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Product Details of [ 83-33-0 ]

CAS No. :83-33-0 MDL No. :MFCD00003785
Formula : C9H8O Boiling Point : -
Linear Structure Formula :- InChI Key :QNXSIUBBGPHDDE-UHFFFAOYSA-N
M.W : 132.16 Pubchem ID :6735
Synonyms :
α-Hydrindone
Chemical Name :2,3-Dihydro-1H-inden-1-one

Calculated chemistry of [ 83-33-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 39.49
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) : -5.92 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.7
Log Po/w (XLOGP3) : 1.67
Log Po/w (WLOGP) : 1.82
Log Po/w (MLOGP) : 1.71
Log Po/w (SILICOS-IT) : 2.82
Consensus Log Po/w : 1.94

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.16
Solubility : 0.924 mg/ml ; 0.00699 mol/l
Class : Soluble
Log S (Ali) : -1.64
Solubility : 3.01 mg/ml ; 0.0228 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.08
Solubility : 0.11 mg/ml ; 0.000832 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.22

Safety of [ 83-33-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 83-33-0 ]

* 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 [ 83-33-0 ]
  • Downstream synthetic route of [ 83-33-0 ]

[ 83-33-0 ] Synthesis Path-Upstream   1~41

  • 1
  • [ 83-33-0 ]
  • [ 109-77-3 ]
  • [ 2510-01-2 ]
Reference: [1] Chemistry Letters, 2008, vol. 37, # 6, p. 570 - 571
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[5] Journal of Organic Chemistry, 2005, vol. 70, # 9, p. 3584 - 3591
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[7] Journal of the Chemical Society, 1961, p. 4705 - 4711
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[9] Journal of Organic Chemistry, 2013, vol. 78, # 14, p. 7154 - 7168
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  • 2
  • [ 83-33-0 ]
  • [ 40731-98-4 ]
  • [ 62803-47-8 ]
Reference: [1] Tetrahedron Letters, 1983, vol. 24, # 30, p. 3095 - 3098
[2] Tetrahedron Letters, 1983, vol. 24, # 30, p. 3095 - 3098
  • 3
  • [ 83-33-0 ]
  • [ 40731-98-4 ]
  • [ 62803-47-8 ]
Reference: [1] Tetrahedron Letters, 1983, vol. 24, # 30, p. 3095 - 3098
[2] Tetrahedron Letters, 1983, vol. 24, # 30, p. 3095 - 3098
  • 4
  • [ 33333-00-5 ]
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  • [ 83-33-0 ]
Reference: [1] Australian Journal of Chemistry, 1984, vol. 37, # 11, p. 2295 - 2304
  • 5
  • [ 83-33-0 ]
  • [ 14548-38-0 ]
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  • 6
  • [ 83-33-0 ]
  • [ 24623-25-4 ]
  • [ 24623-24-3 ]
YieldReaction ConditionsOperation in experiment
80%
Stage #1: With sulfuric acid; nitric acid In nitromethane at -10 - -5℃; for 0.75 h;
Stage #2: With water In nitromethaneCooling with ice
To a well-stirred mixture of H2SO4 (13.9 mL of a 98percent solution) and HNO3 (2.6 mL of a 65percent solution) was added at -10 °C a solution of 1-indanone (1.0 g, 7.6 mmol) in nitromethane (1.1 mL). The addition rate was carefully adjusted to raise the temperature from -10 to -5 °C during 30 min. The reaction mixture was stirred further for 15 min at this temperature (attention has to be paid to temperature and reaction time.). After ice-water hydrolysis (200 mL), the yellow precipitate was collected and extracted with CH2Cl2 (2 .x. 20 mL). The organic phase was washed with a KHCO3 solution 5percent (2 .x. 15 mL) washed with saturated brine (10 mL), dried over anhydrous Na2SO4 and evaporated in vacuo. The residue was separated by flash chromatography using hexane-ethyl acetate (1:0.2) as eluent. Compound 25, yield: 0.94 g, 80percent, mp: 98-100 °C (mp 15 100-101 °C) 1H NMR (CDCl3) δ ppm: 2.80 (m, 2H, CH2), 3.53 (m, 2H, CH2), 7.61 (m, 1H, H-Ar), 8.08 (d, J = 8.5 Hz, 1H, H-Ar), 8.47 (d, J = 8.3 Hz, 1H, H-Ar). Compound 26, yield: 0.23 g, 20percent, mp: 73-74 °C (mp lit.16 72-73 °C). 1H NMR (CDCl3) δ ppm: 2.83 (m, 2H, CH2), 3.28 (m, 2H, CH2), 7.61 (d, J = 8.5 Hz, 1H, H-Ar), 8.44 (dd, J = 2.2 Hz, J = 8.5 Hz, 1H, H-Ar), 8.56 (d, J = 2.2 Hz, 1H, H-Ar).
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[6] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 10, p. 2849 - 2853
[7] Patent: US2004/167128, 2004, A1, . Location in patent: Page 39
  • 7
