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[ CAS No. 66-77-3 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 66-77-3
Chemical Structure| 66-77-3
Chemical Structure| 66-77-3
Structure of 66-77-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 66-77-3 ]

CAS No. :66-77-3 MDL No. :MFCD00004003
Formula : C11H8O Boiling Point : -
Linear Structure Formula :- InChI Key :SQAINHDHICKHLX-UHFFFAOYSA-N
M.W :156.18 Pubchem ID :6195
Synonyms :

Calculated chemistry of [ 66-77-3 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 49.34
TPSA : 17.07 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.56 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.78
Log Po/w (XLOGP3) : 2.39
Log Po/w (WLOGP) : 2.65
Log Po/w (MLOGP) : 2.48
Log Po/w (SILICOS-IT) : 3.16
Consensus Log Po/w : 2.49

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.86
Solubility : 0.213 mg/ml ; 0.00137 mol/l
Class : Soluble
Log S (Ali) : -2.39
Solubility : 0.637 mg/ml ; 0.00408 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.01
Solubility : 0.0154 mg/ml ; 0.0000984 mol/l
Class : Moderately soluble

Medicinal Chemistry

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

Safety of [ 66-77-3 ]

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 [ 66-77-3 ]

* 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 [ 66-77-3 ]
  • Downstream synthetic route of [ 66-77-3 ]

[ 66-77-3 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 66-77-3 ]
  • [ 3163-27-7 ]
Reference: [1] Tetrahedron Letters, 2000, vol. 41, # 27, p. 5161 - 5164
[2] Journal of the Chemical Society, 1957, p. 2796,2799
[3] Chemical Communications, 2014, vol. 50, # 28, p. 3692 - 3694
[4] Organic Letters, 2014, vol. 16, # 2, p. 484 - 487
[5] Organic Letters, 2014, vol. 16, # 17, p. 4424 - 4427
  • 2
  • [ 90-12-0 ]
  • [ 6627-78-7 ]
  • [ 13098-88-9 ]
  • [ 66-77-3 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1981, vol. 54, # 9, p. 2724 - 2727
  • 3
  • [ 64-19-7 ]
  • [ 90-12-0 ]
  • [ 6627-78-7 ]
  • [ 13098-88-9 ]
  • [ 66-77-3 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1981, vol. 54, # 9, p. 2724 - 2727
  • 4
  • [ 506-59-2 ]
  • [ 66-77-3 ]
  • [ 16413-71-1 ]
YieldReaction ConditionsOperation in experiment
92%
Stage #1: With sodium acetate; sodium tris(acetoxy)borohydride; acetic acid In tetrahydrofuran for 12 h;
Stage #2: With sodium hydrogencarbonate In dichloromethane; water
To 1-naphthaldehyde (1.50 g, 9.62 mmol, 1.00 equiv) in 40 mL THF is added NaOAc (0.79 g, 9.62 mmol, 1.00 equiv), Me2NH-HCl (863 mg, 10.6 mmol, 1.10 equiv), and AcOH (0.11 mL, 1.9 mmol, 0.20 equiv) at 23 0C. NaBH(OAc)3 (4.08 g, 19.3 mmol, 2.00 equiv) is added in three portions over five minutes. The suspension is stirred for 12 hours before solvent is removed in vacuo. To the residue is added 10 mL sat. NaHCO3(aq) and 10 mL CH2Cl2. The phases are separated and the aqueous phase is extracted with CH2Cl2 (3 x 10 mL). The combined organic phase is concentrated in vacuo. The residue is purified by chromatography on silica gel eluting with hexanes/EtOAc 3:2 (v/v) to afford 1.64 g of the title compound as a colorless liquid (92percent yield). R/= 0.38 (hexane/EtOAc 2:3 (v/v)). NMR Spectroscopy: 1H NMR (600 MHz, CDCl3,23 0C, δ): 8.27 (d, J = 8.5 Hz, IH), 7.85 (d, J= 8.2 Hz, IH), 7.79 (dd, J= 6.7 Hz, 2.9 Hz, IH), 7.53 (ddd, J = 8.0 Hz, 6.5 Hz, 1.0 Hz, IH), 7.48 (ddd, J= 6.5 Hz, 5.5 Hz, 1.0 Hz, IH), 7.43- 7.40 (m, 2H), 3.82 (s, 2H), 2.31 (s, 6H). 13C NMR (125 MHz, CDCl3, 23 0C, δ): 134.85, 133.84, 132.52, 128.40, 127.95, 127.38, 125.98, 125.56, 125.06, 124.49, 62.60, 45.69. Mass <n="81"/>Spectrometry: HRMS-FIA (m/z): calcd for [Ci3Hi5N + H], 186.1277. Found, 186.1286. These spectroscopic data correspond to reported data (Gay, R.L.; Hauser, CR. J. Am. Chem. Soc. 1967, 89, 2297-2303; incorporated herein by reference).
Reference: [1] Patent: WO2009/149347, 2009, A1, . Location in patent: Page/Page column 79-80
  • 5
  • [ 66-77-3 ]
  • [ 124-40-3 ]
  • [ 16413-71-1 ]
Reference: [1] Patent: WO2009/100014, 2009, A1, . Location in patent: Page/Page column 206
  • 6
  • [ 66-77-3 ]
  • [ 41790-30-1 ]
Reference: [1] Helvetica Chimica Acta, 1979, vol. 62, # 3, p. 882 - 893
[2] Helvetica Chimica Acta, 1979, vol. 62, # 3, p. 882 - 893
  • 7
  • [ 66-77-3 ]
  • [ 74-89-5 ]
  • [ 14489-75-9 ]
Reference: [1] Journal of Medicinal Chemistry, 1981, vol. 24, # 2, p. 140 - 145
[2] Helvetica Chimica Acta, 1952, vol. 35, p. 1348,1351
[3] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 21, p. 6671 - 6676,6
[4] Organic Letters, 2014, vol. 16, # 2, p. 358 - 361
  • 8
  • [ 66-77-3 ]
  • [ 14489-75-9 ]
Reference: [1] Organic Letters, 2011, vol. 13, # 4, p. 600 - 603
  • 9
  • [ 593-51-1 ]
  • [ 66-77-3 ]
  • [ 14489-75-9 ]
Reference: [1] Analytical Chemistry, 1981, vol. 53, # 7, p. 1122 - 1125
  • 10
  • [ 66-77-3 ]
  • [ 28095-56-9 ]
Reference: [1] Journal of the Indian Chemical Society, 1958, vol. 35, p. 287,289
  • 11
  • [ 66-77-3 ]
  • [ 269066-75-3 ]
Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 10, p. 2819 - 2828
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