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[ CAS No. 7478-69-5 ] {[proInfo.proName]}

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Chemical Structure| 7478-69-5
Chemical Structure| 7478-69-5
Structure of 7478-69-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 7478-69-5 ]

CAS No. :7478-69-5 MDL No. :MFCD00192575
Formula : C18H22N2 Boiling Point : -
Linear Structure Formula :- InChI Key :HBWITNNIJDLPLS-UHFFFAOYSA-N
M.W : 266.38 Pubchem ID :81995
Synonyms :

Calculated chemistry of [ 7478-69-5 ]

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.22
Num. rotatable bonds : 4
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 89.43
TPSA : 6.48 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.5 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.3
Log Po/w (XLOGP3) : 4.83
Log Po/w (WLOGP) : 3.88
Log Po/w (MLOGP) : 3.86
Log Po/w (SILICOS-IT) : 3.35
Consensus Log Po/w : 3.84

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.71
Solubility : 0.00514 mg/ml ; 0.0000193 mol/l
Class : Moderately soluble
Log S (Ali) : -4.7
Solubility : 0.00532 mg/ml ; 0.00002 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.58
Solubility : 0.000694 mg/ml ; 0.00000261 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.08

Safety of [ 7478-69-5 ]

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 [ 7478-69-5 ]

* 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 [ 7478-69-5 ]
  • Downstream synthetic route of [ 7478-69-5 ]

