[ CAS No. 130-15-4 ]

Name: 130-15-4|1,4-Naphthoquinone|97%
Brand: Ambeed
SKU: A457360
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{[proInfo.proName]} (Synonyms:1,4-Naphthoquinone) ,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

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Quality Control of [ 130-15-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 130-15-4 ]

SDS Specification

Alternatived Products of [ 130-15-4 ]

Product Details of [ 130-15-4 ]

CAS No. :	130-15-4	MDL No. :	MFCD00001676
Formula :	C₁₀H₆O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FRASJONUBLZVQX-UHFFFAOYSA-N
M.W :	158.15	Pubchem ID :	8530
Synonyms :	1,4-Naphthoquinone

Calculated chemistry of [ 130-15-4 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	44.24
TPSA :	34.14 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.05 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.44
Log Po/w (XLOGP3) :	1.71
Log Po/w (WLOGP) :	1.62
Log Po/w (MLOGP) :	0.91
Log Po/w (SILICOS-IT) :	2.29
Consensus Log Po/w :	1.59

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.27
Solubility :	0.854 mg/ml ; 0.0054 mol/l
Class :	Soluble
Log S (Ali) :	-2.04
Solubility :	1.43 mg/ml ; 0.00907 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.8
Solubility :	0.25 mg/ml ; 0.00158 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	1.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.3

Safety of [ 130-15-4 ]

Signal Word:	Danger	Class:	8,6.1
Precautionary Statements:	P272-P280-P264-P270-P271-P284-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P403+P233-P405-P501	UN#:	2923
Hazard Statements:	H314-H317-H331-H335-H410-H301+H311	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 130-15-4 ]

* 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 [ 130-15-4 ]
Downstream synthetic route of [ 130-15-4 ]

[ 130-15-4 ] Synthesis Path-Upstream 1~5

1
[ 130-15-4 ]
[ 3846-71-7 ]

Reference： [1] Patent: US4642350, 1987, A,
[2] Patent: US4642350, 1987, A,

2
[ 6627-34-5 ]
[ 130-15-4 ]
[ 20103-09-7 ]

Yield	Reaction Conditions	Operation in experiment
96%	With sodium hydroxide; hydrazine hydrate In water	EXAMPLE 2 A reaction vessel was charged with 200 g of water, 41.4 g of pulverized 2,5-dichloro-p-nitroaniline, 6 g of sodium hydroxide, 0.3 g of 1,4-naphthoquinone and 25 g of an 80percent solution of hydrazine hydrate in water. The contents of the vessel were agitated at 85° to 95° C. for 9 hours to complete the reaction. The reaction product was filtered, washed with water and dried to give 34.0 of 2,5-dichloro-p-phenylenediamine. Yield: 96percent Purity determined by G.C. analysis: 99.6percent
91%	With sodium hydroxide; hydrazine hydrate In water	EXAMPLE 1 A reaction vessel was charged with 60 g of isopropyl alcohol, 50 g of water, 41.4 g of 2,5-dichloro-p-nitroaniline, 6 g of sodium hydroxide and 0.3 g of 1,4-naphthoquinone. The temperature of the mixture was controlled to be 75° to 80° C., and 22 g of an 80percent solution of hydrazine hydrate in water was added dropwise to the mixture over 2 hours. After the addition, the reaction mixture was refluxed with stirring for 3 hours to complete the reaction. After cooling to 5° C., the reaction product was filtered, washed with water and dried, to give 32.2 g of 2,5-dichloro-p-phenylenediamine. Yield: 91percent Purity determined by G.C. analysis: 99.9percent

Reference： [1] Patent: US5041672, 1991, A,
[2] Patent: US5041672, 1991, A,

3
[ 63-74-1 ]
[ 130-15-4 ]
[ 19992-50-8 ]

Reference： [1] Chemische Berichte, 1944, vol. 77/79, p. 478,481
[2] Svensk Kemisk Tidskrift, 1942, vol. 54, p. 200,202
[3] Patent: WO2014/201016, 2014, A2, . Location in patent: Paragraph 00167; 00370

4
[ 64-17-5 ]
[ 63-74-1 ]
[ 130-15-4 ]
[ 19992-50-8 ]

Reference： [1] Svensk Kemisk Tidskrift, 1942, vol. 54, p. 200,202

5
[ 130-15-4 ]
[ 95233-18-4 ]

Reference： [1] Organic Process Research and Development, 2014, vol. 18, # 5, p. 618 - 625
[2] Organic Process Research and Development, 2014, vol. 18, # 5, p. 618 - 625

[ 130-15-4 ] Synthesis Path-Downstream 1~68

1
[ 123-91-1 ]
[ 7478-69-5 ]
[ 130-15-4 ]
[ 571-60-8 ]
2-[2,2-bis-(4-dimethylamino-phenyl)-vinyl]-[1,4]naphthoquinone [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1944,vol. 66,p. 124,129

2
diacetyl-orthonitric acid [ No CAS ]
[ 90-15-3 ]
[ 607-24-9 ]
[ 130-15-4 ]

