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[ CAS No. 680596-79-6 ] {[proInfo.proName]}

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Chemical Structure| 680596-79-6
Chemical Structure| 680596-79-6
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Product Details of [ 680596-79-6 ]

CAS No. :680596-79-6 MDL No. :MFCD04115656
Formula : C14H23BO4 Boiling Point : -
Linear Structure Formula :- InChI Key :JCHWHOHZZYWUMP-UHFFFAOYSA-N
M.W : 266.14 Pubchem ID :3697076
Synonyms :

Calculated chemistry of [ 680596-79-6 ]

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.86
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 73.86
TPSA : 36.92 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.7 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.73
Log Po/w (WLOGP) : 2.47
Log Po/w (MLOGP) : 1.16
Log Po/w (SILICOS-IT) : 1.65
Consensus Log Po/w : 1.4

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.51
Solubility : 0.815 mg/ml ; 0.00306 mol/l
Class : Soluble
Log S (Ali) : -2.12
Solubility : 2.01 mg/ml ; 0.00756 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.92
Solubility : 0.32 mg/ml ; 0.0012 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 4.38

Safety of [ 680596-79-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 680596-79-6 ]

* 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 [ 680596-79-6 ]
  • Downstream synthetic route of [ 680596-79-6 ]

[ 680596-79-6 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 680596-79-6 ]
  • [ 40503-87-5 ]
Reference: [1] Patent: WO2018/54365, 2018, A1,
  • 2
  • [ 680596-79-6 ]
  • [ 105640-07-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 18, p. 5577 - 5582
  • 3
  • [ 680596-79-6 ]
  • [ 84892-43-3 ]
Reference: [1] Patent: WO2018/54365, 2018, A1,
  • 4
  • [ 73183-34-3 ]
  • [ 170011-47-9 ]
  • [ 680596-79-6 ]
YieldReaction ConditionsOperation in experiment
99% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 110℃; for 10 h; Inert atmosphere 1,4-dioxaspiro [4.5] sunene-7-ene-8-trifluoromethanesulfonate (500 mg, 1.73 mmol)1,4-dioxane (8 mL)Potassium acetate (260 mg, 2.64 mmol) was added sequentially to the solution,Which aliphatic alcohol (530mg, 2.08mmol) with boronic acid,Pd (dppf) Cl2 (130 mg, 0.17 mmol), nitrogen,110 ° C for 10 hours, filtered,Concentrated column chromatography (petroleum ether / ethyl acetate (v / v) = 2/1) gave 540 mg of a yellow oil in 99percent yield.
95% With potassium acetate In 1,4-dioxane at 80℃; Inert atmosphere Synthesis of 4,4,5,5-tetramethyl-2-(1,4-dioxaspiro[4,5]dec-7-en-8-yl)-1,3,2-dioxaborolane
A solution of 1,4-dioxaspiro[4.5]dec-7-en-8-yl trifluoromethane-sulfonate (1.0 equiv.) in dioxane (0.5 M) was purged with nitrogen for 30 min.
Then 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (1.0 equiv.), KOAc (3.0 equiv.), Pd(dppf)Cl2-DCM (0.2 equiv.) were added and the solution was stirred in a sealed bomb at 80° C.
The reaction was filtered over a pad of celite, then to the filtrate was added ethyl acetate, and washed with brine, dried over MgSO4, filtered, and concentrated.
The residue was purified by column (ethyl acetate:hexanes=1:1) to give 4,4,5,5-tetramethyl-2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-1,3,2-dioxaborolane (95percent). LC/MS (m/z): MH+=267.1, Rt=0.95.
81% With potassium acetate In 1,4-dioxane at 80℃; for 16 h; To a stirred solution of 1,4-dioxaspiro[4.5]dec-7-en-8-yl trifluoromethanesulfonate (2.20 g, 7.64 mmol) in dioxane (38 mL) was added bis(pinacolato)diboron (2.33 g, 9.17 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with DCM (1:1) (0.187 g, 0.23 mmol), 1,1'-bis(diphenylphosphino)ferrocene (0.127 g, 0.23 mmol), and potassium acetate (2.25 g, 22.92 mmol). The mixture was degassed by purging the reaction flask with vacuum/then N2 back-fill (3.x.). Under N2, the reaction was then heated to 80° C. and stirred overnight (approx. 16 hrs). The reaction was cooled to rt and diluted with H2O. The mixture was extracted with EtOAc (3.x.). The combined organic layers were washed with brine, dried over MgSO4, filtered, then purified by silica gel chromatography to give the title compound of step B (1.65 g, 6.20 mmol, 81percent) as a clear oil, that upon sitting in the fridge overnight changed to a white solid. MS (ESI): 267 [M+H]+.
66% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; sodium bromide In 1,4-dioxane A mixture of crude Preparation 14A (600 g,2.08mol ,1eq), B2Pin2 (687.1 g, 2.71 mol, 1.3eq), KOAc (613 g, 6.24 mol, 3eq) , NaBr (86 g 0.833mol,0.4 eq) and Pd(dppf)Cl2 (76 g, 0.1 mol, 0.05eq) in dioxane (6.5 L) was heated to reflux overnight. Once the reaction was complete, the mixture was concentrated and purified by FCC (2percent ^10percent ^20percent EtOAc/PE) to give Preparation 14B (369g, 66percent). Preparation 14B: LC-MS: 267.1 (M+1)+, 1H NMR (400 MHz, CDCl3) δ ^6.46 (s, 1H), 3.98 (s, 4H), 2.37-2.35 (m, 4H), 1.74-1.60 (t, 2H), 1.24 (s, 12H).
59% With bis-triphenylphosphine-palladium(II) chloride; potassium phenolate; triphenylphosphine In toluene at 20 - 50℃; for 28 h; Inert atmosphere In a round–bottom flask 1.1 mmol (1.1 equiv.) of bis(pinacolato)diboron was dissolved in 50 mL of toluene and PdCl2(PPh3)2 (0.03 equiv), triphenylphosphine (0.06 equiv) and potassium phenolate (1.5 equiv) were added. The reaction mixture was flushed with N2 gas and 1 mmol (1 equiv.) of triflate 25 was added. The mixture was stirred at 50 C under a nitrogen atmosphere. After 4 hours the heat source was removed and the reaction was stirred for 24 hours at room temperature. The reaction mixture was partitioned between H2O/EtOAc and the organic layer was washed with brine and dried over MgSO4. Column chromatography was performed using a gradient of 0-10percent EtOAc in DCM as eluent. Yield = 59percent. 1H NMR (400 MHz, CDCl3) δ: 6.47 (s, 1H), 3.98 (s, 4H), 2.39–2.36 (m, 4H), 1.73 (t, J = 6.4 Hz, 2H), 1.25 (s, 12H). 13C NMR (100 MHz, CDCl3) δ: 139.7, 108.0, 83.4, 64.5, 37.2, 31.2, 25.9, 25.0.
49% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 80℃; [00385] Into a 3-L 4-necked round-bottom flask was placed 1,4-dioxaspiro[4.5]dec-7-en-8- yl trifluoromethanesulfonate (80 g, 277.55 mmol, 1.00 equiv), B2Pin2 (85 g, 334.65 mmol, 1.21 equiv), Pd(dppf)C12 (20 g, 27.33 mmol, 0.10 equiv), KOAc (82 g, 835.54 mmol, 3.01 equiv) and 1,4-dioxane (800 mL). The resulting solution was stirred overnight at 80°C using an oil bath then cooled to room temperature and concentrated under vacuum. The residue was extracted with 1 L of ethyl acetate and the organic layer washed with 3x 1 L of brine and dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by flash chromatography on silica gel column using ethyl acetate / petroleum ether (gradient: 5percent to 10percent ethyl acetate) to afford 36 g (49percent) of 2-[1,4-dioxaspiro[4.5]dec-7-en-8-yl]-4,4,5,5- tetramethyl-1,3,2-dioxaborolane as a yellow solid. ‘H-NMR (300 MHz, CDC13): 6.46-6.47 (m, 1H), 3.98(s, 4H), 2.39-2.35(m, 4H), 1.73(t, J=4.8Hz, 2H), 1.26(s, 12H) ppm.
369 g With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; sodium bromide In 1,4-dioxaneReflux A mixture of crude Preparation 40A (600 g,2.O8mol ,leq), B2Pin2 (687.1 g, 2.71mol, 1.3eq), KOAc (613 g, 6.24 mol, 3eq) , NaBr (86 g 0.833mo1,0.4 eq) and Pd(dppf)C12(76 g, 0.1 mol, 0.OSeq) in dioxane (6.5 L) was heated to reflux overnight. Once thereaction was complete, the mixture was concentrated and purified by FCC (2percent - 10percent-20percent EtOAc/PE) to give Preparation 40B (369g, 66percent).Preparation 40B: LC-MS: 267.1 (M+1)+, ‘H NMR (400 MHz, CDC13) ö 6.46 (s, 1H),3.98 (s, 4H), 2.37-2.35 (m, 4H), 1.74-1.60 (t, 2H), 1.24 (s, 12H).
