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[ CAS No. 6850-65-3 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 6850-65-3
Chemical Structure| 6850-65-3
Chemical Structure| 6850-65-3
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Product Details of [ 6850-65-3 ]

CAS No. :6850-65-3 MDL No. :MFCD00042624
Formula : C6H13NO Boiling Point : -
Linear Structure Formula :- InChI Key :IMLXLGZJLAOKJN-UHFFFAOYSA-N
M.W : 115.17 Pubchem ID :81293
Synonyms :

Calculated chemistry of [ 6850-65-3 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 32.71
TPSA : 46.25 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) : -7.05 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.41
Log Po/w (XLOGP3) : -0.06
Log Po/w (WLOGP) : 0.25
Log Po/w (MLOGP) : 0.21
Log Po/w (SILICOS-IT) : 0.39
Consensus Log Po/w : 0.44

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.52
Solubility : 35.1 mg/ml ; 0.305 mol/l
Class : Very soluble
Log S (Ali) : -0.46
Solubility : 39.9 mg/ml ; 0.347 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.1
Solubility : 92.3 mg/ml ; 0.802 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.91

Safety of [ 6850-65-3 ]

Signal Word:Danger Class:9
Precautionary Statements:P264-P270-P271-P272-P280-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P403+P233-P501 UN#:3077
Hazard Statements:H302-H314-H317-H410 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 6850-65-3 ]

* 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 [ 6850-65-3 ]
  • Downstream synthetic route of [ 6850-65-3 ]