Reference： [1]Chemisches Zentralblatt,1903,vol. 74,p. 1109
[2]Chemisches Zentralblatt,1903,vol. 74,p. 1109

3
[ 90-15-3 ]
[ 607-24-9 ]
[ 130-15-4 ]

Reference： [1]Chemisches Zentralblatt,1903,vol. 74,p. 1109

4
[ 64-17-5 ]
[ 63-74-1 ]
[ 130-15-4 ]
[ 19992-50-8 ]

Reference： [1]Svensk Kemisk Tidskrift,1942,vol. 54,p. 200,202

5
[ 63-74-1 ]
[ 130-15-4 ]
[ 19992-50-8 ]

Yield	Reaction Conditions	Operation in experiment
	With cerium(III) chloride heptahydrate; In ethanol; water; at 75.0℃; for 72.0h;	General procedure: Cerium chloride heptahydrate (36 mg; 97 muetaiotaomicron), followed by 4- aminobenzenesulfonamide (689 mg; 4.00 mmol), was added to a suspension of naphthalene- 1 ,4- dione (316 mg; 2.00 mmol) in 95% ethanol (8.0 mL). The reaction vial was capped then put intoa 75 C block. After three days the reaction was cooled to room temperature, then 80 mL of 1.0 M citric acid was added with vigorous stirring. The insoluble material was collected by filtration, washed with water, and dried in vacuo at 45 C affording crude product as a rust colored solid (370 mg). A portion of this (225 mg) was purified by pRPLC yielding 4-((l ,4-dioxo-l ,4- dihydronaphthalen-2-yl)amino)benzenesulfonamide as a rust-colored solid (101 mg). LH NMR (400 MHz, DMSO-i delta 9.45 (s, 1H), 8.09 (dd, J = 1.0, 7.6 Hz, 1H), 7.98 (dd, J = 1.1 , 7.6 Hz, 1H), 7.92 - 7.79 (m, 4H), 7.60 (m, 2H), 7.37 (s, 2H), 6.33 (s, 1H). 13C NMR (125 MHz, DMSO- d6) delta 183.0, 181.3, 145.2, 141.5, 139.6, 134.9, 132.9, 132.3, 130.4, 127.0, 126.2, 125.3, 122.7, 103.8. LC-MS (ESI+): Purity at 214 nm is 100%. HRMS: 329.0591 (calcd for C16H13N204S = [M+H ); 329.0594 (found / [M+H]+)

Reference： [1]Chemische Berichte,1944,vol. 77/79,p. 478,481
[2]Patent: WO2014/201016,2014,A2 .Location in patent: Paragraph 00167; 00370

6
[ 7478-69-5 ]
[ 130-15-4 ]
2-[2,2-bis-(4-dimethylamino-phenyl)-vinyl]-[1,4]naphthoquinone [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1944,vol. 66,p. 124,129

7
[ 130-15-4 ]
[ 2065-37-4 ]

Yield	Reaction Conditions	Operation in experiment
98.7%	With N-chloro-succinimide; copper(II) chloride monohydrate; In acetonitrile; at 82℃; for 2h;	General procedure: To a 50 mL flask, the coumarin (1 mmol), appropriate amount of NXS, the Lewisacid catalyst and 20 mL anhydrous solvent were added in. The mixture was heated toreflux with a condenser under the protection of a drying tube. The reaction progresswas monitored by TLC. When the reaction was completed, the mixture was cooled toroom temperature. The solvent was removed by vacuum rotary evaporation, and theresidue was dispensed in 25 mL 5% sodium hydrogen sulfite (NaHSO3) aqueoussolution and then extracted with 25 mL ethyl acetate (EtOAc) for three times. Theorganic layer was combined, washed with 10 mL water and dried over anhydroussodium sulphate (Na2SO4). After the solvent was removed, the crude product waspurified by silica gel (300-400 mesh) column chromatograph.
97%	With Oxone; ammonium bromide; In water; acetonitrile; for 5h;Reflux;	General procedure: To a solution of olefin (2 mmol) in CH3CN (10 mL) were added NH4Br (4.4 mmol) and Oxone (2.2 mmol) and the mixture was stirred at reflux temperature for the time shown in Table 2. After completion (as indicated by TLC), the reaction mixture was filtered and the solvent evaporated under reduced pressure. The products were purified by column chromatography (Hexane/EtOAc, 98:2) over silica gel.
73%	With Oxone; ammonium bromide; In ethanol; for 5.3h;Reflux;	General procedure: To a solution of olefin (2 mmol) in MeOH/EtOH (10 ml) were added NH4Br (2.2 mmol) and oxone(2.2 mmol) and the mixture was stirred at room/reflux temperature for the time shown in Table 2 and 3. After completion (as indicated by TLC), the reaction mixture was filtered and the solvent evaporated under reducedpressure. The products were purified by column chromatography over silica gel.

