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[ CAS No. 12150-46-8 ] {[proInfo.proName]}

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Chemical Structure| 12150-46-8
Chemical Structure| 12150-46-8
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Product Citations

Product Citations

Gilbert, Robert ; Davis, Christopher W ; Bingham, Tanner W , et al. DOI:

Abstract: A dearomative 1,4-hydroamination of nonactivated arenes has been developed, using a key arene-arenophile photocycloaddition strategy to disrupt aromaticity. Palladium catalysis with K-Selectride® as a hydride source uniquely enables selective reactivity and provides access to a range of substituted 1,4-cyclohexadienes from aromatic starting materials. We demonstrate a few synthetic applications of this scalable procedure by preparing highly-functionalized small molecules in three to four steps from naphthalene.

Keywords: Dearomatization ; Hydroamination ; Arenophiles ; Palladium ; Catalysis

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Product Details of [ 12150-46-8 ]

CAS No. :12150-46-8 MDL No. :MFCD00001422
Formula : C34H28FeP2 Boiling Point : -
Linear Structure Formula :[((P(C6H5)2C5H4)2Fe)] InChI Key :-
M.W : 554.38 Pubchem ID :-
Synonyms :

Calculated chemistry of [ 12150-46-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 37
Num. arom. heavy atoms : 24
Fraction Csp3 : 0.06
Num. rotatable bonds : 8
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 160.09
TPSA : 27.18 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.06 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 7.92
Log Po/w (WLOGP) : 7.82
Log Po/w (MLOGP) : 7.56
Log Po/w (SILICOS-IT) : 7.39
Consensus Log Po/w : 6.14

Druglikeness

Lipinski : 2.0
Ghose : None
Veber : 0.0
Egan : 1.0
Muegge : 1.0
Bioavailability Score : 0.17

Water Solubility

Log S (ESOL) : -8.22
Solubility : 0.00000335 mg/ml ; 0.000000006 mol/l
Class : Poorly soluble
Log S (Ali) : -8.34
Solubility : 0.00000253 mg/ml ; 0.0000000046 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -11.0
Solubility : 0.0000000056 mg/ml ; 0.0 mol/l
Class : Insoluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 6.56

Safety of [ 12150-46-8 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P261-P264-P270-P271-P280-P301+P310-P302+P352-P304+P340-P312-P330-P363-P405-P501 UN#:3467
Hazard Statements:H301 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 12150-46-8 ]

* 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 [ 12150-46-8 ]
  • Downstream synthetic route of [ 12150-46-8 ]

