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[ CAS No. 52598-02-4 ] {[proInfo.proName]}

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Chemical Structure| 52598-02-4
Chemical Structure| 52598-02-4
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Product Details of [ 52598-02-4 ]

CAS No. :52598-02-4 MDL No. :MFCD00974243
Formula : C20H14ClN Boiling Point : -
Linear Structure Formula :- InChI Key :BAEWCDBRAIDXMN-UHFFFAOYSA-N
M.W : 303.79 Pubchem ID :253583
Synonyms :

Calculated chemistry of [ 52598-02-4 ]

Physicochemical Properties

Num. heavy atoms : 22
Num. arom. heavy atoms : 21
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 0.0
Num. H-bond donors : 1.0
Molar Refractivity : 94.18
TPSA : 15.79 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -3.92 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.08
Log Po/w (XLOGP3) : 5.96
Log Po/w (WLOGP) : 6.16
Log Po/w (MLOGP) : 4.77
Log Po/w (SILICOS-IT) : 6.28
Consensus Log Po/w : 5.25

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 1.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -6.05
Solubility : 0.000269 mg/ml ; 0.000000886 mol/l
Class : Poorly soluble
Log S (Ali) : -6.07
Solubility : 0.00026 mg/ml ; 0.000000856 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -8.92
Solubility : 0.000000365 mg/ml ; 0.0000000012 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.53

Safety of [ 52598-02-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 52598-02-4 ]

* 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 [ 52598-02-4 ]
  • Downstream synthetic route of [ 52598-02-4 ]

