[ CAS No. 52147-97-4 ] {[proInfo.proName]}

Name: 52147-97-4|(E)-2-Phenylethene-1-sulfonyl chloride|97%
Brand: Ambeed
SKU: A491072
Price: 5.0 USD
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Quality Control of [ 52147-97-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 52147-97-4 ]

CAS No. :	52147-97-4	MDL No. :	MFCD00007456
Formula :	C₈H₇ClO₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ONWRSBMOCIQLRK-VOTSOKGWSA-N
M.W :	202.66	Pubchem ID :	5369377
Synonyms :

Calculated chemistry of [ 52147-97-4 ] Expand+

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	50.29
TPSA :	42.52 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.85 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.72
Log Po/w (XLOGP3) :	2.37
Log Po/w (WLOGP) :	3.2
Log Po/w (MLOGP) :	1.81
Log Po/w (SILICOS-IT) :	1.77
Consensus Log Po/w :	2.17

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.83
Solubility :	0.301 mg/ml ; 0.00149 mol/l
Class :	Soluble
Log S (Ali) :	-2.9
Solubility :	0.253 mg/ml ; 0.00125 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.03
Solubility :	0.187 mg/ml ; 0.000925 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.46

Safety of [ 52147-97-4 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P260-P280-P303+P361+P353-P301+P330+P331-P304+P340+P310-P305+P351+P338+P310	UN#:	3261
Hazard Statements:	H314	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 52147-97-4 ]

* 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.

Upstream synthesis route of [ 52147-97-4 ]
Downstream synthetic route of [ 52147-97-4 ]

[ 52147-97-4 ] Synthesis Path-Upstream 1~3

1
[ 292638-84-7 ]
[ 52147-97-4 ]

Reference： [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 13, p. 5562 - 5586
[2] Phosphorus, Sulfur and Silicon and the Related Elements, 1990, vol. 53, # 1-4, p. 285 - 290
[3] Organic Preparations and Procedures International, 1991, vol. 23, # 5, p. 633 - 638
[4] Advanced Synthesis and Catalysis, 2009, vol. 351, # 18, p. 3128 - 3132
[5] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1995, vol. 34, # 9, p. 816 - 822
[6] Synthesis, 2005, # 20, p. 3639 - 3643
[7] European Journal of Medicinal Chemistry, 2011, vol. 46, # 10, p. 5034 - 5038
[8] European Journal of Medicinal Chemistry, 2013, vol. 64, p. 488 - 497
[9] Journal of Chemical Research, 2015, vol. 39, # 3, p. 141 - 144
[10] RSC Advances, 2016, vol. 6, # 72, p. 67805 - 67816
[11] Patent: US2017/145026, 2017, A1, . Location in patent: Paragraph 0966; 0967
[12] European Journal of Medicinal Chemistry, 2018, vol. 143, p. 891 - 898
[13] Organic Letters, 2018,

2
[ 14554-08-6 ]
[ 52147-97-4 ]

Reference： [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 25, p. 6326 - 6336

3
[ 98-85-1 ]
[ 52147-97-4 ]

Reference： [1] Journal of Organic Chemistry, 2003, vol. 68, # 20, p. 7911 - 7914

[ 52147-97-4 ] Synthesis Path-Downstream 1~72

1
[ 52147-97-4 ]
[ 64984-09-4 ]

