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[ CAS No. 16466-61-8 ] {[proInfo.proName]}

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Chemical Structure| 16466-61-8
Chemical Structure| 16466-61-8
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Product Details of [ 16466-61-8 ]

CAS No. :16466-61-8 MDL No. :MFCD00015000
Formula : C10H20N2O4 Boiling Point : -
Linear Structure Formula :- InChI Key :TYSZETYVESRFNT-UHFFFAOYSA-N
M.W : 232.28 Pubchem ID :85431
Synonyms :

Calculated chemistry of [ 16466-61-8 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.8
Num. rotatable bonds : 7
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 59.21
TPSA : 76.66 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) : -6.42 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.7
Log Po/w (XLOGP3) : 1.83
Log Po/w (WLOGP) : 1.95
Log Po/w (MLOGP) : 1.54
Log Po/w (SILICOS-IT) : -0.06
Consensus Log Po/w : 1.59

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.97
Solubility : 2.48 mg/ml ; 0.0107 mol/l
Class : Very soluble
Log S (Ali) : -3.06
Solubility : 0.202 mg/ml ; 0.000871 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.79
Solubility : 3.77 mg/ml ; 0.0162 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.88

Safety of [ 16466-61-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P271-P280-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 16466-61-8 ]

* 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 [ 16466-61-8 ]
  • Downstream synthetic route of [ 16466-61-8 ]

