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[ CAS No. 104-58-5 ] {[proInfo.proName]}

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Chemical Structure| 104-58-5
Chemical Structure| 104-58-5
Structure of 104-58-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 104-58-5 ]

CAS No. :104-58-5 MDL No. :MFCD00023781
Formula : C8H17NO Boiling Point : -
Linear Structure Formula :- InChI Key :PLRXAFVBCHEMGD-UHFFFAOYSA-N
M.W : 143.23 Pubchem ID :66032
Synonyms :

Calculated chemistry of [ 104-58-5 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 46.43
TPSA : 23.47 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) : -6.62 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.2
Log Po/w (XLOGP3) : 0.78
Log Po/w (WLOGP) : 0.47
Log Po/w (MLOGP) : 0.9
Log Po/w (SILICOS-IT) : 1.38
Consensus Log Po/w : 1.15

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.02
Solubility : 13.6 mg/ml ; 0.0952 mol/l
Class : Very soluble
Log S (Ali) : -0.85
Solubility : 20.1 mg/ml ; 0.14 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.22
Solubility : 8.65 mg/ml ; 0.0604 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.19

Safety of [ 104-58-5 ]

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

Application In Synthesis of [ 104-58-5 ]

* 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 [ 104-58-5 ]
  • Downstream synthetic route of [ 104-58-5 ]