Yield	Reaction Conditions	Operation in experiment
82%	With ammonium hydroxide; In water; for 0.5h;Reflux;	Example 7: Synthesis of 6-oxa-2-thia-3-azabicyclor3.1.01hexane-4-methanol 2,2-dioxide (40, Figure 7)[(l£)-2-phenylethenyl]sulfonyl chloride 31 (1Og, 49.3 mmol) was dissolved in a 25% aqueous solution of ammonium hydroxide (100 ml) and the mixture was warmed to reflux for 30 minutes. After cooling at 00C, the precipitate was filtered and then dissolved in ethyl <n="21"/>acetate, dried (MgSO4) and the pure [(l£)-2-phenylethenyl]sulfbnamide 32 was recovered as a white solid (7.39 g, 40.3 mmol, 82% yield) after solvent evaporation in vacuo.
38%	With ammonium hydroxide; In water; acetonitrile; at 0 - 20℃;	Trans-2-phenyl-ethenesulfonic acid amide (compound 28).; 3.3 g (1 mol equiv.) Trans-2-phenyl-ethenesulfonyl chloride was dissolved in 33 mL acetonitrile and cooled to 0C. Dropwise, 7.7 mL (3 eq) ammoniumhydroxide was added and the reaction mixture was stirred at room temperature for 10 min. Volatiles were removed under reduced pressure, and the solid residue was washed with water and dried in vacuo to afford 1 .13 g (38%) trans-2-phenvl-ethenesulfonic acid amide. 1H NMR (400 MHz, DMSO-c/6) delta 7.1 1 (br.s., 2H), 7.23 (d, J=16.0 Hz, 1 H), 7.31 (d, J=16.0 Hz, 1 H), 7.41-7.45 (m, 3H), 7.64-7.71 (m, 2H).
	With ammonia; In acetonitrile; at 0 - 5℃; for 0.5h;	(E)-2-phenylethenesulfonyl chloride (1.0 g, 4.93 mmol) was dissolved in Acetonitrile (20 ml) to give a colorless solution. Ammonia gas was introduced to the reaction mixture at 0-5C for 30 min. Acetonitrile was distilled & chilled water (50 ml) was added , stirred and solid material formed was filtered through Buchner funnel to give product. (0118) 1H NMR (400 MHz, DMSO-d6): delta = 7.68- 7.65 (m, 2H), 7.44- 7.40 (m, 3H), 7.30 (d, J = 15.6 Hz, 1H), 7.22 (d, J = 15.6 Hz, 1H), 7.10 (s, 2H); MS (ESI): m/z (%) = 183.15 (100%) (M+H)+, 181.35 (100%) (M-1) (100%)

Reference： [1]Patent: WO2009/118712,2009,A2 .Location in patent: Page/Page column 18-19
[2]Patent: WO2011/92226,2011,A1 .Location in patent: Page/Page column 32
[3]Journal of Organic Chemistry,1938,vol. 3,p. 186
[4]Journal of Organic Chemistry,2003,vol. 68,p. 7911 - 7914
[5]European Journal of Medicinal Chemistry,2018,vol. 143,p. 891 - 898
[6]Patent: WO2019/43610,2019,A1 .Location in patent: Page/Page column 18

2
[ 52147-97-4 ]
[ 405-18-5 ]

Yield	Reaction Conditions	Operation in experiment
98%	With potassium hydrogen difluoride; In water; acetonitrile; at 20℃; for 21h;	General procedure: A round-bottomed flask was charged with KHF2 (15.6 g, 200 mmol)and H2O (40.17 g) and the mixture was stirred at r.t. for 1 h. Then, asolution of the required sulfonyl chloride (100 mmol) in MeCN (45mL) was added, and the mixture was vigorously stirred for 20 h. Then,the mixture was transferred to a separatory funnel, extracted withDCM (2 × 100 mL), and the combined organic phases were dried(MgSO4). The mixture was filtered, evaporated, and dried in vacuo toobtain the desired sulfonyl fluoride. The crude products 1b, 1c, 1g,and 1i were analytically pure.

Reference： [1]Synthesis,2019,vol. 51,p. 2278 - 2286
[2]Angewandte Chemie - International Edition,2015,vol. 54,p. 11780 - 11784
Angew. Chem.,2015,p. 11780 - 11784,5
[3]Journal of the American Chemical Society,1954,vol. 76,p. 3230

3
[ 110-91-8 ]
[ 52147-97-4 ]
[ 17299-32-0 ]

Yield	Reaction Conditions	Operation in experiment
50.6%	With triethylamine; In dichloromethane; at 0 - 20℃; for 16h;	Synthesis of (E)-4-(styrylsulfonyl)morpholine (2) To a solution of morpholine, (0.65 mL, 355.3 mmol) in dichloromethane (700 mL) at 0 C., triethylamine (109.4 mL, 888.2 mmol) and solution of (E)-2-phenylethene-1-sulfonyl chloride (1, 60.0 mL, 296.0 mmol) in dichloromethane was added drop wise over a period of 15 min. The reaction mass was slowly brought to room temperature and stirred for additional 16 h. After completion, the reaction mass was diluted with dichloromethane (500 mL) and water (250 mL). The organic layer was separated, washed with water, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude was purified by silica gel column chromatography using 20% ethyl acetate in hexanes as eluent. The desired fractions were concentrated to afford (E)-4-(styrylsulfonyl)morpholine (2) as white solid. Yield: 38.0 g, 50.6%; MS (ESI) m/z 254.19[M-1]+.

