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[ CAS No. 321-38-0 ] {[proInfo.proName]}

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Chemical Structure| 321-38-0
Chemical Structure| 321-38-0
Structure of 321-38-0 * Storage: {[proInfo.prStorage]}
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Product Details of [ 321-38-0 ]

CAS No. :321-38-0 MDL No. :MFCD00003873
Formula : C10H7F Boiling Point : -
Linear Structure Formula :- InChI Key :CWLKTJOTWITYSI-UHFFFAOYSA-N
M.W : 146.16 Pubchem ID :9450
Synonyms :

Calculated chemistry of [ 321-38-0 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 43.91
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
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) : -5.04 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.12
Log Po/w (XLOGP3) : 3.03
Log Po/w (WLOGP) : 3.4
Log Po/w (MLOGP) : 3.76
Log Po/w (SILICOS-IT) : 3.44
Consensus Log Po/w : 3.15

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.33
Solubility : 0.0687 mg/ml ; 0.00047 mol/l
Class : Soluble
Log S (Ali) : -2.7
Solubility : 0.295 mg/ml ; 0.00202 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.33
Solubility : 0.00684 mg/ml ; 0.0000468 mol/l
Class : Moderately soluble

Medicinal Chemistry

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

Safety of [ 321-38-0 ]

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 [ 321-38-0 ]

* 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 [ 321-38-0 ]
  • Downstream synthetic route of [ 321-38-0 ]

