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[ CAS No. 6921-45-5 ] {[proInfo.proName]}

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Chemical Structure| 6921-45-5
Chemical Structure| 6921-45-5
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Product Details of [ 6921-45-5 ]

CAS No. :6921-45-5 MDL No. :MFCD00102381
Formula : C11H12O Boiling Point : -
Linear Structure Formula :- InChI Key :SWHHCKFQUJBPPQ-UHFFFAOYSA-N
M.W : 160.21 Pubchem ID :263692
Synonyms :

Calculated chemistry of [ 6921-45-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.36
Num. rotatable bonds : 2
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 49.1
TPSA : 17.07 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) : -5.4 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.2
Log Po/w (XLOGP3) : 2.65
Log Po/w (WLOGP) : 2.7
Log Po/w (MLOGP) : 2.3
Log Po/w (SILICOS-IT) : 3.25
Consensus Log Po/w : 2.62

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.74
Solubility : 0.291 mg/ml ; 0.00182 mol/l
Class : Soluble
Log S (Ali) : -2.66
Solubility : 0.351 mg/ml ; 0.00219 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.32
Solubility : 0.0765 mg/ml ; 0.000478 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 6921-45-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 6921-45-5 ]

* 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 [ 6921-45-5 ]
  • Downstream synthetic route of [ 6921-45-5 ]