Reference： [1]Patent: US2017/145026,2017,A1 .Location in patent: Paragraph 1135; 1136
[2]Journal of Organic Chemistry,1968,vol. 33,p. 3849 - 3851

4
[ 292638-84-7 ]
[ 52147-97-4 ]
[ 886-65-7 ]

Reference： [1]Chemistry Letters,1985,p. 705 - 708
[2]Journal of Organic Chemistry,1985,vol. 50,p. 5045 - 5050
[3]Bulletin of the Chemical Society of Japan,1988,vol. 61,p. 1231 - 1236
[4]Synlett,2006,p. 3155 - 3157
[5]Chemistry - A European Journal,2005,vol. 11,p. 2633 - 2641

5
[ 292638-84-7 ]
[ 52147-97-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuryl dichloride; N,N-dimethyl-formamide; at 60℃; for 8h;	To a stirred mixture of DMF (1 mL) at 0 C, sulfuryl chloride (1.25 mL, 15 mmol) temperature. Then styrene (0.97 mL, 7.5 mmol) was added and the mixture heated to 60 C. The progress of the reaction was monitored by TLC. After completion of the reaction (8 h), cold water was poured into the mixture and it was extracted with CH2Cl2. The organic phase was washed with saturated NaCl (2 × 20 mL) and dried. The product was obtained as an oil
	With sulfuryl dichloride; In N,N-dimethyl-formamide; at 0 - 90℃; for 2h;Inert atmosphere;	Synthesis of (E)-2-phenylethene-1-sulfonyl chloride (3) Sulfuryl dichloride (2, 77.70 mL, 960.1 mmol) was added drop wise to anhydrous dimethylformamide (80 mL) at 0 C. under nitrogen and the reaction mixture was stirred at room temperature for 30 min. Styrene (1, 50.0 g, 478.4 mmol) was added and the reaction mixture was heated at 90 C. for 2 h. After completion, the mixture was quenched with ice cold water (1000 ml), the precipitated solid was filtered and dried under vacuum to afford (E)-2-phenylethene-1-sulfonyl chloride (3) as light brown solid. Yield: 60.0 g crude.
	With sulfuryl dichloride; In N,N-dimethyl-formamide; at 90℃; for 3h;Inert atmosphere;	Styrene (5.56 ml, 48.0 mmol) was added to a solution of Sulfuryl Chloride (7.81 ml, 96 mmol) in DMF (50.0 ml) at room temperature in three portions under Nitrogen atmosphere conditions & heated at 90C for 3h. The reaction was cooled & then poured into cold water (100 ml), extract with Et2O (50 mL x2), organic layers were collected, dried over sodium sulfate and distilled under vacuum to give crude product. The crude product was used for next reaction. (0115) 1H NMR (400 MHz, DMSO-d6): delta = 7.75 (d, J = 15.6 Hz, 1H), 7.58- 7.52 (m, 3H), 7.52- 7.47 (m, 2H), 7.25 (d, J = 15.6 Hz, 1H)

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 5562 - 5586
[2]Phosphorus, Sulfur and Silicon and the Related Elements,1990,vol. 53,p. 285 - 290
[3]Organic Preparations and Procedures International,1991,vol. 23,p. 633 - 638
[4]Advanced Synthesis and Catalysis,2009,vol. 351,p. 3128 - 3132
[5]ACS Medicinal Chemistry Letters,2019,vol. 10,p. 1061 - 1067
[6]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1995,vol. 34,p. 816 - 822
[7]Synthesis,2005,p. 3639 - 3643
[8]European Journal of Medicinal Chemistry,2011,vol. 46,p. 5034 - 5038
[9]European Journal of Medicinal Chemistry,2013,vol. 64,p. 488 - 497
[10]Journal of Chemical Research,2015,vol. 39,p. 141 - 144
[11]RSC Advances,2016,vol. 6,p. 67805 - 67816
[12]Patent: US2017/145026,2017,A1 .Location in patent: Paragraph 0966; 0967
[13]European Journal of Medicinal Chemistry,2018,vol. 143,p. 891 - 898
[14]Organic Letters,2018,vol. 20,p. 6516 - 6519
[15]Patent: WO2019/43610,2019,A1 .Location in patent: Page/Page column 18
[16]Journal of Medicinal Chemistry,2020