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  • [ 24623-25-4 ]
YieldReaction ConditionsOperation in experiment
23% at 0℃; for 1 h; 4-Nitro-2,3-dihydro-1H-inden-1-one (IC1a) and 6-Nitro-2,3-dihydro-1H-inden-1-one (IC1b)
To a solution of 1-Indanone (20 g, 151 mmol) in concentrated H2SO4 (210 mL) at 0° C. was added KNO3 (15.3 g, 151 mmol) in several portions.
The reaction mixture was allowed to stir for 1 h and poured over ice (1 L).
The mixture was extracted with EtOAc and the organic phase was washed with brine and dried over Na2SO4.
After filtration and removal of the solvent, the residue was purified by flash column chromatography (EtOAc/hexanes) to afford IC1a as a yellow solid (3.00 g, 23percent)1H NMR (CDCl3, 600 MHz) δ 8.48 (d, J=8.4 Hz, 1H), 8.09 (d, J=7.2 Hz, 1H), 7.62 (dd, J=7.8, 7.8 Hz, 1H), 3.66 (t, J=6.0 Hz, 2H), 2.83-2.79 (m, 2H); and IC1b as a yellow solid (4.00 g, 30percent)1H NMR (CDCl3, 600 MHz) δ 8.57 (s, 1H), 8.45 (d, J=7.8 Hz, 1H), 7.67 (d, J=8.4 Hz, 1H), 3.28 (t, J=6.0 Hz, 2H), 2.86-2.82 (m, 2H).
18% at 0℃; for 1.08333 h; 4-Nitro-2,3-dihydro-lH-inden-l-one. To a 0 °C solution of indanone (1.1 mL,9.16 mmol, 1.0 equiv) in concentrated H2SO4 (9 mL) was added KNO3 (926 mg, 9.16 mmol, 1.0 equiv) as a solid in several portions over 5 min. After stirring for 1 h, the reaction mixture was poured onto ice. The aqueous suspension was extracted with EtOAC (3 x 30 mL), and the combined organic layers were washed with brine, dried over sodium sulfate, and concentrated in vacuo. Purification by silica gel chromatography (20percent - 50percent EtOAc/Hexanes) provided the desired compound as a yellow solid (288 mg, 18percent).
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  • 8
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YieldReaction ConditionsOperation in experiment
43 %Chromat. With sodium bromate; sulfuric acid; sodium bromide In water at 20℃; for 24 h; General procedure: A total of 1.0 g of 1-octanol (7.69 mmol) was taken in a 50-mL round-bottomed flask, to it NaBr 0.523 g (0.66 eq.), NaBrO 3 0.383 g (0.33 eq.), and 10 mL of H 2 O [comprises the bromide and bromate in 2:1 molar ratio] were added[6f]. The reaction mixture was stirred vigorously to dissolve the contents completely. To the above reaction mixture, the aqueous H 2 SO 4 solution (0.5 eq.) was added slowly under stirring over a period of 2.5 h at room temperature (prepared by adding 0.21 mL of 98percent H 2 SO 4 to 1 mL of water). The reaction mixture was allowed to stir for up to 24 h. After the completion of reaction, the product was extracted with CH 2 Cl 2 (3 15 mL), the organic layer was dried with Na 2 SO 4 and removal of the solvent obtained octyloctanoate in 98percent yield (0.953 g) as colorless liquid. The product was confirmed by GC–MS as well as by NMR.
Reference: [1] Synthetic Communications, 2018, vol. 48, # 13, p. 1663 - 1670
  • 9
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  • [ 28272-96-0 ]
  • [ 83-33-0 ]
  • [ 615-13-4 ]
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  • 10
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[2] Chemical Communications, 1999, # 5, p. 467 - 468
[3] Chemical and Pharmaceutical Bulletin, 1978, vol. 26, # 6, p. 1776 - 1785
  • 11
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[2] Journal of Organic Chemistry, 2017, vol. 82, # 14, p. 7621 - 7627
  • 12
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[2] European Journal of Organic Chemistry, 2016, vol. 2016, # 5, p. 918 - 920
[3] Advanced Synthesis and Catalysis, 2018, vol. 360, # 15, p. 2869 - 2878
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[6] Organic Letters, 2015, vol. 17, # 12, p. 3070 - 3073
[7] Advanced Synthesis and Catalysis, 2016, vol. 358, # 12, p. 1934 - 1941
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  • 13
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  • 14
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  • [ 83-33-0 ]
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  • 15
  • [ 83-33-0 ]
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  • 16
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  • 17
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  • 18
