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[ CAS No. 96835-17-5 ] {[proInfo.proName]}

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Chemical Structure| 96835-17-5
Chemical Structure| 96835-17-5
Structure of 96835-17-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 96835-17-5 ]

CAS No. :96835-17-5 MDL No. :MFCD08702763
Formula : C8H14O3 Boiling Point : -
Linear Structure Formula :- InChI Key :BCXINTIRMSZYKA-UHFFFAOYSA-N
M.W : 158.20 Pubchem ID :13467581
Synonyms :

Calculated chemistry of [ 96835-17-5 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.88
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 40.83
TPSA : 35.53 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.7 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.22
Log Po/w (XLOGP3) : 0.79
Log Po/w (WLOGP) : 0.98
Log Po/w (MLOGP) : 0.69
Log Po/w (SILICOS-IT) : 1.54
Consensus Log Po/w : 1.24

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.12
Solubility : 12.0 mg/ml ; 0.0758 mol/l
Class : Very soluble
Log S (Ali) : -1.12
Solubility : 12.1 mg/ml ; 0.0764 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.25
Solubility : 8.98 mg/ml ; 0.0568 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.93

Safety of [ 96835-17-5 ]

Signal Word:Warning Class:
Precautionary Statements:P264-P270-P301+P312-P330 UN#:
Hazard Statements:H302 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 96835-17-5 ]

* 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 [ 96835-17-5 ]
  • Downstream synthetic route of [ 96835-17-5 ]

[ 96835-17-5 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 96835-17-5 ]
  • [ 14774-37-9 ]
YieldReaction ConditionsOperation in experiment
96%
Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 1 h;
Stage #2: With water; sodium hydroxide In tetrahydrofuran; ethyl acetate for 0.5 h;
Ethyl tetrahydro-2H-pyran-4-carboxylate (5.0 g, 34.7 mmol) was added to a stirred solution of LiAlH4 (4.0 g, 104 mmol) in THF (100 mE) at 0° C. and the reaction mixture was stirred for 1 h. Ethyl acetate (20 mE) was added dropwise to the reaction mixture followed by addition of 10percent aq.NaOH and the resulting mixture was stirred for additional 30 mm. Reaction mass was filtered through Celite and the filtrate was concentrated under reduced pressure to give (tetrahydro-2H-pyran-4-yl)methanol (9) as a colorless oil. Yield (3.9 g, 96percent); ‘H NMR (400 MHz, DMSO-d5) δ 4.46 (bs, 1H), 3.82 (dd, J=i0.8, 8.0 Hz, 2H), 3.25-3.22 (m, 4H), 1.62-1.52 (m, 3H), 1.18-1.04 (m, 1H).
Reference: [1] Patent: US2014/275043, 2014, A1, . Location in patent: Paragraph 0415; 0416
[2] Justus Liebigs Annalen der Chemie, 1936, vol. 525, p. 292,294
[3] Patent: WO2010/96371, 2010, A2, . Location in patent: Page/Page column 156
  • 2
  • [ 96835-17-5 ]
  • [ 50675-18-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 5, p. 2058 - 2073
  • 3
  • [ 5382-77-4 ]
  • [ 96835-17-5 ]
YieldReaction ConditionsOperation in experiment
92% With lithium iodide In N,N-dimethyl-formamide 1.
Alternative Preparation of a Compound of Formula (8) where R 1 and R 2 taken together with the Carbon to which they are attached represent Tetrahydropyran
To a solution of tetrahydropyran-4,4-dicarboxylic acid diethyl ester (400 mg, 1.74 mmol) in N,N-dimethylformamide (4 ml), was added lithium iodide (1.16 g, 8.66 mmol), followed by sodium cyanide (94 mg, 1.91 mmol).
The mixture was heated at 130°C for 7 hours, 140°C for 25 hours, after which GC analysis indicated the reaction to be >95percent complete.
The mixture was partitioned between 33percent diethyl ether/hexanes (100 ml) and brine (25 ml).
The organic layer was washed with additional brine (25 ml), dried (MgSO4) and concentrated in vacuoto afford the tetrahydropyran-4-carboxylic acid ethyl ester (253 mg, 92percent). Note:
92% With lithium iodide In N,N-dimethyl-formamide 1.
To a solution of tetrahydropyran-4,4-dicarboxylic acid diethyl ester (400 mg, 1.74 mmol) in N,N-dimethylformamide (4 mL), was added lithium iodide (1.16 g, 8.66 mmol), followed by sodium cyanide (94 mg, 1.91 mmol).
The mixture was heated at 130° C. for 7 hours, 140° C. for 25 hours, after which GC analysis indicated the reaction to be >95percent complete.
The mixture was partitioned between 33percent diethyl ether/hexanes (100 mL) and brine (25 mL).
The organic layer was washed with additional brine (25 mL), dried (MgSO4) and concentrated in vacuo to afford the tetrahydropyran-4-carboxylic acid ethyl ester (253 mg, 92percent). Note:
Reference: [1] Patent: EP780386, 1997, A1,
[2] Patent: US5932595, 1999, A,
[3] Patent: US6342639, 2002, B1, . Location in patent: Scheme D
  • 4
  • [ 5337-03-1 ]
  • [ 64-17-5 ]
  • [ 96835-17-5 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1932, vol. 4, p. 259,263
[2] Patent: WO2016/138532, 2016, A1, . Location in patent: Paragraph 0474
  • 5
  • [ 5337-03-1 ]
  • [ 96835-17-5 ]
Reference: [1] Journal of the Chemical Society, 1930, p. 2525,2529
  • 6
  • [ 40191-32-0 ]
  • [ 64-17-5 ]
  • [ 96835-17-5 ]
Reference: [1] Journal of the Chemical Society, 1930, p. 2525,2529
  • 7
  • [ 96835-17-5 ]
  • [ 65626-22-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 5, p. 1903 - 1907
[2] Patent: WO2015/95767, 2015, A1,
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