Home Cart 0 Sign in  
X

[ CAS No. 3984-34-7 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 3984-34-7
Chemical Structure| 3984-34-7
Chemical Structure| 3984-34-7
Structure of 3984-34-7 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 3984-34-7 ]

Related Doc. of [ 3984-34-7 ]

Alternatived Products of [ 3984-34-7 ]

Product Details of [ 3984-34-7 ]

CAS No. :3984-34-7 MDL No. :MFCD00002794
Formula : C10H9ClO3 Boiling Point : -
Linear Structure Formula :- InChI Key :AHVASTJJVAYFPY-UHFFFAOYSA-N
M.W : 212.63 Pubchem ID :77604
Synonyms :

Calculated chemistry of [ 3984-34-7 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.2
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 53.03
TPSA : 54.37 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) : -6.15 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.55
Log Po/w (XLOGP3) : 2.04
Log Po/w (WLOGP) : 2.39
Log Po/w (MLOGP) : 1.88
Log Po/w (SILICOS-IT) : 2.44
Consensus Log Po/w : 2.06

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.85

Water Solubility

Log S (ESOL) : -2.5
Solubility : 0.678 mg/ml ; 0.00319 mol/l
Class : Soluble
Log S (Ali) : -2.81
Solubility : 0.329 mg/ml ; 0.00155 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.15
Solubility : 0.15 mg/ml ; 0.000705 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.34

Safety of [ 3984-34-7 ]

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

Application In Synthesis of [ 3984-34-7 ]

* 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.

  • Upstream synthesis route of [ 3984-34-7 ]
  • Downstream synthetic route of [ 3984-34-7 ]

[ 3984-34-7 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 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
  • 2
  • [ 3984-34-7 ]
  • [ 26673-32-5 ]
  • [ 529-34-0 ]
Reference: [1] Patent: US5502048, 1996, A,
  • 3
  • [ 3984-34-7 ]
  • [ 4619-18-5 ]
YieldReaction ConditionsOperation in experiment
96% With potassium hydroxide; hydrazine hydrate In dichloromethane; water; diethylene glycol 4-(p-chlorophenyl)butanoic acid (34a)
A mixture of 3-(4-chlorobenzoyl) propionic acid (33) (2.50 g, 12.0 mmol), KOH (s) (1.75 g, 31.2 mmol), and hydrazine monohydrate (1.25 mL, 25.8 mmol) in 12.5 mL of diethylene glycol was refluxed azeotropically at 120-130° C. for 90 min to remove water.
The reaction mixture was then refluxed at 170° C. for 3 h, cooled to RT, diluted with 12.5 mL of water, and poured into 15 mL 2.5 N HCl(aq).
The precipate was filtered off, dissolved in CH2Cl2, and the solvent removed to give 34a (2.23 g, 96percent) as a white solid. UV λmax 223 (8980, 95percent ETHANOL); 1H NMR (400 MHz, CDCl3) δ 7.26 (d, J=7 Hz, 2H), 7.12 (d, J=8 Hz, 2H), 2.66 (t, J=4 Hz, 2H), 2.38 (t, J=4 Hz, 2H), 1.96 (m, 2H); 13C NMR (CDCl3) δ 179.3, 140.0, 132.2, 130.2, 128.9, 34.7, 33.4, 26.4; IR (drift) 3063 (s), 3051 (s), 2955 (s), 2923 (s,b), 2905 (s), 2814, 2797, 2493 (b), 2466, 2413, 2367 (b), 2321, 1706 (s), 1492 (s), 1212 (s), cm-1; MS (El) m/z (rel. intensity) 198 (M+, 22), 200 (7), 198 (22), 140 (32), 139 (17), 138 (99), 127 (15), 125 (48), 103 (10), 89 (13), 60 (9); HRMS (EI) calcd for 198.0448, found 198.0441.
89% With potassium hydroxide; hydrazine In ethylene glycol at 120 - 190℃; for 8 h; Heating / reflux A mixture of 4-(4-chlorophenyl)4-oxobutanoic acid (1 eq.), KOH (3 eq.) and hydrazine hydrate (2.2 eq.) in ethylene glycol was refluxed azeotropically at 120-130° C. for 5 hours, the temperature was increased gradually to 180° C. Heating under reflux was then continued at 190° C. for 3 hours. The reaction mixture was cooled to 25° C., diluted with water and poured into a solution 2.5N HCl to give white crystals of 4-(4-chlorophenyl)butanoic acid (89percent).
89% With hydrazine hydrate; potassium hydroxide In diethylene glycol at 120 - 200℃; for 5 h; Dean-Stark 4-(4-Chlorophenyl)butanoic acid: 4-(4-Chlorophenyl)-4-oxobutanoic acid (1.06 g, 5 mmol) and KOH (85percent by wt, 0.79 g, 12 mmol) were placed in a round-bottomed flask fitted with a Dean-Stark apparatus and a reflux condenser and suspended in diethylene glycol (10 mL) at RT. Then, hydrazine monohydrate (50percent by wt., 1.20 g, 12 mmol) was added slowly to the reaction at RT after which it was heated to 120- 130 °C for 2 h. The reaction became homogenous after heating for approximately 45 min. After 2 h, the temperature was increased to 180-200 °C and the reaction stirred for an additional 3 h to remove residual hydrazine and water via the Dean-Stark trap. The reaction was then cooled to RT, diluted with H20 (10 mL), and poured into a 2.5 N aqueous solution of HQ (20 mL). The suspension was cooled in an ice bath and the resulting precipitate was isolated by filtration. To remove residual diethylene glycol, the solid was dissolved in a saturated aqueous solution of K2CO3 (20 mL), diluted with H20 (20 niL), and poured into a 2.5 N aqueous solution of HC1 (20 mL). The suspension was again cooled in an ice bath and the precipitate isolated by filtration, washed with cold H20 (2x 15 mL), and dried under vacuum. The title compound was isolated as a white solid (0.89 g, 89percent). NMR (500 MHz, DMSO- d6): δ 12.06 (br, 1H), 7.32 (d, J= 8.5 Hz, 2H), 7.21 (d, J= 8.5 Hz, 2H), 2.57 (t, J= (0563) 7.4 Hz, 2H), 2.20 (t, J= 7.3 Hz, 2H), 1.77 (q, J= 7.5 Hz, 2H). 13C NMR (125 MHz, DMSO-i/6): δ 174.16, 140.57, 130.41, 130.17, 128.20, 33.63, 32.95, 26.1 1. ESI- LRMS: [M-H]- = m/z 284.3. ESI-HRMS: calcd. for C10H1 1C102: [M-H]- = m/z 197.0375, found: [M-H]- = m/z 197.0379.
79% With hydrazine hydrate; potassium hydroxide In diethylene glycol at 120 - 180℃; for 4.5 h; Dean-Stark A heterogeneous mixture of 3-(4-chlorobenzoyl)-propionic acid (20 g, 188.1 mmol), potassium hydroxide (11.7 g, 208.7 mmol), hydrazine monohydrate (10 mL, 205.1 mmol), and diethylene glycol (84 mL) were heated in a flask equipped with a Dean-Stark trap and condenser. The mixture became homogeneous on heating. The mixture maintained at 120-130oC for 1.5 h and raised to 180oC for 3 h. The reaction mixture was cooled to room temperature, diluted with water and added 2.5M HCl. The mixture was allowed to stand for 16 h and the white solid collected by filtration. To remove the residual diethylene glycol, the solid dissolved in sat. K2CO3and water. The clear solution was poured into stirred 2.5M HCl. White solid was collected by filtration, washed with water (30.0 g, 79 percent).1H NMR (400 MHz, CDCl3) δ 2.12 -2.14 (m, 2H), 2.37 (t,J= 9.0, 2H), 2.56 (t,J= 6.0, 2H), 7.12 (s, 2H), 7.26 (s, 2H).