[ 12150-46-8 ] Synthesis Path-Upstream   1~23

  • 1
  • [ 405164-68-3 ]
  • [ 12150-46-8 ]
YieldReaction ConditionsOperation in experiment
94% With tributylphosphine; iodine In tetrahydrofuran; acetonitrile at 20℃; for 0.166667 h; Inert atmosphere EXAMPLE 4100 mg (0.171 mmol) of l,l'-Bis(diphenyloxyphosphino)ferrocene were treated with I2 4 mg (16 μιηο) and tributylphosphine 170 μ^ (0.68 mmol) in acetonitrile/THF (1 : 1 v/v) 1 mL. The mixture was stirred at room temperature for 10 minutes under nitrogen atmosphere before it was quenched with H20 (100 μ). The reaction mixture was diluted with ethyl acetate (lOmL) and was washed with portions of sat. NaHC03 (3x5 mL). The organic fraction was dried with Na2S04, filtered and the solvent evaporated under vacuum. The resulting residue was recrystallized from ethanol, the resulting crystals were filtered, washed and dried in vacuum, giving 89 mg (0.160 mmol, 94percent>) of Ι,Γ- Bis(diphenylphosphino)ferrocene (dppf).
Reference: [1] Patent: WO2011/123037, 2011, A1, . Location in patent: Page/Page column 23
  • 2
  • [ 32660-24-5 ]
  • [ 12150-46-8 ]
YieldReaction ConditionsOperation in experiment
93 %Chromat. With [AlH3(triethylamine)] In hexane at 20℃; for 0.166667 h; Inert atmosphere; Schlenk technique General procedure: Triphenylphosphine oxide or sulfide (1 mmol), dry hexane (1 mL), and Ic (1 mmol) were added to a Schlenk tube under the atmosphere of nitrogen. The reaction was carried out at room temperature for 10 min and monitored by TLC. Upon completion of the process the reaction mixture was filtered by silica gel and washed several times with ethyl acetate. Ethyl acetate was evaporated and the residue purified by flash chromatography on silica gel with pure cyclohexane toafford the desired phosphine. The yield was determined by GC without additional purification.
Reference: [1] Chemistry - A European Journal, 2017, vol. 23, # 58, p. 14434 - 14438
[2] ChemCatChem, 2017, vol. 9, # 24, p. 4460 - 4464
[3] Russian Journal of General Chemistry, 2015, vol. 85, # 5, p. 1156 - 1160[4] Zh. Obshch. Khim.,
  • 3
  • [ 102-54-5 ]
  • [ 1079-66-9 ]
  • [ 12150-46-8 ]
Reference: [1] Chemistry - A European Journal, 2012, vol. 18, # 39, p. 12267 - 12277
  • 4
  • [ 591-51-5 ]
  • [ 1079-66-9 ]
  • [ 12150-46-8 ]
Reference: [1] Journal of Organometallic Chemistry, 1980, vol. 185, # 1, p. C1 - C5
[2] Organometallics, 1982, vol. 1, p. 1275 - 1282
  • 5
  • [ 83272-80-4 ]
  • [ 12150-46-8 ]
  • [ 403815-19-0 ]
  • [ 878190-65-9 ]
Reference: [1] Organometallics, 2006, vol. 25, # 4, p. 989 - 995
  • 6
  • [ 717901-49-0 ]
  • [ 540-72-7 ]
  • [ 12150-46-8 ]
Reference: [1] Journal of Organometallic Chemistry, 2004, vol. 689, # 11, p. 1978 - 1990
  • 7
  • [ 12098-17-8 ]
  • [ 1079-66-9 ]
  • [ 12150-46-8 ]
Reference: [1] Organometallics, 1986, vol. 5, p. 2537 - 2542
  • 8
  • [ 201543-21-7 ]
  • [ 672-66-2 ]
  • [ 12150-46-8 ]
  • [ 717901-65-0 ]
Reference: [1] Journal of Organometallic Chemistry, 2004, vol. 689, # 11, p. 1978 - 1990
  • 9
  • [ 75-09-2 ]
  • [ 148-18-5 ]
  • [ 12150-46-8 ]
Reference: [1] Journal of Organometallic Chemistry, 2004, vol. 689, # 11, p. 1978 - 1990
  • 10
  • [ 33272-09-2 ]
  • [ 14311-22-9 ]
  • [ 12150-46-8 ]
Reference: [1] Organometallics, 1992, vol. 11, p. 2543 - 2550
  • 11
  • [ 105019-26-9 ]
  • [ 591-51-5 ]
  • [ 12150-46-8 ]
Reference: [1] Organometallics, 1986, vol. 5, p. 2537 - 2542
  • 12
  • [ 12150-46-8 ]
  • [ 72287-26-4 ]
YieldReaction ConditionsOperation in experiment
