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[ CAS No. 4056-78-4 ]

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Chemical Structure| 4056-78-4
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Product Details of [ 4056-78-4 ]

CAS No. :4056-78-4 MDL No. :MFCD01735467
Formula : C7H10O4 Boiling Point : -
Linear Structure Formula :- InChI Key :LNGJOYPCXLOTKL-UHFFFAOYSA-N
M.W :158.15 g/mol Pubchem ID :107216
Synonyms :

Calculated chemistry of [ 4056-78-4 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.71
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 37.19
TPSA : 74.6 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) : -7.17 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.75
Log Po/w (XLOGP3) : 0.14
Log Po/w (WLOGP) : 0.57
Log Po/w (MLOGP) : 0.21
Log Po/w (SILICOS-IT) : 0.03
Consensus Log Po/w : 0.34

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.78
Solubility : 26.4 mg/ml ; 0.167 mol/l
Class : Very soluble
Log S (Ali) : -1.26
Solubility : 8.63 mg/ml ; 0.0546 mol/l
Class : Very soluble
Log S (SILICOS-IT) : 0.46
Solubility : 454.0 mg/ml ; 2.87 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.4

Safety of [ 4056-78-4 ]

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 [ 4056-78-4 ]

* 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.

  • Upstream synthesis route of [ 4056-78-4 ]
  • Downstream synthetic route of [ 4056-78-4 ]