[ 16466-61-8 ] Synthesis Path-Upstream   1~24

  • 1
  • [ 24424-99-5 ]
  • [ 16466-61-8 ]
YieldReaction ConditionsOperation in experiment
84% With hydrazine hydrate In methanol at 20℃; for 3 h; Cooling with ice 50ml methanol solution under ice-cooling, over 30min Hydrazine monohydrate (5.85g, 85percent, 200mmol) was added dropwise into the 50ml of BOC anhydride (48g, 220mmol), and the resulting mixture was stirred at rt for 3h, spin dry methanol , 250ml of n-hexane was added, the resulting white solid was suction filtered and washed with n-hexane to give a white solid 19.34 g, 84percent yield.
66% With hydrazine hydrate In methanol at -10 - 20℃; for 3 h; A solution of di-tert-butyl dicarbonate (5.3 g, 24 mmol) in methanol (4 mL) was cooled to −10 °C and stirred for 10 min. Hydrazine monohydrate (64–65percent, 0.83 mL, 11 mmol) dissolved in methanol (10 mL) was added dropwise to the solution at −10 °C. After the addition was complete, the mixture was warmed to ambient temperature and stirred for 3 h. After methanol and excess di-tert-butyl dicarbonate was removed in vacuo, hexane (100 mL) was added to the residue. The precipitate was filtered and washed with hexane (2 × 100 mL) to afford a white precipitate, which was dried in vacuo to obtain the corresponding product 7 (1.7 g, 66 percent) as a white solid. 1H NMR (600 MHz, CDCl3) δ 1.47 (s, 18H), 6.22 (s, 2H); 13C NMR (150 MHz, CDCl3) δ 28.3, 81.7, 155.9.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 20, p. 2715 - 2717
[2] Chemical Communications, 2011, vol. 47, # 1, p. 373 - 375
[3] Patent: CN104387418, 2016, B, . Location in patent: Paragraph 0088; 0089; 0090
[4] Journal of the American Chemical Society, 2012, vol. 134, # 45, p. 18581 - 18584
[5] Patent: WO2014/22454, 2014, A1, . Location in patent: Paragraph 0160
[6] Bulletin of the Korean Chemical Society, 2018, vol. 39, # 1, p. 126 - 129
[7] Journal of Antibiotics, 1993, vol. 46, # 12, p. 1866 - 1882
[8] Journal of Organic Chemistry USSR (English Translation), 1977, vol. 13, # 12, p. 2352 - 2355[9] Zhurnal Organicheskoi Khimii, 1977, vol. 13, # 12, p. 2531 - 2535
[10] Heterocycles, 2009, vol. 79, # C, p. 851 - 863
  • 2
  • [ 870-50-8 ]
  • [ 1129-28-8 ]
  • [ 16466-61-8 ]
  • [ 1048669-58-4 ]
YieldReaction ConditionsOperation in experiment
74% With ammonium chloride; zinc In tetrahydrofuran; water for 3 h; General procedure: To 0.13 g (2 mmol) of Zn metal in 1 mL saturated aqueous NH4Cl solution was added 0.23 g (1 mmol) of 4. Stirring was begun and a solution of the appropriate benzyl bromide (2 mmol) in 2 mL of THF was added via pipette. The reaction vessel was capped and the mixture allowed to stir until the yellow color of 4 was discharged (generally ~3 h). The reaction mixture was filtered through a plug of glass wool into a centrifuge tube. The organic layer was removed. The aqueous layer was washed 2 × 2 mL of THF. The combined organic layers were dried over Na2SO4, filtered, and concentrated. Column chromatography on SiO2 using appropriate mixtures of ethylacetate and hexanes provided the desired compounds.
Reference: [1] Synthetic Communications, 2014, vol. 44, # 8, p. 1128 - 1136
  • 3
  • [ 6044-68-4 ]
  • [ 870-50-8 ]
  • [ 16466-61-8 ]
Reference: [1] Journal of the American Chemical Society, 2006, vol. 128, # 35, p. 11693 - 11712
  • 4
  • [ 870-50-8 ]
  • [ 16466-61-8 ]
Reference: [1] Angewandte Chemie - International Edition, 2006, vol. 45, # 14, p. 2305 - 2308
  • 5
  • [ 24608-52-4 ]
  • [ 16466-61-8 ]
Reference: [1] Organic and Biomolecular Chemistry, 2017, vol. 15, # 9, p. 1970 - 1975
  • 6
  • [ 870-50-8 ]
  • [ 16466-61-8 ]
  • [ 1219020-59-3 ]
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 30, p. 4102 - 4104
  • 7
  • [ 870-46-2 ]
  • [ 16466-61-8 ]
Reference: [1] Organic Letters, 2003, vol. 5, # 22, p. 4129 - 4131
  • 8
  • [ 870-50-8 ]
  • [ 16466-61-8 ]
  • [ 185456-26-2 ]
Reference: [1] Organic Letters, 2006, vol. 8, # 1, p. 43 - 45
  • 9
  • [ 35454-04-7 ]
  • [ 16466-61-8 ]
Reference: [1] Journal of the American Chemical Society, 1960, vol. 82, p. 2725 - 2727
  • 10
  • [ 29518-83-0 ]
  • [ 16466-61-8 ]
Reference: [1] Journal of the American Chemical Society, 1960, vol. 82, p. 2725 - 2727
  • 11
  • [ 50624-94-7 ]
  • [ 16466-61-8 ]
Reference: [1] Journal of the American Chemical Society, 1960, vol. 82, p. 2725 - 2727
  • 12
  • [ 870-46-2 ]
  • [ 16466-61-8 ]
Reference: [1] Patent: US5494889, 1996, A,
  • 13
  • [ 870-50-8 ]
  • [ 16466-61-8 ]
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 30, p. 4102 - 4104
[2] Synthetic Communications, 2014, vol. 44, # 8, p. 1128 - 1136
  • 14
  • [ 870-50-8 ]
  • [ 98-80-6 ]
  • [ 16466-61-8 ]
  • [ 65578-58-7 ]
Reference: [1] Journal of Organic Chemistry, 2005, vol. 70, # 21, p. 8631 - 8634
  • 15
  • [ 1070-19-5 ]
  • [ 870-46-2 ]
  • [ 16466-61-8 ]
Reference: [1] Journal of the American Chemical Society, 1957, vol. 79, p. 4427,4429
  • 16
  • [ 870-46-2 ]
  • [ 57022-34-1 ]
  • [ 16466-61-8 ]
Reference: [1] Journal of the American Chemical Society, 1960, vol. 82, p. 2725 - 2727
  • 17
  • [ 870-46-2 ]
  • [ 24424-99-5 ]
  • [ 16466-61-8 ]
Reference: [1] Tetrahedron, 2008, vol. 64, # 28, p. 6788 - 6793
  • 18
  • [ 14618-58-7 ]
  • [ 16466-61-8 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1981, vol. 17, # 9, p. 1795[2] Zhurnal Organicheskoi Khimii, 1981, vol. 17, # 9, p. 2011 - 2012
  • 19
  • [ 39982-09-7 ]
  • [ 16466-61-8 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1981, vol. 17, # 9, p. 1795[2] Zhurnal Organicheskoi Khimii, 1981, vol. 17, # 9, p. 2011 - 2012
  • 20
  • [ 870-50-8 ]
  • [ 16851-56-2 ]
  • [ 120-72-9 ]
  • [ 16466-61-8 ]
Reference: [1] RSC Advances, 2016, vol. 6, # 99, p. 96693 - 96699
  • 21
  • [ 2168-84-5 ]
  • [ 870-50-8 ]
  • [ 16466-61-8 ]
  • [ 65813-90-3 ]
  • [ 140869-67-6 ]
Reference: [1] Liebigs Annalen der Chemie, 1992, # 9, p. 927 - 932
  • 22
  • [ 56816-01-4 ]
  • [ 870-50-8 ]
  • [ 16466-61-8 ]
  • [ 119645-81-7 ]
  • [ 119645-77-1 ]
Reference: [1] Tetrahedron, 1988, vol. 44, # 17, p. 5553 - 5562
[2] Tetrahedron, 1988, vol. 44, # 17, p. 5553 - 5562
  • 23
  • [ 16466-61-8 ]
  • [ 870-50-8 ]
Reference: [1] Journal of Chemical Research, 2005, # 10, p. 661 - 662
[2] Organic and Biomolecular Chemistry, 2017, vol. 15, # 9, p. 1970 - 1975
[3] Chemical Communications, 2011, vol. 47, # 1, p. 373 - 375
[4] Chemistry - A European Journal, 2018, vol. 24, # 67, p. 17681 - 17685
[5] Journal of the American Chemical Society, 2012, vol. 134, # 45, p. 18581 - 18584
[6] Patent: WO2014/22454, 2014, A1, . Location in patent: Paragraph 0160
[7] Journal of Organic Chemistry, 1961, vol. 26, p. 4336 - 4340
[8] Organic Letters, 2016, vol. 18, # 24, p. 6300 - 6303
[9] Chemistry Letters, 2018, vol. 47, # 2, p. 144 - 147
  • 24
  • [ 16466-61-8 ]
  • [ 28899-97-0 ]
  • [ 870-50-8 ]
Reference: [1] Tetrahedron Letters, 2002, vol. 43, # 35, p. 6213 - 6215
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