6
[ 1073-67-2 ]
[ 52147-97-4 ]
[ 37985-13-0 ]

Yield	Reaction Conditions	Operation in experiment
93%	In benzene at 150℃; for 43h;
93%	With tris(triphenylphosphine)ruthenium(II) chloride In benzene at 150℃; for 43h;
55%	In xylene at 140℃;

Reference： [1]Kamigata, Nobumasa; Ozaki, Jun-ichi; Kobayashi, Michio [Chemistry Letters, 1985, p. 705 - 708]
[2]Kamigata, Nobumasa; Ozaki, Jun-ichi; Kobayashi, Michio [Journal of Organic Chemistry, 1985, vol. 50, # 25, p. 5045 - 5050]
[3]Dubbaka, Srinivas Reddy; Vogel, Pierre [Chemistry - A European Journal, 2005, vol. 11, # 9, p. 2633 - 2641]

7
[ 52147-97-4 ]
[ 142373-57-7 ]
4-(4-{4-[(S)-2-Methoxycarbonyl-2-((E)-2-phenyl-ethenesulfonylamino)-ethyl]-phenoxy}-butyl)-piperidine-1-carboxylic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate In ethyl acetate for 18h; Ambient temperature;

Reference： [1]Egbertson, Melissa S.; Chang, Charles T.-C.; Duggan, Mark E.; Gould, Robert J.; Halczenko, Wasyl; et al. [Journal of Medicinal Chemistry, 1994, vol. 37, # 16, p. 2537 - 2551]

8
[ 7755-70-6 ]
[ 52147-97-4 ]
(E)-N-(2-formylphenyl)-N-methyl-2-phenylethenesulfonamide [ No CAS ]

Reference： [1]Journal of the Iranian Chemical Society,2013,vol. 10,p. 1057 - 1065
[2]Tetrahedron,1997,vol. 53,p. 13855 - 13866
[3]Journal of the Iranian Chemical Society,2015,vol. 12,p. 379 - 387

9
[ 52147-97-4 ]
[ 122-07-6 ]
[ 198694-02-9 ]

Reference： [1]Tetrahedron,1997,vol. 53,p. 13855 - 13866

10
[ 52147-97-4 ]
[ 4720-29-0 ]
[ 198694-14-3 ]

Reference： [1]Tetrahedron,1997,vol. 53,p. 13855 - 13866

11
[ 73356-19-1 ]
[ 52147-97-4 ]
(E)-2-Phenyl-ethenesulfonic acid anthracen-9-ylmethyl-methyl-amide [ No CAS ]

Reference： [1]Tetrahedron Letters,2000,vol. 41,p. 2323 - 2326

12
[ 52147-97-4 ]
[ 39994-75-7 ]
[ 406951-12-0 ]

Reference： [1]Journal of Organic Chemistry,2002,vol. 67,p. 1536 - 1547

13
[ 52147-97-4 ]
[ 396682-63-6 ]
trans-2-Phenyl-ethenesulfonic acid(1-acetyl-2,3-dihydro-1H-indol-6-yl)-(1-benzyl-piperidin-4-yl)-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With triethylamine; In dichloromethane; at 20℃; for 20h;	A mixture of 1-[6-(1-benzyl-piperidin-4-ylamino)-2,3-dihydro-indol-1-yl]-ethanone (0.10 g, 0.29 mmol), 2-phenyl-ethenesulfonyl chloride (87 mg, 0.43 mmol), and TEA (0.08 mL, 0.57 mmol) in CH2Cl2 (5 mL) was stirred at rt for 20 h. The reaction mixture was concentrated, and the residue was purified on silica gel (60-70% EtOAc/hexanes) to afford the title compound (138 mg, 92%). 1H NMR (500 MHz, CDCl3): 8.12 (s, 1H), 7.50-7.48 (m, 2H), 7.43 (s, 1H), 7.41-7.39 (m, 3H), 7.25 (d, J=6.8 Hz, 2H), 7.20 (t, J=7.0 Hz, 3H), 7.15 (d, J=7.9 Hz, 1H), 6.91 (d, J=7.8 Hz, 1H), 6.86 (d, J=15.0 Hz, 1H), 4.13 (t, J=8.0 Hz, 2H), 3.98-3.40 (m, 1H), 3.41 (s, 2H), 3.20 (t, J=8.5 Hz, 2H), 2.87 (d, J=10.5 Hz, 2H), 2.20 (s, 3H), 2.06-2.02 (m, 2H), 1.88 (d, J=10.7 Hz, 2H), 1.61-1.55 (m, 2H). MS: exact mass calculated for C30H33N3O3S, 515.22; m/z found, 516.3 [M+H]+.