40%	With Oxone; ammonium bromide; at 20℃; for 24h;Green chemistry;	General procedure: An olefin was slowly added to a well stirred (30 min) solution of NH4Br (2.2 mmol) and oxone (2.2 mmol) in DMF/DMA (10 mL) and the reaction mixture was stirred at room temperature until the olefin completely disappeared (monitored by TLC) or an appropriate time, quenched with ice water and extracted with Et2O (2 x 15 mL). The combined organic layers were dried (Na2SO4) and concentrated in vacuo. The resulting crude residue was purified by column chromatography (silica gel, 5-50%EtOAc-hexane) to give pure products that were identified by means of 1HNMR and 13C NMR spectroscopy
	With hydrogenchloride; bromine; In 1,4-dioxane; chloroform; at 0 - 20℃; for 2h;Inert atmosphere;	The 1, 4 - naphthoquinone (150 mg, 0 . 95 mmol) dissolved in 8 ml CHCl3In, will be 4 mol/L HCl dioxane solution of (0.26 ml) are added to a reaction solution, N2The reaction under the protection of the cooling to 0 C, will be soluble in CHCl3(2 Ml) of bromine (50 mul, 0 . 95 mmol) using the dropping funnel is added in the mixed solution (20 minutes drop end). After the completion of the dropping, the reaction temperature is raised to room temperature, N2Under the protection of the sustained reaction 2 h. After the reaction, the solvent is removed in vacuo, the mixture of ice water for washing, filtering, the filter cake is washed vacuum drying, get intermediate 2-bromo-1,4-naphthoquinone (14).

Reference： [1]Synlett,2019,vol. 30,p. 630 - 634
[2]Synthetic Communications,1996,vol. 26,p. 887 - 892
[3]Tetrahedron Letters,2012,vol. 53,p. 1401 - 1405
[4]Chemical Science,2016,vol. 7,p. 3780 - 3784
[5]Synthetic Communications,2013,vol. 43,p. 3121 - 3129
[6]Australian Journal of Chemistry,2008,vol. 61,p. 768 - 784
[7]Synthetic Communications,1993,vol. 23,p. 2083 - 2089
[8]Tetrahedron Letters,2014,vol. 55,p. 3926 - 3933
[9]Journal of the American Chemical Society,1944,vol. 66,p. 1077,1082
[10]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5324 - 5328
[11]Journal of the Chemical Society. Perkin transactions II,1983,p. 271 - 280
[12]Chemische Berichte,1894,vol. 27,p. 2757
[13]Patent: CN109438471,2019,A .Location in patent: Paragraph 0199-200

8
[ 108-97-4 ]
[ 130-15-4 ]
[ 99113-67-4 ]
[ 99113-68-5 ]

Reference： [1]Journal of Organic Chemistry,1985,vol. 50,p. 5546 - 5550

9
[ 3131-52-0 ]
[ 130-15-4 ]
[ 112097-20-8 ]

Reference： [1]Tetrahedron,1987,vol. 43,p. 2749 - 2754

10
[ 90-15-3 ]
[ 491-31-6 ]
[ 607-24-9 ]
[ 130-15-4 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1988,vol. 36,p. 4567 - 4575

11
[ 90-11-9 ]
[ 62784-48-9 ]
[ 2065-37-4 ]
[ 18099-96-2 ]
[ 130-15-4 ]

Reference： [1]Tetrahedron,1994,vol. 50,p. 3575 - 3586

12
[ 90-11-9 ]
[ 2065-37-4 ]
[ 18099-96-2 ]
[ 130-15-4 ]

Reference： [1]Tetrahedron,1994,vol. 50,p. 3575 - 3586

13
[ 122-88-3 ]
[ 130-15-4 ]
[ 130837-04-6 ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 8330 - 8339
[2]Journal of the Chemical Society. Perkin transactions I,1990,p. 2163 - 2174

14
[ 1001-53-2 ]
[ 130-15-4 ]
[ 75473-68-6 ]

Reference： [1]Archiv der Pharmazie,1980,vol. 313,p. 603 - 611

15
[ 821-38-5 ]
[ 130-15-4 ]
[ 132080-51-4 ]

Reference： [1]Liebigs Annalen der Chemie,1991,p. 315 - 321

16
[ 35202-54-1 ]
[ 130-15-4 ]
[ 53995-99-6 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1974,vol. 22,p. 2159 - 2163

17
[ 10304-09-3 ]
[ 130-15-4 ]
[ 68749-78-0 ]

Reference： [1]Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry,1978,vol. 32,p. 347 - 353

18
[ 130-15-4 ]
[ 59-46-1 ]
[ 97356-57-5 ]

Reference： [1]Pharmazie,1961,vol. 16,p. 266 - 272

19
[ 43036-06-2 ]
[ 130-15-4 ]
3-[2-(1,4-dioxo-1,4-dihydronaphthalen-2-yl)-pyrrol-1-yl]propionitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	In chloroform; water;	Example 6 Preparation of 3-[2-(1,4-Dioxo-1,4-dihydronaphthalen-2-yl)pyrrol-1-yl]propionitrile STR15 6.32 millimol of 1,4-naphthoquinone and 3.16 millimol of 3-(1-pyrrolyl) propionitrile were stirred in 50 ml of chloroform in a round-bottomed flask for 5 hours at room temperature, the reaction being catalysed by addition of a few milligrams of para-toluenesulphonic acid. The reaction medium was diluted with 50 ml of chloroform and then washed four times with 50 ml of water and finally with saturated aqueous NaCl solution. The resulting organic phase was dried over Na2 SO4 and then concentrated under vacuum. The product 3-[2-(1,4-dioxo-1,4-dihydronaphthalen-2-yl)pyrrol-1-yl]propionitrile was thus isolated in a yield of 42% after purification by chromatography on a column of silica. Melting point: 127-128 C.