Reference: [1] Patent: US6410585, 2002, B1,
[2] Journal of Medicinal Chemistry, 1982, vol. 25, # 8, p. 947 - 952
[3] Patent: US2005/165004, 2005, A1, . Location in patent: Page/Page column 28
[4] Patent: WO2015/134973, 2015, A1, . Location in patent: Page/Page column 97; 98
[5] Angewandte Chemie - International Edition, 2017, vol. 56, # 41, p. 12476 - 12480[6] Angew. Chem., 2017, vol. 129, p. 12650 - 12654,5
[7] Journal of Medicinal Chemistry, 2013, vol. 56, # 23, p. 9427 - 9440
[8] Journal of Medicinal Chemistry, 2009, vol. 52, # 21, p. 6768 - 6781
[9] Patent: WO2017/150904, 2017, A1, . Location in patent: Paragraph 309-311
[10] Justus Liebigs Annalen der Chemie, 1928, vol. 462, p. 147
[11] Patent: US5492905, 1996, A,
[12] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 20, p. 5586 - 5590
[13] Australian Journal of Chemistry, 2010, vol. 63, # 2, p. 211 - 226
[14] Chemical Communications, 2016, vol. 52, # 56, p. 8757 - 8760
[15] Advanced Synthesis and Catalysis, 2018, vol. 360, # 15, p. 2894 - 2899
[16] Patent: US5502048, 1996, A,
  • 4
  • [ 3984-34-7 ]
  • [ 4619-18-5 ]
YieldReaction ConditionsOperation in experiment
96% With potassium hydroxide; hydrazine hydrate In dichloromethane; water; diethylene glycol 4-(p-chlorophenyl)butanoic acid (35a).
A mixture of 3-(4-chlorobenzoyl) propionic acid (34) (2.50 g, 12.0 mmol), KOH (s) (1.75 g, 31.2 mmol), and hydrazine monohydrate (1.25 mL, 25.8 mmol) in 12.5 mL of diethylene glycol was refluxed azeotropically at 120-130° C. for 90 min to remove water.
The reaction mixture was then refluxed at 170° C. for 3 h, cooled to RT, diluted with 12.5 mL of water, and poured into 15 mL 2.5 N HCl(aq).
The precipate was filtered off, dissolved in CH2Cl2, and the solvent removed to give 35a (2.23 g, 96percent) as a white solid. UV λmax 223 (8980, 95percent ETHANOL); 1H NMR (400 MHz, CDCl3) δ 7.26 (d, J=7 Hz, 2H), 7.12 (d, J=8 Hz, 2H), 2.66 (t, J=4 Hz, 2H), 2.38 (t, J=4 Hz, 2H), 1.96 (m, 2H); 13C NMR (CDCl3) δ 179.3, 140.0, 132.2, 130.2, 128.9, 34.7, 33.4, 26.4; IR (drift) 3063 (s), 3051 (s), 2955 (s), 2923 (s,b), 2905 (s), 2814, 2797, 2493 (b), 2466, 2413, 2367 (b), 2321, 1706 (s), 1492 (s), 1212 (s), cm-1; MS (EI) m/z (rel. intensity) 198 (M+, 22), 200 (7), 198 (22), 140 (32), 139 (17), 138 (99), 127 (15), 125 (48), 103 (10), 89 (13), 60 (9); HRMS (EI) calcd for 198.0448, found 198.0441.
Reference: [1] Patent: US6410585, 2002, B1,
  • 5
  • [ 3984-34-7 ]
  • [ 279687-54-6 ]
Reference: [1] Patent: EP2687528, 2014, A1,
[2] Patent: WO2014/12614, 2014, A1,
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 3984-34-7 ]