Reference： [1]Patent: US2005/70534,2005,A1 .Location in patent: Page/Page column 15
[2]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 1239 - 1242

14
[ 52147-97-4 ]
[ 58186-45-1 ]
[ 866323-92-4 ]

Yield	Reaction Conditions	Operation in experiment
70%	With sodium hydrogencarbonate; In 1,4-dioxane; water;	Example 132 3-{3-[(E)-2-Phenylethenesulfonylamino]phenyl}acrylic acid methyl ester (25a) A solution of (E)-2-phenylethenesulfonyl chloride (24a) (0.59 g, 2.82 mmol) in dioxane (3 ml) was added to a mixture of 3-(3-aminophenyl)-acrylic acid methyl ester (23) (0.50 g, 2.82 mmol) in dioxane (12 ml) and NaHCO3 (0.36 g, 4.28 mmol) in water (8 ml), and the resultant solution was stirred at room temperature until the completion of the reaction (control by TLC). The reaction mixture was evaporated and the residue was partitioned between ethyl acetate and 2N HCl. The organic layer was washed successively with water, saturated NaCl, and dried (Na2SO4). The solvent was removed and the residue was chromatographed on silica gel with chloroform-ethyl acetate (100:2, v/v) as eluent to give the title compound (0.68 g, 70%) as a white solid. 1H NMR (CDCl3, HMDSO), delta: 3.78 (3H, s); 6.39 (1H, d, J=16.0 Hz); 6.77 (1H, d, J=15.8 Hz); 6.78 (1H, s); 7.17-7.48 (9H, m); 7.49 (1H, d, J=15.8 Hz); 7.58 (1H, d, J=16.0 Hz).

Reference： [1]Helvetica Chimica Acta,2005,vol. 88,p. 1630 - 1657
[2]Patent: US2004/77726,2004,A1

15
[ 1126-09-6 ]
[ 52147-97-4 ]
[ 260441-70-1 ]

Yield	Reaction Conditions	Operation in experiment
89%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 15h;	To a solution of (E)-2-phenylethene-1-sulfonyl chloride (1.29 g, 6.36 minol) in DCM(25 mL) at r.t. was added DIPEA (2.1 mL, 12.72 minol). Ethyl piperidine-4-carboxylate (1 g,6.36 minol) was added dropwise to the stirred solution. The reaction was stuffed at r.t. for 15 h. The solvent was removed under reduced pressure and the resulting crude product was purified by automated flash column chromatography (100% heptane to 50:50 heptane: EtOAc) to afford the requires ester as a white solid. 1.84 g (89%)LC/MS tR 1.40 min; MS (ESj m/z 324 [M+H] (D) 1H NMR (500 MHz, CDC13) oe 7.56 - 7.37 (m, 6H), 6.68 (d, 1H), 4.16 (q, 2H), 3.77 - 3.63 (m, 2H), 2.90 - 2.76 (m, 2H), 2.48 - 2.34 (m, 1H), 2.13 - 1.97 (m, 2H), 1.95 - 1.80 (m, 2H), 1.27 (t, 3H)
	With triethylamine; In dichloromethane; at 0 - 20℃; for 20h;	A solution of ethyl piperidine-4-carboxate (3.0 ML) and triethylamine (2.7 ML) in dichloromethane (10 ML) was added dropwise to a cooled (ice bath) solution of trans-beta-styrenesulphonyl chloride (3.95 g) in dichloromethane (10 ML).. The reaction mixture was allowed to warm to ambient temperature and stirring was continued for 20 hours.. The reaction mixture was evaporated to dryness, the residue was diluted with water and extracted with ethyl acetate (2*25 ML).. The combined ethyl acetate extracts were washed with brine and dried (MgSO4) to give ethyl-(1-trans-beta-styrenesulphonyl)-piperidine-4-carboxylate 5.76 g, M+H=324.

