[ CAS No. 142770-42-1 ] {[proInfo.proName]}

Name: 142770-42-1|1-Chloro-4-propoxy-9H-thioxanthen-9-one|97%
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Quality Control of [ 142770-42-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 142770-42-1 ]

SDS Specification

Alternatived Products of [ 142770-42-1 ]

Product Details of [ 142770-42-1 ]

CAS No. :	142770-42-1	MDL No. :	MFCD00191928
Formula :	C₁₆H₁₃ClO₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VKQJCUYEEABXNK-UHFFFAOYSA-N
M.W :	304.79	Pubchem ID :	5212856
Synonyms :

Calculated chemistry of [ 142770-42-1 ]

Physicochemical Properties

Num. heavy atoms :	20
Num. arom. heavy atoms :	14
Fraction Csp3 :	0.19
Num. rotatable bonds :	3
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	86.72
TPSA :	54.54 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.61 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.09
Log Po/w (XLOGP3) :	5.0
Log Po/w (WLOGP) :	4.86
Log Po/w (MLOGP) :	3.61
Log Po/w (SILICOS-IT) :	6.08
Consensus Log Po/w :	4.53

Druglikeness

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

Water Solubility

Log S (ESOL) :	-5.2
Solubility :	0.00192 mg/ml ; 0.00000631 mol/l
Class :	Moderately soluble
Log S (Ali) :	-5.89
Solubility :	0.000397 mg/ml ; 0.0000013 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-6.88
Solubility :	0.00004 mg/ml ; 0.000000131 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.9

Safety of [ 142770-42-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 142770-42-1 ]

* 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 [ 142770-42-1 ]
Downstream synthetic route of [ 142770-42-1 ]

[ 142770-42-1 ] Synthesis Path-Upstream 1~1

1
[ 59803-22-4 ]
[ 106-94-5 ]
[ 142770-42-1 ]

Yield	Reaction Conditions	Operation in experiment
95.4%	at 80℃;	(2) etherification reaction: adding 29 g of potassium carbonate to the above organic layer,33 grams of bromopropane, heated to 80 ° C under stirring for more than 5 hours,HPLC detection was carried out until the intermediate reaction was complete and the temperature was lowered to 40 °C.(3) To the above reaction system, 340 g of water was added for washing, and the layers were allowed to stand, and the obtained organic layer was decomposed under reduced pressure. After desolvation, the temperature was lowered slightly, 250 g of ethanol was added, 10 g of activated carbon was added, and the temperature was raised to 60 ° C. After stirring for 1 hour, the mixture was filtered, and the filtrate was placed in a rotating refrigerator overnight, suction filtered, and dried in vacuo to give 55.7 g of pale yellow solid powder.The measurement result was 95.4percent based on 2-mercaptobenzoic acid, the melting point was 99-103 ° C, and the purity of the product was determined by HPLC.99.1percent.

Reference： [1] Patent: CN108440495, 2018, A, . Location in patent: Paragraph 0035; 0037; 0038

[ 142770-42-1 ] Synthesis Path-Downstream 1~42

1
[ 142770-42-1 ]
[ 591773-95-4 ]

Yield	Reaction Conditions	Operation in experiment
72.7%	With ammonium cerium(IV) nitrate; In water; acetonitrile; at 50℃; for 1h;	EXAMPLE 9; . 0. 0g (0.0328moles) of <strong>[142770-42-1]1-chloro-4-propoxythioxanthone</strong> (CPTX) were dissolved in 630mol of a mixture of acetonitrile and water (75% acetonitrile, 25% water). Gentle heating was required to dissolve the CPTX (50C). 71.93g of Ceric ammonium nitrate (0.1312moles) were added in one batch. The reaction was followed by TLC. The reaction mixture was stirred for 1 hour. At this stage TLC indicated that the reaction was complete. The reaction was allowed to cool to room temperature and 400ml of water added. A small amount of precipitate formed. The mixture was extracted with 1000ml of diethyl ether. The ether solution was dried with magnesium sulphate, and the ether was removed on a rotary evaporator to yield the product that was subsequently dried in a vacuum oven. Product yield 6.74g (72.7%) of a yellow/orange solid. The product was analysed by HPLC, LC-MS and IR.
	With ammonium cerium(IV) nitrate; In water; acetonitrile; at 20℃; for 2h;	EXAMPLE 22 1-chloro-4-propyloxy-10-oxythioxanthone was prepared as follows. A solution of <strong>[142770-42-1]1-chloro-4-propyloxy-thioxanthone</strong> (5.0 g, 0.016 mol) in acetonitrile (400 mL) and water (80 mL) was stirred at room temperature. Ammonium cerium (IV) nitrate (44 g, 0.080 mol) was added and the resulting mixture was stirred for 2 h at room temperature. The reaction was followed by GC-MS. The reaction mixture was then quenched with water (500 mL) and was extracted with chloroform. After removal of the solvent, the obtained solid was recrystallized from benzene to give the title product as yellow crystals with mp 155-157 C. The identity of this compound was shown by 1H NMR and GC-MS to have the following structure:

Reference： [1]Russian Journal of Organic Chemistry,2006,vol. 42,p. 298 - 301
[2]Patent: WO2003/72567,2003,A1 .Location in patent: Page/Page column 21
[3]Patent: EP1538149,2005,A2 .Location in patent: Page/Page column 22

2
[ 142770-42-1 ]
4-propoxy-1-chloro-9H-thioxanthen-9-one 10,10-dioxide [ No CAS ]

Reference： [1]Russian Journal of Organic Chemistry,2006,vol. 42,p. 298 - 301

3
[ 142770-42-1 ]
4-propoxy-1-chloro-9-oxo-10-(4-heptoxyphenyl)-9H-thioxanthenium [ No CAS ]

Reference： [1]Russian Journal of Organic Chemistry,2006,vol. 42,p. 298 - 301

4
[ 134216-06-1 ]
[ 142770-42-1 ]
C₅₂H₇₀ClO₄S₂⁽¹⁺⁾*F₆Sb^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 20 A sulfonium salt containing <strong>[142770-42-1]1-chloro-4-propoxythioxanthone</strong> and bis(dodecyloxy) substituted phenyl groups was prepared as follows. A solution of 1-chloro-4-dodecyoxythioxanthone (2.1 g, 6.9 mmol), 4,4'-didodecylphenylsulfoxide (4.0 g, 7.0 mmol) in chloroform (100 mL) and acetic anhydride (25 mL) was stirred at 10-20º C. Concentrated sulfuric acid (98 %, 4.0 g, 40 mmol) was added slowly. The reaction was then warmed to room temperature and stirred for 48 h. Water (30 mL) and NaSbF6 (2.0 g, 7.7 mmol) were then added and the mixture was stirred at room temperature for additional 12 h. The mixture was washed with water and the organic layer was dried with MgSO4. After removal of the solvent, the obtained solid was recrystalized from MeOH to give a sulfonium salt as an orange solid. The identity of this compound was shown by 1H NMR to have the following structure:

Reference： [1]Patent: EP1538149,2005,A2 .Location in patent: Page/Page column 21

Yield	Reaction Conditions	Operation in experiment
75.5%		The solid was filtered and washed with water the resulting damp solid recrystallized from ethanol (50 ml) to afford the title compound (6.9 g; 75.5%) of mp 102-3. Analysis C16 H13 ClO2 S=304.777 Requires C 63.05%; H 4.30%; Cl 11.63%; S 10.52% Found C 63.14%; H 4.37%; Cl 11.66%; S 10.63%

6
[ 110-89-4 ]
[ 142770-42-1 ]
[ 1351934-53-6 ]

Reference： [1]Biochemical Pharmacology,2012,vol. 83,p. 57 - 68

7
[ 67-56-1 ]
[ 142770-42-1 ]
[ 156-87-6 ]
[ 1351934-50-3 ]
[ 1351934-52-5 ]

Reference： [1]Biochemical Pharmacology,2012,vol. 83,p. 57 - 68

8
[ 72-19-5 ]
[ 142770-42-1 ]
[ 1351934-55-8 ]

Reference： [1]Biochemical Pharmacology,2012,vol. 83,p. 57 - 68

9
[ 13889-98-0 ]
[ 142770-42-1 ]
[ 1351934-58-1 ]

Reference： [1]Biochemical Pharmacology,2012,vol. 83,p. 57 - 68

10
[ 54-85-3 ]
[ 142770-42-1 ]
[ 1351934-61-6 ]

