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[ CAS No. 578743-87-0 ] {[proInfo.proName]}

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Chemical Structure| 578743-87-0
Chemical Structure| 578743-87-0
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Product Details of [ 578743-87-0 ]

CAS No. :578743-87-0 MDL No. :MFCD09264276
Formula : C27H36ClCuN2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 487.59 Pubchem ID :-
Synonyms :

Calculated chemistry of [ 578743-87-0 ]

Physicochemical Properties

Num. heavy atoms : 31
Num. arom. heavy atoms : 17
Fraction Csp3 : 0.44
Num. rotatable bonds : 6
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 132.51
TPSA : 9.86 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -2.83 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 9.08
Log Po/w (WLOGP) : 8.53
Log Po/w (MLOGP) : 5.82
Log Po/w (SILICOS-IT) : 6.23
Consensus Log Po/w : 5.93

Druglikeness

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

Water Solubility

Log S (ESOL) : -8.59
Solubility : 0.00000124 mg/ml ; 0.0000000026 mol/l
Class : Poorly soluble
Log S (Ali) : -9.18
Solubility : 0.000000322 mg/ml ; 0.0000000007 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -8.58
Solubility : 0.00000127 mg/ml ; 0.0000000026 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 3.79

Safety of [ 578743-87-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 578743-87-0 ]

* 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 [ 578743-87-0 ]
  • Downstream synthetic route of [ 578743-87-0 ]

