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[ CAS No. 1000623-95-9 ] {[proInfo.proName]}

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Chemical Structure| 1000623-95-9
Chemical Structure| 1000623-95-9
Structure of 1000623-95-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1000623-95-9 ]

CAS No. :1000623-95-9 MDL No. :MFCD16619382
Formula : C30H38Br2N2O2S2 Boiling Point : -
Linear Structure Formula :- InChI Key :JVVGLKKTAZYUQU-UHFFFAOYSA-N
M.W :682.57 Pubchem ID :53439694
Synonyms :

Calculated chemistry of [ 1000623-95-9 ]

Physicochemical Properties

Num. heavy atoms : 38
Num. arom. heavy atoms : 18
Fraction Csp3 : 0.53
Num. rotatable bonds : 14
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 174.62
TPSA : 100.48 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -3.41 cm/s

Lipophilicity

Log Po/w (iLOGP) : 5.82
Log Po/w (XLOGP3) : 9.93
Log Po/w (WLOGP) : 9.97
Log Po/w (MLOGP) : 6.15
Log Po/w (SILICOS-IT) : 11.75
Consensus Log Po/w : 8.72

Druglikeness

Lipinski : 2.0
Ghose : None
Veber : 1.0
Egan : 1.0
Muegge : 2.0
Bioavailability Score : 0.17

Water Solubility

Log S (ESOL) : -9.75
Solubility : 0.00000012 mg/ml ; 0.0000000002 mol/l
Class : Poorly soluble
Log S (Ali) : -11.97
Solubility : 0.0000000007 mg/ml ; 0.0 mol/l
Class : Insoluble
Log S (SILICOS-IT) : -11.2
Solubility : 0.0000000043 mg/ml ; 0.0 mol/l
Class : Insoluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 5.52

Safety of [ 1000623-95-9 ]

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

Application In Synthesis of [ 1000623-95-9 ]

* 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 [ 1000623-95-9 ]
  • Downstream synthetic route of [ 1000623-95-9 ]

[ 1000623-95-9 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 1185885-86-2 ]
  • [ 1000623-95-9 ]
YieldReaction ConditionsOperation in experiment
71% With N-Bromosuccinimide In chloroform at -0.16℃; for 2 h; Compound 3 (1.01 g, 2.05 mmol) was charged in a 100 mLsingle-neck round–bottom flask filled with 50 mL of CHCl3.The mixture was cooled to 273 K and stirred while Nbromosuccinimide(NBS) was added in small portions. Themixture was allowed to warm to room temperature and stirredfor 2 h following complete addition of NBS. The reactionmixture was poured in water and extracted with CHCl3.Then CHCl3 was evaporated, the resulting red solid (darkred) was purified by column chromatography using CHCl3/petroleum ether as eluent. 0.95 g of 4 [31] were isolated (71percentyield). 1H NMR (500 MHz, CDCl3): (ppm) = 8.30 (d,J = 3.7 Hz, 2 H), 6.62 (d, J = 3.7 Hz, 2 H), 3.99 (add,J = 2.7 Hz, 7.4 Hz, 4 H), 1.78–1.68 (m, 2 H), 1.39–1.24 (m,16 H), 0.92 (t, J = 7.5 Hz, 6 H), 0.88 (t, J = 7.0 Hz, 6 H). 13C(75 MHz, CDCl3): (ppm) = 161.1, 146.4, 132.9, 126.4, 122.4,115.7, 106.4, 46.4, 40.2, 30.7, 28.9, 23.9, 23.3, 14.2, 10.8. FTIR(KBr) ν max = 3422, 3084, 2957, 2926, 2859, 1657, 1556,1504.9, 1450, 1406, 1308, 1261, 1233, 1165, 1100, 1072,1027, 967, 833, 810, 731, 709, 635, 466, 430 cm−
71% With N-Bromosuccinimide In chloroform at 0℃; for 12 h; Darkness Charge a 500-ml eggplant-shape flask with the above- prepared compound (b) (3.0 g, 5.7 mmol), N-bromosuccinimide (2.5 g, 13.8 mmol), and chloroform (200 ml). Agitate the flask content for 12 hours at 0° C. under light shielding condition. After distilling the solvent away under reducedpressures, add MeOR (100 ml) to the flask. Separate the precipitate by filtration. Thus, a dark green powder (4.8 g, 71.0percent) is obtained. mlz=683.1 (M+H)
70% With N-Bromosuccinimide; acetic acid In chloroform at 20℃; for 12 h; 3.56 g of 2,5-diethylhexyl-3,6-dithiophen-2-ylpyrrolo[3,4-c]pyrrolo-1,4-dione dissolved in 150 ml chloroform (CF) was added to a 500 ml two-necked flask. 2.50 g of N-bromosuccinimide (NBS) was added, a small amount of acetic acid was added, and the mixture was stirred at room temperature for 12 hours. After the reaction was completed by confirming thin-layer chromatography (TLC), the solvent was concentrated to about 20 ml under reduced pressure, and ethanol was added and a solid precipitate was filtered through a filter. The solid thus separated was again dissolved in chloroform, and short column was carried out using silica to obtain a black powder. (Yield: 70percent).
65% With N-Bromosuccinimide; acetic acid In tetrahydrofuran at 0℃; for 12 h; the formula (5) Compound 6 (2.00g, 3.81mmol) was dissolved in 50ml of tetrahydrofuran (THF), cooled to 0 ° C, then added in three portions N- bromosuccinimide (NBS ) (1. 42g, 8. OOmmol), while dropping a few drops of glacial acetic acid. After 12 hours under reduced pressure the reaction solvent was distilled off, boiling range 60 ° C -90 ° C petroleum ether as eluent over a silica gel column to give 1. 69g of the formula (5) Compound 7 in a yield of 65percent.

