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[ CAS No. 107-86-8 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 107-86-8
Chemical Structure| 107-86-8
Chemical Structure| 107-86-8
Structure of 107-86-8 * Storage: {[proInfo.prStorage]}
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Product Citations

Zhang, Yueteng ; Ji, Peng ; Meng, Xiang , et al. DOI: PubMed ID:

Abstract: A simple arylamine-catalyzed Mannich-cyclization cascade reaction was developed for facile synthesis of substituted 2H-benzo[h]chromenes, e.g., I (R1 = Ph, 2-MeOC6H4, furan-2-yl, 2-bromopyridin-3-yl, etc.; R2 = H, Cl, O2N, AcNH, etc.). The notable feature of the process includes the efficient generation of ortho-quinone methides (o-QMs) catalyzed by o-phenylenediamine. The mild reaction conditions allows for a broad spectrum of 1- and 2-naphthols and trans-cinnamaldehydes R1CH:CHCHO to engage in the cascade sequence with high efficiency.

Keywords: aminocatalysis ; cascade reaction ; chromenes ; organocatalysis ; quinone methide

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Product Details of [ 107-86-8 ]

CAS No. :107-86-8 MDL No. :MFCD00010291
Formula : C5H8O Boiling Point : -
Linear Structure Formula :HOCCHC(CH3)2 InChI Key :SEPQTYODOKLVSB-UHFFFAOYSA-N
M.W : 84.12 Pubchem ID :61020
Synonyms :

Calculated chemistry of [ 107-86-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 6
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.4
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 25.87
TPSA : 17.07 Ų

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) : -5.98 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.48
Log Po/w (XLOGP3) : 1.17
Log Po/w (WLOGP) : 1.15
Log Po/w (MLOGP) : 0.9
Log Po/w (SILICOS-IT) : 0.83
Consensus Log Po/w : 1.11

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.03
Solubility : 7.8 mg/ml ; 0.0928 mol/l
Class : Very soluble
Log S (Ali) : -1.12
Solubility : 6.33 mg/ml ; 0.0752 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.58
Solubility : 22.0 mg/ml ; 0.261 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.55

Safety of [ 107-86-8 ]

Signal Word:Danger Class:8,3
Precautionary Statements:P210-P233-P240-P241-P242-P243-P261-P264-P270-P271-P272-P273-P280-P301+P312+P330-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P312-P333+P313-P362+P364-P370+P378-P403+P233-P403+P235-P405-P501 UN#:2920
Hazard Statements:H226-H302-H313-H314-H317-H331-H402 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 107-86-8 ]

* 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 [ 107-86-8 ]
  • Downstream synthetic route of [ 107-86-8 ]