Aryls

Chemical Structure| 36978-49-1

[ 36978-49-1 ]

5-(4-Chlorophenyl)-5-oxopentanoic acid

Similarity: 1.00

Chemical Structure| 898765-73-6

[ 898765-73-6 ]

7-(3-Chlorophenyl)-7-oxoheptanoic acid

Similarity: 1.00

Chemical Structure| 898765-75-8

[ 898765-75-8 ]

8-(3-Chlorophenyl)-8-oxooctanoic acid

Similarity: 1.00

Chemical Structure| 75381-46-3

[ 75381-46-3 ]

5-(3-Chlorophenyl)-5-oxovaleric acid

Similarity: 1.00

Chemical Structure| 898765-71-4

[ 898765-71-4 ]

6-(3-Chlorophenyl)-6-oxohexanoic acid

Similarity: 1.00

Chlorides

Chemical Structure| 36978-49-1

[ 36978-49-1 ]

5-(4-Chlorophenyl)-5-oxopentanoic acid

Similarity: 1.00

Chemical Structure| 898765-73-6

[ 898765-73-6 ]

7-(3-Chlorophenyl)-7-oxoheptanoic acid

Similarity: 1.00

Chemical Structure| 898765-75-8

[ 898765-75-8 ]

8-(3-Chlorophenyl)-8-oxooctanoic acid

Similarity: 1.00

Chemical Structure| 75381-46-3

[ 75381-46-3 ]

5-(3-Chlorophenyl)-5-oxovaleric acid

Similarity: 1.00

Chemical Structure| 898765-71-4

[ 898765-71-4 ]

6-(3-Chlorophenyl)-6-oxohexanoic acid

Similarity: 1.00

Ketones

Chemical Structure| 36978-49-1

[ 36978-49-1 ]

5-(4-Chlorophenyl)-5-oxopentanoic acid

Similarity: 1.00

Chemical Structure| 898765-73-6

[ 898765-73-6 ]

7-(3-Chlorophenyl)-7-oxoheptanoic acid

Similarity: 1.00

Chemical Structure| 898765-75-8

[ 898765-75-8 ]

8-(3-Chlorophenyl)-8-oxooctanoic acid

Similarity: 1.00

Chemical Structure| 75381-46-3

[ 75381-46-3 ]

5-(3-Chlorophenyl)-5-oxovaleric acid

Similarity: 1.00

Chemical Structure| 898765-71-4

[ 898765-71-4 ]

6-(3-Chlorophenyl)-6-oxohexanoic acid

Similarity: 1.00

Carboxylic Acids

Chemical Structure| 36978-49-1

[ 36978-49-1 ]

5-(4-Chlorophenyl)-5-oxopentanoic acid

Similarity: 1.00

Chemical Structure| 898765-73-6

[ 898765-73-6 ]

7-(3-Chlorophenyl)-7-oxoheptanoic acid

Similarity: 1.00

Chemical Structure| 898765-75-8

[ 898765-75-8 ]

8-(3-Chlorophenyl)-8-oxooctanoic acid

Similarity: 1.00

Chemical Structure| 75381-46-3

[ 75381-46-3 ]

5-(3-Chlorophenyl)-5-oxovaleric acid

Similarity: 1.00

Chemical Structure| 898765-71-4

[ 898765-71-4 ]

6-(3-Chlorophenyl)-6-oxohexanoic acid

Similarity: 1.00