369 g With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; sodium bromide In 1,4-dioxaneReflux [00165] A mixture of crude Preparation A (600 g,2.08mol ,leq), Β2ΡΠ12 (687.1 g, 2.71 mol, 1.3eq), KOAc (613 g, 6.24 mol, 3eq) , NaBr (86 g 0.833mol,0.4 eq) and Pd(dppf)Cb (76 g, 0.1 mol, 0.05eq) in dioxane (6.5 L) was heated to reflux overnight. Once the reaction was complete, the mixture was concentrated and purified by FCC (2percent - 10percent - 20percent EtOAc/PE) to give Preparation B (369g, 66percent). (0233) Preparation B: LC-MS: 267.1 (M+l)+, XH NMR (400 MHz, CDCb) δ 6.46 (s, 1H), 3.98 (s, 4H), 2.37-2.35 (m, 4H), 1.74-1.60 (t, 2H), 1.24 (s, 12H).
369 g With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; sodium bromide In 1,4-dioxaneReflux [00179] A mixture of intermediate 2A (600 g,2.08mol ,leq), B2Pin2 (687.1 g, 2.71 mol, 1.3eq), KOAc (613 g, 6.24 mol, 3eq) , NaBr (86 g 0.833mol,0.4 eq) and Pd(dppf)C12 (76 g, 0.1 mol, 0.05eq) in dioxane (6.5 L) was heated to reflux overnight. Once the reaction was complete, the mixture was concentrated and purified by via silica gel column chromatography to give Intermediate 2B (369 g, 66percent yield). LC-MS Anal. Calc'd for C14H23BO4 266.17, found [M+H] 267.1. 1H NMR (400 MHz, CDCI3) δ 6.46 (s, 1H), 3.98 (s, 4H), 2.37-2.35 (m, 4H), 1.74-1.60 (t, 2H), 1.24 (s, 12H).
369 g With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; sodium bromide In 1,4-dioxaneReflux A mixture of crude Preparation 4A (600 g,2.O8mol ,leq), B2Pin2 (687.1 g, 2.71 mol, 1.3eq), KOAc (613 g, 6.24 mol, 3eq) , NaBr (86 g 0.833mo1,0.4 eq) and Pd(dppf)C12 (76 g, 0.1 mol, 0.OSeq) in dioxane (6.5 L) was heated to reflux overnight. Once the reaction was complete, the mixture was concentrated and purified by FCC (2percent -10percent -20percent EtOAc/PE) to give Preparation 4B (369g, 66percent).Preparation 4B: LC-MS: 267.1 (M+1)+, ‘HNMR(400 MHz, CDC13) ö 6.46 (s, 1H), 3.98 (s, 4H), 2.37-2.35 (m, 4H), 1.74-1.60 (t, 2H), 1.24 (s, 12H).
369 g With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; sodium bromide In 1,4-dioxaneReflux j00169j A mixture of crude Preparation 1A(600 g,2.O8mol ,leq), B2Pin2 (687.1 g, 2.71 mol, 1.3eq), KOAc (613 g, 6.24 mol, 3eq) , NaBr (86 g 0.833mo1,0.4 eq) and Pd(dppf)C12 (76 g,0.1 mol, 0.OSeq) in dioxane (6.5 L) was heated to reflux overnight. Once the reaction was complete, the mixture was concentrated and purified by FCC (2percent -10percent -20percent EtOAc/PE) to give Preparation lB (369g, 66percent).Preparation 1B: LC-MS: 267.1 (M+1)+, ‘HNMR(400 MHz, CDC13) ö 6.46 (s, 1H), 3.98 (s, 4H), 2.37-2.35 (m, 4H), 1.74-1.60 (t, 2H), 1.24 (s, 12H).
369 g With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; sodium bromide In 1,4-dioxaneReflux A mixture of crude Preparation IA (60() g, 2O8moi ,leq), B2Pin2 (687.1g. 271 mol, 1.3eq), KOAc (613 g, 6.24 mol, 3eq) , NaBr (86g. 0.833mo1,0.4 eq) and Pd(dppf)C12(76 g, 0.1 mol, 0OSeq) in dioxane (6.5 L) was heated to reflux overnight, Once the reaction was complete, the mixture was concentrated and purified by FCC (2percent 10percent 20percent EtOAc/PE) to give Preparation lB (369g, 66percent).Preparation 1B: LC--MS: 267. 1 (M--1)--. ‘HNMR (400 MHz, CDG3) ö 6.46 (s, 1H), 3.98 (s, 4H), 2.37—2.35 (in, 4H), 1.74—I. 60 (L, 2H), 1.24 (s, 12H).
3.6 g With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; sodium bromide In 1,4-dioxaneReflux Compound 4.1 (6.0 g), dipinacol boronate(6.87 g, 27.1 mmol), potassium acetate (6.13 g,62.4 mmol), sodium bromide (8.6 g, 8.33 mmol) and Pd(dppf)Cl2 (0.76 g, 1.0 mmol) in 1,4-dioxane(65 mL) The mixture was stirred at reflux overnight.Then the reaction system was cooled to room temperature and the solvent was removed under reduced pressure.The residue was purified by flash column chromatography (petroleum ether/ethyl acetate = 50/1 to 10/1) to give Compound 4.2 (3.6 g, two-step yield: 70percent) as a yellow solid.