Reference： [1]Journal of Heterocyclic Chemistry,2000,vol. 37,p. 1635 - 1640
[2]Patent: US6022379,2000,A

20
[ 28868-76-0 ]
[ 130-15-4 ]
[ 401465-93-8 ]

Reference： [1]Tetrahedron,2001,vol. 57,p. 9615 - 9621

21
[ 63-25-2 ]
[ 90-15-3 ]
[ 130-15-4 ]
(phthalic acid-O-)yl N-methylcarbamate [ No CAS ]

Reference： [1]Journal of agricultural and food chemistry,2002,vol. 50,p. 2331 - 2337
[2]Journal of Agricultural and Food Chemistry,2003,vol. 51,p. 5382 - 5390

22
[ 604-44-4 ]
[ 130-15-4 ]
4-chloro-4-fluoro-4H-naphthalen-1-one [ No CAS ]

Reference： [1]Tetrahedron,2004,vol. 60,p. 6629 - 6638

23
[ 15799-79-8 ]
[ 130-15-4 ]
2-[4-(dimethylamino)-2-methoxyphenyl]naphthalene-1,4-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
18%	With phosphotungstic acid; In acetic acid; dimethyl sulfoxide; at 100℃; for 24h;	General procedure: (Scheme 1: cat.= H3PW12O40, oxidant= air, solvent= DMSO/CH3CO2H). A 50mL flask equipped with a magnetic stirrer was charged with 1,4-naphthoquinone (1) (20mmol; 3.16g), aromatic compounds (10mmol), 15mL of CH3COOH and H3PW12O40 (288mg; 1mol%). The flask was heated at 100C for 24h. After that time, the flask was cooled down to room temperature and 15mL of chloroform was added. The solution was washed with 20mL of brine. The organic phase was separated and dried by MgSO4. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography on silica gel, using a gradient hexane/acetone mixture as eluent.

Reference： [1]Advanced Synthesis and Catalysis,2006,vol. 348,p. 229 - 235
[2]European Journal of Medicinal Chemistry,2016,vol. 124,p. 252 - 252

24
[ 6627-34-5 ]
[ 130-15-4 ]
[ 20103-09-7 ]

Yield	Reaction Conditions	Operation in experiment
96%	With sodium hydroxide; hydrazine hydrate; In water;	EXAMPLE 2 A reaction vessel was charged with 200 g of water, 41.4 g of pulverized 2,5-dichloro-p-nitroaniline, 6 g of sodium hydroxide, 0.3 g of 1,4-naphthoquinone and 25 g of an 80% solution of hydrazine hydrate in water. The contents of the vessel were agitated at 85 to 95 C. for 9 hours to complete the reaction. The reaction product was filtered, washed with water and dried to give 34.0 of 2,5-dichloro-p-phenylenediamine. Yield: 96% Purity determined by G.C. analysis: 99.6%
91%	With sodium hydroxide; hydrazine hydrate; In water;	EXAMPLE 1 A reaction vessel was charged with 60 g of isopropyl alcohol, 50 g of water, 41.4 g of 2,5-dichloro-p-nitroaniline, 6 g of sodium hydroxide and 0.3 g of 1,4-naphthoquinone. The temperature of the mixture was controlled to be 75 to 80 C., and 22 g of an 80% solution of hydrazine hydrate in water was added dropwise to the mixture over 2 hours. After the addition, the reaction mixture was refluxed with stirring for 3 hours to complete the reaction. After cooling to 5 C., the reaction product was filtered, washed with water and dried, to give 32.2 g of 2,5-dichloro-p-phenylenediamine. Yield: 91% Purity determined by G.C. analysis: 99.9%

