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[ CAS No. 26673-32-5 ] {[proInfo.proName]}

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Chemical Structure| 26673-32-5
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Product Details of [ 26673-32-5 ]

CAS No. :26673-32-5 MDL No. :MFCD01928386
Formula : C10H9ClO Boiling Point : -
Linear Structure Formula :- InChI Key :IIMAYXKDBHTQHC-UHFFFAOYSA-N
M.W : 180.63 Pubchem ID :256677
Synonyms :

Calculated chemistry of [ 26673-32-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 49.31
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) : -5.52 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.12
Log Po/w (XLOGP3) : 2.65
Log Po/w (WLOGP) : 2.86
Log Po/w (MLOGP) : 2.57
Log Po/w (SILICOS-IT) : 3.64
Consensus Log Po/w : 2.77

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.0
Solubility : 0.181 mg/ml ; 0.001 mol/l
Class : Soluble
Log S (Ali) : -2.66
Solubility : 0.396 mg/ml ; 0.00219 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.01
Solubility : 0.0177 mg/ml ; 0.0000977 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.7

Safety of [ 26673-32-5 ]

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 [ 26673-32-5 ]

* 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 [ 26673-32-5 ]
  • Downstream synthetic route of [ 26673-32-5 ]

[ 26673-32-5 ] Synthesis Path-Upstream   1~21

  • 1
  • [ 96-48-0 ]
  • [ 108-90-7 ]
  • [ 26673-30-3 ]
  • [ 26673-32-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 8, p. 2281 - 2284
  • 2
  • [ 4619-18-5 ]
  • [ 26673-32-5 ]
YieldReaction ConditionsOperation in experiment
81% at 90℃; for 0.166667 h; Polyphosphoric acid (20 g, excess) was place in a beaker and heated to 90oC. 4-(4-chlorophenyl)butanoic acid (Preparation example 31, 3 g, 17 mmol) was added in portions. The mixture was stirred for 5 min an additional portion of polyphosphoric acid (20 g, excess) was added and heated to 90oC for 5 min. The thick, homogenous viscous orange oil was cooled to 60oC before water was added. When the reaction was completed, the mixture was cooled to room temperature and extracted with EtOAc. The organic layer was washed with water, 1N NaOH and water, dried over MgSO4, and evaporated under reduced pressure. The crude product was purified by silica gel column chromatography to give as a white solid (2.5 g, 81 percent).1H NMR (400 MHz, CDCl3) δ 2.12-2.18 (m, 2H), 2.67 (t,J= 6.8, 2H), 2.95 (t,J= 6.8, 2H), 7.22 (d,J= 8.0, 1H), 7.42 (dd,J= 10.2, 2.4, 1H), 7.85 (d,J= 2.4, 1H).
Reference: [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 41, p. 12476 - 12480[2] Angew. Chem., 2017, vol. 129, p. 12650 - 12654,5
[3] Journal of Medicinal Chemistry, 2009, vol. 52, # 21, p. 6768 - 6781
[4] Patent: WO2017/150904, 2017, A1, . Location in patent: Paragraph 312-314
[5] Synthetic Communications, 1991, vol. 21, # 8-9, p. 981 - 987
[6] Advanced Synthesis and Catalysis, 2018, vol. 360, # 15, p. 2894 - 2899
[7] Journal of the Chemical Society, 1950, p. 1027,1032
[8] Phytochemistry (Elsevier), 1984, vol. 23, # 2, p. 313 - 318