Reference： [1]Biochemical Pharmacology,2012,vol. 83,p. 57 - 68

11
[ 16369-05-4 ]
[ 142770-42-1 ]
C₂₁H₂₅NO₃S [ No CAS ]

Reference： [1]Biochemical Pharmacology,2012,vol. 83,p. 57 - 68

12
[ 29518-68-1 ]
[ 142770-42-1 ]
[ 1351934-65-0 ]

Reference： [1]Biochemical Pharmacology,2012,vol. 83,p. 57 - 68

13
[ 115955-90-3 ]
[ 142770-42-1 ]
[ 1351934-63-8 ]

Reference： [1]Biochemical Pharmacology,2012,vol. 83,p. 57 - 68

14
C₁₂H₁₇NO₆ [ No CAS ]
[ 142770-42-1 ]
C₂₈H₂₉NO₈S [ No CAS ]

Reference： [1]Biochemical Pharmacology,2012,vol. 83,p. 57 - 68

15
[ 926-39-6 ]
[ 142770-42-1 ]
[ 1351934-62-7 ]

Reference： [1]Biochemical Pharmacology,2012,vol. 83,p. 57 - 68

16
[ 1944-96-3 ]
[ 142770-42-1 ]
[ 1351934-69-4 ]

Reference： [1]Biochemical Pharmacology,2012,vol. 83,p. 57 - 68

17
[ 539-48-0 ]
[ 142770-42-1 ]
[ 1351934-59-2 ]

Reference： [1]Biochemical Pharmacology,2012,vol. 83,p. 57 - 68

18
[ 24954-67-4 ]
[ 142770-42-1 ]
[ 1351934-68-3 ]

Reference： [1]Biochemical Pharmacology,2012,vol. 83,p. 57 - 68

19
[ 616-86-4 ]
[ 142770-42-1 ]
[ 1351934-70-7 ]

Reference： [1]Biochemical Pharmacology,2012,vol. 83,p. 57 - 68

20
[ 1484-85-1 ]
[ 142770-42-1 ]
[ 1351934-66-1 ]

Reference： [1]Biochemical Pharmacology,2012,vol. 83,p. 57 - 68
[2]Archives of Toxicology,2015,vol. 89,p. 1783 - 1800

21
[ 78-81-9 ]
[ 142770-42-1 ]
[ 1351934-51-4 ]

Reference： [1]Biochemical Pharmacology,2012,vol. 83,p. 57 - 68
[2]Archives of Toxicology,2015,vol. 89,p. 1783 - 1800

22
[ 1664-40-0 ]
[ 142770-42-1 ]
[ 1351934-60-5 ]

Reference： [1]Biochemical Pharmacology,2012,vol. 83,p. 57 - 68

23
[ 5763-61-1 ]
[ 142770-42-1 ]
[ 1351934-67-2 ]

Reference： [1]Biochemical Pharmacology,2012,vol. 83,p. 57 - 68

24
[ 75-31-0 ]
[ 142770-42-1 ]
[ 1351934-54-7 ]

Reference： [1]Biochemical Pharmacology,2012,vol. 83,p. 57 - 68
[2]Archives of Toxicology,2015,vol. 89,p. 1783 - 1800

25
[ 100-36-7 ]
[ 142770-42-1 ]
[ 1351934-57-0 ]

Yield	Reaction Conditions	Operation in experiment
	With copper(I) oxide; potassium carbonate; In methanol; at 100℃; for 24h;	Four individual mixtures of TX (500 mg; 2.0 mmol), amine A1 (0.44 mL, 4.0 mmol), K2CO3 (442 mg; 4.0 mmol), Cu2O (2 mg) and MeOH (20 mL) were placed in closed vessels. The mixtures were allowed to react in parallel at 100 C, with no stirring, during 24 h. The reaction mixtures were recombined, filtered and concentrated under reduced pressure furnishing a dark brown crude product. The crude product was dissolved with diethyl ether (30 mL), made alkaline with an aqueous solution of NaOH 20% and washed with water (3 30 mL). The ether fraction was dried (Na2SO4), filtered and concentrated under vacuum. This concentrate was used to the next reaction without further purification.