Reference： [1]Patent: US5041672,1991,A
[2]Patent: US5041672,1991,A

25
2-Nitro-2'-hydroxy-3',5'-di-tert-butyl-azobenzene [ No CAS ]
[ 130-15-4 ]
[ 3846-71-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; sodium; sodium hydrogensulfite; In water; isopropyl alcohol;	EXAMPLE 2 A suspension of 9.2 g of sodium in 400 g of isopropanol is refluxed in a 1.5 liter sulfonating flask until a solution is formed. To this are added, at 60° C., 3.2 g of 1,4-naphthoquinone, 2.1 g of sodium bisulfite and 71 g of 2-nitro-2'-hydroxy-3',5'-bis-tert.-butylazobenzene. The mixture is stirred at 60° C. for between half an hour and a full hour. 20 g of 17 percent by volume aqueous sulfuric acid and 100 ml of warm water at 60°-70° C. are then added dropwise. The precipitated crystals are filtered and are washed with warm 60 percent by weight aqueous methanol and with warm water. Drying at 70°-80° C. n vacuo produces 2,4-di-tert.-butyl-6-(2'-benzotriazolyl)-phenol in a high yield.
	With sodium hydroxide; sulfuric acid; sodium hydrogensulfite; In water; isopropyl alcohol;	EXAMPLE 5 200 g of isopropanol are heated to 60° C. in a 750 ml sulfonating flask, and 1 g of sodium bisulfite, 1.6 g of 1,4-naphthoquinone, 14 g of sodium hydroxide and 35.5 g of 2-nitro-2'-hydroxy-3',5'-bis-tert.-butylazobenzene are then added. The mixture is stirred at 75°-80° C. for two hours, and 18 g of 17 percent by volume aqueous sulfuric acid and 50 ml of warm water are then added dropwise. The precipitated crystals are washed with warm methanol and then with warm water. The product is a high yield of 2,4-di-tert.-butyl-6-(2'-benzotriazolyl)-phenol.

Reference： [1]Patent: US4642350,1987,A
[2]Patent: US4642350,1987,A

26
[ 2840-44-0 ]
[ 130-15-4 ]

Yield	Reaction Conditions	Operation in experiment
5.6g (37%)		Autoxidation of <strong>[2840-44-0]7-fluoro-1-tetralone</strong> (13g) as described in example 8(b) gave 5.6g (37percent) of the naphthoquinone which after recrystallization from chloroform had m.p. 206°-210° C. (Found; C, 62.50; H, 2.70; C10 H5 FO3 requires; C, 62.51; H, 2.62percent).

Reference： [1]Patent: US4014907,1977,A

27
[ 52522-40-4 ]
[ 5259-72-3 ]
[ 130-15-4 ]
[ 544707-91-7 ]

Reference： [1]Journal of Organometallic Chemistry,1983,vol. 246,p. 203 - 212

28
[ 52522-40-4 ]
[ 130-15-4 ]
bis(1,4-naphthoquinone)palladium⁽⁰⁾ [ No CAS ]

Reference： [1]Journal of Organometallic Chemistry,1983,vol. 246,p. 203 - 212

29
[ 52522-40-4 ]
[ 130-15-4 ]
[ 478548-99-1 ]
[ 1083211-26-0 ]

Yield	Reaction Conditions	Operation in experiment
89%	In acetone; at 20℃; for 1h;Inert atmosphere;	0.1328 g (0.4057 mmol) of 8-diphenylphosphine-2-methylquinoline, 0.0674 g (0.4261 mmol) of naphthoquinone and 0.2003 g(0.1935 mmol) of [Pd2(DBA)3CHCl3] were dissolved under inert atmosphere (Ar) in 30 ml of anhydrous acetone in a 100 ml necked flask. The mixture was stirred for 60 min at RT, the resulting orange solution treated with activated charcoal, filtered on a celite filter and concentrated under vacuum. The title complexwas precipitated as a paleorange solid by slow addition of diethylether, filtered off on a gooch, and washed with diethylether and n-pentane. 0.2039g (yield 89percent) of complex 1'b was obtained. 1H-NMR (300 MHz, CDCl3, T = 298 K, ppm) delta: 3.12 (s, 3H, quinoline-CH3), 4.98-5.05 (m, 2H, CH=CH) 7.06e7.13 (m, 2H, aryl naphthoquinone), 7.29-7.71 (m, 13H, H3, PPh2, aryl naphthoquinone), 7.79 (ddd,1H, J = 8.1, 7.5,1.4 Hz, H6), 7.90 (d,1H, J = 8.1, H7), 8.05 (dd, 1H, J = 7.5, 1.6 Hz, H5), 8.19 (dd, 1H, J = 8.4, 1.4 Hz, H4). 13C{1H}-NMR (CDCl3, T = 298 K, ppm) delta: 30.3 (CH3, quinoline-CH3), 62.7 (CH, CH=CH trans-N), 66.3 (d, CH, JCP = 21 Hz, CH=CH transP), 123.9 (CH, C3), 125.1 (CH, C5), 131.1 (CH, C7), 137.8 (CH, C6), 138.4 (CH, C4), 165.7 (d, C, JCP = 22.1 Hz, C9),165.7 (C, C2),184.0 (d, C, JCP = 6.2 Hz, CO transP), 185.2 (C, CO transN). 31P{1H}-NMR (CD2Cl2, T = 298 K, ppm) delta: 23.4. IR (KBr, pellet, cm-1): 1641 (nCO). Anal. Calcd. for C32H24NO2PPd: C 64.93, H 4.09, N 2.37. Found: C 65.06, H 3.98, N 2.21.

