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[ CAS No. 493-08-3 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 493-08-3
Chemical Structure| 493-08-3
Chemical Structure| 493-08-3
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Product Details of [ 493-08-3 ]

CAS No. :493-08-3 MDL No. :MFCD00138123
Formula : C9H10O Boiling Point : -
Linear Structure Formula :- InChI Key :VZWXIQHBIQLMPN-UHFFFAOYSA-N
M.W : 134.18 Pubchem ID :136319
Synonyms :

Calculated chemistry of [ 493-08-3 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.33
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 40.59
TPSA : 9.23 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) : -5.34 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.07
Log Po/w (XLOGP3) : 2.5
Log Po/w (WLOGP) : 2.01
Log Po/w (MLOGP) : 2.06
Log Po/w (SILICOS-IT) : 2.84
Consensus Log Po/w : 2.3

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.69
Solubility : 0.273 mg/ml ; 0.00204 mol/l
Class : Soluble
Log S (Ali) : -2.34
Solubility : 0.614 mg/ml ; 0.00458 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.93
Solubility : 0.156 mg/ml ; 0.00116 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.68

Safety of [ 493-08-3 ]

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 [ 493-08-3 ]

* 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 [ 493-08-3 ]
  • Downstream synthetic route of [ 493-08-3 ]

[ 493-08-3 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 122-97-4 ]
  • [ 254-03-5 ]
  • [ 493-08-3 ]
  • [ 491-37-2 ]
  • [ 19090-04-1 ]
Reference: [1] Journal of Organic Chemistry, 1983, vol. 48, # 25, p. 4914 - 4917
  • 2
  • [ 122-97-4 ]
  • [ 254-04-6 ]
  • [ 254-03-5 ]
  • [ 493-08-3 ]
  • [ 491-37-2 ]
  • [ 19090-04-1 ]
  • [ 100-52-7 ]
Reference: [1] Journal of Organic Chemistry, 1983, vol. 48, # 25, p. 4914 - 4917
  • 3
  • [ 493-08-3 ]
  • [ 3875-78-3 ]
Reference: [1] Journal of Chemical Research, Miniprint, 1997, # 12, p. 2701 - 2733
[2] Annales de Chimie (Cachan, France), 1954, vol. <12> 9, p. 431,363
[3] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1984, vol. 20, # 8, p. 838 - 841[4] Khimiya Geterotsiklicheskikh Soedinenii, 1984, vol. 20, # 8, p. 1035 - 1038
  • 4
  • [ 493-08-3 ]
  • [ 3875-78-3 ]
Reference: [1] Annales de Chimie (Cachan, France), 1954, vol. <12> 9, p. 431,363
  • 5
  • [ 56-23-5 ]
  • [ 128-08-5 ]
  • [ 493-08-3 ]
  • [ 94-36-0 ]
  • [ 3875-78-3 ]
Reference: [1] Annales de Chimie (Cachan, France), 1954, vol. <12> 9, p. 431,363
  • 6
  • [ 56-23-5 ]
  • [ 493-08-3 ]
  • [ 7726-95-6 ]
  • [ 3875-78-3 ]
Reference: [1] Annales de Chimie (Cachan, France), 1954, vol. <12> 9, p. 431,363
  • 7
  • [ 493-08-3 ]
  • [ 68-12-2 ]
  • [ 55745-97-6 ]
YieldReaction ConditionsOperation in experiment
55.1% With trichlorophosphate In 1,2-dichloro-ethane at 50 - 85℃; for 12.5 h; To a solution of chromane (LVI) (3 g, 22.4 mmol, 1.0 eq) and DMF (3.3 g, 45.2 mmol, 2 eq) in DCE (20 mL) was added phosphorus oxychloride (3.4 g, 45.2 mmol, 2 eq) dropwise over 30 min below 50° C. The mixture was stirred at 85° C. for 12 h. The reaction was quenched by water and extracted with EtOAc (3×300 mL). The combined organic phase was dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel (PE:EtOAc=8:1) to give chromane-6-carbaldehyde (LVII) as yellow oil. (2.0 g, 12.3 mmol, 55.1percent yield). 1H NMR (CDCl3, 400 MHz) δ ppm 2.01 (q, J=45.8 Hz, 2H), 2.82 (t, J=6.4 Hz, 2H), 4.24 (t, J=5.2 Hz, 2H), 6.85 (d, J=8.4 Hz, 1H), 7.52-7.64 (m, 2H), 9.79 (s, 1H); ESIMS found C10H10O2 m/z 163.1 (M+H).
Reference: [1] Patent: US2014/243349, 2014, A1, . Location in patent: Paragraph 1738; 1740
[2] Journal of the Indian Chemical Society, 1959, vol. 36, p. 76,80
  • 8
  • [ 493-08-3 ]
  • [ 55745-97-6 ]
Reference: [1] Patent: WO2013/12649, 2013, A1,
  • 9
  • [ 493-08-3 ]
  • [ 74-90-8 ]
  • [ 55745-97-6 ]
Reference: [1] Journal of the Chemical Society, 1956, p. 2455,246
  • 10
  • [ 493-08-3 ]
  • [ 103203-84-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 24, p. 8219 - 8248
[2] Journal of Heterocyclic Chemistry, 1994, vol. 31, # 2, p. 457 - 480
  • 11
  • [ 493-08-3 ]
  • [ 327183-32-4 ]
YieldReaction ConditionsOperation in experiment
60% With n-butyllithium In tetrahydrofuran; <i>N</i>-methyl-acetamide 8-Chromanylacetic acid can be prepared in three stages from chroman, with an overall yield of 60percent, as illustrated by Synth. Comm., 12, 763-70 (1982).
On treatment with n-butyllithium and then with dimethylformamide in tetrahydrofuran, chroman results in 8-chromanal, which is then treated with trimethylsilyl cyanide in the presence of zinc iodide in dichloromethane.
Reference: [1] Patent: US5936097, 1999, A,
  • 12
  • [ 493-08-3 ]
  • [ 73183-34-3 ]
  • [ 1002727-88-9 ]
YieldReaction ConditionsOperation in experiment
84% With potassium acetate In N,N-dimethyl-formamide at 95℃; for 5 h; A solution of the 6-iodochroman 11c (1.0 g, 3.85 mmol), bis[pinocolato]diborane (1.22 g, 4.81 mmol) and potassium acetate (1.1O g, 11.5 mmol) in DMF (36 mL) is degassed with Ar for 5 min followed by the addition of the PdCI2dppf-DCM complex (314 mg, 0.38 mmol). The reaction mixture is then degassed for an additional 5 min before being heated to 950C for 5 h. The reaction is then cooled to RT. The crude reaction mixture is diluted with water and the product is extracted with EtOAc (3 x 100 mL). The combined organics are washed with water (100 mL) and brine (100 mL). The organic phase is then dried over MgSO4 and filtered and concentrated. The crude mixture is further purified by CombiFlash.(R). Companion using a gradient of EtOAc/hexanes to afford the borane fragment 11d (840 mg, 84percent yield).
Reference: [1] Patent: WO2009/62289, 2009, A1, . Location in patent: Page/Page column 79; 80
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