[ 107-86-8 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 107-86-8 ]
  • [ 55876-82-9 ]
Reference: [1] Journal of Chemical Research, Miniprint, 1985, # 8, p. 2801 - 2817
  • 2
  • [ 107-86-8 ]
  • [ 95-01-2 ]
  • [ 54287-99-9 ]
YieldReaction ConditionsOperation in experiment
50% With calcium hydroxide In methanol at 20℃; for 48 h; 2,4-Dihydroxybenzaldehyde (15) (3 g/20.17 mmol), calcium hydroxide (1.543 g/20.8 mmol) and 150 mL of methanol were place in a two-necked round-bottom flask. Then, prenal (9.135 g/108.6 mmol) was added dropwise. The mixture was allowed to stir at room temperature for 48 h. The reaction was quenched with HCl 1 M until pH 1–2. The methanol was evaporated and the aqueous phase was extracted with 3 × 150 mL of ethyl acetate. The organic phase was washed with 2 × 100 mL of brine, dried over sodium sulfate anhydrous, filtered and the organic solvent evaporated. The crude product was purified by silica gel flash chromatography (n-hexane/ethyl acetate 9:1). Compound 16 was crystallized from n-hexane/ethyl acetate 3:1 as a yellow solid (2.06 g/50percent).
50% With calcium hydroxide In methanol at 20℃; for 48 h; 2,4-Dihydroxybenzaldehyde (42) (3g/20.17mmol), calcium hydroxide (1.543g/20.8mmol) and 150mL of methanol were placed in a round-bottom flask. Then, prenal (9.135g/108.6mmol) was added dropwise. The mixture was stirred at room temperature for 48h. The reaction was quenched with HCl 1M until pH 1–2. The methanol was evaporated and the aqueous phase was extracted with 3×150mL of ethyl acetate. The organic phase was washed with 2×100mL of brine, dried over sodium sulfate anhydrous, filtered and the organic solvent evaporated. The crude product was purified by silica gel flash chromatography (n-hexane/ethyl acetate 9:1). Compound 43 was crystallized from n-hexane/ethyl acetate 3:1 as a yellow solid (2.06g/50percent).6-Formyl-5-hydroxy-2,2-dimethyl-2H-benzopyran (43). Mp: 68–69°C. IR νmax (cm−1) (KBr): 3464, 2967, 2922, 2857, 1628, 1484, 1330, 1294, 1247, 1176, 1107, 1081, 748. 1H NMR (300.13MHz, CDCl3) δ (ppm): 11.65 (OH), 9.66 (s, CHO), 7.29 (d, J=8.6), 6.88 (d, J=10.0), 6.44 (d, J=8.6), 5.61 (d, J=10.0), 1.46 (s, 6H). 13C NMR (100.63MHz, CDCl3) δ (ppm): 194.5, 160.6, 158.7, 134.7, 128.6, 115.2, 115.1, 109.4, 108.8, 78.2, 28.4. EIMS m/z (percent): 205 (5, [M+1]+.), 204 (10 [M]+.), 190 (15), 189 (100), 187 (60), 159 (12), 131 (12), 103 (10), 77 (12), 51 (6). HRMS (ESI) m/z calcd for C12H13O3 [M+H]+: 205.08570, found: 205.08592.
0.68 g With calcium hydroxide In methanol at 20℃; for 12 h; A 1 g portion of 2,4-2 hydroxybenzaldehyde (Compound 2 shown in Figure 1)0.514 g Ca (OH) 2, methanol150mL.3.045 g of prenyl aldehyde (compound 1 shown in FIG. 1) was then added dropwise.Stir at room temperature for 12h.Quench with HCl (1 M) until the pH is 1-2.Methanol was evaporated and the aqueous phase was extracted with 3 * 150 mL of ethyl acetate.The organic phase was washed with 2 * 100 mL saturated brine, dried over anhydrous Na2SO4,Vacuum filtration, and spin dry. The crude product was passed through a column of silica gel (petroleum ether: ethyl acetate = 9: 1)Crystallization gave product 3 (0.68 g) as shown in FIG.
Reference: [1] Journal of Medicinal Chemistry, 2018,
[2] Journal of Organic Chemistry, 2015, vol. 80, # 22, p. 11460 - 11467
[3] Angewandte Chemie - International Edition, 2012, vol. 51, # 32, p. 8092 - 8096
[4] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 11, p. 2941 - 2959
[5] European Journal of Medicinal Chemistry, 2013, vol. 69, p. 798 - 816
[6] Tetrahedron, 2001, vol. 57, # 25, p. 5335 - 5338
[7] Tetrahedron Letters, 2009, vol. 50, # 36, p. 5075 - 5079
[8] Advanced Synthesis and Catalysis, 2005, vol. 347, # 4, p. 555 - 562
[9] Patent: CN106187974, 2016, A, . Location in patent: Paragraph 0044
  • 3
  • [ 107-86-8 ]
  • [ 95-01-2 ]
  • [ 54287-99-9 ]
  • [ 33279-69-5 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1999, vol. 72, # 2, p. 259 - 263
  • 4
  • [ 107-86-8 ]
  • [ 33143-29-2 ]
Reference: [1] Journal of Molecular Catalysis A: Chemical, 2015, vol. 398, p. 11 - 16
[2] Tetrahedron, 2016, vol. 72, # 51, p. 8406 - 8416
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