[9] Australian Journal of Chemistry, 2010, vol. 63, # 2, p. 211 - 226
  • 3
  • [ 22009-40-1 ]
  • [ 26673-32-5 ]
YieldReaction ConditionsOperation in experiment
3.05 mmol, 98% With sodium nitrite In hydrogenchloride; water Step B:
7-chloro-1-tetralone
7-Amino-1-tetralone (500 mg, 3.1 mmol) was suspended in 3 mL of water and treated with 3 mL of concentrated hydrochloric acid with stirring.
The mixture was cooled in an ice bath and treated dropwise with vigorous stirring with a solution of 241 mg of sodium nitrite in 1.5 mL of water (3.5 mmol, 1.1 eq).
The mixture was stirred at 0°-5° for 15 minutes then added dropwise to a cold solution of 366 mg of CuCl (3.7 mmol, 1.2 eq) in 6 mL of concentrated hydrochloric acid.
The mixture was stirred for 5 minutes at 0° and 1 hour at room temperature.
The mixture was extracted with methylene chloride (3*15 mL); the combined extracts were washed with brine, dried over magnesium sulfate, filtered and evaporated to dryness under vacuum at room temperature to give 550 mg (3.05 mmol, 98percent) of the product. 1 H NMR (300 MHz, CDCl3): 2.16 (m,2H), 2.67 (t,6 Hz,2H), 2.95 (t,6 Hz,2H), 7.22 (d,8 Hz,1H), 7.44 (dd;2,8 Hz;1H), 8.01 (d,2 Hz,1H). FAB-MS: calculated for C10 H9 ClO 180; found 181 (M+H,10percent).
94% With sodium nitrite In hydrogenchloride; conc HCl; water (ii)
7-Chloro-1-tetralone
NaNO2 (0.7 g; 10 mmol) dissolved in water (10 mL) was added with stirring to an ice-cold solution of 7-amino-1-tetralone (1.4 g; 8.8 mmol; from step (i) above) in conc HCl (aq.) over a period of 5 minutes.
The resultant cold solution was then added slowly to an ice-cold solution of CuCl (1.5 g, 15 mmol) in conc. HCl (aq.), whereafter the resultant solution was stirred at RT for 2 hours and at 60° C. for 30 minutes.
The slurry was cooled with ice, and the resultant precipitate was suction filtered, washed with water, and air dried.
Yield 1.50 g (94percent).
1H-NMR (500 MHz; CDCl3): δ8.00 (d, 1H); 7.41 (dd, 1H); 7.20 (d, 1H); 2.95 (t, 2H); 2.66 (m, 2H); 2.14 (m, 2H)
Reference: [1] Justus Liebigs Annalen der Chemie, 1927, vol. 451, p. 53
[2] Patent: US5206235, 1993, A,
[3] Patent: US6265397, 2001, B1,
[4] Journal of the American Chemical Society, 2018, vol. 140, # 3, p. 940 - 946
  • 4
  • [ 4619-18-5 ]
  • [ 26673-32-5 ]
  • [ 529-34-0 ]
Reference: [1] Patent: US5492905, 1996, A,
[2] Patent: US5502048, 1996, A,
  • 5
  • [ 56820-67-8 ]
  • [ 26673-32-5 ]
YieldReaction ConditionsOperation in experiment
89.3% With PPA In (2S)-N-methyl-1-phenylpropan-2-amine hydrate C.
7-chloro-1-tetralone (III)
101 g (0.51 mole) of (II) is added to 1.25 kg polyphosphoric acid and the mixture is heated to 70° with stirring.
The temperature rises spontaneously so heating is reduced, maintaining an internal temperature between 90°-100° for a total reaction time of one hour.
The rust-colored solution is poured into 1.2 liters of ice water, stirred for 30 minutes and the crude product is filtered.