Reference: [1] Journal of the American Chemical Society, 2010, vol. 132, # 44, p. 15547 - 15549
[2] Australian Journal of Chemistry, 2014, vol. 67, # 8-9, p. 1330 - 1337
[3] RSC Advances, 2015, vol. 5, # 25, p. 19520 - 19527
[4] Journal of Materials Chemistry A, 2013, vol. 1, # 8, p. 2795 - 2805
[5] Journal of Fluorescence, 2016, vol. 26, # 6, p. 1939 - 1949
[6] Patent: US9590187, 2017, B2, . Location in patent: Page/Page column 40
[7] Patent: KR101676526, 2016, B1, . Location in patent: Paragraph 0197-0199
[8] European Journal of Organic Chemistry, 2017, vol. 2017, # 33, p. 4896 - 4904
[9] RSC Advances, 2016, vol. 6, # 11, p. 9023 - 9036
[10] European Journal of Organic Chemistry, 2016, vol. 2016, # 15, p. 2617 - 2627
[11] Patent: CN103360397, 2016, B, . Location in patent: Paragraph 0031-0033; 0038
[12] RSC Advances, 2014, vol. 4, # 101, p. 58027 - 58035
[13] Journal of Materials Chemistry A, 2015, vol. 3, # 8, p. 4229 - 4238
[14] Journal of Polymer Science, Part A: Polymer Chemistry, 2010, vol. 48, # 7, p. 1669 - 1675
[15] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 3, p. 1983 - 1994
[16] Organic Letters, 2014, vol. 16, # 13, p. 3508 - 3511
[17] Dyes and Pigments, 2012, vol. 95, # 1, p. 126 - 133
[18] Collection of Czechoslovak Chemical Communications, 2012, vol. 77, # 6, p. 462 - 469
[19] Patent: WO2008/664, 2008, A1, . Location in patent: Page/Page column 43
[20] Patent: WO2009/47104, 2009, A2, . Location in patent: Page/Page column 33; 34
[21] Chemistry of Materials, 2013, vol. 25, # 12, p. 2549 - 2556
[22] Physical Chemistry Chemical Physics, 2014, vol. 16, # 32, p. 17253 - 17265
[23] Electrochimica Acta, 2014, vol. 144, p. 211 - 220
[24] Dyes and Pigments, 2016, vol. 127, p. 37 - 44
  • 2
  • [ 1185885-86-2 ]
  • [ 1000623-95-9 ]
  • [ 1308671-90-0 ]
YieldReaction ConditionsOperation in experiment
73% With N-Bromosuccinimide In chloroform at 20℃; for 0.5 h; Inert atmosphere; Darkness Cmpd 1 (857.1 mg, 1.633 mmol) was solubilized in 60 mL CHCl3 previously deacidified onbasic alumina. The solution was stirred in the dark, degassed and an argon flow wasmaintained during the entire reaction. NBS (467.5 mg, 2.627 mmol, 1.6 equiv) was added inone portion. The reaction medium was evaporated, taken up in CH2Cl2, washed with water and brine, driedover Na2SO4. Bis- and mono-brominated products were separated by repetitive chromatography columns onsilica gel using at first a gradient of toluene/petroleum ether (50/50 to 100/0) as eluent, then a gradient ofCH2Cl2/petroleum ether (70/30 to 100/0). The bis-brominated product (3) was obtained as a deep purplesolid (73percent, 815.1 mg) and the mono brominated (2) as a fushia-purple solid (107.0 mg, 11percent).
53% With N-Bromosuccinimide In chloroform at 20℃; for 0.5 h; Inert atmosphere; Darkness NBS (230.5 mg, 1.295 mmol, 1.2 equiv) was added to a degassed solution of cmpd 1 (555.0mg, 1.058 mmol) in deacidified CHCl3. The reaction medium was stirred in the dark underan argon flow at rt for 30 min. The solution was evaporated and the residue was taken up inCH2Cl2, washed with water, brine and dried over Na2SO4. Purification on silica gel column chromatographyusing a gradient of CH2Cl2/toluene/petroleum ether (5/55/40, 13/50/37, 100/0/0) afforded the monobrominatedcmpd (2) in 53percent as a fushia-purple solid. The bis-brominated product (3) was also isolated in26 percent as a dark purple solid and 19 percent of the starting material was recovered.