Reference： [1]Journal of Organometallic Chemistry,2017,vol. 834,p. 10 - 21
[2]Journal of Organometallic Chemistry,2009,vol. 694,p. 411 - 419
[3]Journal of Organometallic Chemistry,2008,vol. 693,p. 3324 - 3330

30
[ 52522-40-4 ]
[ 28225-52-7 ]
[ 130-15-4 ]
[ 1132766-64-3 ]

Reference： [1]Journal of Organometallic Chemistry,2009,vol. 694,p. 411 - 419

31
[ 216961-61-4 ]
[ 130-15-4 ]
C₂₅H₃₆N₂O₄ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 5463 - 5467

32
[ 383-70-0 ]
[ 130-15-4 ]
[ 1196068-56-0 ]
[ 1196068-79-7 ]

Reference： [1]European Journal of Organic Chemistry,2009,p. 4882 - 4892

33
[ 3172-52-9 ]
[ 130-15-4 ]
[ 602-25-5 ]

Reference： [1]Journal of Chemical Research,2009,p. 732 - 736

34
[ 127-71-9 ]
[ 130-15-4 ]
[ 1204290-36-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 5576 - 5592

35
[ 54323-50-1 ]
[ 130-15-4 ]
[ 1246308-57-5 ]

Reference： [1]Journal of Heterocyclic Chemistry,2010,vol. 47,p. 960 - 966

36
[ 367-34-0 ]
[ 130-15-4 ]
[ 1276184-21-4 ]

Yield	Reaction Conditions	Operation in experiment
70%	With copper diacetate; acetic acid; at 70℃; for 2h;	General procedure: The substituted naphthoquinones were prepared by the method reported in the literature with several modifications [9]. 1,4-Naphthoquinone (1 mmol), a substituted aniline (1 mmol) and an amount (0.1 mmol) of Cu(AcO)2 were solubilized by gently warming in AcOH (2 mL) for 30 min. The reaction mixture was gently warmed in a water bath for two hours at 70 °C. The solid that precipitated was separated by filtration and washed with an aqueous solution of NaHCO3 (10 percent) to neutralize the remaining acid. The reaction mixture was dissolved in a small amount of CH2Cl2 and was passed through a small silica gel column to remove the remaining copper salts. 4.9 Characterization of 2-(<strong>[367-34-0]2,4,5-trifluoroaniline</strong>)-1,4-naphthoquinone (3h) 1H (400MHz, DMSO-d6): delta 5.62 (d, 1H, 3, J=3.1Hz), 7.63 (dt, 1H, 6?, JoHF=10.8Hz, JmHF=7.9Hz), 7.76 (td, 2H, 3?, JoHF=10Hz, JmHF=7.4Hz), 7.80 (td, 1H, 7, Jo=7.5Hz, Jm=1.4Hz), 7.87 (td, 1H, 6, Jo=7.5Hz, Jm=1.3Hz), 7.95 (dd, 1H, 5, Jo=7.6Hz, Jm=0.98Hz), 8.07 (dd, 1H, 8, Jo=7.61Hz, Jm=0.97Hz), 9.12 (s, 1H, A); 13C{1H} (100MHz, DMSO-d6): delta 103.68 (3), 106.95 (dd, 3?, 2JC?F=26Hz, 2JC?F=22Hz), 116.19 (d, 6?, 2JC?F=20Hz), 122.06 (m, 1?), 125.40 (5), 126.12 (8), 130.27 (9), 132.34 (10), 132.87 (7), 134.97 (6), 145.92 (dm, 4?, 1JC?F=240Hz) [22], 146.69 (2), 147.64 (dm, 5?, 1JC?F=235Hz) [22], 151.92 (dd, 2?, 1JC?F=247Hz, 3JC?F=11Hz), 180.97 (1), 182.55 (4); High-Resolution EI-MS C16H8F3NO2 m/z calcd: 303.0507, found: 303.0507.
		General procedure: These compounds were prepared by a method previously reported in the literature by us [38?41]. 1,4-Naphthoquinone or 5-hydroxy-1,4-naphthoquinone (1 mmol) was dissolved in ethanol (10 mL) and an amount (0.1 mmol) of catalyst (FeCl3 or CeCl3) was added. The reaction mixture was stirred for 15 min to allow the reaction between the Lewis base (1,4-naphthoquinone) and catalyst. A solution of the substituted aniline (1 mmol) in ethanol (10 mL) was slowly added and the mixture was refluxed for 4 h. TLC analysis indicated only one product was formed. The resulting solid was filtered, washed with cold ethanol and recrystallized from ethanol. Total characterization of compounds 3a?k has been previously reported [38?41].