The light yellow product is then taken up in ether (2.0 liters) and washed successively with water (1.0 liter), 5percent sodium hydroxide (1.0 liter), water (1.0 liter), 5percent acetic acid (500 ml), 5percent sodium bicarbonate (500 ml) and water (1.0 liter).
The organic phase is dried over anhydrous sodium sulfate, filtered and evaporated. Yield: 82.0 g (89.3percent), mp 92°-93°.
The product is dried overnight in vacuo at room temperature.
Reference: [1] Patent: US3985731, 1976, A,
  • 6
  • [ 529-34-0 ]
  • [ 26673-32-5 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1983, vol. 20, # 3, p. 663 - 666
[2] Justus Liebigs Annalen der Chemie, 1927, vol. 451, p. 53
  • 7
  • [ 3984-34-7 ]
  • [ 26673-32-5 ]
Reference: [1] Journal of medicinal chemistry, 1970, vol. 13, # 1, p. 87 - 89
[2] Journal of medicinal chemistry, 1971, vol. 14, # 2, p. 90 - 94
[3] Australian Journal of Chemistry, 2010, vol. 63, # 2, p. 211 - 226
[4] Patent: WO2017/150904, 2017, A1,
[5] Angewandte Chemie - International Edition, 2017, vol. 56, # 41, p. 12476 - 12480[6] Angew. Chem., 2017, vol. 129, p. 12650 - 12654,5
[7] Advanced Synthesis and Catalysis, 2018, vol. 360, # 15, p. 2894 - 2899
  • 8
  • [ 108-90-7 ]
  • [ 26673-32-5 ]
Reference: [1] Chemical Communications, 2016, vol. 52, # 56, p. 8757 - 8760
[2] Angewandte Chemie - International Edition, 2017, vol. 56, # 41, p. 12476 - 12480[3] Angew. Chem., 2017, vol. 129, p. 12650 - 12654,5
[4] Advanced Synthesis and Catalysis, 2018, vol. 360, # 15, p. 2894 - 2899
  • 9
  • [ 54654-08-9 ]
  • [ 26673-32-5 ]
Reference: [1] Phytochemistry (Elsevier), 1984, vol. 23, # 2, p. 313 - 318
  • 10
  • [ 40353-34-2 ]
  • [ 26673-32-5 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1927, vol. 451, p. 53
[2] Journal of the American Chemical Society, 2018, vol. 140, # 3, p. 940 - 946
  • 11
  • [ 96-48-0 ]
  • [ 108-90-7 ]
  • [ 26673-30-3 ]
  • [ 26673-32-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 8, p. 2281 - 2284
  • 12
  • [ 22991-05-5 ]
  • [ 26673-32-5 ]
Reference: [1] Chemical Communications, 2016, vol. 52, # 56, p. 8757 - 8760
  • 13
  • [ 62903-14-4 ]
  • [ 26673-32-5 ]
Reference: [1] Chemical Communications, 2016, vol. 52, # 56, p. 8757 - 8760
  • 14
  • [ 51114-94-4 ]
  • [ 26673-32-5 ]
Reference: [1] Chemical Communications, 2016, vol. 52, # 56, p. 8757 - 8760
  • 15
  • [ 56820-66-7 ]
  • [ 26673-32-5 ]
Reference: [1] Patent: US3985731, 1976, A,
  • 16
  • [ 56820-70-3 ]
  • [ 26673-32-5 ]
Reference: [1] Patent: US3985731, 1976, A,
  • 17
  • [ 3984-34-7 ]
  • [ 26673-32-5 ]
  • [ 529-34-0 ]
Reference: [1] Patent: US5502048, 1996, A,
  • 18
  • [ 17151-48-3 ]
  • [ 26673-32-5 ]
Reference: [1] Synthetic Communications, 1991, vol. 21, # 8-9, p. 981 - 987
  • 19
  • [ 1821-12-1 ]
  • [ 26673-32-5 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1927, vol. 451, p. 53
  • 20
  • [ 96-48-0 ]
  • [ 108-90-7 ]
  • [ 26673-32-5 ]
Reference: [1] Archiv der Pharmazie, 1975, vol. 308, # 2, p. 94 - 109
  • 21
  • [ 108-30-5 ]
  • [ 108-90-7 ]
  • [ 26673-32-5 ]
Reference: [1] Journal of the Chemical Society, 1952, p. 279
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