Reference： [1]Biochemical Pharmacology,2012,vol. 83,p. 57 - 68
[2]Molecules,2016,vol. 21

26
[ 10272-07-8 ]
[ 142770-42-1 ]
[ 1351934-64-9 ]

Reference： [1]Biochemical Pharmacology,2012,vol. 83,p. 57 - 68

27
[ 24313-88-0 ]
[ 142770-42-1 ]
[ 1351934-71-8 ]

Reference： [1]Biochemical Pharmacology,2012,vol. 83,p. 57 - 68

28
[ 142770-42-1 ]
[ 147053-83-6 ]

Reference： [1]Biochemical Pharmacology,2012,vol. 83,p. 57 - 68

29
[ 142770-42-1 ]
[ 1351934-73-0 ]
[ 105659-92-5 ]

Reference： [1]Biochemical Pharmacology,2012,vol. 83,p. 57 - 68

30
[ 142770-42-1 ]
[ 59803-22-4 ]

Reference： [1]Biochemical Pharmacology,2012,vol. 83,p. 57 - 68
[2]Archives of Toxicology,2015,vol. 89,p. 1783 - 1800

31
[ 142770-42-1 ]
[ 156-87-6 ]
[ 1351934-52-5 ]

Reference： [1]Archives of Toxicology,2015,vol. 89,p. 1783 - 1800

32
[ 2749-11-3 ]
[ 142770-42-1 ]
(S)-1-((1-hydroxypropan-2-yl)amino)-4-propoxy-9H-thioxanthen-9-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.97%	With copper(l) iodide; potassium carbonate; In methanol; at 100℃; for 48h;	General procedure: 1-Chloro-4-propoxy-9H-thioxanthen-9-one (Tx, 450 mg, 1.48 mmol) and a suitable chiral aminoalcohol (9-16, 1.72 mmol) were dissolved in methanol (30 mL) and CuI (0.15 mmol) and K2CO3(1.92 mmol) were added. The reaction mixture was heated at 100 C in a muffle furnace for 48 h.After the completion of the reaction, the crude material was filtrated, washed with dichloromethane,and the organic solvents were evaporated under reduced pressure. Then, the obtained solid wasdissolved in 50 mL of dichloromethane and extracted with HCl 1M(3 50 mL). The aqueous layer wasbasified with NaOH 20% and extracted with dichloromethane (3 100 mL). The organic layers weregathered, washed with water (3 50 mL), dried over anhydrous sodium sulphate and the solvent wasevaporated under reduced pressure. Then, a solid phase extraction using a cation exchange cartridgeDiscovery DSC-SCX was applied to further purify the extracted material. First, an activation ofthe cartridge with dichloromethane (50 mL) was performed followed by loading the cartridge withthe sample (previously incorporated in silica). Then, elution was carried out with the followingsolvents: dichloromethane, a mixture of dichloromethane/methanol 5:5 (v/v), methanol 100% andNH3 2% in methanol. The fractions containing the chiral ATxs were gathered and the solvent wasevaporated under reduced pressure. A flash column chromatography with n-hexane/ethyl acetate ingradient and crystallization from chloroform and petroleum ether (4:1) were also performed to obtainpure compounds.(S)-1-((1-Hydroxypropan-2-yl)amino)-4-propoxy-9H-thioxanthen-9-one (ATx 1 (+)). Yield: 1.97%. m.p.:116-118 C (dec.); [alpha]25D +112 (c = 3.4 103 g/mL in dichloromethane). IR (KBr) numax: 3419, 3270,2962, 2925, 2873, 2359, 2341, 1618, 1568, 1507, 1435, 1293, 1269, 1252, 1225, 746 cm1. 1H-NMR(300.13 MHz, CDCl3): delta: 8.50 (1H, d, J = 8.0 Hz, H-8), : 7.56 (2H, m, H-5 and H-6), : 7.43 (1H, m, H-7),: 7.13 (1H, d, J = 9.0 Hz, H-3), : 6.85 (1H, d, J = 9.0 Hz, H-2), : 4.03 (2H, t, J = 6.5 Hz, H-a), : 3.81 (3H,m, H-10 and CH2OH), : 1.90 (2H, m, H-b), : 1.32 (3H, d, J = 6.2 Hz, H-20), : 1.12 (3H, t, J = 7.4 Hz,H-c). 13C-NMR (75.47 MHz, CDCl3): delta: 183.55 (C-9), 146.50 (C-4), 144.02 (C-1), 136.85 (C-6), 131.92(C-8a), 129.85 (C-4a), 129.24 (C-9a), 126.08 (C-8), 125.98 (C-7), 125.20 (C-5), 119.12 (C-3), 114.10 (C-10a),109.80 (C-2), 72.48 (C-a), 65.96 (C-CH2OH), 51.91 (C-10), 22.66 (C-b), 16.86 (C-20), 10.71 (C-c). e.e. > 99%(HPLC; column: Lux Amylose-1 (250 4.6 mm i.d., 5 m), Mobile phase: n-hexane:ethanol (70:30v/v), 0.5 mL/min, max 254 nm).