[ 578743-87-0 ] Synthesis Path-Upstream   1~20

  • 1
  • [ 250285-32-6 ]
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YieldReaction ConditionsOperation in experiment
94% With sodium t-butanolate In tetrahydrofuran at 20℃; for 20 h; Synthesis of [(IPr)CuCl]. This synthesis is as reported in the literature; see H. Kaur et al., Organometallics 2004, 23, 1157-1160. In a 250 mL Schlenk flask were added copper(I) chloride (1.0 g, 10.10 mmol), 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride (IPr.HCl; 4.29 g, 10.10 mmol), and sodium tert-butoxide (0.97 g, 10.10 mmol). To this flask, dry tetrahydrofuran (100 mL) was added under an inert atmosphere of argon, and the mixture was magnetically stirred for 20 hours at room temperature. After the mixture was filtered through a plug of Celite and then evaporating the solvent under vacuum, a white solid was obtained (4.59 g, 9.40 mmol, 94percent). 1H NMR: (400 MHz, acetone-d6, ppm) δ=1.21 (d, J=6.8 Hz, 12H); 1.30 (d, J=6.8 Hz, 12H); 2.57 (hep, J=6.8 Hz, 4H); 7.12 (s, 2H). 7.29 (d, J=7.8 Hz, 4H); 7.49 (t, J=7.8 Hz, 2H). 13C NMR: (100 MHz, acetone-d6, ppm) δ=182.32; 145.61; 134.41; 130.62; 124.25; 123.13; 28.76; 24.82; 23.87. Elemental analysis calcd for C27H36ClCuN2: C 66.64percent, H, 7.46percent, N, 5.76percent; found C, 66.70percent, H, 7.48percent, N, 6.06percent.
Reference: [1] Organometallics, 2004, vol. 23, # 5, p. 1157 - 1160
[2] Patent: US2009/69569, 2009, A1, . Location in patent: Page/Page column 6
[3] Organometallics, 2013, vol. 32, # 15, p. 4279 - 4283
[4] Organic and Biomolecular Chemistry, 2012, vol. 10, # 47, p. 9334 - 9337
[5] Journal of the American Chemical Society, 2017, vol. 139, # 36, p. 12855 - 12862
[6] Journal of the American Chemical Society, 2015, vol. 137, # 4, p. 1424 - 1427
[7] Dalton Transactions, 2017, vol. 46, # 27, p. 8756 - 8762
  • 2
  • [ 244187-81-3 ]
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YieldReaction ConditionsOperation in experiment
45% With sodium t-butanolate In tetrahydrofuran at 30℃; for 2 h; Inert atmosphere General procedure: To a stirred solution of imidazolium salts (0.045 mmol), NaOtBu (4.3 mg, 0.045 mmol) and CuCl (4.5mg, 0.045 mmol) was added THF (0.5 mL, 0.09 M) at 30 oC under argon atmosphere. After stirring for 2 h, the solution of K+[CF3B(OMe)3] (63.5 mg, 0.3 mmol, 6.0 equiv) in DMF (0.5 mL) was added dropwise. Then the mixture was kept stirring at 30 oC for 10 h. After that, the reaction was quenched with water. Aqueous layer was extracted with EtOAc (15 mL x 3), and the combined organic layers was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. Then the crude product was purified by column chromatography on silica gel to give the imidazolinone 3b-d.
Reference: [1] Journal of Organometallic Chemistry, 2013, vol. 743, p. 44 - 48
  • 3
  • [ 12775-96-1 ]
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YieldReaction ConditionsOperation in experiment
40% at 80 - 90℃; for 30 h; Add ligand L8850mg (2.0mmol), copper powder 128mg (2.0mmol) in 50mL flask, water 30 mL, 80 ~ 90 in an oil bath, the reaction was stirred for 30 hours, the reaction mixture was cooled to room temperature, filtered, the filter cake was washed 3 times with water, the filter cake dissolved in acetonitrile and filtered to remove unreacted copper powder, the solvent was evaporated under reduced pressure to give 390 mg of colorless crystals, a yield of 40percent.
Reference: [1] Dalton Transactions, 2015, vol. 44, # 4, p. 1836 - 1844
[2] Chemical Science, 2017, vol. 8, # 2, p. 1086 - 1089
[3] Chemical Communications, 2012, vol. 48, # 40, p. 4887 - 4889
[4] Patent: CN105585584, 2016, A, . Location in patent: Paragraph 0046; 0047; 0048
  • 4
  • [ 250285-32-6 ]
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Reference: [1] Dalton Transactions, 2010, vol. 39, # 19, p. 4489 - 4491
[2] Organic Letters, 2013, vol. 15, # 5, p. 996 - 999
[3] Inorganic Chemistry, 2014, vol. 53, # 17, p. 9181 - 9191
[4] Organometallics, 2010, vol. 29, # 7, p. 1518 - 1521
[5] RSC Advances, 2017, vol. 7, # 9, p. 4912 - 4920
[6] RSC Advances, 2016, vol. 6, # 85, p. 82401 - 82408
  • 5
  • [ 106-43-4 ]
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  • [ 14621-04-6 ]
Reference: [1] Chemical Communications, 2014, vol. 50, # 64, p. 8927 - 8929
  • 6
  • [ 1317-39-1 ]
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Reference: [1] Organometallics, 2013, vol. 32, # 23, p. 7225 - 7233
  • 7
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Reference: [1] Dalton Transactions, 2015, vol. 44, # 4, p. 1836 - 1844
  • 8
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Reference: [1] Journal of the American Chemical Society, 2006, vol. 128, # 5, p. 1446 - 1447
[2] Organometallics, 2007, vol. 26, # 6, p. 1483 - 1493
  • 9
  • [ 74663-75-5 ]
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Reference: [1] Journal of Organometallic Chemistry, 2013, vol. 743, p. 44 - 48
  • 10
  • [ 55718-76-8 ]
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Reference: [1] Dalton Transactions, 2018, vol. 47, # 15, p. 5318 - 5327
  • 11
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Reference: [1] Inorganic Chemistry, 2005, vol. 44, # 24, p. 8647 - 8649
  • 12
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Reference: [1] Inorganic Chemistry, 2009, vol. 48, # 14, p. 6353 - 6355
  • 13
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Reference: [1] Heteroatom Chemistry, 2012, vol. 23, # 6, p. 605 - 609
  • 14
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Reference: [1] Heteroatom Chemistry, 2012, vol. 23, # 6, p. 605 - 609
  • 15
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Reference: [1] Dalton Transactions, 2018, vol. 47, # 15, p. 5318 - 5327
  • 16
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Reference: [1] Organometallics, 2008, vol. 27, # 12, p. 2682 - 2684
  • 17
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Reference: [1] Dalton Transactions, 2018, vol. 47, # 15, p. 5318 - 5327
  • 18
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Reference: [1] Dalton Transactions, 2018, vol. 47, # 15, p. 5318 - 5327
  • 19
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Reference: [1] Dalton Transactions, 2018, vol. 47, # 15, p. 5318 - 5327
  • 20
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Reference: [1] Dalton Transactions, 2018, vol. 47, # 15, p. 5318 - 5327
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