, 131.78, 128.20, 128.12, 127.98, 127.96, 126.70, 126.54, 126.53, 115.19. IR (KBr, ν, cm-1): 3476, 3378, 3009.
51.2%	With pyridine; titanium tetrachloride; zinc In tetrahydrofuran Inert atmosphere; Reflux;
51.6%	With pyridine; titanium tetrachloride; zinc In tetrahydrofuran Inert atmosphere; Reflux;
38%	With titanium tetrachloride; zinc In tetrahydrofuran Inert atmosphere; Reflux;
10%	With pyridine; titanium tetrachloride; zinc In tetrahydrofuran at -10℃; for 3h; Inert atmosphere; Reflux;
	With titanium tetrachloride; zinc In tetrahydrofuran Reflux;
4.16 g	With titanium tetrachloride; zinc In tetrahydrofuran at -78 - 80℃; Inert atmosphere;	1.1; 9 1) Synthesis of compound TPE-NH2 Add zinc powder (3.3g), 4-aminobenzophenone (2.5g), benzophenone (2.5g) to a fully dried 250mL two-necked round-bottomed flask and evacuate and fill the argon gas for 3 times. 100 mL of ultra-dry tetrahydrofuran was injected under an atmosphere. The mixture was placed in a liquid nitrogen acetone bath and cooled to -78°C, and titanium tetrachloride (2.9 mL) was slowly added dropwise. After the addition was completed, the reaction mixture was continuously stirred for 15 min. The liquid nitrogen acetone bath was removed, and the reaction system was gradually returned to room temperature and stirring was continued for half an hour. Finally, it was heated to 80°C and refluxed for 12 hours. After the reaction is complete, quench the reaction with 1mol/L hydrochloric acid, filter with suction, take the filtrate, extract with ethyl acetate, spin dry, use 10:1 ratio of dichloromethane: methanol as eluent, and separate by column chromatography to obtain the compound A1: 1-(4-aminophenyl)-1,2,2-triphenylethylene (4.16g).
	With titanium tetrachloride; zinc In tetrahydrofuran Inert atmosphere; Schlenk technique;
	With titanium tetrachloride; zinc In tetrahydrofuran
	With pyridine; titanium tetrachloride; zinc In tetrahydrofuran

Reference： [1]Chen, Shengxin; Qiu, Rongmao; Yu, Qiuhan; zhang, Xueyan; Wei, Ming; Dai, Zhenya [Tetrahedron Letters, 2018, vol. 59, # 27, p. 2671 - 2678]
[2]Current Patent Assignee: CHANGZHOU UNIVERSITY - CN109369543, 2019, A Location in patent: Paragraph 0021; 0023
[3]Duan, Xin-Fang; Zeng, Jing; Lue, Jia-Wei; Zhang, Zhan-Bin [Synthesis, 2007, # 5, p. 713 - 718]
[4]Lee, Yi-Ting; Chang, Yung-Ting; Chen, Chao-Tsen; Chen, Chin-Ti [Journal of Materials Chemistry C, 2016, vol. 4, # 29, p. 7020 - 7025]
[5]Chen, Weijie; Zhang, Chen; Han, Xie; Liu, Sheng Hua; Tan, Ying; Yin, Jun [Journal of Organic Chemistry, 2019, vol. 84, # 22, p. 14498 - 14507]
[6]Li, Wen-Bo; Luo, Wei-Jian; Li, Kai-Xuan; Yuan, Wang-Zhang; Zhang, Yong-Ming [Chinese Chemical Letters, 2017, vol. 28, # 6, p. 1300 - 1305]
[7]Cai, Yunbo; Li, Lingzhi; Wang, Zongtan; Sun, Jing Zhi; Qin, Anjun; Tang, Ben Zhong [Chemical Communications, 2014, vol. 50, # 64, p. 8892 - 8895]
[8]Wang, Yi Jia; Li, Zeyu; Tong, Jiaqi; Shen, Xiao Yuan; Qin, Anjun; Sun, Jing Zhi; Tang, Ben Zhong [Journal of Materials Chemistry C, 2015, vol. 3, # 15, p. 3559 - 3568]
[9]Liang, Chunshuang [RSC Advances, 2020, vol. 10, # 48, p. 29043 - 29050]
[10]Fan, Ying; Hu, Yuchen; Luo, Tingrong; Wu, Wen; Xia, Xuefeng; Zhang, Jinqiang; Zhang, Qianyu [Chemical Communications, 2021, vol. 57, # 93, p. 12520 - 12523]
[11]Sk, Bahadur; Patra, Abhijit [CrystEngComm, 2016, vol. 18, # 23, p. 4290 - 4294]
[12]Current Patent Assignee: HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY - WO2017/8743, 2017, A1 Location in patent: Paragraph 112
[13]Current Patent Assignee: SOUTH CHINA NORMAL UNIVERSITY - CN111116418, 2020, A Location in patent: Paragraph 0044; 0048-0052; 0086-0088
[14]Ma, Xiaoxie; Chi, Weijie; Han, Xie; Wang, Chao; Liu, Shenghua; Liu, Xiaogang; Yin, Jun [Chinese Chemical Letters, 2021, vol. 32, # 5, p. 1790 - 1794]
[15]Hu, Yi-Xiong; Li, Wei-Jian; Wang, Wei; Wang, Xu-Qing; Xu, Lin; Xu, Wei-Tao; Yang, Hai-Bo; Zhang, Dan-Yang [Angewandte Chemie - International Edition, 2021, vol. 60, # 34, p. 18761 - 18768][Angew. Chem., 2021, vol. 133, # 34, p. 18909 - 18916]
[16]Lv, Hong-Min; Jiang, Zi-Ke; Wang, Jing; Wang, Tao; Zhang, Xiao-Nan; Hu, Yi-Meng; Ma, Yan-Yan [New Journal of Chemistry, 2021, vol. 45, # 41, p. 19521 - 19530]

