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[ CAS No. 53590-49-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 53590-49-1
Chemical Structure| 53590-49-1
Chemical Structure| 53590-49-1
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Product Details of [ 53590-49-1 ]

CAS No. :53590-49-1 MDL No. :MFCD06800428
Formula : C9H6ClNO Boiling Point : -
Linear Structure Formula :- InChI Key :ZFWBIHAXMSSQOO-UHFFFAOYSA-N
M.W :179.60 Pubchem ID :12203318
Synonyms :

Calculated chemistry of [ 53590-49-1 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 48.7
TPSA : 32.86 Ų

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) : -5.64 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.61
Log Po/w (XLOGP3) : 2.47
Log Po/w (WLOGP) : 2.63
Log Po/w (MLOGP) : 1.45
Log Po/w (SILICOS-IT) : 3.29
Consensus Log Po/w : 2.29

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.0
Solubility : 0.18 mg/ml ; 0.001 mol/l
Class : Soluble
Log S (Ali) : -2.8
Solubility : 0.282 mg/ml ; 0.00157 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.85
Solubility : 0.0256 mg/ml ; 0.000143 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.21

Safety of [ 53590-49-1 ]

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

Application In Synthesis of [ 53590-49-1 ]

* 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 [ 53590-49-1 ]
  • Downstream synthetic route of [ 53590-49-1 ]

[ 53590-49-1 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 53590-47-9 ]
  • [ 53590-49-1 ]
YieldReaction ConditionsOperation in experiment
82% With manganese(IV) oxide In tetrahydrofuran for 1.5 h; The product (1 eq.) from above was dissolved in THF (0.5 M) and treated with manganese dioxide (3 eq), and stirred for 1.5 hours until TLC analysis indicated that reaction was complete. The reaction was filtered through celite, dried over magnesium sulfate, and concentrated to yield the desired crude aldehyde in 82percent yield.
76% With manganese(IV) oxide In N,N-dimethyl-formamide at 20℃; for 12 h; Inert atmosphere General procedure: A suspension of the alcohol 12 (1 mmol) and active MnO2(10 mmol) in DMF (30 mL) was stirred at rt for 12 h. The reactionmixture was filtrated through a Celite pad. The filtrate was evaporatedin vacuo. The residue was purified by column chromatographyusing EtOAc-hexane as an eluent to give the indole-2-carbaldehyde 13.
66% With manganese(IV) oxide In tetrahydrofuran at 60℃; General procedure: In round-bottom flask 112 containing the corresponding indole alcohol (1 eq.) in THF, 6 eq. of freshly prepared 113 MnO2 were added and the reaction was kept under magnetic stirring at 60 C, until the 114 completion of the reaction was detected by TLC (2 – 4 hours). The reaction mixture was 115 filtered through a quantitative filter paper (pore size of 8 μm), washed with THF, followed by MeOH and the filtered was evaporated under reduced pressure.
Reference: [1] Synlett, 2007, # 11, p. 1707 - 1710
[2] Chemical Communications, 2013, vol. 49, # 28, p. 2894 - 2896
[3] Patent: US2008/9485, 2008, A1, . Location in patent: Page/Page column 41
[4] European Journal of Medicinal Chemistry, 2016, vol. 121, p. 561 - 577
[5] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 6, p. 1889 - 1900
[6] Journal of Medicinal Chemistry, 2014, vol. 57, # 2, p. 364 - 377
[7] Journal of Organic Chemistry, 2015, vol. 80, # 16, p. 8122 - 8133
  • 2
  • [ 53590-58-2 ]
  • [ 53590-49-1 ]
Reference: [1] Synthesis (Germany), 2015, vol. 47, # 13, p. 1913 - 1921
  • 3
  • [ 10517-21-2 ]
  • [ 53590-49-1 ]
Reference: [1] Synlett, 2007, # 11, p. 1707 - 1710
[2] Chemical Communications, 2013, vol. 49, # 28, p. 2894 - 2896
[3] Journal of Medicinal Chemistry, 2013, vol. 56, # 9, p. 3725 - 3732
[4] Journal of Medicinal Chemistry, 2014, vol. 57, # 2, p. 364 - 377
[5] Journal of Organic Chemistry, 2018, vol. 83, # 4, p. 2486 - 2493
  • 4
  • [ 4792-67-0 ]
  • [ 53590-49-1 ]
Reference: [1] Journal of Organic Chemistry, 2015, vol. 80, # 16, p. 8122 - 8133
[2] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 6, p. 1889 - 1900
[3] Journal of Organic Chemistry, 2018, vol. 83, # 4, p. 2486 - 2493
  • 5
  • [ 87802-11-7 ]
  • [ 53590-49-1 ]
Reference: [1] Synlett, 2007, # 11, p. 1707 - 1710
[2] European Journal of Medicinal Chemistry, 2016, vol. 121, p. 561 - 577
  • 6
  • [ 27034-51-1 ]
  • [ 53590-49-1 ]
Reference: [1] Synthesis (Germany), 2015, vol. 47, # 13, p. 1913 - 1921
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