86% for 8 h; Inert atmosphere; Schlenk technique; Reflux To a dichloromethane solution (15 cm3) of dppf (189 mg, 0.34 mmol), a methanolic solution of Na2PdCl4 (100 mg, 0.34 mmol) was added with continuous stirring. The resulting reaction mixture was refluxed for 8 hours. The solvents were evaporated in vacuo and the residue was washed thoroughly with diethyl ether to remove excess phosphine. The residue was extracted with dichloromethane, filtered and passed through a Florisil column. The resulting solution on refrigeration at –5 oC afforded reddish orange crystals.(yield 214 mg, 86percent). Anal. Calcd. for C34H28P2FePdCl2 : C, 55.81 ; H, 3.86 percent. Found: C, 55.86; H, 3.85 percent. 1H NMR (CDCl3) δ: 4.26 (br, 4H, C5H4), 4.71 (br, 4H, C5H4), 7.41-7.49 (m, Ph), 7.56-7.82 (m, Ph); 31P{1H}NMR (CDCl3) δ : 34.1 ppm.
Reference: [1] Inorganica Chimica Acta, 2018, vol. 478, p. 125 - 129
[2] Organometallics, 1990, vol. 9, p. 1617 - 1623
  • 13
  • [ 12150-46-8 ]
  • [ 75-09-2 ]
  • [ 72287-26-4 ]
YieldReaction ConditionsOperation in experiment
95% With hydrogenchloride In ethanol for 3 h; Reflux The solution of dppf (1.6632g, 3mmol)in 15ml CH2Cl2 was added to a solution of PdCl2(0.5320g, 3mmol) that dissolved in 2 cm3 ethanoland 2 cm3 concentrate HCl. The mixture was reuxfor 3 hrs. And then the solvent was evaporate at roomtemperature to give red precipitate. A small portion ofthis complex was dissolve in CH2Cl2 and set to slowevaporation at room temperature after a few days, thered colored needle crystals were formed suitable forsingle-crystal diffraction analysis15. The melting pointis 253°C, yield is 2.086gm (95percent), formula: [Pd(k2-dppf)Cl2] and M.wt.is 816.58 gm/mole, as shown inFigure 1.
Reference: [1] Oriental Journal of Chemistry, 2017, vol. 33, # 2, p. 584 - 592
  • 14
  • [ 12150-46-8 ]
  • [ 14323-43-4 ]
  • [ 72287-26-4 ]
Reference: [1] Patent: WO2007/29031, 2007, A1, . Location in patent: Page/Page column 6
  • 15
  • [ 12150-46-8 ]
  • [ 72287-26-4 ]
Reference: [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 10, p. 2667 - 2671[2] Angew. Chem., 2018, vol. 130, p. 2697 - 2701,5
  • 16
  • [ 12150-46-8 ]
  • [ 15617-18-2 ]
  • [ 72287-26-4 ]
Reference: [1] Organometallics, 2006, vol. 25, # 11, p. 2750 - 2760
  • 17
  • [ 12150-46-8 ]
  • [ 72287-26-4 ]
Reference: [1] Journal of Organometallic Chemistry, 2003, vol. 678, # 1-2, p. 48 - 55
[2] Dalton Transactions, 2015, vol. 44, # 32, p. 14453 - 14464
  • 18
  • [ 12150-46-8 ]
  • [ 12317-46-3 ]
  • [ 72287-26-4 ]
Reference: [1] Journal of Organometallic Chemistry, 2001, vol. 637-639, p. 691 - 697
  • 19
  • [ 12150-46-8 ]
  • [ 12107-56-1 ]
  • [ 72287-26-4 ]
Reference: [1] Polyhedron, 1993, vol. 12, p. 721 - 730
  • 20
  • [ 12150-46-8 ]
  • [ 21264-30-2 ]
  • [ 72287-26-4 ]
Reference: [1] Journal of the Chemical Society, Chemical Communications, 1995, # 11, p. 1103 - 1104
  • 21
  • [ 12150-46-8 ]
  • [ 67292-34-6 ]
Reference: [1] Organometallics, 2014, vol. 33, # 8, p. 2012 - 2018
[2] Organic Letters, 2017, vol. 19, # 8, p. 2118 - 2121
[3] Journal of Organometallic Chemistry, 2001, vol. 637-639, p. 683 - 690
[4] Organic Process Research and Development, 2003, vol. 7, # 1, p. 10 - 16
  • 22
  • [ 12150-46-8 ]
  • [ 14264-16-5 ]
  • [ 67292-34-6 ]
Reference: [1] Journal of the American Chemical Society, 2015, vol. 137, # 3, p. 1109 - 1115
  • 23
  • [ 12150-46-8 ]
  • [ 67292-34-6 ]
Reference: [1] Inorganica Chimica Acta, 1989, vol. 157, p. 259 - 266
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