Reference： [1]Journal of Fluorine Chemistry,2011,vol. 132,p. 94 - 101
[2]Journal of Fluorine Chemistry,2015,vol. 180,p. 152 - 160
[3]Research on Chemical Intermediates,2017,vol. 43,p. 1813 - 1827

37
[ 2835-96-3 ]
[ 130-15-4 ]
[ 1370231-45-0 ]

Reference： [1]Russian Journal of Organic Chemistry,2012,vol. 48,p. 234 - 240

38
[ 5751-52-0 ]
[ 130-15-4 ]
[ 1384433-64-0 ]

Reference： [1]Chemical Communications,2012,vol. 48,p. 7191 - 7193

39
[ 383-70-0 ]
[ 130-15-4 ]
[ 1196068-56-0 ]

Reference： [1]European Journal of Organic Chemistry,2012,p. 5774 - 5788,15

40
[ 3025-95-4 ]
[ 130-15-4 ]
[ 1417603-15-6 ]

Reference： [1]European Journal of Organic Chemistry,2012,p. 5774 - 5788,15

41
[ 5751-52-0 ]
[ 130-15-4 ]
[ 1415426-45-7 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 6108 - 6111

42
[ 69189-19-1 ]
[ 130-15-4 ]
[ 126963-18-6 ]

Reference： [1]Research on Chemical Intermediates,2013,vol. 39,p. 139 - 146

43
[ 3172-52-9 ]
[ 130-15-4 ]
C₁₄H₈Cl₂O₃S [ No CAS ]

Reference： [1]Journal of Physical Organic Chemistry,2013,vol. 26,p. 367 - 375

44
[ 75-15-0 ]
[ 17609-47-1 ]
[ 130-15-4 ]
ethyl 2-(4,9-dioxo-4,9-dihydronaphtho[2,3-d][1,3]dithiol-2-imino)-3-methylbutanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79.3%	With triethylamine; In dichloromethane; at 0℃; for 4h;	General procedure: Typically, a mixture of 1,4-naphthoquinone (1a, 1.0 mmol, 0.158 g, 1.0 equiv), phenylalanine ethyl ester hydrochloride (2a, 1.2 mmol, 0.276 g, 1.2 equiv), CS2 (3a, 5 mmol, 0.381 g, 5.0 equiv), triethylamine (1.2 mmol, 0.121 g 1.2 equiv) in CH2Cl2 (5.0 mL) was stirred at 0 C under air condition for 4 h, determined by GC-MS and TLC. The solvent was removed under vacuum and the resulting crude product was purified by chromatography on silica gel eluted using CH2Cl2 as the eluent to afford the desired product 4a as red solid (0.3735 g, yield 88.2%, mp=149-150 C).

Reference： [1]Tetrahedron,2013,vol. 69,p. 5221 - 5226

45
[ 75-15-0 ]
[ 15572-56-2 ]
[ 130-15-4 ]
[ 65160-10-3 ]
[ 1438263-33-2 ]

Yield	Reaction Conditions	Operation in experiment
Ca. 10%; 81%	With triethylamine; In dichloromethane; at 0℃; for 4h;	General procedure: Typically, a mixture of 1,4-naphthoquinone (1a, 1.0 mmol, 0.158 g, 1.0 equiv), phenylalanine ethyl ester hydrochloride (2a, 1.2 mmol, 0.276 g, 1.2 equiv), CS2 (3a, 5 mmol, 0.381 g, 5.0 equiv), triethylamine (1.2 mmol, 0.121 g 1.2 equiv) in CH2Cl2 (5.0 mL) was stirred at 0 C under air condition for 4 h, determined by GC-MS and TLC. The solvent was removed under vacuum and the resulting crude product was purified by chromatography on silica gel eluted using CH2Cl2 as the eluent to afford the desired product 4a as red solid (0.3735 g, yield 88.2%, mp=149-150 C).

Reference： [1]Tetrahedron,2013,vol. 69,p. 5221 - 5226

46
[ 122-88-3 ]
[ 130-15-4 ]
[ 1449692-39-0 ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 8330 - 8339

47
[ 52522-40-4 ]
[ 130-15-4 ]
[ 653570-21-9 ]
[Pd(η²-naphthoquinone)(2-methyl-8-(tert-butylthio)quinoline)] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	In acetone; for 0.5h;Inert atmosphere; Darkness;	General procedure: To 64.3 mg (0.278 mmol) of TTbQ-Me dissolved in anhydrous acetone (20 ml) in a two necked flask, 30 mg (0.278 mmol) of p-benzoquinone and 120 mg (0.116 mmol) of Pd2DBA3CHCl3 were added in sequence under inert atmosphere (Ar). The resulting mixture was stirred in the dark for 30 min, filtered on a celite filter and evaporated under vacuum to a small volume. Addition of Et2O induces the precipitation of the complex which was filtered off and dried in a desiccator for 5 h. 82.2 mg of the title compound as a red solid were obtained (yield 80percent).

