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[ CAS No. 2186-92-7 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 2186-92-7
Chemical Structure| 2186-92-7
Structure of 2186-92-7 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 2186-92-7 ]

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Product Details of [ 2186-92-7 ]

CAS No. :2186-92-7 MDL No. :MFCD00036507
Formula : C10H14O3 Boiling Point : No data available
Linear Structure Formula :CH3OC6H4CH(CH3O)2 InChI Key :NNHYAHOTXLASEA-UHFFFAOYSA-N
M.W : 182.22 Pubchem ID :75140
Synonyms :

Calculated chemistry of [ 2186-92-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.4
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 49.68
TPSA : 27.69 ?2

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) : -6.33 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.33
Log Po/w (XLOGP3) : 1.53
Log Po/w (WLOGP) : 1.66
Log Po/w (MLOGP) : 1.63
Log Po/w (SILICOS-IT) : 1.88
Consensus Log Po/w : 1.8

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.01
Solubility : 1.78 mg/ml ; 0.00975 mol/l
Class : Soluble
Log S (Ali) : -1.72
Solubility : 3.47 mg/ml ; 0.019 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.83
Solubility : 0.271 mg/ml ; 0.00149 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.47

Safety of [ 2186-92-7 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 2186-92-7 ]

* 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.

  • Downstream synthetic route of [ 2186-92-7 ]

[ 2186-92-7 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 2186-92-7 ]
  • [ 54439-75-7 ]
  • 2
  • [ 2186-92-7 ]
  • [ 48149-72-0 ]
  • (4aR,6S,7R,8R,8aR)-6-Allyloxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol [ No CAS ]
  • 3
  • [ 67442-07-3 ]
  • [ 2186-92-7 ]
  • [ 905927-08-4 ]
  • 4
  • [ 81-13-0 ]
  • [ 2186-92-7 ]
  • [ 1196055-91-0 ]
  • 5
  • [ 2186-92-7 ]
  • [ 73522-17-5 ]
  • C12H16O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With camphor-10-sulfonic acid; In dichloromethane;Reflux; Into a 50 mL round bottom flask, diol 22 (0.2 g, 3.3 mmol), CSA (catalytic amount), anisaldehyde dimethyl acetal (0.91 g, 5.0 mmol) and CH2Cl2 (12 mL) were added and refluxed for 20 h. The reaction mixture was quenched with triethylamine (2 mL). The solvent was removed with a rotary evaporator and the resulting crude acetal was directly utilized for the next reaction without further purification. The crude acetal (0.5 g) was dissolved in 15 mL of dry CH2Cl2 and cooled to -78 C. To this, diisobutyaluminium hydride (2.6 mL, 3.6 mmol, and 1.4 M solution in toluene) was added and stirred for 2 h at -30 C. The reaction mixture was quenched with saturated sodium potassium tartrate solution and stirred for 6 h at room temperature. The reaction mixture was extracted with CH2Cl2 (3 * 10 mL). The combined organic layers were dried over anhydrous Na2SO4 and concentrated under reduced pressure. The resulting crude was purified by column chromatography to afford compound 13 (0.38 g, 1.8 mmol, 80%) as a colorless oil. (c 1.5, CHCl3). IR [NEAT]: 3426, 2926, 2875, 1612, 1586, 1513, 1247, 1034, 820, 516 cm-1. 1H NMR, (300 MHz, CDCl3): delta 7.30-7.26 (m, 2H), 6.90-6.87 (m, 2H), 4.56 (d, J = 11.2 Hz, 1H), 4.46 (d, J = 11.2 Hz, 1H), 3.80 (s, 3H), 3.80-3.72 (m, 1H), 3.70-3.65 (m, 1H), 3.55-3.39 (m, 1H), 1.97 (br s, 1H), 1.72-1.39 (m, 2H), 0.92 (t, J = 7.5 Hz, 3H) ppm. 13C NMR (75 MHz, CDCl3): delta 159.2, 129.3, 128.6, 113.9, 80.7, 71.1, 64.9, 55.2, 23.5, 9.6 ppm. MS(ESI): m/z 233 [M+Na]+. HRMS(ESI) m/z calculated for C12H18O3Na 233.11482, found: 233.11446.
  • 6
  • [ 67-56-1 ]
  • [ 2186-92-7 ]
  • [ 135544-68-2 ]
  • [ 1397-89-3 ]
  • C68H91NO21 [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% A suitable fully protected intermediate was quickly generated from AmB (Scheme 3, FIG. 16). This sequence involved Alloc protection of the amine, C3/C5 and C9/C11 rho-methoxyphenyl acetal formation, TES silylation of the remaining alcohols, and lastly TMSE formation of the C16 carboxylate to form fully protected intermediate 5. Exposure of 5 to NaHMDS at low temperatures smoothly eliminated the C3 alcohol, generating an alpha-beta unsaturated lactone. Stryker reduction of this intermediate efficiently reduced the unsaturation yielding 6, leaving only a deprotection sequence to generate C3deOAmB. Exposure of 6 to HF cleanly removed the TES groups, followed by TBAF-promoted TMSE removal. Methyl ketal and PMP ketal hydrolysis was achieved concomitantly under acidic conditions with HCl. Efforts are currently underway to achieve the final Alloc deprotection of 7 and synthesize C3deOAmB.
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