[ 6921-45-5 ] Synthesis Path-Upstream   1~21

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Reference: [1] Journal of Organic Chemistry, 1959, vol. 24, p. 1261,1266
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  • [ 99-90-1 ]
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YieldReaction ConditionsOperation in experiment
95% With potassium phosphate tribasic heptahydrate; C45H53ClFeNO2PPd In water; toluene at 100℃; for 8 h; Inert atmosphere General procedure: Potassium phosphate (0.75 mmol) and IIe (1 mol percent) was added to the solution of aryl halides (0.25 mmol) and cyclopropylboronic acid (0.5 mmol) in toluene (2.0 mL) and water (100 μL). The mixture was heated to 100 °C for a proper time under nitrogen atmosphere and cooled to room temperature. Water (10 mL) was added and the mixture was extracted with EtOAc (3.x.15 mL), evaporated and purified by chromatography on silica gel.
1.0 g With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In water; dimethyl sulfoxide at 100℃; for 48 h; To a solution of 1-(4-bromophenyl)ethanone (3.Og, 0.0150 mmol) in mixture of DMSO: water (3:1, 30 mL) was added tripotassium phosphate (9.5 g, 0.045 mmol), 1,1 ‘-bi s(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane (0.200 g,0.245 mmol) and cyclopropylboronic acid (1.9 g, 0.022 mmol). The reactionmixture was heated at 100 °C for 48 h. The reaction mass was quenched with water and extracted with EtOAc. The organic layer were washed with water and brine, dried over Na2504 and concentrated. The obtained solid was purified by column chromatography on silica gel to afford 1.0 g of the title product. ‘H NIVIR (300 IVIFIz, DMSO d6): 7.86-7.83 (d, J = 7.8 Hz, 2H), 7.13.7.10 (d, J = 7.8 Hz, 2H), 2.57 (s,3H), 1.94 (m, 1H), 1.07-1.05 (q, J= 7.2 Hz, 2H),0.79-0.77 (d, J= 4.8 Hz, 2H).
Reference: [1] Tetrahedron, 2012, vol. 68, # 3, p. 900 - 905
[2] Synthetic Communications, 2006, vol. 36, # 1, p. 121 - 128
[3] Patent: WO2015/59618, 2015, A1, . Location in patent: Page/Page column 42
[4] Journal of the American Chemical Society, 2016, vol. 138, # 20, p. 6598 - 6609
[5] Patent: WO2016/201168, 2016, A1, . Location in patent: Paragraph 0662
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  • [ 4333-56-6 ]
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Reference: [1] Organic Letters, 1999, vol. 1, # 8, p. 1267 - 1269
  • 4
  • [ 99-90-1 ]
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YieldReaction ConditionsOperation in experiment
99%
Stage #2: With potassium phosphate In MeTHF; water; toluene at 100℃; for 3 h; Inert atmosphere
Example 3: Use of cyclopropyldioxazaborocane in the Suzuki coupling reaction; The boronic acid coupling products were obtained under the conditions recorded in the table below, by applying procedures 3a) and 3b).+ catalyst + ligand + K3PO4 solvent SIMes : 1 ,3-bis(2,4,6-trimethylphenyl)imidazolin-2-ylideneThe Suzuki coupling process has many advantages. The first is that the conditions are extremely simple to implement using catalysts which are readily available and usable (u n l i ke the rare model s issu ing from the l iteratu re relating to cyclopropylboronic acid) [19, 11]. The particularly short reaction times are also an element that simplifies the implementation of the process. Finally, it has been possible to carry out Suzuki couplings both with brominated derivatives and with chlorinated derivatives.Example 3a): Coupling with brominated derivatives: Procedure:Cyclopropyldioxazaborocane (1.5 eq.) is dissolved in a solution of 1 N HCI/NaClsat (1 ml/mmol of dioxazaborocane); boronic acid is then extracted with MeTHF (1.5 ml/mmol of dioxazaborocane). It is added to a solution containing aryl bromide (1 eq .), PdCI2dppf (0.5 eq.), PPh3 (0.1 eq.) and K3PO4 (2 eq .) in toluene (1.5 ml/mmol), anhydrous. The mixture is then heated at 1000C for 3 hours, under argon. After cooling, the organic phase is washed with water and then dried over MgSO4 and evaporated. The residue is then purified by flash chromatography (eluant: pure DCM). The fractions containing the product are then combined and evaporated.4-cyclopropylacetophenone:Yellowish liquid (41 1 mg, 2.57 mmol, 99percent). 1H NMR (CDCI3, 300 MHz), δ = 7.87 (d, 3JHH = 8.5 Hz, 2H, H5), 7.14 (d, 3JHH = 8.5 Hz, 2H, H4), 2.58 (s, 3H, H8), 1 .96 (tt, 3JHH = 8.4 Hz, 3JHH = 5.0 Hz, 1 H, H1), 1 .08 (ddd, 3JHH = 8.4 Hz, 3JHH = 5.0 Hz, 2Jgem = 6.6 Hz, 2H, H2), 0.80 (td, 3JHH = 4.8 Hz, 2Jgem = 6.7 Hz, 1 H, H2). 13C NMR (CDCI3, 75.5 MHz), δ = 197.7 (C7), 150.4 (C6), 134.6 (C3), 128.5 (C5), 125.5 (C4), 26.5 (Ce), 15.8 (CO, 10.4 (C2). Rf = 0.30 (DCM/EP 70 :30).
Reference: [1] Patent: WO2010/18211, 2010, A1, . Location in patent: Page/Page column 14-15
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YieldReaction ConditionsOperation in experiment
90%
Stage #2: With potassium phosphate In MeTHF; toluene at 100℃; for 48 h; Inert atmosphere