[ 321-38-0 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 321-38-0 ]
  • [ 341-41-3 ]
YieldReaction ConditionsOperation in experiment
91.5% for 2 h; Reflux 1-Fluoronaphthalene (20.0 g, 0.137 mol) and carbon tetrachloride (120.0 mL) were added to a 500 mL one-necked flask, and bromine (10.9 g, 0.068 mol) was added dropwise and refluxed for 2 h. After completion of the reaction, the concentrated solution was concentrated under reduced pressure, and the concentrated solution was poured into methanol (80.0 mL). The solid was precipitated at room temperature overnight, and 28.2 g of 1-bromo-4-fluoronaphthalene. The yield was 91.5percent.
Reference: [1] Patent: CN106478376, 2017, A, . Location in patent: Paragraph 0009; 0020; 0021; 0029; 0030; 0038; 0039; 0047
[2] Journal of Medicinal Chemistry, 2004, vol. 47, # 6, p. 1575 - 1586
[3] Justus Liebigs Annalen der Chemie, 1931, vol. 487, p. 270,282
[4] Patent: US2001/49379, 2001, A1,
[5] Patent: US6211208, 2001, B1,
  • 2
  • [ 56-23-5 ]
  • [ 321-38-0 ]
  • [ 7726-95-6 ]
  • [ 341-41-3 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1931, vol. 487, p. 270,282
  • 3
  • [ 321-38-0 ]
  • [ 341-92-4 ]
Reference: [1] Journal of Organic Chemistry, 2011, vol. 76, # 19, p. 7975 - 7984
[2] Justus Liebigs Annalen der Chemie, 1931, vol. 487, p. 270,282
[3] Bulletin des Societes Chimiques Belges, 1966, vol. 75, p. 577 - 581
[4] Israel Journal of Chemistry, 1977, vol. 16, p. 299 - 303
  • 4
  • [ 321-38-0 ]
  • [ 7697-37-2 ]
  • [ 64-19-7 ]
  • [ 341-92-4 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1931, vol. 487, p. 270,282
  • 5
  • [ 321-38-0 ]
  • [ 1583-67-1 ]
Reference: [1] Canadian Journal of Chemistry, 1980, vol. 58, p. 2484 - 2490
  • 6
  • [ 321-38-0 ]
  • [ 438-32-4 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1931, vol. 487, p. 270,282
[2] Bulletin des Societes Chimiques Belges, 1966, vol. 75, p. 577 - 581
[3] Journal of Organic Chemistry, 2011, vol. 76, # 19, p. 7975 - 7984
  • 7
  • [ 321-38-0 ]
  • [ 315-53-7 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 13, p. 3481 - 3486
[2] Journal of Organic Chemistry, 1995, vol. 60, # 20, p. 6592 - 6594
[3] Patent: CN105566284, 2016, A,
[4] Patent: CN106478376, 2017, A,
[5] Patent: CN106478376, 2017, A,
[6] Patent: CN106478376, 2017, A,
  • 8
  • [ 321-38-0 ]
  • [ 144-62-7 ]
  • [ 132335-49-0 ]
  • [ 132335-47-8 ]
YieldReaction ConditionsOperation in experiment
75.6%
Stage #1: With sodium hydride In N,N-dimethyl acetamide at 70℃; for 0.333333 h;
Stage #2: at 110℃; for 1 h;
DX-A 03 (2.0 g, 0.011 mol)Was dissolved in dimethylacetamide (100 mL)A solution of 60percent sodium hydride (463 mg, 0.012 mol)Dropwise.The resulting mixture was heated at 70 ° C. for 20 minutes.1-Fluoronaphthalene (1.27 mL, 0.012 mol)Was added dropwise to this mixed solution,And heated at 110 ° C. for 60 minutes.The reaction mixture was diluted with water,And extracted twice with diethyl ether.The extracts are combined,Wash with water,Then washed with saturated sodium chloride solution,It was dried over anhydrous sodium sulfate,After concentration under reduced pressure,To obtain an oily compound (DX-A 04, 3.28 g, 75.6percent).
Reference: [1] Patent: JP2016/172704, 2016, A, . Location in patent: Paragraph 0027; 0053
  • 9
  • [ 321-38-0 ]
  • [ 144-62-7 ]
  • [ 132335-44-5 ]
  • [ 132335-47-8 ]
Reference: [1] Organic Process Research and Development, 2009, vol. 13, # 5, p. 854 - 856
[2] Patent: WO2009/87463, 2009, A2, . Location in patent: Page/Page column 7-8
  • 10
  • [ 13636-02-7 ]
  • [ 321-38-0 ]
  • [ 144-62-7 ]
  • [ 132335-47-8 ]
Reference: [1] Patent: WO2011/33366, 2011, A2, . Location in patent: Page/Page column 23
  • 11
  • [ 321-38-0 ]
  • [ 132335-47-8 ]
YieldReaction ConditionsOperation in experiment
80 % With oxalic acid In ISOPROPYLAMIDE; water; (S)-3-dimethylamino-1-(2-thienyl)propan-1-ol; ethyl acetate; mineral oil Example 4
Synthesis of (S)-N,N-dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine oxalate
In 50 ml of dimethylacetamide 0.5 g of sodium hydride (suspension in mineral oil) is suspended.
Suspension is stirred and in few portions 2 g of (s)-3-(dimethylamino)-1-(thienyl)-propan-1-ol is added.
After the addition is completed the suspension is warmed up to 70°C. 1.27 ml of 1-fluoronaphthalene is added and the reaction mixture is heated to 110°C.
At this temperature the solution is stirred for another three hours.
Then the reaction solution is dissolved with 300 ml of water and extracted twice with 100 ml ether.
Combined ether phases are rinsed with water, dried with sodium sulphate end evaporated to dryness.
Obtained oil is dissolved in 50 ml ethyl acetate and 0.9 g of oxalic acid is added.
The suspension is further stirred for one hour, filtered off the product and washed with ethyl acetate.
The product is dried to obtain 3.5 g (80 percent) of (S)-N,N-dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine oxalate.
Reference: [1] Patent: EP2133072, 2009, A1,
  • 12
  • [ 321-38-0 ]
  • [ 132335-44-5 ]
  • [ 132335-47-8 ]
Reference: [1] Tetrahedron Letters, 1990, vol. 31, # 45, p. 7101 - 7104
  • 13
  • [ 4885-02-3 ]
  • [ 321-38-0 ]
  • [ 172033-73-7 ]
YieldReaction ConditionsOperation in experiment
87%
Stage #1: With tin(IV) chloride In dichloromethane at 0℃; for 0.75 h;
Stage #2: at 20℃;
A solution OF A, A-DICHLOROMETHYL methyl ether (5.9 mL, 65 mmol) in CH2C12 (30 mL) was cooled in an ice bath and then treated dropwise over 15 min with SNCL4 (7.6 mL, 65 mmol). After stirring for 45 min, a solution of 1-FLUORONAPHTHALENE (5.5 mL, 50 mmol) in CH2C12 (30 mL) was added. The mixture was allowed to slowly warm to room temperature while stirring overnight. The mixture was poured in ice water (100 mL) and diluted with CH2C12 (50 mL). The layers were separated. The organic layer was diluted with CH2C12 (100 mL), washed with H20 (3 x 50 mL), dried over NA2S04, filtered, and the solvent was removed in vacuo to give the title compound (7.62 g, 87percent) as a pale yellow solid: MS (ESI) mle 175 (M + H) +.
55%
Stage #1: With tin(IV) chloride In dichloromethane at -5 - 0℃; for 0.5 h;
Stage #2: at 20℃; for 18 h;
To a 250 mL flask was added dichloromethane (30 mL) and dichloromethyl methyl ether (0.81 mL, 8.89 mmol, 1.3equivalent).The clear solution was cooled to -5 & lt; 0 & gt;Tin (IV) chloride (1.04 ml, 8.89 mmol, 1.3 eq.) Was then slowly addedGt; C), keeping the temperature below 0 & lt; 0 & gt; C. The solution was stirred at 0 & lt; 0 & gt; C for 30 minutes and then 1-fluoronaphthalene in dichloromethane (10 ml) was added(1.0 g, 6.84 mmol). The reaction mixture was allowed to equilibrate to room temperature. After about 18 hours, the dark green was mixedThe mixture was poured into ice water (40 mL) and transferred to a separatory funnel. The layers were separated and the aqueous layer was extracted with dichloromethane(3 x 20 mL). The combined organic layers were washed with water (150 mL) and saturated sodium chloride (150 mL). WillThe organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure to give a beige solid. By Biotage color(Gradient elution: 5percent to 50percent dichloromethane / hexane) to give 0.60 g (55percent) of 8 asAn off-white solid
Reference: [1] Journal of Organic Chemistry, 1995, vol. 60, # 20, p. 6592 - 6594
[2] Patent: WO2004/52890, 2004, A1, . Location in patent: Page 78
[3] Patent: CN105566284, 2016, A, . Location in patent: Paragraph 0267; 0268
[4] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 13, p. 3481 - 3486
[5] Patent: WO2008/407, 2008, A1, . Location in patent: Page/Page column 57
[6] Patent: WO2008/409, 2008, A1, . Location in patent: Page/Page column 153
[7] Patent: WO2010/79077, 2010, A1, . Location in patent: Page/Page column 32; 33
  • 14
  • [ 321-38-0 ]
  • [ 182344-25-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 6, p. 1575 - 1586
[2] Patent: CN106478376, 2017, A,
[3] Patent: CN106478376, 2017, A,
[4] Patent: CN106478376, 2017, A,
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