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Chemical Structure| 1664-57-9
Chemical Structure| 1664-57-9
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Product Details of [ 1664-57-9 ]

CAS No. :1664-57-9 MDL No. :MFCD01310835
Formula : C9H9NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :ZOANOABZUNJOJT-UHFFFAOYSA-N
M.W :195.17 Pubchem ID :2760224
Synonyms :

Calculated chemistry of [ 1664-57-9 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 4
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 51.62
TPSA : 83.12 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.18 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.14
Log Po/w (XLOGP3) : 1.84
Log Po/w (WLOGP) : 1.61
Log Po/w (MLOGP) : 0.89
Log Po/w (SILICOS-IT) : -0.25
Consensus Log Po/w : 1.05

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.26
Solubility : 1.07 mg/ml ; 0.00547 mol/l
Class : Soluble
Log S (Ali) : -3.21
Solubility : 0.121 mg/ml ; 0.000622 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.97
Solubility : 2.12 mg/ml ; 0.0108 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.67

Safety of [ 1664-57-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1664-57-9 ]

* 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 [ 1664-57-9 ]
  • Downstream synthetic route of [ 1664-57-9 ]

[ 1664-57-9 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 1664-57-9 ]
  • [ 58161-35-6 ]
Reference: [1] Patent: CN103370324, 2016, B,
  • 2
  • [ 2033-24-1 ]
  • [ 99-61-6 ]
  • [ 1664-57-9 ]
YieldReaction ConditionsOperation in experiment
72% With formic acid; triethylamine In N,N-dimethyl-formamideLarge scale General procedure: NEt3 (56.6 g, 0.56 mol) was added dropwise to stirred formicacid (64.4 g, 1.4 mol) at 5 8C. To the resulting reagent were addedDMF (150 ml), Meldrum’s acid (57.6 g, 0.4 mol) and aldehyde 2a–c(60.4 g, 0.4 mol). The reaction mixture was heated at reflux for 4 h.The solvent was evaporated under vacuum.The residue was triturated with water (1000 ml) and acidifiedwith conc. aq HCl to pH = 2. The formed product was filtered off,dried on air, and crystallized from EtOAc (3a) or CCl4 (3b,c) toobtain the pure material.
Reference: [1] Journal of Fluorine Chemistry, 2015, vol. 171, p. 174 - 176
[2] Archiv der Pharmazie, 2011, vol. 344, # 12, p. 840 - 842
  • 3
  • [ 555-68-0 ]
  • [ 1664-57-9 ]
Reference: [1] Journal of Medicinal Chemistry, 1995, vol. 38, # 4, p. 636 - 646
  • 4
  • [ 555-68-0 ]
  • [ 1664-57-9 ]
Reference: [1] Journal of Medicinal Chemistry, 1989, vol. 32, # 9, p. 2104 - 2110
  • 5
  • [ 7116-33-8 ]
  • [ 1664-57-9 ]
YieldReaction ConditionsOperation in experiment
18%
Stage #1: With water; sodium hydroxide In ethanolReflux
Stage #2: With hydrogenchloride In water
To a solution of Intermediate 79 (48.76 g, 0.23 mol) in ethanol (50 mL) was added sodium hydroxide 2N (400 mL).
The mixture was refluxed overnight.
The crude reaction was cooled and the aqueous phase was treated with hydrochloric acid and extracted with ether.
The solvent was removed under reduced pressure obtaining an oil, which was purified by column chromatography with silica gel, eluding with methylene chloride/methanol (98:2).
The title compound was obtained as a solid (8.13 g, 18percent).
Reference: [1] Patent: EP2096105, 2009, A1, . Location in patent: Page/Page column 31
  • 6
  • [ 13331-27-6 ]
  • [ 79-10-7 ]
  • [ 1664-57-9 ]
Reference: [1] Synlett, 2011, # 17, p. 2517 - 2520
  • 7
  • [ 1772-65-2 ]
  • [ 1664-57-9 ]
  • [ 1504-76-3 ]
Reference: [1] Journal of the American Chemical Society, 1992, vol. 114, # 26, p. 10110 - 10112
  • 8
  • [ 501-52-0 ]
  • [ 16642-79-8 ]
  • [ 1664-57-9 ]
  • [ 2001-32-3 ]
Reference: [1] Journal of Organic Chemistry, 1998, vol. 63, # 4, p. 952 - 958
  • 9
  • [ 619-23-8 ]
  • [ 1664-57-9 ]
Reference: [1] Journal of the Chemical Society, 1929, p. 1674
  • 10
  • [ 54405-44-6 ]
  • [ 1664-57-9 ]
Reference: [1] Chemische Berichte, 1882, vol. 15, p. 846
[2] Chemische Berichte, 1882, vol. 15, p. 846
  • 11
  • [ 7151-20-4 ]
  • [ 1664-57-9 ]
Reference: [1] Journal of the Chemical Society, 1929, p. 1674
[2] Journal of the Chemical Society, 1929, p. 1674
  • 12
  • [ 501-52-0 ]
  • [ 16642-79-8 ]
  • [ 1664-57-9 ]
  • [ 2001-32-3 ]
Reference: [1] Journal of Organic Chemistry, 1998, vol. 63, # 4, p. 952 - 958
  • 13
  • [ 1664-57-9 ]
  • [ 1664-54-6 ]
Reference: [1] Chemische Berichte, 1882, vol. 15, p. 846
[2] Patent: US2003/225125, 2003, A1, . Location in patent: Page 9
  • 14
  • [ 1664-57-9 ]
  • [ 83304-13-6 ]
YieldReaction ConditionsOperation in experiment
59%
Stage #1: With sodium azide; sulfuric acid In chloroform at 50℃; for 4 h;
Stage #2: With potassium carbonate In chloroform
To a solution of Intermediate 80 (7.75 g, 39.71 mmol) in sulphuric acid (19 mL) was added chloroform (10 mL).
The mixture was stirred at 50°C and sodium azide (3.8 g, 58.45 mmol) was slowly added (addition time: 2 hours).
The reaction was stirred at 50°C for 2 hours.
The crude was poured into potassium carbonate (40 g) to neutralize the reaction, then water was added (30 mL) and the crude was extracted with ethyl acetate.
The crude was purified by column chromatography with silica gel, eluding with methylene chloride/methanol (from 98:2 to 9:1) to give the title compound as an oil (3.92 g, 59percent).
Reference: [1] Patent: EP2096105, 2009, A1, . Location in patent: Page/Page column 31
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