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  • [ 34598-49-7 ]
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  • 19
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  • 20
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  • [ 35095-07-9 ]
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  • 21
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  • 22
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  • 23
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  • 24
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  • [ 24425-40-9 ]
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  • 25
  • [ 83-33-0 ]
  • [ 40774-41-2 ]
YieldReaction ConditionsOperation in experiment
62% With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 1.5 h; Heating / reflux Synthesis of 3-bromo-indan-1-one; 390 g (2.2 mol) N-bromosuccinimde (powder with no lumps) and 0.5 g benzoyl peroxide were added to 264 g indan-1-one in 1500 mL CCl4 and refluxed with mechanical stirring for 1.5 hours. The colour of the reaction mixture suddenly changed to yellow and all N-bromosuccinimde (heavier than CCl4) was converted to succinimide (lighter than CCl4). The reaction mixture was cooled to 20° C., filtered and concentrated in vacuo. Crude 3-bromo-indan-1-one was dissolved in 600 mL ethyl acetate/heptane (1:2), cooled 2 hours on an ice bath and then left in a freezer over night to give 257 g crystals of 3-bromo-indan-1-one (62percent yield).
51% With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 1 h; Inert atmosphere; Reflux 3-Bromo-2,3-dihydro-lH-inden-l-one was generated as described by Treibs and Schroth 34. 2,3-Dihydro- lH-indan-1-one (528 mg, 4 mmol), N-bromosuccinimide (684 mg, 4 mmol) and benzoyl peroxide (30 mg, 0.12 mmol) were dissolved in CCl4 (10 mL) and heated to reflux for Ih under an N2 atmosphere. After cooling, succinimide was removed by filtration and the filtrate concentrated under high vacuum to yield the title compound as a straw-colored oil of >; 99percent purity as seen by GC-MS and NMR that was used without further purification (428 mg, 51percent yield). 1H NMR (600 MHz, CDCl3): δ 3.064 (dd, IH, /=19.7, /=2.3 Hz, CH2), 3.370 (dd, IH, /=19.7Hz, /=7.2Hz, CH2) 5.609 (dd, IH, /=7.2Hz, /=2.6Hz, C3-H), 7.468-7.520 (m, IH), 7.702-7.775 (m, 3H); 13C NMR (150 MHz, CDCl3): δ 40.28, 50.30, 127.29, 128.81, 128.86, 133.72, 138.00, 204.55; MS (EI) m/z (relative intensity): 208 ([77Br]M+', 22). CAS Registry No: [40774-41-2].
50% With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 2 h; Reflux To a solution of indan-1-one (5.00 g, 37.83 mmol) in carbon tetrachloride (25 mL), was added N-bromosuccinimide (7.41 g, 41.61 mmol) and a catalytic quantity of benzoyl peroxide. The reaction was refluxed for 2 h, after which time the reaction mixture was cooled and partitioned between diethyl ether and water. Purification by flash column chromatography on silica gel (eluant; petroleum ether:ethyl acetate, 9:1) afforded the title compound (2), a yellow oil (4.00g, 50percent) with the following physical properties: IR (DCM, υ) 1543, 1717, 2010, 2157 cm-1; 1HNMR (CDCl3, 400MHz) δppm = 3.06 (dd, J1= 19.8 Hz, J2= 2.3 Hz, 1H, CH2), 3.37 (dd, J1=19.8 Hz, J2=7.2 Hz, 1H, CH2), 5.61 (dd, J1=7.0 Hz, J2=2.1 Hz, 1H, CHBr), 7.49 (dt, J1=7.8 Hz, J2=4.0 Hz, 1H, Ar-H), 7.74 (m, 3 x Ar-H).
11 g With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In chloroform for 3 h; Inert atmosphere; Reflux 1-Indanone (8) (10 g, 0.0758 mol, 1.0 eq) react with N-bromosuccinimide (NBS) (13.8 g, 0.0758 mol 1.0 eq) in a catalyst azobisisobutyronitrile (AIBN), was refluxed in CHCl3 (100 mL) solvent for 3 h. After completion of reaction the reaction mixture was quenched with water, extracted with CHCl3, washed with water, dried over sodium sulphate and concentrated under reduced pressure to obtain the 11 g compound 9. 1H NMR (400 MHz, CDCl3); δ 7.70 (dd, 3H, Ar-H), 7.47 (m, 1H, Ar-H), 5.59 (q, 1H, CH-Br), 3.34 (dd, 2H, CH2-CO), 3.03 (dd, 1H, CH2-CO). Mass: m/z calcd. 211, found m/z 212 (M+1)+. HPLC purity (percent): 98.58.

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