Reference： [1]Molecules,2018,vol. 23

33
[ 35320-23-1 ]
[ 142770-42-1 ]
(R)-1-((1-hydroxypropan-2-yl)amino)-4-propoxy-9H-thioxanthen-9-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
5.91%	With copper(l) iodide; potassium carbonate; In methanol; at 100℃; for 48h;	General procedure: 1-Chloro-4-propoxy-9H-thioxanthen-9-one (Tx, 450 mg, 1.48 mmol) and a suitable chiral aminoalcohol (9-16, 1.72 mmol) were dissolved in methanol (30 mL) and CuI (0.15 mmol) and K2CO3(1.92 mmol) were added. The reaction mixture was heated at 100 C in a muffle furnace for 48 h.After the completion of the reaction, the crude material was filtrated, washed with dichloromethane,and the organic solvents were evaporated under reduced pressure. Then, the obtained solid wasdissolved in 50 mL of dichloromethane and extracted with HCl 1M(3 50 mL). The aqueous layer wasbasified with NaOH 20% and extracted with dichloromethane (3 100 mL). The organic layers weregathered, washed with water (3 50 mL), dried over anhydrous sodium sulphate and the solvent wasevaporated under reduced pressure. Then, a solid phase extraction using a cation exchange cartridgeDiscovery DSC-SCX was applied to further purify the extracted material. First, an activation ofthe cartridge with dichloromethane (50 mL) was performed followed by loading the cartridge withthe sample (previously incorporated in silica). Then, elution was carried out with the followingsolvents: dichloromethane, a mixture of dichloromethane/methanol 5:5 (v/v), methanol 100% andNH3 2% in methanol. The fractions containing the chiral ATxs were gathered and the solvent wasevaporated under reduced pressure. A flash column chromatography with n-hexane/ethyl acetate ingradient and crystallization from chloroform and petroleum ether (4:1) were also performed to obtainpure compounds.

Reference： [1]Molecules,2018,vol. 23

34
[ 2799-17-9 ]
[ 142770-42-1 ]
(S)-1-((2-hydroxypropyl)amino)-4-propoxy-9H-thioxanthen-9-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
7.86%	With copper(l) iodide; potassium carbonate; In methanol; at 100℃; for 48h;	General procedure: 1-Chloro-4-propoxy-9H-thioxanthen-9-one (Tx, 450 mg, 1.48 mmol) and a suitable chiral aminoalcohol (9-16, 1.72 mmol) were dissolved in methanol (30 mL) and CuI (0.15 mmol) and K2CO3(1.92 mmol) were added. The reaction mixture was heated at 100 C in a muffle furnace for 48 h.After the completion of the reaction, the crude material was filtrated, washed with dichloromethane,and the organic solvents were evaporated under reduced pressure. Then, the obtained solid wasdissolved in 50 mL of dichloromethane and extracted with HCl 1M(3 50 mL). The aqueous layer wasbasified with NaOH 20% and extracted with dichloromethane (3 100 mL). The organic layers weregathered, washed with water (3 50 mL), dried over anhydrous sodium sulphate and the solvent wasevaporated under reduced pressure. Then, a solid phase extraction using a cation exchange cartridgeDiscovery DSC-SCX was applied to further purify the extracted material. First, an activation ofthe cartridge with dichloromethane (50 mL) was performed followed by loading the cartridge withthe sample (previously incorporated in silica). Then, elution was carried out with the followingsolvents: dichloromethane, a mixture of dichloromethane/methanol 5:5 (v/v), methanol 100% andNH3 2% in methanol. The fractions containing the chiral ATxs were gathered and the solvent wasevaporated under reduced pressure. A flash column chromatography with n-hexane/ethyl acetate ingradient and crystallization from chloroform and petroleum ether (4:1) were also performed to obtainpure compounds.