[ 4056-78-4 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 498-66-8 ]
  • [ 4056-78-4 ]
YieldReaction ConditionsOperation in experiment
58% With ruthenium trichloride; sodium periodate In water; ethyl acetate; acetonitrile at 5 - 39℃; Industry scale A 22-L, 3-neck, round bottom flask was equipped with a mechanical stirrer, a J-KEM temperature controller, and anitrogen inlet. The flask was charged with norbornene (200 g, 2.123 mol), ethyl acetate(1.95 L), and acetonitrile (1.95 L). The reaction mixture was cooled to 5 °C using anacetone/dry ice bath. Ruthenium trichloride (9.69 g, 46.72 mmol) was added in oneportion followed by the slow addition of a suspension of sodium periodate (1.816 kg,8.707 mol) in water (2.925 L) over 30 min. The reaction slowly began to exotherm and was monitored to keep the temperature between 10 °C and 15 °C. After 90 min thereaction mixture suddenly thickened to the point where stirring was difficult andexothermed rapidly up to 39 °C (a large amount of dry ice was added to the cooling bath to control the exotherm). The reaction mixture was allowed to cool to 20 °C, the dryice/acetone bath was removed, and the mixture was stirred at room temperature overnight.The solids were removed by filtration through a pad of celite and the filtrate wasconcentrated to a solid which was triturated with hexane (2 L), filtered, and rinsed with hexane (2 x 500 mL) to yield 195 g (58percent) of cyclopentane-l,3-dicarboxylic acid.1H NMR (500 Hz, DMSO-<3/4) δ ppm 12.07 (s, 2H), 2.66-2.73 (m, 2H), 2.06-2.12 (m, 1H), 1.85-1.89 (m, 1H), 1.72-1.85 (m, 4H).
53% With sodium periodate; water In chloroform at 20℃; for 48 h; A mixture of commercially available norbonene (15 g) and RuCl3 (0.3 g) in CHCl3 (100 mL) was stirred at room temperature for 5 min. Then a solution OfNaIO4 (163 g) in H2O (1200 mL) was added and the mixture was stirred at room temperature for 2 d. The mixture was filtered through a pad of celite.(R). and the organic phase was separated. The aqueous phase was saturated with NaCl and extracted with EtOAc (3 x 500 mL). The combined organic phases were treated with MgSO4 and charcoal, filtered and concentrated to afford the crude title compound as thick slightly purple liquid (13.5 g, 53percent). [MH]+ = 159.
Reference: [1] Tetrahedron Letters, 2005, vol. 46, # 18, p. 3201 - 3203
[2] Russian Journal of Applied Chemistry, 2011, vol. 84, # 2, p. 236 - 242
[3] Tetrahedron Letters, 2010, vol. 51, # 23, p. 3123 - 3126
[4] Australian Journal of Chemistry, 1985, vol. 38, # 11, p. 1705 - 1718
[5] Journal of Medicinal Chemistry, 2011, vol. 54, # 10, p. 3480 - 3491
[6] Patent: WO2012/145569, 2012, A1, . Location in patent: Page/Page column 179
[7] Patent: WO2006/128184, 2006, A2, . Location in patent: Page/Page column 167
[8] Journal of Organic Chemistry, 1993, vol. 58, # 17, p. 4745
[9] Journal of Organic Chemistry, 1963, vol. 28, p. 2537 - 2541
  • 2
  • [ 497-38-1 ]
  • [ 4056-78-4 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1961, vol. 9, p. 391 - 403
  • 3
  • [ 18084-03-2 ]
  • [ 4056-78-4 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1961, vol. 9, p. 391 - 403
  • 4
  • [ 71720-43-9 ]
  • [ 4056-78-4 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1961, vol. 9, p. 391 - 403
  • 5
  • [ 87238-75-3 ]
  • [ 4056-78-4 ]
Reference: [1] Monatshefte fuer Chemie, 1961, vol. 92, p. 1080 - 1083
  • 6
  • [ 67-56-1 ]
  • [ 4056-78-4 ]
  • [ 2435-36-1 ]
YieldReaction ConditionsOperation in experiment
100% at 7 - 12℃; for 16 h; Reflux A 5-L, 3-neck, roundbottom flask was equipped with a mechanical stirrer, a J-KEM temperature controller, and a reflux condenser. The flask was charged with cyclopentane-l,3-dicarboxylic acid(357 g, 2.262 mol) and methanol (1.75 L). The solution was cooled to 7 °C using anice/water bath. Concentrated sulfuric acid (70 mL) was added dropwise over 30 minresulting in an exotherm up to 12 °C. The reaction mixture was heated to reflux andstirred for 16 h when TLC analysis (10 percent methanol/ethyl acetate) indicated that thereaction was complete. The reaction mixture was concentrated, redissolved in methyl- 179 -ATI-2514175vl tert-butyl ether, and washed with saturated aqueous sodium bicarbonate (2 x 150 mL) and brine (2 x 150 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated. The resulting clear oil was dissolved in hexane (2 L) and treated with a 2 N aqueous sodium hydroxide solution (950 mL) until the pH ~ 10. The layers were separated and the aqueous layer was extracted with hexane (4 x 1 L). The organic layers were combined, dried over sodium sulfate, filtered, and concentrated to provide 360 g (100percent) of dimethyl cyclopentane-l,3-dicarboxylate as a clear oil. 1H NMR (500 Hz, CDCls) δ ppm 3.67 (s, 6H), 2.75-2.83 (m, 2H), 2.20-2.26 (m, 1H), 2.05-2.12 (m, 1H), 1.90-2.0 (m, 4H).
88% With sulfuric acid In water at 0 - 90℃; Step A:
Dimethyl cyclopentane-1,3-dicarboxylate.
A solution of cyclopentane-1,3-dicarboxylic acid (70.0 g, 443 mmol) and anhydrous methanol (300 mL) was cooled to 0° C. in an ice water bath.
Concentrated sulfuric acid (14 mL) was added dropwise, maintaining the temperature at <15° C.
After the addition, the reaction was heated to 90° C. and stirred overnight.
The reaction was cooled to room temperature and concentrated to dryness.
The residue was treated with MTBE (500 mL) and H2O (100 mL).
The aqueous layer was separated and extracted with MTBE (2*100 mL).
The combined organic extracts were washed with saturated sodium bicarbonate (2*100 mL), brine (100 mL), dried over anhydrous MgSO4, filtered, and concentrated to dryness to provide the title compound (72.5 g, 88percent) as a pale yellow oil. 1H NMR (400 MHz, CDCl3) δ 3.65 (s, 6H), 2.84-2.72 (m, 2H), 2.26-2.17 (m, 1H), 2.11-2.02 (m, 1H), 1.96-1.88 (m, 4H).
88% at 15 - 90℃; . A solution of cyclopentane-1,3- dicarboxylic acid (70.0 g, 443 mmol) and anhydrous methanol (300 mL) was cooled to 0 °C in an ice water bath. Concentrated sulfuric acid (14 mL) was added dropwise, maintaining the temperature at < 15 °C. After the addition, the reaction was heated to 90 °C and stirred overnight. The reaction was cooled to room temperature and concentrated to dryness. Theresidue was treated with MTBE (500 mL) and H20 (100 mL). The aqueous layer was separated and extracted with MTBE (2 x 100 mL). The combined organic extracts were washed with saturated sodium bicarbonate (2 x 100 mL), brine (100 mL), dried over anhydrous Mg504, filtered, and concentrated to dryness to provide the title compound (72.5 g, 88percent) as a pale yellow oil. ‘HNMR(400 IVIFIz, CDC13) 3.65 (s, 6H), 2.84-2.72 (m, 2H), 2.26-2.17 (m, 1H),2.11 -2.02(m, 1H), 1.96- 1.88(m,4H).
64% at 20℃; for 15 h; Heating / reflux To a solution of the title compound from Step A above (11.2 g) in MeOH (250 mL) was added concentrated H2SO4 (0.5 mL) at room temperature. The mixture was heated to reflux for 15 h, cooled to room temperature, filtrated and concentrated. The remaining residue was diluted with EtOAc (100 mL), washed with saturated aqueous NaHCO3 (3 x 50 mL) and saturated aqueous NaCl (50 mL), dried (MgSO4), filtered, concentrated and purified by chromatography (silica, cyclohexane/EtOAc) to afford the title compound as a colorless solid (8.43 g, 64percent). [MH]+ = 187.

Reference: [1] Patent: WO2012/145569, 2012, A1, . Location in patent: Page/Page column 179; 180
[2] Journal of Medicinal Chemistry, 2011, vol. 54, # 10, p. 3480 - 3491
[3] Patent: US2018/170931, 2018, A1, . Location in patent: Paragraph 0188
[4] Patent: WO2018/112382, 2018, A1, . Location in patent: Page/Page column 174
[5] Tetrahedron Letters, 2005, vol. 46, # 18, p. 3201 - 3203
[6] Patent: WO2006/128184, 2006, A2, . Location in patent: Page/Page column 167
[7] Australian Journal of Chemistry, 1985, vol. 38, # 11, p. 1705 - 1718
[8] Patent: WO2016/106623, 2016, A1, . Location in patent: Page/Page column 113
[9] Patent: WO2016/106624, 2016, A1, . Location in patent: Page/Page column 64
  • 7
  • [ 4056-78-4 ]
  • [ 15448-76-7 ]
Reference: [1] Patent: WO2016/106623, 2016, A1,
[2] Patent: WO2016/106624, 2016, A1,
[3] Patent: US2018/170931, 2018, A1,
[4] Patent: WO2012/145569, 2012, A1,
[5] Patent: WO2018/112382, 2018, A1,
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