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[ CAS No. 619-73-8 ] {[proInfo.proName]}

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Chemical Structure| 619-73-8
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Product Details of [ 619-73-8 ]

CAS No. :619-73-8 MDL No. :MFCD00007376
Formula : C7H7NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :JKTYGPATCNUWKN-UHFFFAOYSA-N
M.W : 153.14 Pubchem ID :69275
Synonyms :

Calculated chemistry of [ 619-73-8 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 41.39
TPSA : 66.05 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.34 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.28
Log Po/w (XLOGP3) : 1.26
Log Po/w (WLOGP) : 0.94
Log Po/w (MLOGP) : 0.34
Log Po/w (SILICOS-IT) : -0.49
Consensus Log Po/w : 0.67

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.85
Solubility : 2.14 mg/ml ; 0.014 mol/l
Class : Very soluble
Log S (Ali) : -2.25
Solubility : 0.87 mg/ml ; 0.00568 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.59
Solubility : 3.92 mg/ml ; 0.0256 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.42

Safety of [ 619-73-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P273 UN#:N/A
Hazard Statements:H302-H412 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 619-73-8 ]

* 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 [ 619-73-8 ]
  • Downstream synthetic route of [ 619-73-8 ]

[ 619-73-8 ] Synthesis Path-Upstream   1~23

  • 1
  • [ 619-73-8 ]
  • [ 95-54-5 ]
  • [ 2963-77-1 ]
  • [ 729-13-5 ]
Reference: [1] ACS Catalysis, 2017, vol. 7, # 11, p. 7456 - 7460
  • 2
  • [ 110-91-8 ]
  • [ 619-73-8 ]
  • [ 6425-46-3 ]
Reference: [1] Journal of Organic Chemistry, 2017, vol. 82, # 13, p. 6604 - 6614
  • 3
  • [ 619-73-8 ]
  • [ 6425-46-3 ]
Reference: [1] Journal of the Chemical Society - Perkin Transactions 1, 1998, # 15, p. 2239 - 2241
  • 4
  • [ 619-73-8 ]
  • [ 16687-60-8 ]
Reference: [1] Journal of Chemical Research, 2017, vol. 41, # 1, p. 25 - 29
  • 5
  • [ 619-73-8 ]
  • [ 19916-73-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2011, vol. 54, # 21, p. 7720 - 7728
  • 6
  • [ 75-44-5 ]
  • [ 619-73-8 ]
  • [ 4457-32-3 ]
Reference: [1] Synthetic Communications, 1984, vol. 14, # 7, p. 613 - 620
[2] Justus Liebigs Annalen der Chemie, 1898, vol. 302, p. 262
[3] Journal of the American Chemical Society, 1952, vol. 74, p. 3818,3819
[4] Journal of the Chemical Society, 1963, p. 2731 - 2736
[5] Journal of the Chemical Society - Perkin Transactions 1, 1999, # 19, p. 2759 - 2770
[6] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 13, p. 3986 - 3991
[7] ACS Medicinal Chemistry Letters, 2012, vol. 3, # 12, p. 1024 - 1028
  • 7
  • [ 619-73-8 ]
  • [ 503-38-8 ]
  • [ 4457-32-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 8, p. 1716 - 1727
  • 8
  • [ 619-73-8 ]
  • [ 100-27-6 ]
Reference: [1] European Journal of Organic Chemistry, 2015, vol. 2015, # 32, p. 7009 - 7019
  • 9
  • [ 100-51-6 ]
  • [ 619-73-8 ]
  • [ 612-25-9 ]
Reference: [1] Tetrahedron Letters, 2001, vol. 42, # 38, p. 6767 - 6769
[2] Phosphorus, Sulfur and Silicon and the Related Elements, 2004, vol. 179, # 2, p. 221 - 226
  • 10
  • [ 619-73-8 ]
  • [ 80936-82-9 ]
Reference: [1] Chemistry - A European Journal, 2007, vol. 13, # 4, p. 1291 - 1299
[2] Journal of the Chemical Society. Perkin Transactions 1, 2001, # 9, p. 955 - 977
  • 11
  • [ 619-73-8 ]
  • [ 2086-26-2 ]
Reference: [1] European Journal of Medicinal Chemistry, 2016, vol. 108, p. 564 - 576
  • 12
  • [ 619-73-8 ]
  • [ 24835-08-3 ]
Reference: [1] European Journal of Organic Chemistry, 2018, vol. 2018, # 1, p. 41 - 47
  • 13
  • [ 2033-24-1 ]
  • [ 619-73-8 ]
  • [ 77359-11-6 ]
YieldReaction ConditionsOperation in experiment