Reference： [1]Patent: WO2018/172251,2018,A1 .Location in patent: Paragraph 0086; 0087; 0088
[2]Patent: US6734184,2004,B1 .Location in patent: Page/Page column 51

16
[ 5382-16-1 ]
[ 52147-97-4 ]
[ 61348-47-8 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; at 20℃;	Triethylamine (8. 0g, 0. [079MOL)] was added to a stirred solution of [E- (3-] styrenesulphonyl chloride [(12.] 0g, 0. [059MOL)] and 4-hydroxypiperidine (8. 0g, 0. [079MOL)] in THF (100ml) at RT. Stirring was continued overnight before the reaction mixture was reduced to low volume and partitioned between EtOAc followed by aqueous 1M [HC1,] saturated [NAHCO3] and brine. The organic fraction was then dried [(NA2SO4)] and evaporated to give a solid product. (12.75g ; 0. 046mol) ; NMR (CDC13) : 1.5-1. 8 (m, 4H), 1.9-2. 1 (m, 2H), 3.0-3. 2 (m, 2H), 3.4-3. 6 (m, 2H), 3.85 (s, 1H), 6.65 (s, 1H), 7.3-7. 6 (m, 6H); MS: 268.

Reference： [1]Patent: WO2004/6926,2004,A1 .Location in patent: Page/Page column 47

17
[ 843676-19-7 ]
[ 52147-97-4 ]
[ 866931-24-0 ]

Yield	Reaction Conditions	Operation in experiment
95%	With polystyrene supported morpholine; In 1,2-dichloro-ethane; at 20℃;	Example 8; {4- [( {4-[ ( 4-butylphenyl)ethynyl]benzyl} [(E)- 2-phenylviny I] sulfonyl}"' amino) ineLhyllphenoLcyl acetic acid; Step a); Formation ofmethyl (at)'4-('((at)4-((4-butylphenyl)ethyhylJbe(at)zyl(at)(at)(at)(E)-2 phenyluiuylJ- (at)M//OKy//(at)7MMo)yKe(at)//pAeHox)(at)ace(at)(at); A solution of methyl {4-[({4-[(4-butylphenyl)ethynyl]benzyl}amino)methyl]phenoxy}- acetate (42 mg, 0.10 mmol) and p-styrene sulfonyl chloride (Aldrich, 23 mg, 0.11 mmol) in DCM (2 mL) was stirred at rt overnight in presence of a morpholine resin (1.5 eq., Novabiochem HL, 3.8 mmol/g) (1.5 eq). Trisamine resin (1 eq, Novabiochem, 3.5 mmol/g) was then added and the mixture stirred at rt for an additional 2 hrs. The reaction mixture was then filtrated and the solvent was removed under reduced pressure to give 55 mg (95%) of the title compound. HPLC, Rt: 5.8 min (purity: 83%).

Reference： [1]Patent: WO2005/97773,2005,A1 .Location in patent: Page/Page column 68

18
[ 843675-76-3 ]
[ 52147-97-4 ]
[ 866931-13-7 ]

Yield	Reaction Conditions	Operation in experiment
53%	With triethylamine; In dichloromethane; at 20℃;	Example 4; 5-( {4-[(4-butylphenyl)ethynyl]benzyl} I [(Ei-2-phenvlvinvll sulfonvli anwxoi- 2-hydroxybenzoic acid; Step a); Formation of (E) N f4-(at)(4-butylphenyl)ethynyl(at)benzyl(at) N (2,2-dimethyl-4-oxo-4H l, 3-benzodioxin-6-yl)-2-phenylethylenesuNo.lonamide; A solution of 6-({4-[(4-butylphenyl)ethynyl]benzyl}amino)-2,2-dimethyl-4H-1,3- benzodioxin-4-one (33mg, 0.08 mmol) , 0-styrene sulfonyl chloride (Aldrich, 18 mg, 0.09 mmol) and TEA (26 mul, 0.19 mmol) in DCM (2 mL) was stirred at rt overnight. Trisamine resin (0.5 eq, Novabiochem, 3.5 mmol/g) was added and the mixture was stirred at rt for an additional 2 hrs. It was then filtrated and the filtrate was washed twice with an aqueous saturated solution of ammonium chloride and with brine. It was dried over MgS04, filtrated and concentrated to give 24 mg (53%) of the title compound. HPLC, Rt: 5.90 min (purity: 88.9%).

