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[ CAS No. 157688-46-5 ] {[proInfo.proName]}

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Chemical Structure| 157688-46-5
Chemical Structure| 157688-46-5
Structure of 157688-46-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 157688-46-5 ]

CAS No. :157688-46-5 MDL No. :MFCD00800239
Formula : C12H21NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :ZXFLMSIMHISJFV-UHFFFAOYSA-N
M.W : 243.30 Pubchem ID :1512539
Synonyms :

Calculated chemistry of [ 157688-46-5 ]

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.83
Num. rotatable bonds : 5
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 67.98
TPSA : 66.84 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) : -6.83 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.49
Log Po/w (XLOGP3) : 1.35
Log Po/w (WLOGP) : 1.73
Log Po/w (MLOGP) : 1.31
Log Po/w (SILICOS-IT) : 0.88
Consensus Log Po/w : 1.55

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.87
Solubility : 3.29 mg/ml ; 0.0135 mol/l
Class : Very soluble
Log S (Ali) : -2.36
Solubility : 1.07 mg/ml ; 0.00441 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.06
Solubility : 21.2 mg/ml ; 0.0873 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.13

Safety of [ 157688-46-5 ]

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 [ 157688-46-5 ]

* 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 [ 157688-46-5 ]
  • Downstream synthetic route of [ 157688-46-5 ]