Reference: [1] Synlett, 2015, vol. 26, # 15, p. 2109 - 2116
[2] Synlett, 2015, vol. 26, # 15, p. 2109 - 2116
  • 3
  • [ 1003-31-2 ]
  • [ 1000623-95-9 ]
Reference: [1] Dyes and Pigments, 2012, vol. 95, # 1, p. 126 - 133
[2] RSC Advances, 2014, vol. 4, # 101, p. 58027 - 58035
[3] Electrochimica Acta, 2014, vol. 144, p. 211 - 220
[4] RSC Advances, 2015, vol. 5, # 25, p. 19520 - 19527
[5] Dyes and Pigments, 2016, vol. 127, p. 37 - 44
[6] Patent: CN103360397, 2016, B,
[7] Journal of Fluorescence, 2016, vol. 26, # 6, p. 1939 - 1949
[8] Patent: US9590187, 2017, B2,
[9] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 3, p. 1983 - 1994
  • 4
  • [ 18908-66-2 ]
  • [ 1000623-95-9 ]
Reference: [1] Electrochimica Acta, 2014, vol. 144, p. 211 - 220
[2] Journal of Materials Chemistry A, 2015, vol. 3, # 8, p. 4229 - 4238
[3] Patent: KR101676526, 2016, B1,
[4] European Journal of Organic Chemistry, 2017, vol. 2017, # 33, p. 4896 - 4904
  • 5
  • [ 18908-66-2 ]
  • [ 1000623-95-9 ]
Reference: [1] Dyes and Pigments, 2012, vol. 95, # 1, p. 126 - 133
[2] Chemistry of Materials, 2013, vol. 25, # 12, p. 2549 - 2556
[3] Collection of Czechoslovak Chemical Communications, 2012, vol. 77, # 6, p. 462 - 469
[4] Synlett, 2015, vol. 26, # 15, p. 2109 - 2116
  • 6
  • [ 1000623-95-9 ]
  • [ 73183-34-3 ]
  • [ 1269004-46-7 ]
YieldReaction ConditionsOperation in experiment
53.4% With 1,1'-bis-(diphenylphosphino)ferrocene; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 120℃; for 15 h; Inert atmosphere After making the gas in the 100 mL flask under a nitrogen gas air current atmosphere,Compound 13 (manufactured by Luminescence Technology, 3.70 g, 5.4 mmoll), bis (pinacolato) diboron(3.00 g, 11.8 mmol), potassium acetate(2.59 g, 26.4 mmol),[1,1'-bis (diphenylphosphino) ferrocene] palladium (II)Dichloride dichloromethane adduct (0.09 g, 0.1 mmol),1,1'-bis (diphenylphosphino) ferrocene(0.06 g, 0.1 mmol) and anhydrous 1,4-dioxane (300 mL)At room temperature, and the mixture was heated under stirring at 120 ° C. for 15 hours.The obtained reaction solution was filtered through Celite, and the obtained Celite was dissolved in chloroform(200 mL) for 5 times.The obtained filtrate was concentrated by an evaporator, and to the obtained residue was added chloroform(200 mL), and the mixture was heated and stirred at 80 ° C., then acetonitrile(400 mL) was added, and the mixture was allowed to cool to room temperature while stirring,The mixture was further stirred at room temperature for 1 hour. The obtained solid was collected by filtration,After washing twice with acetonitrile (100 mL)And dried under reduced pressure to obtain Compound 14.The yield of compound 14 was 2.25 g (0.24 mmol), and the yield was 53.4percent.
Reference: [1] Patent: JP6140482, 2017, B2, . Location in patent: Paragraph 0210
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