Reference： [1]Molecules,2018,vol. 23

35
[ 2799-16-8 ]
[ 142770-42-1 ]
(R)-1-((2-hydroxypropyl)amino)-4-propoxy-9H-thioxanthen-9-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
23.62%	With copper(l) iodide; potassium carbonate; In methanol; at 100℃; for 48h;	General procedure: 1-Chloro-4-propoxy-9H-thioxanthen-9-one (Tx, 450 mg, 1.48 mmol) and a suitable chiral aminoalcohol (9-16, 1.72 mmol) were dissolved in methanol (30 mL) and CuI (0.15 mmol) and K2CO3(1.92 mmol) were added. The reaction mixture was heated at 100 C in a muffle furnace for 48 h.After the completion of the reaction, the crude material was filtrated, washed with dichloromethane,and the organic solvents were evaporated under reduced pressure. Then, the obtained solid wasdissolved in 50 mL of dichloromethane and extracted with HCl 1M(3 50 mL). The aqueous layer wasbasified with NaOH 20% and extracted with dichloromethane (3 100 mL). The organic layers weregathered, washed with water (3 50 mL), dried over anhydrous sodium sulphate and the solvent wasevaporated under reduced pressure. Then, a solid phase extraction using a cation exchange cartridgeDiscovery DSC-SCX was applied to further purify the extracted material. First, an activation ofthe cartridge with dichloromethane (50 mL) was performed followed by loading the cartridge withthe sample (previously incorporated in silica). Then, elution was carried out with the followingsolvents: dichloromethane, a mixture of dichloromethane/methanol 5:5 (v/v), methanol 100% andNH3 2% in methanol. The fractions containing the chiral ATxs were gathered and the solvent wasevaporated under reduced pressure. A flash column chromatography with n-hexane/ethyl acetate ingradient and crystallization from chloroform and petroleum ether (4:1) were also performed to obtainpure compounds.

Reference： [1]Molecules,2018,vol. 23

36
[ 7533-40-6 ]
[ 142770-42-1 ]
(S)-1-((1-hydroxy-4-methylpentan-2-yl)amino)-4-propoxy-9H-thioxanthen-9-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
19.59%	With copper(l) iodide; potassium carbonate; In methanol; at 100℃; for 48h;	General procedure: 1-Chloro-4-propoxy-9H-thioxanthen-9-one (Tx, 450 mg, 1.48 mmol) and a suitable chiral aminoalcohol (9-16, 1.72 mmol) were dissolved in methanol (30 mL) and CuI (0.15 mmol) and K2CO3(1.92 mmol) were added. The reaction mixture was heated at 100 C in a muffle furnace for 48 h.After the completion of the reaction, the crude material was filtrated, washed with dichloromethane,and the organic solvents were evaporated under reduced pressure. Then, the obtained solid wasdissolved in 50 mL of dichloromethane and extracted with HCl 1M(3 50 mL). The aqueous layer wasbasified with NaOH 20% and extracted with dichloromethane (3 100 mL). The organic layers weregathered, washed with water (3 50 mL), dried over anhydrous sodium sulphate and the solvent wasevaporated under reduced pressure. Then, a solid phase extraction using a cation exchange cartridgeDiscovery DSC-SCX was applied to further purify the extracted material. First, an activation ofthe cartridge with dichloromethane (50 mL) was performed followed by loading the cartridge withthe sample (previously incorporated in silica). Then, elution was carried out with the followingsolvents: dichloromethane, a mixture of dichloromethane/methanol 5:5 (v/v), methanol 100% andNH3 2% in methanol. The fractions containing the chiral ATxs were gathered and the solvent wasevaporated under reduced pressure. A flash column chromatography with n-hexane/ethyl acetate ingradient and crystallization from chloroform and petroleum ether (4:1) were also performed to obtainpure compounds.