Reference： [1]Patent: WO2005/97773,2005,A1 .Location in patent: Page/Page column 59-60

19
ethyl acetate n-hexane [ No CAS ]
[ 52147-97-4 ]
[ 184105-34-8 ]
(3S,4S)-3-{N-(trans-3-phenylpropenoyl)-L-phenylalanyl}-amino-4-acetoxy-azetidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With hydrogen; triethylamine;palladium on activated carbon; In ethyl acetate;	EXAMPLE 11 (3S,4S)-3-{N-(trans-3-phenylpropenoyl)-L-phenylalanyl}-amino-4-acetoxy-azetidin-2-one (11) (3S,4S)-3-(N-benzyloxycarbonyl-L-phenylalanyl)-amino-4-acetoxy-azetidin-2-one (200 mg, 0.47 mmol) obtained in example 7, was hydrogenated with 300 mg of 10% palladium on activated carbon in 50 ml of ethyl acetate at 50 psi hydrogen pressure at room temperature for 2 hrs. After removal of catalyst by filtration, the desubstituted (3S,4S)-3-(L-phenylalanyl)-amino-4-acetoxy-azetidin-2-one in ethyl acetate was cooled to -15 C. Then triethylamine (50 mg, 0.5 mmol) and trans-beta-styrenesulfonyl chloride (95 mg, 0.47 mmol) were added at -15 C. Stirring was continued at a bath temperature of -10 to 5 C. for 2 hr. The reaction mixture was diluted with ethyl acetate, washed with water, brine and dried over sodium sulfate. After removal of solvent, the residue was purified by silica gel column chromatography using hexane-ethyl acetate (1:1) as eluent and the title compound (200 mg) was obtained as a white solid. Yield: 93%; m.p.: 103-105 C.; IR (KBr, cm-1): 3315, 1785, 1748, 1672, 1523, 1321, 1227; 1 H NMR(DMSO-d6), delta (ppm): 2.03 (3H, s), 2.77 (1H, dd, J=14, 10), 2.92 (1H, dd, J=14, 5), 3.99 (1H, m), 4.57 (1H, d, J=8), 5.59 (1H, s), 6.55 (1H, d, J=16), 7.10-7.55 (1H, m), 7.94 (1H, d, J=8), 8.86 (1H, d, J=8), 9.19 (1H, s).

Reference： [1]Patent: US5986108,1999,A

20
C₂₄H₂₂NO₄Pol [ No CAS ]
[ 52147-97-4 ]
[ 101555-63-9 ]
[ 143824-78-6 ]
(S)-1-((E)-2-phenyl-ethenesulfonyl)-piperidine-2-carboxylic acid [(S)-1-amido-2-(1H-indol-3-yl)-ethyl]-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A sample of Rink amide resin (0.06 g, 1 mmol/g) was loaded with Fmoc-Trp(Boc)-OH and Fmoc-pip-OH using the conditions in Method A. After deprotection and washing of the dipeptide, dichloroethane was added followed by N,N-diisopropylethylamine (0.1 mL, 0.44 mmol). The resin was shaken for 5 minutes then treated with -styrenesulfonyl chloride (0.06 g). The resin was placed in a FlexChem.(R). rotational oven (Robbins) and rotated at 45 C overnight. After allowing it to cool to ambient temperature, the resin was washed with dichloroethane (2.x.), CH2Cl2 (3.x.), THF (2.x.), THF/H2O (2.x.), THF (3.x.), and CH2Cl2 (3.x.). The product was cleaved from the resin as in Method A. LC-MS: RT=3.28 minutes (100percent by ELSD); MS (ES+) 436 (M-CONH2).