83% at 80℃; Inert atmosphere To a flame dried 150 mL pressure tube under argon was added Meldrum’s acid (5.00 g, 34.7 mmol) and anhydrous MeCN (40 mL). To the resulting solution was added p-nitrobenzyl alcohol (5.58 g, 36.4 mmol), the tube was tightly capped, and refluxed overnight. The reaction was concentrated under reduced pressure and purified with column chromatography (55/45 hexanes/EtOAc) to give 16a (6.86 g, 27.1 mmol) as an off-white solid in 83percent yield. A small crop of this material (1.00 g) was recrystallized from t-butanol/hexanes to give 16a (225 mg, 0.889 mmol) as a white solid.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 21, p. 4933 - 4936
[2] Tetrahedron, 2001, vol. 57, # 9, p. 1837 - 1847
[3] Tetrahedron Letters, 2003, vol. 44, # 40, p. 7499 - 7502
  • 14
  • [ 619-73-8 ]
  • [ 77359-11-6 ]
YieldReaction ConditionsOperation in experiment
59% With malonic acid; toluene-4-sulfonic acid In toluene a)
Preparation of mono-p-nitrobenzyl malonate by esterification of malonic acid with p-nitrobenzyl alcohol:
A mixture of 27.5 g of p-nitrobenzyl alcohol, 28.1 g of malonic acid, 0.4 g of p-toluene sulfonic acid and 180 ml of toluene was heated to reflux (from 100° to 115° C.) for 6 hours in a 300 ml flask.
During this period, the water formed was separated as the toluene azeotrope.
The reaction mixture was cooled to room temperature, and thus formed precipitates were collected by filtration, washed with toluene and dried to give 48 g of crude mono-p-nitrobenzyl malonate (crude yield: 59percent, purity: 52.9percent)
Reference: [1] Patent: US5087734, 1992, A,
  • 15
  • [ 2033-24-1 ]
  • [ 619-73-8 ]
  • [ 28509-24-2 ]
  • [ 77359-11-6 ]
Reference: [1] Patent: US4576746, 1986, A,
  • 16
  • [ 109-01-3 ]
  • [ 555-16-8 ]
  • [ 7556-55-0 ]
  • [ 619-73-8 ]
  • [ 70261-81-3 ]
Reference: [1] Chemistry of Heterocyclic Compounds, 2007, vol. 43, # 12, p. 1540 - 1543
  • 17
  • [ 674-82-8 ]
  • [ 619-73-8 ]
  • [ 61312-84-3 ]
YieldReaction ConditionsOperation in experiment
97% With triethylamine In dichloromethane at 0 - 20℃; for 3 h; 4-Nitrobenzyl alcohol (1.53 g, 10 mmol) was introduced into a round bottomedflask, and dichloromethane (10 mNo. ) was added thereto. After the solution was cooledusing an ice bath, diketene (1.26 g, 15 mmol) was slowly added, and triethyknine(0.14 m-6 , 1 mmol) was added. This solution was warmed to room temperature, stirredfor 3 hours, and water (10 m-6 ) was added. The organic kyer was dried over MgSOand distilled under reduced pressure to give 4-nitrobenzyl acetoacetate (2.30 g,Yield=97percent). The resulting 4-nitrobenzyl acetoacelate was reacted according to thesame procedure as Example 1 to give the title compound in the yield of 68percent (2.09 g).1 H NMR(CDC1): 5 8.25(d, 2H), 7.53(s, 1H), 7.5l(d, 2H), 6.57(s, 1H), 5.27(s,32H), 4.21(s, 2H), 2.54(s, 3H)MS(M+1): 308
Reference: [1] Patent: WO2004/111013, 2004, A1, . Location in patent: Page 39-40
  • 18
  • [ 619-73-8 ]
  • [ 141-97-9 ]
  • [ 61312-84-3 ]
Reference: [1] Synthetic Communications, 2000, vol. 30, # 10, p. 1725 - 1730
[2] Canadian Journal of Chemistry, 1984, vol. 62, # 12, p. 2936 - 2940
[3] Synthetic Communications, 2001, vol. 31, # 13, p. 2063 - 2066
[4] Journal of the Chemical Society. Perkin Transactions 1, 2001, # 8, p. 662 - 667
  • 19
  • [ 619-73-8 ]
  • [ 105-45-3 ]
  • [ 61312-84-3 ]
Reference: [1] RSC Advances, 2015, vol. 5, # 24, p. 18972 - 18976
  • 20
  • [ 619-73-8 ]
  • [ 5394-63-8 ]
  • [ 61312-84-3 ]
Reference: [1] Synthetic Communications, 2000, vol. 30, # 10, p. 1725 - 1730
  • 21
  • [ 619-73-8 ]
  • [ 94838-58-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 5, p. 691 - 701
  • 22
  • [ 619-73-8 ]
  • [ 131230-76-7 ]
Reference: [1] Journal of Organic Chemistry, 2006, vol. 71, # 26, p. 9628 - 9636
[2] Journal of the American Chemical Society, 2000, vol. 122, # 28, p. 6535 - 6551
[3] Journal of Medicinal Chemistry, 2000, vol. 43, # 10, p. 2049 - 2063
[4] Patent: WO2015/23355, 2015, A1,
[5] Chemical Communications, 2015, vol. 51, # 46, p. 9567 - 9570
  • 23
  • [ 619-73-8 ]
  • [ 94838-55-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 5, p. 691 - 701
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