[ 104-58-5 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 110-89-4 ]
  • [ 627-30-5 ]
  • [ 104-58-5 ]
Reference: [1] Pharmazie, 2005, vol. 60, # 2, p. 97 - 106
[2] Tetrahedron, 1992, vol. 48, # 38, p. 8295 - 8308
[3] European Journal of Medicinal Chemistry, 2014, vol. 86, p. 578 - 588
[4] Journal of the American Chemical Society, 1949, vol. 71, p. 3366,3368
[5] Tetrahedron Letters, 1994, vol. 35, # 11, p. 1715 - 1718
[6] Chemische Berichte, 1907, vol. 40, p. 424,426
[7] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 10, p. 3522 - 3529
[8] Journal of Medicinal Chemistry, 2002, vol. 45, # 18, p. 4000 - 4010
[9] Journal of Medicinal Chemistry, 2002, vol. 45, # 5, p. 1128 - 1141
[10] Australian Journal of Chemistry, 2007, vol. 60, # 4, p. 236 - 242
[11] Patent: EP1216244, 2003, B1,
[12] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 8, p. 2172 - 2175
[13] Organic Letters, 2010, vol. 12, # 11, p. 2578 - 2581
[14] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 19, p. 5883 - 5886
[15] European Journal of Medicinal Chemistry, 2018, vol. 148, p. 487 - 497
  • 2
  • [ 23573-93-5 ]
  • [ 104-58-5 ]
YieldReaction ConditionsOperation in experiment
4.0g With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 2 h; Step 2:
Synthesis of 3-(piperidin-1-yl)propanol
To a three-neck flask was added anhydrous tetrahydrofuran (80mL), and then the environment was cooled to 0°C.
To the flask was added in batch lithium aluminum hydride (3.5g, 93.4mmol), and then dropwise added a solution of methyl 3-(piperidin-1-yl)propanoate (8.0g, 46.7mmol) in tetrahydrofuran.
After the completion of the dropwise addition, the mixture was warmed up to room temperature and reacted for 2 hours.
After the completion of the reaction, the reaction mixture was cooled down to 0°C.
To the cooled mixture were successively added purified water (10mL), an aqueous NaOH solution (15percent, 10mL) and purified water (30mL).
A white solid separated out.
The resulting mixture was filtered.
The filtrate was concentrated to produce a yellow oil (4.0g), which was directly used in the next step.
Reference: [1] Tetrahedron, 2007, vol. 63, # 52, p. 12903 - 12911
[2] Patent: EP3181554, 2017, A1, . Location in patent: Paragraph 0253
  • 3
  • [ 503-30-0 ]
  • [ 110-89-4 ]
  • [ 104-58-5 ]
Reference: [1] Tetrahedron Letters, 1994, vol. 35, # 5, p. 761 - 764
[2] Journal of the American Chemical Society, 1954, vol. 76, p. 2789
  • 4
  • [ 110-89-4 ]
  • [ 693-03-8 ]
  • [ 104-58-5 ]
Reference: [1] Journal of the American Chemical Society, 1954, vol. 76, p. 2789
  • 5
  • [ 110-89-4 ]
  • [ 627-18-9 ]
  • [ 104-58-5 ]
Reference: [1] Journal of the American Chemical Society, 1955, vol. 77, p. 3648
  • 6
  • [ 110-89-4 ]
  • [ 107-18-6 ]
  • [ 104-58-5 ]
Reference: [1] Chemical Communications, 2015, vol. 51, # 35, p. 7459 - 7462
  • 7
  • [ 503-30-0 ]
  • [ 110-89-4 ]
  • [ 124-38-9 ]
  • [ 104-58-5 ]
Reference: [1] Synthetic Communications, 1999, vol. 29, # 18, p. 3207 - 3214
  • 8
  • [ 110-89-4 ]
  • [ 627-32-7 ]
  • [ 104-58-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 6, p. 2607 - 2622
  • 9
  • [ 110-89-4 ]
  • [ 104-58-5 ]
Reference: [1] Patent: EP3181554, 2017, A1,
  • 10
  • [ 5470-02-0 ]
  • [ 934-90-7 ]
  • [ 104-58-5 ]
Reference: [1] Journal of the American Chemical Society, 2015, vol. 137, # 40, p. 12796 - 12799
  • 11
  • [ 110-89-4 ]
  • [ 57-57-8 ]
  • [ 104-58-5 ]
Reference: [1] Journal of Organic Chemistry, 1957, vol. 22, p. 1225,1227
  • 12
  • [ 19653-33-9 ]
  • [ 104-58-5 ]
Reference: [1] Zhurnal Obshchei Khimii, 1934, vol. 4, p. 253,266[2] Archiv der Pharmazie (Weinheim, Germany), 1933, vol. 271, p. 569,579[3] Chem. Zentralbl., 1935, vol. 106, # I, p. 2984
[4] Chemische Berichte, 1942, vol. 75, p. 123,129
  • 13
  • [ 110-89-4 ]
  • [ 20907-32-8 ]
  • [ 104-58-5 ]
Reference: [1] Yakugaku Zasshi, 1954, vol. 74, p. 763[2] Chem.Abstr., 1955, p. 11646
[3] Chemische Berichte, 1942, vol. 75, p. 123,129
  • 14
  • [ 14446-67-4 ]
  • [ 934-90-7 ]
  • [ 104-58-5 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1980, vol. 2, # 11-12, p. 565 - 570
  • 15
  • [ 104-58-5 ]
  • [ 1458-63-5 ]
Reference: [1] European Journal of Medicinal Chemistry, 2014, vol. 86, p. 578 - 588
[2] Tetrahedron, 2007, vol. 63, # 52, p. 12903 - 12911
[3] Journal of the American Chemical Society, 1957, vol. 79, p. 5667,5670
[4] Journal of the Chemical Society, 1951, p. 1800,1802
[5] Zhurnal Obshchei Khimii, 1934, vol. 4, p. 253,266[6] Archiv der Pharmazie (Weinheim, Germany), 1933, vol. 271, p. 569,579[7] Chem. Zentralbl., 1935, vol. 106, # I, p. 2984
[8] Journal of the American Chemical Society, 1957, vol. 79, p. 5667,5670
[9] Journal of the Chemical Society, 1951, p. 1800,1802
[10] Zhurnal Obshchei Khimii, 1934, vol. 4, p. 253,266[11] Archiv der Pharmazie (Weinheim, Germany), 1933, vol. 271, p. 569,579[12] Chem. Zentralbl., 1935, vol. 106, # I, p. 2984
[13] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 8, p. 2172 - 2175
[14] European Journal of Medicinal Chemistry, 2018, vol. 148, p. 487 - 497
  • 16
  • [ 104-58-5 ]
  • [ 5472-49-1 ]
Reference: [1] Archiv der Pharmazie, 2004, vol. 337, # 10, p. 533 - 545
[2] Pharmazie, 2005, vol. 60, # 2, p. 97 - 106
[3] Journal of Medicinal Chemistry, 2002, vol. 45, # 5, p. 1128 - 1141
  • 17
  • [ 104-58-5 ]
  • [ 24424-99-5 ]
  • [ 156185-63-6 ]
Reference: [1] Patent: US6362188, 2002, B1,
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