[ 7478-69-5 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 1779-49-3 ]
  • [ 90-94-8 ]
  • [ 7478-69-5 ]
YieldReaction ConditionsOperation in experiment
92%
Stage #1: With potassium <i>tert</i>-butylate In tetrahydrofuran at 0℃; for 2 h; Inert atmosphere
Stage #2: at 0℃; Reflux
The synthesis of BDADPE was conducted by the classic Wittig reaction using 4,4′-bis(dimethylamino)benzophenone as substrate under an argon atmosphere (described in detail by Hirao [29]). Typically, methyltriphenylphosphonium bromide (45.58g, 127.6mmol) and freshly distilled THF (500mL) were added into a round bottom flask equipped with a reflux condenser and a magnetic bar. Potassium tert-butoxide (138.4mL of a 1.0M solution in THF, 138.4mmol) was then added dropwise to the reaction flask via constant pressure funnel. The reaction mixture was stirred for 2h at 0°C. Then the solution of 4,4′-bis(dimethylamino)benzophenone (21.4g, 79.75mmol) in dry THF (690mL) was dropped to the reaction mixture via constant pressure funnel at 0°C. The orange–brown reaction mixture was heated to reflux for 7h with stirring and then quenched with distilled water. The resultant mixture was extracted with ether three times. Such ethereal layer was washed with aqueous NaHCO3 solution and saturated aqueous NaCl solution and then dried over MgSO4. After filtration, the ethereal layer was poured into hexane to precipitate triphenylphosphine oxide. Flash column chromatography (petroleum ether/ethyl acetate 2:1 v/v) gave BDADPE in 92percent yield (19.52g, 73.37mmol) and Rf=0.76. 1H NMR (CDCl3, 400MHz): δ 2.96 (s, 12H, 2×N(CH3)2), 5.19 (s, 2H, CH2=C), 6.68–6.70 (d, 4H, aromatic proton ortho to N(CH3)2), 7.25-7.28 (d, 4H, aromatic proton meta to N(CH3)2).
Reference: [1] Polymer, 2013, vol. 54, # 12, p. 2958 - 2965
  • 2
  • [ 78-08-0 ]
  • [ 586-77-6 ]
  • [ 7478-69-5 ]
  • [ 2039-80-7 ]
  • [ 22210-79-3 ]
Reference: [1] Chemical Communications, 2007, # 39, p. 4056 - 4058
  • 3
  • [ 1309-60-0 ]
  • [ 7478-69-5 ]
YieldReaction ConditionsOperation in experiment
74% With sodium hydroxide In benzene EXAMPLE 30
Synthesis of 1,1-bis(4-dimethylaminophenyl)ethylene
Into 400 ml of benzene was dissolved 10 g of 2,2-bis(4-dimethylaminophenyl)propionic acid.
Thereto was added 10 g of lead dioxide and the mixture was reacted at room temperature with stirring for 30 minutes.
The lead compound was removed by filtration and the benzene layer was washed with 200 ml of 5percent aqueous solution of sodium hydroxide.
Benzene was removed by distillation at a reduced pressure.
The residue was recrystallized from methanol to obtain 6.3 g (yield 74percent) of 1,1-bis(4-dimethylaminophenyl)ethylene, having a melting point of 123°~123.5° C.
Reference: [1] Patent: US4898941, 1990, A,
  • 4
  • [ 90-94-8 ]
  • [ 74-88-4 ]
  • [ 7478-69-5 ]
YieldReaction ConditionsOperation in experiment
65% With magnesium In diethyl ether; benzene (1)
Synthesis of 1,1-bis(4'-dimethylaminophenyl)ethylene
After adding 100 ml of benzene to a diethyl ether solution of methylmagnesium iodide prepared from 1.7 g of magnesium, 9.9 g of methyl iodide, and 100 ml of diethyl ether, 16.6 of 4,4'-bis-dimethylaminobenzophenone was gradually added thereto.
After stirring at room temperature for 10 hours, the reaction mixture was decomposed by a saturated aqueous ammonium chloride solution, followed by stirring as it was for 2 hours.
After separating and water-washing an organic layer, the solvent was distilled off, and the residue was recrystallized from ethanol to obtain 10.7 g of 1,1-bis(4'-dimethylaminophenyl)ethylene.
The melting point was 121° to 122° C., and the theoretical yield was 65percent.
Reference: [1] Patent: US4751163, 1988, A,
  • 5
  • [ 78-08-0 ]
  • [ 586-77-6 ]
  • [ 7478-69-5 ]
  • [ 22210-79-3 ]
Reference: [1] Chemical Communications, 2007, # 39, p. 4056 - 4058
  • 6
  • [ 33905-89-4 ]
  • [ 7478-69-5 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1994, vol. 67, # 6, p. 1753 - 1755
  • 7
  • [ 90-94-8 ]
  • [ 7478-69-5 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1928, vol. 461, p. 145
[2] Bulletin of the Chemical Society of Japan, 1994, vol. 67, # 6, p. 1753 - 1755
  • 8
  • [ 75-16-1 ]
  • [ 90-94-8 ]
  • [ 7478-69-5 ]
  • [ 58379-76-3 ]
Reference: [1] Journal of Organic Chemistry, 1958, vol. 23, p. 1056
  • 9
  • [ 75-16-1 ]
  • [ 90-94-8 ]
  • [ 7478-69-5 ]
  • [ 16273-85-1 ]
Reference: [1] Journal of Organic Chemistry, 1958, vol. 23, p. 1056
  • 10
  • [ 27200-84-6 ]
  • [ 90-94-8 ]
  • [ 7478-69-5 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1990, vol. 63, # 6, p. 1748 - 1752
  • 11
  • [ 917-64-6 ]
  • [ 90-94-8 ]
  • [ 7478-69-5 ]
Reference: [1] Journal of Organic Chemistry, 1993, vol. 58, # 22, p. 6049 - 6056
[2] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1909, vol. 149, p. 349
[3] Journal fuer Praktische Chemie (Leipzig), 1927, vol. &lt;2&gt;115, p. 40
[4] Chemische Berichte, 1907, vol. 40, p. 3888
[5] Chemische Berichte, 1906, vol. 39, p. 1118
[6] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1913, vol. 157, p. 724
[7] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1909, vol. 149, p. 349
[8] Journal fuer Praktische Chemie (Leipzig), 1927, vol. &lt;2&gt;115, p. 40
[9] Chemische Berichte, 1907, vol. 40, p. 3888
[10] Chemische Berichte, 1906, vol. 39, p. 1118
[11] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1913, vol. 157, p. 724
[12] Journal of Materials Chemistry, 1998, vol. 8, # 12, p. 2677 - 2683
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