[ 6850-65-3 ] Synthesis Path-Upstream   1~25

  • 1
  • [ 100-02-7 ]
  • [ 2615-25-0 ]
  • [ 15827-56-2 ]
  • [ 27489-62-9 ]
  • [ 6850-65-3 ]
Reference: [1] ChemCatChem, 2018, vol. 10, # 17, p. 3689 - 3693
  • 2
  • [ 106-50-3 ]
  • [ 2615-25-0 ]
  • [ 15827-56-2 ]
  • [ 6850-65-3 ]
  • [ 108-91-8 ]
  • [ 108-93-0 ]
Reference: [1] Russian Journal of Applied Chemistry, 2014, vol. 87, # 3, p. 397 - 403[2] Zh. Prikl. Khim. (S.-Peterburg, Russ. Fed.), 2014, vol. 87, # 3, p. 397 - 403,7
  • 3
  • [ 100-02-7 ]
  • [ 6850-65-3 ]
  • [ 108-93-0 ]
Reference: [1] ACS Catalysis, 2017, vol. 7, # 7, p. 4446 - 4450
  • 4
  • [ 556-48-9 ]
  • [ 3114-70-3 ]
  • [ 6850-65-3 ]
Reference: [1] Patent: US6369274, 2002, B1, . Location in patent: Page column 3
  • 5
  • [ 100-02-7 ]
  • [ 6850-65-3 ]
  • [ 123-30-8 ]
Reference: [1] Catalysis Communications, 2012, vol. 18, p. 55 - 59
  • 6
  • [ 106-50-3 ]
  • [ 2615-25-0 ]
  • [ 15827-56-2 ]
  • [ 6850-65-3 ]
  • [ 108-91-8 ]
  • [ 108-93-0 ]
Reference: [1] Russian Journal of Applied Chemistry, 2014, vol. 87, # 3, p. 397 - 403[2] Zh. Prikl. Khim. (S.-Peterburg, Russ. Fed.), 2014, vol. 87, # 3, p. 397 - 403,7
  • 7
  • [ 41295-20-9 ]
  • [ 6850-65-3 ]
  • [ 82166-21-0 ]
Reference: [1] Chemical Communications, 2013, vol. 49, # 40, p. 4567 - 4569
  • 8
  • [ 556-48-9 ]
  • [ 3114-70-3 ]
  • [ 6850-65-3 ]
  • [ 108-91-8 ]
Reference: [1] Journal of Catalysis, 1999, vol. 182, # 2, p. 289 - 291
  • 9
  • [ 123-31-9 ]
  • [ 27489-62-9 ]
  • [ 6850-65-3 ]
Reference: [1] ChemCatChem, 2018, vol. 10, # 17, p. 3689 - 3693
  • 10
  • [ 100-02-7 ]
  • [ 2615-25-0 ]
  • [ 15827-56-2 ]
  • [ 27489-62-9 ]
  • [ 6850-65-3 ]
Reference: [1] ChemCatChem, 2018, vol. 10, # 17, p. 3689 - 3693
  • 11
  • [ 123-30-8 ]
  • [ 27489-62-9 ]
  • [ 6850-65-3 ]
Reference: [1] Journal of the American Chemical Society, 1958, vol. 80, p. 6412,6419
  • 12
  • [ 100-02-7 ]
  • [ 27489-62-9 ]
  • [ 6850-65-3 ]
Reference: [1] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1923, vol. 177, p. 159
[2] Technology Reports of the Osaka University, 1955, vol. 5, p. 205,208
  • 13
  • [ 6850-65-3 ]
  • [ 108-24-7 ]
  • [ 27489-60-7 ]
  • [ 27489-61-8 ]
Reference: [1] European Journal of Medicinal Chemistry, 1980, vol. 15, # 1, p. 77 - 84
  • 14
  • [ 6850-65-3 ]
  • [ 16801-63-1 ]
Reference: [1] Synthetic Communications, 1990, vol. 20, # 7, p. 1073 - 1082
[2] Journal of Organic Chemistry, 1968, vol. 33, # 8, p. 3182 - 3187
[3] Journal of Materials Chemistry, 2011, vol. 21, # 18, p. 6677 - 6682
[4] Patent: WO2014/194242, 2014, A2,
[5] Patent: WO2015/164374, 2015, A1,
  • 15
  • [ 6850-65-3 ]
  • [ 104618-32-8 ]
Reference: [1] Journal of medicinal chemistry, 1993, vol. 36, # 13, p. 1918 - 1919
  • 16
  • [ 22509-74-6 ]
  • [ 6850-65-3 ]
  • [ 104618-31-7 ]
YieldReaction ConditionsOperation in experiment
81% for 0.0833333 h; Heating 4-Amino-cyclohexanol (2.627 g, 22.81 mmol) and 1,3-Dioxo-1,3-dihydro-isoindole-2-carboxylic acid ethyl ester (5 g, 22.81 mmol) were placed in a large test-tube and heated with a heat gun until both had melted and then for an additional 5 minutes. The resulting solution was allowed to cool and a solid formed. This solid was transferred to a flask, taken up in CH2Cl2 and purified via chromatography (75percent EtOAc/Hex) to give 4.57 g of 2-(4-Hydroxy-cyclohexyl)-isoindole-1,3-dione (81percent yield). LCMS (m/z): M+H+MeCN=287.1.
56.82% With potassium carbonate In water at 20℃; for 2 h; [00486] To a solution of ethyl 1 ,3-dioxoisoindoline-2-carboxylate (1 .67 g, 7.19 mmol) in water (16 mL) was added 4-aminocyclohexanol (1 .31 g, 8.63 mmol), followed by K2CO3 (1 .59 g, 1 1 .5 mmol). The mixture was stirred at room temperature for 2 h. TLC (PE: EA = 1 :1 ) showed the reaction was complete. The mixture was filtered and the solid was dried under vacuum to give 2-(4- hydroxycyclohexyl)isoindoline-1 ,3-dione (1 g, 56.82percent) as a brown solid.
56.82% at 20℃; for 2 h; To a solution of ethyl 1,3-dioxoisoindoline-2-carboxylate (1.67 g, 7.19 mmol) in water (16 mL) was added 4-aminocyclohexanol (1.31 g, 8.63 mmol), followed by K2CO3 (1.59 g, 11.5 mmol). The mixture was stirred at room temperature for 2 h. TLC (PE:EA=1:1) showed the reaction was complete. The mixture was filtered and the solid was dried under vacuum to give 2-(4-hydroxycyclohexyl)isoindoline-1,3-dione (1 g, 56.82percent) as a brown solid.
Reference: [1] Patent: US2008/269193, 2008, A1, . Location in patent: Page/Page column 33
[2] Patent: WO2013/13188, 2013, A1, . Location in patent: Paragraph 00486
[3] Patent: US9416132, 2016, B2, . Location in patent: Page/Page column 183; 184
[4] Journal of medicinal chemistry, 1993, vol. 36, # 13, p. 1918 - 1919
  • 17
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  • [ 179321-49-4 ]
Reference: [1] Patent: US2013/190249, 2013, A1,