Example 3b): Coupling with chlorinated derivatives:; Procedure:Cyclopropyldioxazaborocane (1.5 eq.) is dissolved in a solution of 1 N HCI/NaClsat(1 ml/mmol of d ioxazaborocane), and the boron ic acid then formed is subsequently extracted with MeTHF (1.5 ml/mmol of dioxazaborocane). It is added to a solution of aryl chloride (1 eq.), Pd(OAc)2 (0.05 eq.), IMes (0.1 eq.) and K3PO4 (2 eq.) in toluene (same volume as MeTHF) containing several drops of water. The mixture is then heated at 1000C for 48 hours, under argon. After cooling, the organic phase is washed with water and then dried over MgSO4 and evaporated. The residue is then purified by flash chromatography (eluant: pure DCM). The fractions containing the product are then combined and evaporated.4-cyclopropylacetophenone:Yellowish liquid (72 mg, 0.45 mmol, 90percent). 1H NMR (CDCI3, 300 MHz), δ = 7.87 (d, 3JHH = 8.5 Hz, 2H, H5), 7.14 (d, 3JHH = 8.5 Hz, 2H, H4), 2.58 (s, 3H, H8), 1.96 (tt, 3JHH = 8.4 Hz, 3JHH = 5.0 Hz, 1 H, H1), 1.08 (ddd, 3JHH = 8.4 Hz, 3JHH = 5.0 Hz, 2Jgem = 6.6 Hz, 2H, H2), 0.80 (td, 3JHH = 4.8 Hz, 2Jgem = 6.7 Hz, 1 H, H2). 13C NMR (CDCI3, 75.5 MHz), δ = 197.7 (C7), 150.4 (C6), 134.6 (C3), 128.5 (C5), 125.5 (C4), 26.5 (C8), 15.8 (C?), 10.4 (C2). Rf = 0.30 (DCM/EP 70 :30).In this case, the coupling remains extremely effective in terms of isolated yield, but the reaction times are increased considerably. The cost of and ease of access to the chlorinated derivative nevertheless remain a major advantage and illustrate even more the flexibility of the method.
Reference: [1] Patent: WO2010/18211, 2010, A1, . Location in patent: Page/Page column 14; 16
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Reference: [1] Journal of Organic Chemistry, 2008, vol. 73, # 9, p. 3604 - 3607
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Reference: [1] Journal of Organic Chemistry, 2008, vol. 73, # 9, p. 3604 - 3607
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YieldReaction ConditionsOperation in experiment
15.7 mg With (η3-allyl)(N,N'-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene)chloropalladium(II); sodium carbonate; lithium chloride In N,N-dimethyl-formamide at 80℃; for 16 h; Inert atmosphere; Sealed tube General procedure: Method A: A sealed tube equiped with a magnetic stirring bar was charged with the arylhalide (1) or (5) (1.0 equiv), sodium carbonate (2.0 equiv), anhydrous lithium chloride (2.0equiv) and (SIPr)Pd(allyl)Cl (0.05 equiv). Tricyclopropylbismuth (2a) (1.0 equiv), preparedas described above, was dissolved in anhydrous DMF (0.1 M) under argon and was addedinto the sealed tube. Carbon monoxide was bubbled in the reaction mixture for 45 seconds,then the tube was sealed and heated at 40 °C for 16 hours. The reaction mixture was cooledto room temperature, transferred in a separatory funnel containing 20 mL of an aq. sat.NaHCO3 solution and was extracted with EtOAc (3 x 20 mL). The combined organic layerswere washed with brine (30 mL), dried over anhydrous Na2SO4 and concentrated underreduced pressure. The residue was purified by flash column chromatography using theindicated solvent system to afford the desired aryl cyclopropyl ketone (3) or (6).Method B: Same as method A except that 1.5 equivalents of tricyclopropylbismuth 2ainstead of 1.0 equivalent and 0.1 equivalents of (SIPr)Pd(allyl)Cl instead of 0.05 equivalentswere used and that the reaction was heated at 80 C instead of 40 C.
Reference: [1] Synlett, 2017, vol. 28, # 20, p. 2833 - 2838
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Reference: [1] Journal of the American Chemical Society, 2001, vol. 123, # 18, p. 4155 - 4160
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Reference: [1] Journal of the American Chemical Society, 2001, vol. 123, # 18, p. 4155 - 4160
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  • [ 873-49-4 ]
  • [ 75-36-5 ]
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Reference: [1] Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 1995, vol. 258, p. 229 - 238
[2] Journal of Organic Chemistry, 1959, vol. 24, p. 1261,1266
[3] Journal of the American Chemical Society, 1975, vol. 97, # 10, p. 2895 - 2898
[4] J. Gen. Chem. USSR (Engl. Transl.), 1963, vol. 33, p. 358 - 363[5] Zhurnal Obshchei Khimii, 1963, vol. 33, # 2, p. 365 - 371
[6] Journal of Medicinal Chemistry, 2009, vol. 52, # 14, p. 4329 - 4337
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  • [ 99-91-2 ]
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Reference: [1] Synthetic Communications, 2006, vol. 36, # 1, p. 121 - 128
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Reference: [1] Organic Letters, 2009, vol. 11, # 11, p. 2453 - 2456
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  • [ 99-91-2 ]
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Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 31, p. 4475 - 4477
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Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 31, p. 4475 - 4477
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  • [ 10537-63-0 ]
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Reference: [1] Journal of the American Chemical Society, 2018, vol. 140, # 25, p. 8037 - 8047
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  • [ 13329-40-3 ]
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Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 31, p. 4475 - 4477
  • 18
  • [ 75-11-6 ]
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Reference: [1] Journal of the American Chemical Society, 2016, vol. 138, # 20, p. 6598 - 6609
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Reference: [1] Organic Letters, 2009, vol. 11, # 11, p. 2453 - 2456
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Reference: [1] Bulletin of the Chemical Society of Japan, 1973, vol. 46, p. 204 - 209
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Reference: [1] J. Gen. Chem. USSR (Engl. Transl.), 1963, vol. 33, p. 364 - 368[2] Zhurnal Obshchei Khimii, 1963, vol. 33, # 2, p. 371 - 376
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