2
[ 166264-70-6 ]
[ 919789-80-3 ]

Yield	Reaction Conditions	Operation in experiment
96%	With palladium 10% on activated carbon; hydrazine hydrate In ethanol for 4h; Reflux;
96%	With palladium 10% on activated carbon; hydrazine hydrate In ethanol for 4h; Reflux;
94%	With palladium 10% on activated carbon; hydrazine hydrate In ethanol for 5h; Reflux;	1.2 2) Synthesis of compound b Compound a (3.77 g, 10 mmol) was dissolved in ethanol (100 mL).To the above solution was added 10% Pd/C (1 g) and hydrazine monohydrate (6.00 g, 120 mmol).The mixture was refluxed for 5 hours, then solid Pd/C was filtered and solvent was evaporated in vacuo.The residue was purified by flash column chromatography on silica to afford compound b. Yield: 3.54 g, 94%.

91%	Stage #1: (2-(4-nitrophenyl)ethene-1,1,2-triyl)tribenzene With palladium 10% on activated carbon In ethanol at 20℃; for 0.25h; Stage #2: With hydrazine hydrate In ethyl [2]alcohol for 4h; Reflux;
85%	Stage #1: (2-(4-nitrophenyl)ethene-1,1,2-triyl)tribenzene With palladium 10% on activated carbon In ethanol at 20℃; for 0.25h; Stage #2: With hydrazine hydrate In ethanol for 4h; Reflux;	1.3 (3) Synthesis of compound TPENH2: Compound 2 (1.2 g, 3.18 mmol), 10% Pd / C (100 mg),Was added to ethanol, stirred for 15 min at room temperature, hydrazine hydrate (85%) (5.4 mL, 95.4 mmol) was added to the reaction mixture and refluxed for 4 h,After cooling suction filtration, the filtrate was concentrated and then recrystallized from methanol to give the reduction product TPENH2,The yield is 85%.
51%	With hydrogenchloride; tin(ll) chloride In ethanol; water for 3h; Reflux;	2.3 2.2.3 Synthesis of (2-(4-Aminophenyl)Ethene-1,1,2-Triyl)Tribenzene (TPE-NH₂) Tin(II) chloride (4.015 g, 21.2 mmol) was dissolved in concentrated HCl (36%, 3.5 mL), then the solution was added dropwise to a suspension of compound TPE-HY (1.55 g, 4.1 mmol) in ethanol (3 mL) with rigorous magnetic stirring. After reflux for 3 h, the reaction system was cooled to room temperature. The formed precipitate was collected, and washed with water. The crude product was purified by flash chromatography on silica gel with petroleum ether/ethyl acetate (50:1, v/v) as the eluent and re-crystallized from EtOH to afford a white solid TPE-NH2 with a yield of 51%. 1H NMR (400 MHz, CDCl3) δ 7.08 (m, 13H), 7.01 (m, 2H), 6.81 (d, J = 8.4 Hz, 2H), 6.46 (d, J = 8.4 Hz, 2H), 4.09 (s, 2H); 13C NMR (100 MHz, CDCl3) δ 144.69, 144.36, 144.23, 144.19, 140.95, 139.34, 134.11, 132.52, 131.50, 131.44, 131.39, 127.69, 127.57, 127.54, 126.27, 126.09, 114.39; HR-MS calculated for C26H21N [M + H]+ m/z 348.1747, found [M + H]+ m/z 348.1744.
	With palladium 10% on activated carbon; hydrazine hydrate Reflux;
	Stage #1: (2-(4-nitrophenyl)ethene-1,1,2-triyl)tribenzene With palladium 10% on activated carbon In ethanol for 0.25h; Stage #2: With hydrazine hydrate In ethanol Reflux;	1.3 (3) Synthesis of 1-(4-amino)phenyl-1,2,2-tristyrene Dissolve 1.2g (3.18mmol) of 1-(4-nitro)phenyl-1,2,2-tristyrene and 100mg of 10% palladium on carbon in 50ml of ethanol and stir for 15min. Add 5.4 ml of 85% hydrazine hydrate, and heat to reflux overnight. After the reaction is over, add dichloromethane to dilute, filter with diatomaceous earth, wash three times with water, dry with anhydrous sodium sulfate and evaporate to dryness under reduced pressure. After the crude product is separated by column chromatography, 1-(4-amino)phenyl-1,2,2-tristyrene is obtained as a yellow solid.