Reference: [1] Patent: CN106336413, 2017, A, . Location in patent: Paragraph 0431; 0432; 0433
[2] Patent: US2010/56576, 2010, A1, . Location in patent: Page/Page column 20
[3] Patent: US2008/300242, 2008, A1, . Location in patent: Page/Page column 102
[4] Patent: WO2017/192811, 2017, A1, . Location in patent: Paragraph 00173
[5] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 23, p. 5377 - 5380
[6] Patent: WO2014/153226, 2014, A1, . Location in patent: Paragraph 00385
[7] Patent: WO2008/44217, 2008, A2, . Location in patent: Page/Page column 102
[8] Patent: US2015/329529, 2015, A1, . Location in patent: Paragraph 0563
[9] Patent: WO2016/73774, 2016, A2, . Location in patent: Paragraph 0325; 0353
[10] Patent: WO2017/192813, 2017, A1, . Location in patent: Paragraph 00165
[11] Patent: WO2017/192840, 2017, A1, . Location in patent: Paragraph 00179; 00196
[12] Patent: WO2017/192844, 2017, A1, . Location in patent: Paragraph 00173; 00190
[13] Patent: WO2017/192815, 2017, A1, . Location in patent: Page/Page column 00169
[14] Patent: WO2018/39512, 2018, A1, . Location in patent: Paragraph 00167
[15] Patent: CN107674029, 2018, A, . Location in patent: Paragraph 0210; 0211; 0214; 0215
  • 5
  • [ 25015-63-8 ]
  • [ 170011-47-9 ]
  • [ 680596-79-6 ]
Reference: [1] Patent: US2006/3997, 2006, A1, . Location in patent: Page/Page column 7
  • 6
  • [ 4746-97-8 ]
  • [ 680596-79-6 ]
Reference: [1] Patent: WO2014/153226, 2014, A1,
[2] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 23, p. 5377 - 5380
[3] Patent: US2015/329529, 2015, A1,
[4] Patent: WO2016/73774, 2016, A2,
[5] Patent: CN106336413, 2017, A,
[6] Patent: WO2017/192813, 2017, A1,
[7] Patent: WO2017/192840, 2017, A1,
[8] Patent: WO2017/192844, 2017, A1,
[9] Patent: WO2017/192811, 2017, A1,
[10] Patent: WO2017/192815, 2017, A1,
[11] Patent: WO2018/39512, 2018, A1,
[12] Patent: CN107674029, 2018, A,
  • 7
  • [ 680596-79-6 ]
  • [ 1048916-71-7 ]
Reference: [1] Patent: WO2018/54365, 2018, A1,
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