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[ CAS No. 149990-27-2 ] {[proInfo.proName]}

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Chemical Structure| 149990-27-2
Chemical Structure| 149990-27-2
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Product Details of [ 149990-27-2 ]

CAS No. :149990-27-2 MDL No. :MFCD10698150
Formula : C9H15NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :BWNQTGRBVMERHU-UHFFFAOYSA-N
M.W : 169.22 Pubchem ID :10725815
Synonyms :

Calculated chemistry of [ 149990-27-2 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.67
Num. rotatable bonds : 5
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 48.05
TPSA : 38.33 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) : -6.26 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.6
Log Po/w (XLOGP3) : 1.51
Log Po/w (WLOGP) : 1.61
Log Po/w (MLOGP) : 1.69
Log Po/w (SILICOS-IT) : 1.15
Consensus Log Po/w : 1.71

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.51
Solubility : 5.22 mg/ml ; 0.0309 mol/l
Class : Very soluble
Log S (Ali) : -1.92
Solubility : 2.02 mg/ml ; 0.0119 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.72
Solubility : 3.25 mg/ml ; 0.0192 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.41

Safety of [ 149990-27-2 ]

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 [ 149990-27-2 ]

* 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 [ 149990-27-2 ]
  • Downstream synthetic route of [ 149990-27-2 ]

[ 149990-27-2 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 149990-27-2 ]
  • [ 88211-50-1 ]
YieldReaction ConditionsOperation in experiment
79% With hydrogenchloride; water In dichloromethane at 20℃; Preparation 18; iV-But-3-ynyl-2,2-dimethyl-ρropionamide; But-3-ynyl amine hydrochloride: Dissolve but-3-ynyl-carbamic acid tert-butyl ester (1.81 g, 0.1 mmol) in DCM (5 mL) and add 5N aqueous HCl (5 mL). Stir vigorously at room temperature overnight. Concentrate in vacuo to a minimum amount of volume and then freeze dry to obtain the desired material as a white solid (809 mg, 79percent).iV-But-3-ynyl-2,2-dimethγl-propionamide:; Add triethylamine (3 mL) to a suspension of but-3-ynylamine hydrochloride (200 mg, 2.1 mmol) in DCM (10 mL) and stir for 10 min at room temperature under nitrogen. Add then neat pivaloyl chloride (284.9 μL, 2.31 mmol) and stir at room temperature overnight under nitrogen. Concentrate in vacuo, take up the residue in methanol and filter through a SCX-2 cartridge eluting with methanol to obtain the title compound (265 mg, 65percent).
Reference: [1] Patent: WO2007/28131, 2007, A1, . Location in patent: Page/Page column 50
  • 2
  • [ 24424-99-5 ]
  • [ 14044-63-4 ]
  • [ 149990-27-2 ]
Reference: [1] Bioconjugate Chemistry, 2013, vol. 24, # 9, p. 1624 - 1633
[2] Chemical and Pharmaceutical Bulletin, 1998, vol. 46, # 4, p. 631 - 638
[3] Patent: US2012/94986, 2012, A1, . Location in patent: Page/Page column 14
[4] Patent: US2014/171403, 2014, A1, . Location in patent: Page/Page column
[5] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 23, p. 5310 - 5321
[6] Journal of Medicinal Chemistry, 2018, vol. 61, # 17, p. 7589 - 7613
  • 3
  • [ 6089-09-4 ]
  • [ 75-65-0 ]
  • [ 149990-27-2 ]
YieldReaction ConditionsOperation in experiment
53% at 0 - 85℃; Preparation 16; But-3-ynyl-carbamic acid tert-butyl ester; Add triethylamine (3 mL) to a solution of 4-pentynoic acid (1.96 g, 20 mmol) in tert-butanol (6 mL) at O0C and then add diphenyl phosphoryl azide (CAUTION: reaction starts violently a short period after the addition). Heat the reaction mixture at 850C overnight under nitrogen. Concentrate in vacuo and purify the crude mixture by chromatography on silica gel eluting with dichloromethane to obtain the title compound as a white solid (1.81g, 53percent).
Reference: [1] Patent: WO2007/28131, 2007, A1, . Location in patent: Page/Page column 49
  • 4
  • [ 24424-99-5 ]
  • [ 149990-27-2 ]
Reference: [1] Patent: US6258360, 2001, B1,
  • 5
  • [ 14396-90-8 ]
  • [ 24424-99-5 ]
  • [ 149990-27-2 ]
Reference: [1] Organic Letters, 2015, vol. 17, # 14, p. 3414 - 3417
  • 6
  • [ 142-71-2 ]
  • [ 146-75-8 ]
  • [ 622-79-7 ]
  • [ 149990-27-2 ]
Reference: [1] Patent: US2014/171403, 2014, A1, . Location in patent: Page/Page column
  • 7
  • [ 24424-99-5 ]
  • [ 10451-00-0 ]
  • [ 149990-27-2 ]
Reference: [1] Organic Letters, 2010, vol. 12, # 17, p. 3784 - 3787
  • 8
  • [ 338463-00-6 ]
  • [ 149990-27-2 ]
Reference: [1] Journal of Organic Chemistry, 2012, vol. 77, # 18, p. 7804 - 7814,11
  • 9
  • [ 14044-63-4 ]
  • [ 1538-75-6 ]
  • [ 149990-27-2 ]
Reference: [1] Organic Letters, 2014, vol. 16, # 1, p. 94 - 97
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