Reference： [1]Han, Fangfang; Zhang, Ran; Zhang, Zhaoming; Su, Jianguo; Ni, Zhonghai [RSC Advances, 2016, vol. 6, # 72, p. 68178 - 68184]
[2]Parthiban; Pavithra; Reddy, L. Vinod Kumar; Sen, Dwaipayan; Samuel, Melvin S.; Singh, N. D. Pradeep [Organic and Biomolecular Chemistry, 2018, vol. 16, # 42, p. 7903 - 7909]
[3]Current Patent Assignee: CHINA UNIVERSITY OF MINING AND TECHNOLOGY - CN108546255, 2018, A Location in patent: Paragraph 0016; 0035; 0037; 0038
[4]Xiong, Jia-Bin; Xie, Wen-Zhao; Sun, Jian-Ping; Wang, Jin-Hua; Zhu, Zhi-Hua; Feng, Hai-Tao; Guo, Dong; Zhang, Hui; Zheng, Yan-Song [Journal of Organic Chemistry, 2016, vol. 81, # 9, p. 3720 - 3726]
[5]Current Patent Assignee: UNIV GANNAN NORMAL - CN106905199, 2017, A Location in patent: Paragraph 0028
[6]Xu, Gaoping; Tang, Yonghe; Ma, Yanyan; Xu, An; Lin, Weiying [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2018, vol. 188, p. 197 - 201]
[7]Sun, Ting; Cheng, Dandan; Chai, Yongshuai; Gong, Jian; Sun, Mengyu; Zhao, Feng [Dyes and Pigments, 2019, vol. 170]
[8]Current Patent Assignee: CHINA PHARMACEUTICAL UNIVERSITY - CN112724057, 2021, A Location in patent: Paragraph 0032; 0041-0042