Reference： [1]Molecules,2018,vol. 23

37
[ 7533-40-6 ]
[ 142770-42-1 ]
(R)-1-((1-hydroxy-4-methylpentan-2-yl)amino)-4-propoxy-9H-thioxanthen-9-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
10.4%	With copper(l) iodide; potassium carbonate; In methanol; at 100℃; for 48h;	General procedure: 1-Chloro-4-propoxy-9H-thioxanthen-9-one (Tx, 450 mg, 1.48 mmol) and a suitable chiral aminoalcohol (9-16, 1.72 mmol) were dissolved in methanol (30 mL) and CuI (0.15 mmol) and K2CO3(1.92 mmol) were added. The reaction mixture was heated at 100 C in a muffle furnace for 48 h.After the completion of the reaction, the crude material was filtrated, washed with dichloromethane,and the organic solvents were evaporated under reduced pressure. Then, the obtained solid wasdissolved in 50 mL of dichloromethane and extracted with HCl 1M(3 50 mL). The aqueous layer wasbasified with NaOH 20% and extracted with dichloromethane (3 100 mL). The organic layers weregathered, washed with water (3 50 mL), dried over anhydrous sodium sulphate and the solvent wasevaporated under reduced pressure. Then, a solid phase extraction using a cation exchange cartridgeDiscovery DSC-SCX was applied to further purify the extracted material. First, an activation ofthe cartridge with dichloromethane (50 mL) was performed followed by loading the cartridge withthe sample (previously incorporated in silica). Then, elution was carried out with the followingsolvents: dichloromethane, a mixture of dichloromethane/methanol 5:5 (v/v), methanol 100% andNH3 2% in methanol. The fractions containing the chiral ATxs were gathered and the solvent wasevaporated under reduced pressure. A flash column chromatography with n-hexane/ethyl acetate ingradient and crystallization from chloroform and petroleum ether (4:1) were also performed to obtainpure compounds.

Reference： [1]Molecules,2018,vol. 23

38
[ 2026-48-4 ]
[ 142770-42-1 ]
(S)-1-((1-hydroxy-3-methylbutan-2-yl)amino)-4-propoxy-9H-thioxanthen-9-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
10.12%	With copper(l) iodide; potassium carbonate; In methanol; at 100℃; for 48h;	General procedure: 1-Chloro-4-propoxy-9H-thioxanthen-9-one (Tx, 450 mg, 1.48 mmol) and a suitable chiral aminoalcohol (9-16, 1.72 mmol) were dissolved in methanol (30 mL) and CuI (0.15 mmol) and K2CO3(1.92 mmol) were added. The reaction mixture was heated at 100 C in a muffle furnace for 48 h.After the completion of the reaction, the crude material was filtrated, washed with dichloromethane,and the organic solvents were evaporated under reduced pressure. Then, the obtained solid wasdissolved in 50 mL of dichloromethane and extracted with HCl 1M(3 50 mL). The aqueous layer wasbasified with NaOH 20% and extracted with dichloromethane (3 100 mL). The organic layers weregathered, washed with water (3 50 mL), dried over anhydrous sodium sulphate and the solvent wasevaporated under reduced pressure. Then, a solid phase extraction using a cation exchange cartridgeDiscovery DSC-SCX was applied to further purify the extracted material. First, an activation ofthe cartridge with dichloromethane (50 mL) was performed followed by loading the cartridge withthe sample (previously incorporated in silica). Then, elution was carried out with the followingsolvents: dichloromethane, a mixture of dichloromethane/methanol 5:5 (v/v), methanol 100% andNH3 2% in methanol. The fractions containing the chiral ATxs were gathered and the solvent wasevaporated under reduced pressure. A flash column chromatography with n-hexane/ethyl acetate ingradient and crystallization from chloroform and petroleum ether (4:1) were also performed to obtainpure compounds.