[ 52598-02-4 ] Synthesis Path-Upstream   1~24

  • 1
  • [ 106-47-8 ]
  • [ 501-65-5 ]
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YieldReaction ConditionsOperation in experiment
90% With Cp*Rh(H2O)3(OTf)2; oxygen; acetic anhydride In pentan-1-ol at 100℃; for 24 h; The 4-aminochlorobenzene 1j (76.5 mg, 0 . 6mmol), 1, 2-diphenyl 2a (71.3 mg, 0 . 4mmol), Cp*Rh (H2O)3(OTf)2(11.8 mg, 5mol percent), acetic anhydride (59. 0μL, 0 . 6mmol), adding 2.0 ml in tertiary amyl alcohol , oxygen (1atm), 100 degrees reaction 24 hours after stop the reaction, add NaOH (48 mg, 1 . 2mmol) and methanol 2 ml after stirring one hour, column chromatography to obtain pure product 5-chloro-2,3-diphenyl indole 3ja. The product is white solid, yield 90percent.
Reference: [1] Chemical Communications, 2014, vol. 50, # 33, p. 4331 - 4334
[2] Patent: CN105218426, 2016, A, . Location in patent: Paragraph 0039; 0040
  • 2
  • [ 873-38-1 ]
  • [ 501-65-5 ]
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YieldReaction ConditionsOperation in experiment
55% With 2 mol% Pd/C; sodium carbonate In N,N-dimethyl-formamide at 140℃; for 144 h; Inert atmosphere aryl bromide (1 mmol), alkyne (3 mmol), Na2CO3 (3 mmol), Pd/C (2 mo lpercent) and DMF (2 mL) were introduced in a sealed tube. The reactor was placed under stirring in a preheated oil bath at 120 °C or 140 °C after being flushed by argon. The reaction completion was monitored by GC. After cooling to room temperature, the reaction mixture was filtered through a celite pad, which was washed with EtOAc (100 mL). The resulting organic layer was then washed with Na2CO3 (2 .x. 40 mL) and brine (40 mL). The organic layer was dried over Na2SO4 and the solvent was removed under reduced pressure. If necessary (for the silylated compounds), the crude product could be fully deprotected by treatment with HCl 1 M before being purified by flash chromatography on silica.
Reference: [1] Tetrahedron Letters, 2011, vol. 52, # 16, p. 1916 - 1918
  • 3
  • [ 21259-25-6 ]
  • [ 52598-02-4 ]
Reference: [1] Journal of Chemical Research - Part S, 2003, # 11, p. 696 - 697
[2] Tetrahedron, 2003, vol. 59, # 11, p. 1917 - 1923
  • 4
  • [ 501-65-5 ]
  • [ 52598-02-4 ]
Reference: [1] ACS Catalysis, 2016, vol. 6, # 4, p. 2705 - 2709
  • 5
  • [ 1073-70-7 ]
  • [ 501-65-5 ]
  • [ 52598-02-4 ]
Reference: [1] Advanced Synthesis and Catalysis, 2014, vol. 356, # 7, p. 1571 - 1576
[2] Chemistry - A European Journal, 2014, vol. 20, # 8, p. 2352 - 2356
  • 6
  • [ 21259-25-6 ]
  • [ 52598-02-4 ]
Reference: [1] Tetrahedron, 2003, vol. 59, # 11, p. 1917 - 1923
  • 7
  • [ 62499-16-5 ]
  • [ 501-65-5 ]
  • [ 52598-02-4 ]
Reference: [1] Angewandte Chemie - International Edition, 2013, vol. 52, # 22, p. 5795 - 5798[2] Angew. Chem., 2013, p. 5999
  • 8
  • [ 501-65-5 ]
  • [ 6947-29-1 ]
  • [ 52598-02-4 ]
Reference: [1] Angewandte Chemie - International Edition, 2013, vol. 52, # 47, p. 12426 - 12429[2] Angew. Chem., 2013, vol. 125, # 47, p. 12652 - 12656,4
  • 9
  • [ 103973-44-0 ]
  • [ 52598-02-4 ]
Reference: [1] Tetrahedron, 1985, vol. 41, # 20, p. 4615 - 4620
  • 10
  • [ 501-65-5 ]
  • [ 52598-02-4 ]
Reference: [1] Advanced Synthesis and Catalysis, 2015, vol. 357, # 13, p. 2944 - 2950
  • 11
  • [ 106-49-0 ]
  • [ 106-47-8 ]
  • [ 501-65-5 ]
  • [ 36804-50-9 ]
  • [ 52598-02-4 ]
Reference: [1] Chemical Communications, 2014, vol. 50, # 33, p. 4331 - 4334
  • 12
  • [ 1417819-68-1 ]
  • [ 98-09-9 ]
  • [ 52598-02-4 ]
Reference: [1] Chemical Communications, 2017, vol. 53, # 30, p. 4203 - 4206
  • 13
  • [ 1417717-04-4 ]
  • [ 501-65-5 ]
  • [ 52598-02-4 ]
Reference: [1] Angewandte Chemie - International Edition, 2016, vol. 55, # 9, p. 3208 - 3211[2] Angew. Chem., 2016, vol. 128, # 9, p. 3261 - 3265,5
  • 14
  • [ 1417819-68-1 ]
  • [ 369-57-3 ]
  • [ 52598-02-4 ]
Reference: [1] New Journal of Chemistry, 2017, vol. 41, # 23, p. 14053 - 14056
  • 15
  • [ 106-47-8 ]
  • [ 52598-02-4 ]
Reference: [1] Angewandte Chemie - International Edition, 2013, vol. 52, # 22, p. 5795 - 5798[2] Angew. Chem., 2013, p. 5999
[3] Angewandte Chemie - International Edition, 2013, vol. 52, # 47, p. 12426 - 12429[4] Angew. Chem., 2013, vol. 125, # 47, p. 12652 - 12656,4
[5] Advanced Synthesis and Catalysis, 2014, vol. 356, # 7, p. 1571 - 1576
[6] Chemical Communications, 2014, vol. 50, # 95, p. 14964 - 14967
  • 16
  • [ 451-40-1 ]
  • [ 1073-70-7 ]
  • [ 52598-02-4 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2011, vol. 48, # 5, p. 1095 - 1102
  • 17
  • [ 451-40-1 ]
  • [ 52598-02-4 ]
Reference: [1] Tetrahedron, 1985, vol. 41, # 20, p. 4615 - 4620
  • 18
  • [ 108-86-1 ]
  • [ 52598-02-4 ]
Reference: [1] Angewandte Chemie - International Edition, 2013, vol. 52, # 47, p. 12426 - 12429[2] Angew. Chem., 2013, vol. 125, # 47, p. 12652 - 12656,4
[3] Chemical Communications, 2014, vol. 50, # 95, p. 14964 - 14967
  • 19
  • [ 1073-70-7 ]
  • [ 52598-02-4 ]
Reference: [1] Angewandte Chemie - International Edition, 2013, vol. 52, # 47, p. 12426 - 12429[2] Angew. Chem., 2013, vol. 125, # 47, p. 12652 - 12656,4
  • 20
  • [ 100-00-5 ]
  • [ 52598-02-4 ]
Reference: [1] Advanced Synthesis and Catalysis, 2015, vol. 357, # 13, p. 2944 - 2950
  • 21
  • [ 150-68-5 ]
  • [ 501-65-5 ]
  • [ 52598-02-4 ]
Reference: [1] Chemical Communications, 2014, vol. 50, # 95, p. 14964 - 14967
  • 22
  • [ 501-65-5 ]
  • [ 21650-51-1 ]
  • [ 52598-02-4 ]
Reference: [1] Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1983, vol. 38, # 2, p. 251 - 252
  • 23
  • [ 20265-96-7 ]
  • [ 119-53-9 ]
  • [ 52598-02-4 ]
Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1997, vol. 36, # 3, p. 288 - 292
  • 24
  • [ 451-40-1 ]
  • [ 1073-69-4 ]
  • [ 52598-02-4 ]
Reference: [1] Journal of the Chemical Society, 1957, p. 3175,3180
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