3
[ 919789-80-3 ]
[ 287493-15-6 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
73.2%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine; sodium t-butanolate In toluene for 48h; Inert atmosphere; Schlenk technique; Reflux;	General procedure for the synthesis General procedure: Synthesis of compounds 1-3: A 50 mL two-necked round-bottom flask was evacuated under vacuum and then flushed with dry argon three times. Subsequently, compound I-1 (735.4 mg, 3.0 mmol) or I-2 (903.7 mg, 3.0 mmol) or I-3 (1072.0 mg, 3.0 mmol), Pd2(dba)3 (57.4 mg, 0.1 mmol), and t-BuONa (384.4 mg, 4.0 mmol) were added into the corresponding round-bottom flask. Next, toluene (30 ml), 4-(1,2,2-triphenylvinyl)aniline (347.5 mg, 1.0 mmol), and toluene solution of P(t-Bu)3 (2 ml) were added into the round-bottom flask. After that, the mixture was reuxed for 48 h and then cooled to room temperature. After completion of present reaction, the resulting mixture was extracted with dichloromethane and water, and then washed with brine three times. Organic layer was dried by anhydrous MgSO4, then the organic solvent was removed under vacuum, the residues were purified by column chromatography on silica gel with petroleum ether/dichloromethane (5:1) as eluent, affording the corresponding target product 1 (faint yellow solid), 2 (yellow solid) or 3 (light green solid) in a yield of 75.7%, 73.2% or 74.1%, respectively. 1: 1H NMR (500 MHz, CDCl3): δ (ppm) = 7.70 (d, J = 10 Hz, 2H), 7.64 (d, J = 10 Hz, 2H), 7.50 (d, J = 10 Hz, 2H), 7.35 (t, J = 7.5 Hz, 2H), 7.24 (s, 3H), 7.18-7.03 (m, 18H), 6.89-6.83 (m, 4H), 3.81 (s, 4H). 13C NMR (125 MHz, CDCl3): δ (ppm) = 146.8, 146.3, 144.5, 144.1, 143.8, 143.6, 143.0, 141.5, 140.7, 140.5, 137.7, 136.7, 132.2, 131.4, 131.4, 127.6, 127.6, 127.6, 126.8, 126.4, 126.3, 125.9, 124.9, 123.4, 122.5, 121.1, 120.3, 119.3, 36.9. EI-MS: m/z = 675.30[M]+. Anal. Calcd. For C52H37N: C, 92.41; H, 5.52, N, 2.07. Found: C, 92.50; H, 5.57; N, 2.01. 2: 1H NMR (500 MHz, CDCl3): δ (ppm) = 7.62 (d, J = 5 Hz, 2H), 7.56 (d, J = 10 Hz, 2H), 7.32-7.27 (m, 5H), 7.24-7.15 (m, 5H), 7.12-7.03 (m, 15H), 6.90-6.85 (m, 4H), 1.98-1.81 (m, 8H), 0.32 (t, J = 7.5 Hz, 12H). 13C NMR (125 MHz, CDCl3): δ (ppm) = 151.1, 149.7, 147.0, 146.3, 144.1, 143.8, 143.6, 141.3, 140.7, 140.4, 137.6, 136.4, 132.2, 131.4, 131.4, 127.6, 127.6, 126.8, 126.4, 126.4, 126.3, 126.2, 123.1, 122.7, 122.4, 120.1, 119.0, 118.9, 56.0, 32.7, 8.6. EI-MS: m/z = 787.40[M]+. Anal. Calcd. For C60H53N: C, 91.44; H, 6.78, N, 1.78. Found: C, 91.36; H, 6.85; N, 1.71. 3: 1H NMR (500 MHz, CDCl3): δ (ppm) = 7.61 (d, J = 5 Hz, 2H), 7.53 (d, J = 10 Hz, 2H), 7.30 (t, J = 5 Hz, 4H), 7.25 (s, 1H), 7.24-7.18 (m, 5H), 7.11-6.99 (m, 16H), 6.88 (s, 3H), 1.94-1.79 (m, 8H), 1.09-1.01 (m, 8H), 0.68-0.58 (m, 20H). 13C NMR (125 MHz, CDCl3): δ (ppm) = 151.9, 150.5, 146.8, 146.2, 144.1, 143.8, 143.6, 140.9, 140.8, 140.4, 137.7, 136.0, 132.1, 131.5, 131.4, 131.4, 127.6, 126.7, 126.5, 126.4, 126.3, 126.2, 123.0, 122.7, 122.4, 120.1, 119.0, 118.7, 54.9, 40.0, 26.0, 23.0, 13.9. EI-MS: m/z = 899.65[M]+. Anal. Calcd. For C68H69N: C, 90.72; H, 7.73, N, 1.56. Found: C, 90.79; H, 7.82; N, 1.51.

Reference： [1]Hu, Hao; Chen, Zhao; Pu, Shouzhi [Tetrahedron Letters, 2021, vol. 67]

