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[ CAS No. 188027-95-4 ] {[proInfo.proName]}

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Chemical Structure| 188027-95-4
Chemical Structure| 188027-95-4
Structure of 188027-95-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 188027-95-4 ]

CAS No. :188027-95-4 MDL No. :MFCD15142806
Formula : C14H8Cl2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :OCUBZGSJBOWQLF-UHFFFAOYSA-N
M.W : 295.11 Pubchem ID :23283109
Synonyms :

Calculated chemistry of [ 188027-95-4 ]

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.07
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 72.57
TPSA : 46.53 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.62 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.47
Log Po/w (XLOGP3) : 3.49
Log Po/w (WLOGP) : 4.32
Log Po/w (MLOGP) : 3.45
Log Po/w (SILICOS-IT) : 3.79
Consensus Log Po/w : 3.5

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.85

Water Solubility

Log S (ESOL) : -4.27
Solubility : 0.0159 mg/ml ; 0.0000537 mol/l
Class : Moderately soluble
Log S (Ali) : -4.15
Solubility : 0.0209 mg/ml ; 0.0000708 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.29
Solubility : 0.0015 mg/ml ; 0.00000509 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.52

Safety of [ 188027-95-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P233-P260-P261-P264-P271-P280-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 188027-95-4 ]

* 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.

  • Downstream synthetic route of [ 188027-95-4 ]

[ 188027-95-4 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 188027-95-4 ]
  • [ 342807-55-0 ]
  • [ 202796-71-2 ]
  • 2
  • [ 188027-95-4 ]
  • 4-amino-1-(cyclooctenylmethyl)piperidine [ No CAS ]
  • N-[1-(1-cyclooctenylmethyl)piperidin-4-yl]-2,7-dichloroxanthene-9-carboxamide [ No CAS ]
  • 3
  • [ 82-07-5 ]
  • [ 188027-95-4 ]
YieldReaction ConditionsOperation in experiment
6.98 g (55.2%) With hydrogenchloride; N-chloro-succinimide; In water; acetic acid; EXAMPLE 8 2,7-Dichloroxanthene-9-carboxylic Acid: To a suspension of 10 g of <strong>[82-07-5]xanthene-9-carboxylic acid</strong> and 14 g of N-chlorosuccinimide in 80 mL of acetic acid was added with stirring dropwise 2.0 mL of conc. HCl over a period of 5 minutes. The mixture was stirred at room temperature for 12 hours and quenched by the addition of 150 mL of water. The precipitated solid was removed by filtration, rinsed with water, and dried in air to give 12.6 g (100%) of the crude carboxylic acid as a white solid. Recrystallization from MeOH--EtOAc (2:1) gave 6.98 g (55.2%) of the pure 2,7-dichloro<strong>[82-07-5]xanthene-9-carboxylic acid</strong> as colorless small needles, m.p. 273-275 C. (dec.); IR (KBr): 2970 (b, OH), 1695 (C=O) cm-1; 1 H NMR (DMSO-d6): delta 5.01 s, 1H, CH), 7.05-7.50 (m, 6H, aryl). Anal. Calcd for C14 H8 Cl2 O3: C, 56.98; H, 2.73. Found: C, 57.05; H, 2.74.
With hydrogenchloride; N-chloro-succinimide; acetic acid; In water; at 20℃; for 48h; Intermediate 422,7-dichloro-9H-<strong>[82-07-5]xanthene-9-carboxylic acid</strong>Acetic acid (80 ml.) and N-chlorosuccinimide (14.7 g, 110 mmols) were added to <strong>[82-07-5]xanthene-9-carboxylic acid</strong> (10.0 g, 44 mmols). Hydrochloric acid (2 ml.) was added dropwise to the mixture at room temperature and it was stirred under these conditions for EPO <DP n="77"/>48 hours. Water was added (150 mL) and the precipitate was filtered. The product obtained was used without further purification in the synthesis of example 54.
  • 4
  • B-EtOAc [ No CAS ]
  • [ 188027-95-4 ]
  • 2,7-dichloro-9-xanthenemethanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.21 g (42.36%) With LiAlH4; In tetrahydrofuran; methanol; water; EXAMPLE 9 2,7-Dichloro-9-xanthenemethanol: A. From 2,7-Dichloroxanthene-9-carboxylic Acid: To a suspension of 0.75 g of LiAlH4 in 90 mL of anhydrous ether was added dropwise a solution of 3.0 g of <strong>[188027-95-4]2,7-dichloroxanthene-9-carboxylic acid</strong> in 45 mL of freshly distilled THF over a period of 25 minutes. The mixture was stirred at room temperature until the color had changed from grey to light brown (ca. 6hr). The excess LiAlH4 was decomposed by the slow addition of 10 mL of methanol and 2 mL of water while stirring. The suspended precipitate was filtered, rinsed with ether (2*30 mL) and discarded. The combined filtrate was washed with water (2*40 mL), dried over MgSO4, and evaporated under reduced pressure to give 1.53 g (53.6%) of the alcohol as a white solid. Recrystallization from Skelly B--EtOAc (4:1) gave 1.21 g (42.36%) of the 2,7-dichloro-9-xanthenemethanol as a white fluffy solid, m.p. 134.5-136 C.; IR (KBr): 3250 (b, OH) cm-1; 1 H NMR (CDCl3): δ 1.65 (b, 1H, OH), 3.75 (d, 2H, CH2 O), 4.01 (t, 1H, CH), 6.94-7.40 (m, 6H, aryl). Anal. Calcd for C14 H10 O2 Cl2: C, 59.81; H, 3.59. Found: C, 60.73; H, 3.91. B. From 9-Xanthenemethanol: To a suspension of 3.0 g of 9-xanthenemethanol and 4.2 g of N-chlorosuccinimide in 25 mL of freshly distilled THF and 12.5 mL of water was added dropwise 2.0 mL of conc. HCl over a period of 5 minutes. The mixture was stirred at room temperature for 6 hours and poured into 200 mL of water with stirring. The precipitated solid was filtered, rinsed with water (2*30 mL), and dried in air to afford 3.95 g (100%) of the crude alcohol. Recrystallization from Skelly B--EtOAc (4:1) gave 1.35 g (34%) of 2,7-dichloro-9-xanthenemethanol as a fluffy solid, m.p. 134.5-136 C., identified by the mixture melting point, IR and NMR spectral comparison with an authentic sample obtained by the reduction of <strong>[188027-95-4]2,7-dichloroxanthene-9-carboxylic acid</strong>.
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