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[ CAS No. 32692-19-6 ] {[proInfo.proName]}

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Chemical Structure| 32692-19-6
Chemical Structure| 32692-19-6
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Product Details of [ 32692-19-6 ]

CAS No. :32692-19-6 MDL No. :MFCD00005709
Formula : C8H8N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :WJQWYAJTPPYORB-UHFFFAOYSA-N
M.W : 164.16 Pubchem ID :36219
Synonyms :

Calculated chemistry of [ 32692-19-6 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 50.36
TPSA : 57.85 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) : -5.83 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.39
Log Po/w (XLOGP3) : 2.07
Log Po/w (WLOGP) : 0.99
Log Po/w (MLOGP) : 1.36
Log Po/w (SILICOS-IT) : -0.04
Consensus Log Po/w : 1.16

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.47
Solubility : 0.562 mg/ml ; 0.00342 mol/l
Class : Soluble
Log S (Ali) : -2.91
Solubility : 0.2 mg/ml ; 0.00122 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.37
Solubility : 0.697 mg/ml ; 0.00425 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.66

Safety of [ 32692-19-6 ]

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 [ 32692-19-6 ]

* 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 [ 32692-19-6 ]
  • Downstream synthetic route of [ 32692-19-6 ]

[ 32692-19-6 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 32692-19-6 ]
  • [ 5192-03-0 ]
Reference: [1] Phytochemistry (Elsevier), 1982, vol. 21, # 12, p. 2879 - 2886
[2] Zhurnal Obshchei Khimii, 1959, vol. 29, p. 2541,2550; engl. Ausg. S. 2504, 2511
  • 2
  • [ 33632-27-8 ]
  • [ 32692-19-6 ]
YieldReaction ConditionsOperation in experiment
97.43% With hydrogenchloride In ethanol; water at 5℃; Reflux To a stirred solution of 5-Nitro N-acetyl Indoline (5 g , 31mmol) in ethanol (50 ml ), 30percent aq HCl (10ml ) was added at 50C .The reaction mixture was heated under reflux for 2 h.Reaction mixture was cooled to room temperature and solvent was evaporated under reduced pressure. Residue was basifed with ammonium hydroxide ( pH 9) solution , filtered and dried to afford the product as a yellow solid (3.8 g , 97.43 percent). MS = m/z 164 [M+l].
Reference: [1] Patent: WO2009/109999, 2009, A1, . Location in patent: Page/Page column 80
[2] Chemical Communications, 2017, vol. 53, # 82, p. 11368 - 11371
[3] Journal of Organic Chemistry, 1955, vol. 20, p. 1538,1541
[4] Zhurnal Obshchei Khimii, 1959, vol. 29, p. 2541,2550; engl. Ausg. S. 2504, 2511
[5] Chemical and Pharmaceutical Bulletin, 2000, vol. 48, # 6, p. 817 - 827
  • 3
  • [ 20870-79-5 ]
  • [ 32692-19-6 ]
YieldReaction ConditionsOperation in experiment
54% With borane-THF In tetrahydrofuran at 0℃; for 0.5 h; Heating / reflux Example 67
5-Nitro-indoline (2)
A suspension of compound 1 (5 g, 28.1 mmol) in THF (10 mL) was treated with a BH3-THF complex (84 mL, 84 mmol, 1.0 M in THF) and the resulting brown red suspension was refluxed overnight.
The reaction was cooled in an ice-bath and methanol (125 mL) was added resulting in orange/red solution which was stirred for half an hour and then concentrated.
Methanol (200 mL) was added again and the solution was refluxed for 2 hrs and then concentrated.
The residue was subjected to a large silica gel filter with methanol as eluent resulting in a brown solid (2.5 g, 54percent yield).
1H-NMR (DMSO-d6) δ 7.90 (dd, J=8.7, 2.4 Hz, 1H), 7.83 (s, 1H), 7.26 (s, 1H), 6.44 (d, J=8.7 Hz, 1H), 3.66 (t, J=9.0 Hz, 2H), 3.04 (t, J=9.0 Hz, 2H).
Reference: [1] Patent: US2008/234237, 2008, A1, . Location in patent: Page/Page column 104
  • 4
  • [ 6146-52-7 ]
  • [ 32692-19-6 ]
Reference: [1] Journal of Organic Chemistry, 1981, vol. 46, # 2, p. 355 - 360
[2] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 21, p. 3105 - 3109
[3] Journal of Organic Chemistry, 2016, vol. 81, # 2, p. 396 - 403
  • 5
  • [ 16078-30-1 ]
  • [ 32692-19-6 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 2000, vol. 48, # 6, p. 817 - 827
[2] Journal of Organic Chemistry, 1955, vol. 20, p. 1538,1541
[3] Chemical Communications, 2017, vol. 53, # 82, p. 11368 - 11371
[4] Patent: WO2009/109999, 2009, A1,
  • 6
  • [ 64-17-5 ]
  • [ 100-01-6 ]
  • [ 32692-19-6 ]
Reference: [1] Chemical Communications, 2016, vol. 52, # 13, p. 2776 - 2779
  • 7
  • [ 496-15-1 ]
  • [ 32692-19-6 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 2000, vol. 48, # 6, p. 817 - 827
[2] Chemical Communications, 2017, vol. 53, # 82, p. 11368 - 11371
  • 8
  • [ 120-72-9 ]
  • [ 32692-19-6 ]
Reference: [1] Chemical Communications, 2017, vol. 53, # 82, p. 11368 - 11371
  • 9
  • [ 496-15-1 ]
  • [ 32692-19-6 ]
  • [ 67932-53-0 ]
Reference: [1] Zhurnal Obshchei Khimii, 1959, vol. 29, p. 2541,2550; engl. Ausg. S. 2504, 2511
  • 10
  • [ 108619-08-5 ]
  • [ 32692-19-6 ]
Reference: [1] Nippon Kagaku Zasshi, 1957, vol. 78, p. 1372[2] Chem.Abstr., 1960, p. 491
  • 11
  • [ 6037-73-6 ]
  • [ 32692-19-6 ]
Reference: [1] Nippon Kagaku Zasshi, 1957, vol. 78, p. 1372[2] Chem.Abstr., 1960, p. 491
  • 12
  • [ 496-15-1 ]
  • [ 108-24-7 ]
  • [ 32692-19-6 ]
  • [ 67932-53-0 ]
Reference: [1] Zhurnal Obshchei Khimii, 1959, vol. 29, p. 2541,2550; engl. Ausg. S. 2504, 2511
  • 13
  • [ 32692-19-6 ]
  • [ 87240-07-1 ]
Reference: [1] Phytochemistry (Elsevier), 1982, vol. 21, # 12, p. 2879 - 2886
[2] Patent: US2014/148437, 2014, A1,
[3] Patent: WO2014/81994, 2014, A1,
  • 14
  • [ 32692-19-6 ]
  • [ 129487-92-9 ]
Reference: [1] Patent: US2011/319394, 2011, A1,
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