4
[ 919789-80-3 ]
[ 88223-35-2 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
74.1%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine; sodium t-butanolate In toluene for 48h; Inert atmosphere; Schlenk technique; Reflux;	General procedure for the synthesis General procedure: Synthesis of compounds 1-3: A 50 mL two-necked round-bottom flask was evacuated under vacuum and then flushed with dry argon three times. Subsequently, compound I-1 (735.4 mg, 3.0 mmol) or I-2 (903.7 mg, 3.0 mmol) or I-3 (1072.0 mg, 3.0 mmol), Pd2(dba)3 (57.4 mg, 0.1 mmol), and t-BuONa (384.4 mg, 4.0 mmol) were added into the corresponding round-bottom flask. Next, toluene (30 ml), 4-(1,2,2-triphenylvinyl)aniline (347.5 mg, 1.0 mmol), and toluene solution of P(t-Bu)3 (2 ml) were added into the round-bottom flask. After that, the mixture was reuxed for 48 h and then cooled to room temperature. After completion of present reaction, the resulting mixture was extracted with dichloromethane and water, and then washed with brine three times. Organic layer was dried by anhydrous MgSO4, then the organic solvent was removed under vacuum, the residues were purified by column chromatography on silica gel with petroleum ether/dichloromethane (5:1) as eluent, affording the corresponding target product 1 (faint yellow solid), 2 (yellow solid) or 3 (light green solid) in a yield of 75.7%, 73.2% or 74.1%, respectively. 1: 1H NMR (500 MHz, CDCl3): δ (ppm) = 7.70 (d, J = 10 Hz, 2H), 7.64 (d, J = 10 Hz, 2H), 7.50 (d, J = 10 Hz, 2H), 7.35 (t, J = 7.5 Hz, 2H), 7.24 (s, 3H), 7.18-7.03 (m, 18H), 6.89-6.83 (m, 4H), 3.81 (s, 4H). 13C NMR (125 MHz, CDCl3): δ (ppm) = 146.8, 146.3, 144.5, 144.1, 143.8, 143.6, 143.0, 141.5, 140.7, 140.5, 137.7, 136.7, 132.2, 131.4, 131.4, 127.6, 127.6, 127.6, 126.8, 126.4, 126.3, 125.9, 124.9, 123.4, 122.5, 121.1, 120.3, 119.3, 36.9. EI-MS: m/z = 675.30[M]+. Anal. Calcd. For C52H37N: C, 92.41; H, 5.52, N, 2.07. Found: C, 92.50; H, 5.57; N, 2.01. 2: 1H NMR (500 MHz, CDCl3): δ (ppm) = 7.62 (d, J = 5 Hz, 2H), 7.56 (d, J = 10 Hz, 2H), 7.32-7.27 (m, 5H), 7.24-7.15 (m, 5H), 7.12-7.03 (m, 15H), 6.90-6.85 (m, 4H), 1.98-1.81 (m, 8H), 0.32 (t, J = 7.5 Hz, 12H). 13C NMR (125 MHz, CDCl3): δ (ppm) = 151.1, 149.7, 147.0, 146.3, 144.1, 143.8, 143.6, 141.3, 140.7, 140.4, 137.6, 136.4, 132.2, 131.4, 131.4, 127.6, 127.6, 126.8, 126.4, 126.4, 126.3, 126.2, 123.1, 122.7, 122.4, 120.1, 119.0, 118.9, 56.0, 32.7, 8.6. EI-MS: m/z = 787.40[M]+. Anal. Calcd. For C60H53N: C, 91.44; H, 6.78, N, 1.78. Found: C, 91.36; H, 6.85; N, 1.71. 3: 1H NMR (500 MHz, CDCl3): δ (ppm) = 7.61 (d, J = 5 Hz, 2H), 7.53 (d, J = 10 Hz, 2H), 7.30 (t, J = 5 Hz, 4H), 7.25 (s, 1H), 7.24-7.18 (m, 5H), 7.11-6.99 (m, 16H), 6.88 (s, 3H), 1.94-1.79 (m, 8H), 1.09-1.01 (m, 8H), 0.68-0.58 (m, 20H). 13C NMR (125 MHz, CDCl3): δ (ppm) = 151.9, 150.5, 146.8, 146.2, 144.1, 143.8, 143.6, 140.9, 140.8, 140.4, 137.7, 136.0, 132.1, 131.5, 131.4, 131.4, 127.6, 126.7, 126.5, 126.4, 126.3, 126.2, 123.0, 122.7, 122.4, 120.1, 119.0, 118.7, 54.9, 40.0, 26.0, 23.0, 13.9. EI-MS: m/z = 899.65[M]+. Anal. Calcd. For C68H69N: C, 90.72; H, 7.73, N, 1.56. Found: C, 90.79; H, 7.82; N, 1.51.

Reference： [1]Hu, Hao; Chen, Zhao; Pu, Shouzhi [Tetrahedron Letters, 2021, vol. 67]

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H202	Explosive; severe projection hazard
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H221	Flammable gas
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H223	Flammable aerosol
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H261	In contact with water releases flammable gas
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Health hazards
Code	Phrase
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H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
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H305	May be harmful if swallowed and enters airways
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H311	Toxic in contact with skin
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H313	May be harmful in contact with skin
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H315	Causes skin irritation
H316	Causes mild skin irritation
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H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
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H331	Toxic if inhaled
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H333	May be harmful if inhaled
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H371	May cause damage to organs
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H373	May cause damage to organs through prolonged or repeated exposure
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Code	Phrase
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H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 919789-80-3 ] {[proInfo.proName]}

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