Reference： [1]Patent: US2008/139556,2008,A1 .Location in patent: Page/Page column 50

21
[ 700-44-7 ]
[ 52147-97-4 ]
[ 1339031-04-7 ]

Yield	Reaction Conditions	Operation in experiment
95%	With potassium carbonate; In acetone; at 20℃; for 2h;	General procedure: To a solution of a 2-hydroxybenzaldehyde (610 mg, 5 mmol) and (E)-2-phenylethenesulfonyl chloride (1010 mg, 5 mmol) in acetone (30 mL) was added K2CO3 (690 mg, 5 mmol) and the mixture was stirred for 2 h at room temperature. After evaporation of the solvent at reduced pressure, 30 mL of H2O was added and the organic compound was extracted with CH2Cl2 (30 mL). The solvent was then evaporated under reduced pressure and the crude products were recrystallized from C2H5OH to afford 3a-f.

Reference： [1]Tetrahedron,2011,vol. 67,p. 8484 - 8491

22
[ 2460-58-4 ]
[ 52147-97-4 ]
[ 1339031-02-5 ]

Yield	Reaction Conditions	Operation in experiment
95%	With potassium carbonate; In acetone; at 20℃; for 2h;	General procedure: To a solution of a 2-hydroxybenzaldehyde (610 mg, 5 mmol) and (E)-2-phenylethenesulfonyl chloride (1010 mg, 5 mmol) in acetone (30 mL) was added K2CO3 (690 mg, 5 mmol) and the mixture was stirred for 2 h at room temperature. After evaporation of the solvent at reduced pressure, 30 mL of H2O was added and the organic compound was extracted with CH2Cl2 (30 mL). The solvent was then evaporated under reduced pressure and the crude products were recrystallized from C2H5OH to afford 3a-f.

Reference： [1]Tetrahedron,2011,vol. 67,p. 8484 - 8491

23
[ 22532-62-3 ]
[ 52147-97-4 ]
[ 1339031-01-4 ]

Yield	Reaction Conditions	Operation in experiment
96%	With potassium carbonate; In acetone; at 20℃; for 2h;	General procedure: To a solution of a 2-hydroxybenzaldehyde (610 mg, 5 mmol) and (E)-2-phenylethenesulfonyl chloride (1010 mg, 5 mmol) in acetone (30 mL) was added K2CO3 (690 mg, 5 mmol) and the mixture was stirred for 2 h at room temperature. After evaporation of the solvent at reduced pressure, 30 mL of H2O was added and the organic compound was extracted with CH2Cl2 (30 mL). The solvent was then evaporated under reduced pressure and the crude products were recrystallized from C2H5OH to afford 3a-f.

Reference： [1]Tetrahedron,2011,vol. 67,p. 8484 - 8491

24
[ 52147-97-4 ]
[ 90-02-8 ]
[ 1339030-98-6 ]

Yield	Reaction Conditions	Operation in experiment
96%	With potassium carbonate; In acetone; at 20℃; for 2h;	General procedure: To a solution of a 2-hydroxybenzaldehyde (610 mg, 5 mmol) and (E)-2-phenylethenesulfonyl chloride (1010 mg, 5 mmol) in acetone (30 mL) was added K2CO3 (690 mg, 5 mmol) and the mixture was stirred for 2 h at room temperature. After evaporation of the solvent at reduced pressure, 30 mL of H2O was added and the organic compound was extracted with CH2Cl2 (30 mL). The solvent was then evaporated under reduced pressure and the crude products were recrystallized from C2H5OH to afford 3a-f.

Reference： [1]Tetrahedron,2011,vol. 67,p. 8484 - 8491
[2]Journal of Organic Chemistry,2011,vol. 76,p. 9975 - 9982
[3]Tetrahedron Letters,2013,vol. 54,p. 2685 - 2689
[4]Tetrahedron,2012,vol. 68,p. 3641 - 3648

25
[ 4438-85-1 ]
[ 52147-97-4 ]
[ 90-02-8 ]
rac-(6bR,14S,14aR)-14-phenyl-14,14a-dihydrobenzo[5',6'][1,2]oxathiino[4',3':4,5]pyrano[3,2-c]chromen-7(6bH)-one 1,1-dioxide [ No CAS ]
rac-(6aR,7S,14bR)-7-phenyl-6a,7-dihydrobenzo[5',6'][1,2]oxathiino[4',3':4,5]pyrano[2,3-b]chromen-14(14bH)-one 6,6-dioxide [ No CAS ]