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[ CAS No. 101623-69-2 ] {[proInfo.proName]}

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Chemical Structure| 101623-69-2
Chemical Structure| 101623-69-2
Structure of 101623-69-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 101623-69-2 ]

CAS No. :101623-69-2 MDL No. :MFCD19441847
Formula : C9H8ClNO5 Boiling Point : -
Linear Structure Formula :- InChI Key :DXVQFTPXVZUWIF-UHFFFAOYSA-N
M.W : 245.62 Pubchem ID :10538354
Synonyms :

Calculated chemistry of [ 101623-69-2 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 5
Num. H-bond acceptors : 5.0
Num. H-bond donors : 0.0
Molar Refractivity : 57.84
TPSA : 81.35 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.65 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.78
Log Po/w (XLOGP3) : 3.02
Log Po/w (WLOGP) : 2.7
Log Po/w (MLOGP) : 1.05
Log Po/w (SILICOS-IT) : -0.16
Consensus Log Po/w : 1.68

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.21
Solubility : 0.15 mg/ml ; 0.000612 mol/l
Class : Soluble
Log S (Ali) : -4.39
Solubility : 0.00993 mg/ml ; 0.0000404 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -2.27
Solubility : 1.33 mg/ml ; 0.00543 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 4.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.8

Safety of [ 101623-69-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 101623-69-2 ]

* 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 [ 101623-69-2 ]
  • Downstream synthetic route of [ 101623-69-2 ]

[ 101623-69-2 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 100-02-7 ]
  • [ 50893-53-3 ]
  • [ 101623-69-2 ]
YieldReaction ConditionsOperation in experiment
97% With pyridine In dichloromethane at 0 - 20℃; for 1.5 h; To an ice cold reaction mixture containing p-nitrophenol (1.39 g, 10 mmol) and pyridine (0.81 g, 10 mmol) in dichloromethane (60 mL) was added 1-chloroethyl chloroformate (1.2 mL, 11 mmol). The mixture was stirred at 0° C. for 30 min and then at room temperature for 1 hour. After removing the solvent under reduced pressure, the residue was dissolved in ether, washed with water, 10percent citric acid and water. The ether layer was dried over Na2SO4 and evaporated under reduced pressure to give 2.4 g (97percent) of the title compound (57) as an off-white solid. 1H NMR (CDCl3): 1.93 (d, 3H), 6.55 (q, 1H), 7.42 (d, 2H), 8.28 (d, 2H).
92% With pyridine In dichloromethane at 0 - 20℃; for 6 h; Example 3: 1-iodoethyl 4-nitrophenyl carbonateSTEP A: 1-chloroethyl 4-nitrophenyl carbonate.To a solution of 4-nitrophenol (3.0 g, 21.6 mmol) and pyridine (1.9 mL, 24 mmol) in CH2C12 (48 mL) cooled to 0°C, 1-chloroethyl chloroformate (2.3 mL, 21.6 mmol) was added. The reaction was stirred at room temperature for 5-6 hours, then washed with NaH2PC>4 (5percent) and brine, dried over Na2SC>4 and concentrated affording the title compound (4.88 g, 92percent) as a pale yellow solid.
92% at 0 - 20℃; STEP A: 1-chloroethyl 4-nitrophenyl carbonateTo a solution of 4-nitrophenol (3.0 g, 21.6 mmol) and pyridine (1.9 mL, 24 mmol) cooled to 0°C, 1-chloroethyl chloroformate (2.3 mL, 21.6 mmol) was added. The reaction was stirred at room temperature for 5-6 hours, then washed with Na3/4P04 (5percent) and brine, dried over Na2 S C>4 and concentrated affording the title compound (4.88 g, 92percent) as a pale yellow solid.1H-NMR (CDC13) : 8.32 (2H,m); 7.44 (2H,m); 6.52 ( 1H, q, J=5.8 Hz); 1.94 (3H, d, J=5.5Hz) .
88% With pyridine In chloroform at 0 - 20℃; Step 1:
1-Chloroethylchloroformate (7.8 ml, 72 mmol, 1 eq.) was added to an ice-cold solution of p-nitrophenol (10 g, 72 mmol) in chloroform (100 mL), followed by drop wise addition of pyridine (8.8 ml, 108 mmol, 1.5 eq.) over a period of 20 min.
The mixture was stirred in the ice-cold bath for 15 min, and then at room temperature overnight.
The reaction mixture was sequentially washed with water, 1 N hydrochloric acid, water, 1 N sodium hydroxide, water, and brine.
The organic phase was dried over Na2SO4, and concentrated to give yellow oil which, upon standing, crystallized to afford the corresponding chloroethyl carbonate (15.5 g, 88percent).
85% With triethylamine In dichloromethane at 0 - 20℃; To an ice-cold solution of 4-nitrophenol (2.0 g, 15 mmol) and triethylamine (1.6 g, 16 mmol) in dichloromethane (20 ml) was added a solution of 1-chloroethyl chloroformate (2.1 g, 19 mmol) in dichloromethane, and the mixture was stirred for 15 min at 0 °C and then overnight at room temperature. The mixture was extracted with dichloromethane (50 ml), washed successively with water (50 ml), 0.5 N sodium hydroxide (50 ml), saturated aqueous sodium chloride solution (50 ml), and water (3 x 50 ml), and dried over Na2SO4. The dichloromethane solution was filtered and evaporated under reduced pressure, and the residue was purified by silica gel column chromatography with chloroform (100percent) as eluent to furnish pure 1-chloroethyl 4- nitrophenyl carbonate, as a white solid in 85percent yield.
1.67 g
Stage #1: With pyridine In dichloromethane at 0 - 4℃; for 0.166667 h;
Stage #2: at 20℃;
First, place a 4-nitro phenol 10g on 250ml flask and dissolved in 100ml of methylene chloride. The reaction was cooled to 0 ~ 4 and slowly added 5.92ml of pyridine. After stirring for 10 minutes and added to 1-chloroethyl chloroformate 8.81ml slowly. Warm to room temperature and then stirred for 30 minutes and stirred overnight. After distillation under reduced pressure and the residue was dissolved in diethyl ether and washed with water, 10wtpercent citric acid solution, water order. Distilled under reduced pressure after dried over anhydrous sodium sulfate phenyl 1-chloro-ethyl-4-nitro-carbonate to give the 1.67g.