[2] Patent: WO2013/107291, 2013, A1,
[3] Patent: WO2015/10297, 2015, A1,
[4] Patent: WO2013/107405, 2013, A1,
[5] Patent: WO2015/10626, 2015, A1,
[6] Patent: US2015/31627, 2015, A1,
[7] Patent: US2015/87600, 2015, A1,
  • 18
  • [ 24424-99-5 ]
  • [ 6850-65-3 ]
  • [ 224309-64-2 ]
YieldReaction ConditionsOperation in experiment
87% With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 4 h; Inert atmosphere To a solution of di-tert-butyl dicarbonate (4.087 mL, 21.01 mmol) and diisopropylethylamine (2.87 mL, 17.4 mmol) in THF (60 mL) was added (1R,4R)-4-aminocyclohexanol (2.00 g, 17.4 mmol) and was stirred at rt for 4h. The reaction was concentrated to dryness and the residue was dried under reduced pressure to yield the title Compound as a white solid (3.49 g, 87.0percent yield), which was used without further purification.
79% With triethylamine In tetrahydrofuran at 20℃; To a solution of 4-aminocyclohexanol (23 g, 0.2 mol) and Et3N (60 g, 0.6 mol) in THF (230 mL) was added (Boc)20 (87 g, 0.4 mol). The resulting solution was stirred at r.t. overnight. The solvent was removed under reduced pressure and the residue was extracted with EtOAc (3 x 200 mL). The combined organic layers were washed with water (2 x 200 mL) and brine (200 mL), dried over anhydrous Na2SC>4 and concentrated. The residue was purified by column chromatography on silica gel using DCM/ MeOH (V:V, 20: 1) to afford the desired product as a white solid (34 g, 79percent yield). MS: 216.2 (M+l)+.
Reference: [1] Patent: WO2017/100662, 2017, A1, . Location in patent: Page/Page column 103; 123
[2] Patent: WO2013/107405, 2013, A1, . Location in patent: Page/Page column 48-49
[3] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 7, p. 2017 - 2021
[4] Patent: US5516806, 1996, A,
[5] Patent: WO2013/107291, 2013, A1, . Location in patent: Page/Page column 63; 64
[6] Patent: WO2015/10626, 2015, A1, . Location in patent: Page/Page column 64; 65
[7] Patent: WO2015/10297, 2015, A1, . Location in patent: Page/Page column 64
  • 19
  • [ 6850-65-3 ]
  • [ 96042-30-7 ]
  • [ 224309-64-2 ]
YieldReaction ConditionsOperation in experiment
79% With triethylamine In tetrahydrofuran Step A:
Tert-butyl 4-hydroxycyclohexylcarbamate
To a solution of 4-aminocyclohexanol (23 g, 0.2 mol) and Et3N (60 g, 0.6 mol) in THF (230 mL) was added (Boc)2O (87 g, 0.4 mol).
The resulting solution was stirred at r.t. overnight.
The solvent was removed under reduced pressure and the residue was extracted with EtOAc (3*200 mL).
The combined organic layers were washed with water (2*200 mL) and brine (200 mL), dried over anhydrous Na2SO4 and concentrated.
The residue was purified by column chromatography on silica gel using DCM/MeOH (V:V, 20:1) to afford the desired product as a white solid (34 g, 79percent yield). MS: 216.2 (M+1)+.
Reference: [1] Patent: US2015/87600, 2015, A1, . Location in patent: Page/Page column
[2] Patent: US2013/190249, 2013, A1, . Location in patent: Page/Page column
[3] Patent: US2015/31627, 2015, A1, . Location in patent: Page/Page column
  • 20
  • [ 6850-65-3 ]
  • [ 224309-64-2 ]
YieldReaction ConditionsOperation in experiment
91% With sodium hydrogencarbonate In acetonitrile A.
4-(N-Boc-amino)-1-cyclohexanol
To a stirred solution of 4-aminocyclohexan-1-ol (5.00 g, 43.4 mmol) in sat. aq. NaHCO3 (40 ml) was added (Boc)2 O (9.47 g, 43.4 mmol) in CH3 CN (20 ml) at ice-bath cooling.
The reaction mixture was stirred at room temperature for 24 h.
Diluted with water (100 ml), the mixture was extracted with AcOEt (100 ml*4).
The combined extracts were washed with brine, dried and concentrated in vacuo to afford a white crystalline solid (8.46 g, 91percent yield).
1 H-NMR (CDCl3): δ4.44-4.22 (m, 1H), 3.68-3.52 (m, 1H), 3.51-3.31 (m, 1H), 2.08-1.89 (m, 4H), 1.44 (s, 9H), 1.50-1.07 (m, 4H).
Reference: [1] Patent: US6156752, 2000, A,
  • 21
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  • [ 224309-64-2 ]
Reference: [1] Patent: WO2004/43962, 2004, A1, . Location in patent: Page 37
  • 22
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  • [ 195314-59-1 ]
Reference: [1] Patent: WO2017/100662, 2017, A1,
  • 23
  • [ 6850-65-3 ]
  • [ 675112-67-1 ]
Reference: [1] Patent: US2013/190249, 2013, A1,
[2] Patent: WO2013/107291, 2013, A1,
[3] Patent: WO2015/10297, 2015, A1,
[4] Patent: WO2013/107405, 2013, A1,
[5] Patent: WO2015/10626, 2015, A1,
[6] Patent: US2015/31627, 2015, A1,
[7] Patent: US2015/87600, 2015, A1,
  • 24
  • [ 6850-65-3 ]
  • [ 675112-67-1 ]
  • [ 675112-69-3 ]
Reference: [1] Patent: WO2013/107291, 2013, A1,
[2] Patent: WO2015/10297, 2015, A1,
[3] Patent: WO2013/107405, 2013, A1,
  • 25
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  • [ 675112-70-6 ]
Reference: [1] Patent: US2015/87600, 2015, A1,
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