Reference： [1]Journal of Organometallic Chemistry,2014,vol. 749,p. 379 - 386

48
[ 52522-40-4 ]
[ 6575-13-9 ]
[ 130-15-4 ]
[Pd(η²-naphthoquinone)(Dic)₂] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	In acetone; for 0.5h;Inert atmosphere; Darkness;	General procedure: To 64.3 mg (0.278 mmol) of TTbQ-Me dissolved in anhydrous acetone (20 ml) in a two necked flask, 30 mg (0.278 mmol) of p-benzoquinone and 120 mg (0.116 mmol) of Pd2DBA3CHCl3 were added in sequence under inert atmosphere (Ar). The resulting mixture was stirred in the dark for 30 min, filtered on a celite filter and evaporated under vacuum to a small volume. Addition of Et2O induces the precipitation of the complex which was filtered off and dried in a desiccator for 5 h. 82.2 mg of the title compound as a red solid were obtained (yield 80percent).

Reference： [1]Journal of Organometallic Chemistry,2014,vol. 749,p. 379 - 386

49
[ 65412-03-5 ]
[ 130-15-4 ]
[ 1607447-83-5 ]

Reference： [1]Journal of Organic Chemistry,2014,vol. 79,p. 4553 - 4560

50
[ 65412-03-5 ]
[ 130-15-4 ]
[ 1607448-11-2 ]

Reference： [1]Journal of Organic Chemistry,2014,vol. 79,p. 4553 - 4560

51
[ 699-08-1 ]
[ 130-15-4 ]
2-(4-ethoxyphenyl)[1,4]naphthoquinone [ No CAS ]

Reference： [1]Russian Journal of General Chemistry,2014,vol. 84,p. 1615 - 1621

52
[ 17745-45-8 ]
[ 130-15-4 ]
[ 34491-84-4 ]

Yield	Reaction Conditions	Operation in experiment
35%	With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; In dichloromethane; water; at 20℃; for 12h;	General procedure: To a solution of benzoquinone (0.5 mmol, 1.0 equiv.) and [Cp*IrCl2]2 (0.025mmol, 5%) in dichloromethane (2 mL) was added the phenylboronic acid (0.75 mmol, 1.5 equiv.) and water (2 mL) Then the solution was stirred vigorously at room temperature for 12 h. Upon completion, the reaction was diluted with dichloromethane (5 mL) and washed with 5% sodium bicarbonate. The layers were separated, and the aqueous layer was extracted with dichloromethane (10 X 3 mL), dried over sodium sulfate, and was evaporated to give the residue. The residue was then purified by column chromatography on silica gel (ethyl acetate / petroleumether = 1:10) to provide the corresponding product.

Reference： [1]Journal of Organometallic Chemistry,2015,vol. 780,p. 30 - 33

53
[ 604-44-4 ]
[ 130-15-4 ]

Reference： [1]RSC Advances,2016,vol. 6,p. 12717 - 12725

54
[ 571-57-3 ]
[ 2065-37-4 ]
[ 130-15-4 ]

Reference： [1]RSC Advances,2016,vol. 6,p. 12717 - 12725

55
[ 130-15-4 ]
[ 62784-48-9 ]
[ 2065-37-4 ]

Reference： [1]Chemical Science,2016,vol. 7,p. 3780 - 3784

56
[ 1950-68-1 ]
[ 130-15-4 ]
1,4-dihydroxy-2-(4-methoxyphenylsulfonyl)naphthalene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	In water; at 20℃; for 12h;	Naphthoquinone 22 (80 mg, 0.5 mmol), p-methoxybenzenesulfonylhydrazide 8 (151 mg, 0.75 mmol) was dissolved in H2O(5.0 mL), and the reaction mixture was allowed to react at room temperature for 12 hours. The reaction was complete. The reaction was extracted three times with EtOAc and the combined organic phases were dried over anhydrous sodium sulfate, filtered and the organic solvent was removed by distillation under reduced pressure. The residue was purified by silica gel column chromatography to give 2- (p-methoxybenzenesulfonyl) -1,4-dinaphthol 25 in 87% yield.
87%	With water; at 50℃; for 6h;Green chemistry;	General procedure: A mixture of 1,4-quinone 1 (0.50 mmol, 1.0 equiv.), sulfonyl hydrazide 2 (0.75 mmol, 1.5 equiv.) in H2O (5.0 mL) was stirred at 50 C for 6 h. Upon the completion of the reaction, the mixture was extracted with ethyl acetate (3*20 mL). The combined organic layers were dried over Na2SO4, filtered, and evaporated under reduced pressure to give crude product, which was purified by flash column chromatography on silica gel with ethyl acetate and petroleum ether as eluents to give the corresponding product 3a-p and 5a-i.

Reference： [1]Patent: CN106565554,2017,A .Location in patent: Paragraph 0101; 0102; 0103
[2]Tetrahedron,2017,vol. 73,p. 2760 - 2765
[3]European Journal of Organic Chemistry,2017,vol. 2017,p. 6081 - 6084

57
[ 930-45-0 ]
[ 130-15-4 ]
2-((2-hydroxycyclopentyl)amino)naphthalene-1,4-dione [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2018,vol. 83,p. 4119 - 4130

58
[ 130-15-4 ]
[ 19112-35-7 ]
ethyl 2-(2-chlorophenyl)-5-hydroxynaphtho[1,2-b]furan-3-carboxylate [ No CAS ]