Reference： [1]Molecules,2018,vol. 23

39
[ 4276-09-9 ]
[ 142770-42-1 ]
(R)-1-((1-hydroxy-3-methylbutan-2-yl)amino)-4-propoxy-9H-thioxanthen-9-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
10.24%	With copper(l) iodide; potassium carbonate; In methanol; at 100℃; for 48h;	General procedure: 1-Chloro-4-propoxy-9H-thioxanthen-9-one (Tx, 450 mg, 1.48 mmol) and a suitable chiral aminoalcohol (9-16, 1.72 mmol) were dissolved in methanol (30 mL) and CuI (0.15 mmol) and K2CO3(1.92 mmol) were added. The reaction mixture was heated at 100 C in a muffle furnace for 48 h.After the completion of the reaction, the crude material was filtrated, washed with dichloromethane,and the organic solvents were evaporated under reduced pressure. Then, the obtained solid wasdissolved in 50 mL of dichloromethane and extracted with HCl 1M(3 50 mL). The aqueous layer wasbasified with NaOH 20% and extracted with dichloromethane (3 100 mL). The organic layers weregathered, washed with water (3 50 mL), dried over anhydrous sodium sulphate and the solvent wasevaporated under reduced pressure. Then, a solid phase extraction using a cation exchange cartridgeDiscovery DSC-SCX was applied to further purify the extracted material. First, an activation ofthe cartridge with dichloromethane (50 mL) was performed followed by loading the cartridge withthe sample (previously incorporated in silica). Then, elution was carried out with the followingsolvents: dichloromethane, a mixture of dichloromethane/methanol 5:5 (v/v), methanol 100% andNH3 2% in methanol. The fractions containing the chiral ATxs were gathered and the solvent wasevaporated under reduced pressure. A flash column chromatography with n-hexane/ethyl acetate ingradient and crystallization from chloroform and petroleum ether (4:1) were also performed to obtainpure compounds.

Reference： [1]Molecules,2018,vol. 23

40
[ 59803-22-4 ]
[ 106-94-5 ]
[ 142770-42-1 ]

Yield	Reaction Conditions	Operation in experiment
95.4%	With potassium carbonate; at 80℃;	(2) etherification reaction: adding 29 g of potassium carbonate to the above organic layer,33 grams of bromopropane, heated to 80 C under stirring for more than 5 hours,HPLC detection was carried out until the intermediate reaction was complete and the temperature was lowered to 40 C.(3) To the above reaction system, 340 g of water was added for washing, and the layers were allowed to stand, and the obtained organic layer was decomposed under reduced pressure. After desolvation, the temperature was lowered slightly, 250 g of ethanol was added, 10 g of activated carbon was added, and the temperature was raised to 60 C. After stirring for 1 hour, the mixture was filtered, and the filtrate was placed in a rotating refrigerator overnight, suction filtered, and dried in vacuo to give 55.7 g of pale yellow solid powder.The measurement result was 95.4% based on 2-mercaptobenzoic acid, the melting point was 99-103 C, and the purity of the product was determined by HPLC.99.1%.

Reference： [1]Patent: CN108440495,2018,A .Location in patent: Paragraph 0035; 0037; 0038

41
[ 97-39-2 ]
[ 142770-42-1 ]
(E)‐6‐propoxy‐N,3‐di‐o‐tolylthiochromeno[4,3,2‐de]quinazolin‐2(3H)‐imine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
13%	With copper(l) iodide; potassium carbonate In methanol at 100℃; for 48h; Sealed tube;	3.1.1. General Procedure for the Synthesis of Aminated Tetracyclic Thioxanthenes General procedure: the appropriate guanidine or urea derivative (7-10, 0.2 mmol) in methanol (25 mL),CuI (2 mg) and K2CO3 (0.1 mmol) were added and the suspension was heated at 100 °Cfor 48 h, in a sealed flask. The 1H and 13C NMR spectra and HRMS chromatograms forcompounds 11-14 are present in the Supplementary Materials (Figures S1-S8).

Reference： [1]Amorim, Isabel; Bousbaa, Hassan; Durães, Fernando; Esteves, Cátia I. C.; Gales, Luís; Guieu, Samuel; Novais, Pedro; Pinto, Madalena; Silva, Patrícia M. A.; Sousa, Emília [Molecules, 2021, vol. 26, # 11]

42
[ 97-39-2 ]
[ 142770-42-1 ]
C₃₁H₂₇N₃OS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With copper(l) iodide; potassium carbonate In methanol at 100℃; for 48h; Sealed tube;

Reference： [1]Durães, Fernando; Palmeira, Andreia; Cruz, Bárbara; Freitas-Silva, Joana; Szemerédi, Nikoletta; Gales, Luís; da Costa, Paulo Martins; Remião, Fernando; Silva, Renata; Pinto, Madalena; Spengler, Gabriella; Sousa, Emília [Pharmaceuticals, 2021, vol. 14, # 6]

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[ 142770-42-1 ] Synthesis Path-Upstream 1~1

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