Reference: [1] Journal of Antibiotics, 1999, vol. 52, # 7, p. 643 - 648
[2] Patent: US2006/229361, 2006, A1, . Location in patent: Page/Page column 37
[3] Journal of Pharmacology and Experimental Therapeutics, 2016, vol. 357, # 2, p. 240 - 247
[4] Journal of Medicinal Chemistry, 1988, vol. 31, # 2, p. 318 - 322
[5] Patent: WO2011/92065, 2011, A1, . Location in patent: Page/Page column 60
[6] Patent: WO2011/101245, 2011, A1, . Location in patent: Page/Page column 38
[7] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 14, p. 1811 - 1816
[8] Patent: US2008/146642, 2008, A1, . Location in patent: Page/Page column 45
[9] Patent: WO2007/27248, 2007, A2, . Location in patent: Page/Page column 22
[10] Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 1, p. 191 - 198
[11] Journal of Medicinal Chemistry, 2016, vol. 59, # 14, p. 6658 - 6670
[12] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 21, p. 7593 - 7603
[13] Journal of Medicinal Chemistry, 1999, vol. 42, # 19, p. 3994 - 4000
[14] Patent: US2002/19437, 2002, A1,
[15] Patent: US5602118, 1997, A,
[16] Patent: US2004/138108, 2004, A1,
[17] Patent: WO2008/79839, 2008, A1, . Location in patent: Page/Page column 40
[18] Patent: WO2010/63002, 2010, A2, . Location in patent: Page/Page column 26
[19] Patent: KR2015/106357, 2015, A, . Location in patent: Paragraph 0171-0175
[20] Patent: WO2018/81513, 2018, A1, . Location in patent: Page/Page column 112
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