[ 157688-46-5 ] Synthesis Path-Upstream   1~22

  • 1
  • [ 157688-46-5 ]
  • [ 89151-44-0 ]
Reference: [1] Journal of Medicinal Chemistry, 1994, vol. 37, # 16, p. 2537 - 2551
[2] Tetrahedron Letters, 1995, vol. 36, # 41, p. 7379 - 7382
[3] Patent: US5866685, 1999, A,
[4] Patent: WO2018/106518, 2018, A1, . Location in patent: Page/Page column 79; 80
  • 2
  • [ 13292-87-0 ]
  • [ 157688-46-5 ]
  • [ 89151-44-0 ]
Reference: [1] Patent: US6265434, 2001, B1,
  • 3
  • [ 135716-09-5 ]
  • [ 157688-46-5 ]
Reference: [1] Chinese Chemical Letters, 2012, vol. 23, # 6, p. 707 - 710
[2] Patent: EP1489078, 2004, A1, . Location in patent: Page 188
[3] Patent: US2003/229074, 2003, A1, . Location in patent: Page 20
[4] Patent: EP1386920, 2004, A1, . Location in patent: Page 50
[5] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 6, p. 1880 - 1886
  • 4
  • [ 24424-99-5 ]
  • [ 157688-46-5 ]
Reference: [1] Patent: US5506242, 1996, A,
[2] Patent: US5552419, 1996, A,
[3] Patent: US5646000, 1997, A,
[4] Patent: US5646167, 1997, A,
[5] Patent: US5817822, 1998, A,
[6] Chinese Chemical Letters, 2012, vol. 23, # 6, p. 707 - 710
  • 5
  • [ 24424-99-5 ]
  • [ 51052-78-9 ]
  • [ 157688-46-5 ]
Reference: [1] Tetrahedron Letters, 1995, vol. 36, # 41, p. 7379 - 7382
[2] Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 21, p. 2601 - 2606
[3] Patent: US5866685, 1999, A,
[4] Patent: US5994356, 1999, A,
[5] Journal of Medicinal Chemistry, 2009, vol. 52, # 11, p. 3523 - 3538
  • 6
  • [ 24424-99-5 ]
  • [ 73415-84-6 ]
  • [ 157688-46-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 21, p. 3105 - 3109
[2] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 4, p. 1084 - 1088
  • 7
  • [ 24424-99-5 ]
  • [ 6622-91-9 ]
  • [ 144-55-8 ]
  • [ 157688-46-5 ]
Reference: [1] Patent: US6376514, 2002, B1,
  • 8
  • [ 28356-58-3 ]
  • [ 157688-46-5 ]
Reference: [1] Journal of Medicinal Chemistry, 1994, vol. 37, # 16, p. 2537 - 2551
  • 9
  • [ 6622-91-9 ]
  • [ 157688-46-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 21, p. 3105 - 3109
[2] Tetrahedron Letters, 1995, vol. 36, # 41, p. 7379 - 7382
  • 10
  • [ 59184-90-6 ]
  • [ 24424-99-5 ]
  • [ 161949-04-8 ]
  • [ 157688-46-5 ]
Reference: [1] Patent: US5612373, 1997, A,
  • 11
  • [ 34619-03-9 ]
  • [ 51052-78-9 ]
  • [ 157688-46-5 ]
Reference: [1] Journal of Medicinal Chemistry, 1994, vol. 37, # 16, p. 2537 - 2551
  • 12
  • [ 175213-46-4 ]
  • [ 157688-46-5 ]
Reference: [1] Patent: EP1104754, 2001, A1,
  • 13
  • [ 79099-07-3 ]
  • [ 157688-46-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 6, p. 1880 - 1886
[2] Chinese Chemical Letters, 2012, vol. 23, # 6, p. 707 - 710
  • 14
  • [ 135716-08-4 ]
  • [ 157688-46-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 6, p. 1880 - 1886
[2] Chinese Chemical Letters, 2012, vol. 23, # 6, p. 707 - 710
  • 15
  • [ 41979-39-9 ]
  • [ 157688-46-5 ]
Reference: [1] Chinese Chemical Letters, 2012, vol. 23, # 6, p. 707 - 710
  • 16
  • [ 84358-13-4 ]
  • [ 157688-46-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 15, p. 4646 - 4661
  • 17
  • [ 157688-46-5 ]
  • [ 142247-38-9 ]
Reference: [1] Journal of Medicinal Chemistry, 1994, vol. 37, # 16, p. 2537 - 2551
  • 18
  • [ 64-17-5 ]
  • [ 157688-46-5 ]
  • [ 135716-09-5 ]
YieldReaction ConditionsOperation in experiment
61% With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 25℃; for 24 h; Step A.
Ethyl 1-tert-butoxycarbonyl-4-piperidineacetate
1-tert -Butoxycarbonyl-4-piperidineacetic acid (1 g, 4.1 mmoles) (prepared as described in Preparative Example 17, Step C in INO291K), ethanol (200 proof) (0.284g, 0.362ml, 6.2mmoles), DEC.HCl (1.18g, 6.2mmoles), HOBT (0.8331g, 6.2mmoles) and NMM (0.624g, 0.678ml, 6.2mmoles) are dissolved in anhydrous DMF (30ml) and the mixture is stirred at 25°C under argon for 24h.
The solution is evaporated to dryness and the residue is dissolved in dichloromethane, washed with satd, NaHCO3 aq, water, dried over magnesium sulfate, filtered and evaporated to dryness.
The residue is chromatographed on silica gel using 0.5percent (10percent conc. ammonium hydroxide in methanol)-dichloromethane as the eluant to give the title compound (0.682g, 61 percent), ESIMS: m/z 272.0 (MH+).
Reference: [1] Patent: EP931078, 2006, B1, . Location in patent: Page/Page column 73-74
  • 19
  • [ 75-03-6 ]
  • [ 157688-46-5 ]
  • [ 135716-09-5 ]
Reference: [1] Patent: EP1553074, 2005, A1, . Location in patent: Page/Page column 52
  • 20
  • [ 157688-46-5 ]
  • [ 145508-94-7 ]
Reference: [1] Advanced Synthesis and Catalysis, 2011, vol. 353, # 9, p. 1438 - 1442
  • 21
  • [ 157688-46-5 ]
  • [ 193275-84-2 ]
Reference: [1] Journal of Organic Chemistry, 2003, vol. 68, # 12, p. 4984 - 4987
[2] Journal of Medicinal Chemistry, 1998, vol. 41, # 24, p. 4890 - 4902
  • 22
  • [ 157688-46-5 ]
  • [ 18107-18-1 ]
  • [ 175213-46-4 ]
Reference: [1] Patent: WO2011/2887, 2011, A1, . Location in patent: Page/Page column 100-101
[2] Patent: WO2007/145563, 2007, A1, . Location in patent: Page/Page column 62
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