Home Cart 0 Sign in  
X

[ CAS No. 54664-55-0 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 54664-55-0
Chemical Structure| 54664-55-0
Chemical Structure| 54664-55-0
Structure of 54664-55-0 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 54664-55-0 ]

Related Doc. of [ 54664-55-0 ]

Alternatived Products of [ 54664-55-0 ]

Product Details of [ 54664-55-0 ]

CAS No. :54664-55-0 MDL No. :MFCD11113078
Formula : C8H8ClN Boiling Point : -
Linear Structure Formula :- InChI Key :IGDLNAWHTASKKG-UHFFFAOYSA-N
M.W : 153.61 Pubchem ID :12203327
Synonyms :

Calculated chemistry of [ 54664-55-0 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.38
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 41.87
TPSA : 12.89 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) : -5.7 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.97
Log Po/w (XLOGP3) : 2.17
Log Po/w (WLOGP) : 2.22
Log Po/w (MLOGP) : 2.06
Log Po/w (SILICOS-IT) : 3.25
Consensus Log Po/w : 2.33

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.6
Solubility : 0.383 mg/ml ; 0.00249 mol/l
Class : Soluble
Log S (Ali) : -2.07
Solubility : 1.3 mg/ml ; 0.00844 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.45
Solubility : 0.054 mg/ml ; 0.000352 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.89

Safety of [ 54664-55-0 ]

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 [ 54664-55-0 ]

* 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 [ 54664-55-0 ]
  • Downstream synthetic route of [ 54664-55-0 ]

[ 54664-55-0 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 54664-52-7 ]
  • [ 1073-67-2 ]
  • [ 17422-33-2 ]
  • [ 52537-00-5 ]
  • [ 54664-55-0 ]
Reference: [1] Journal of the American Chemical Society, 1981, vol. 103, # 6, p. 1525 - 1533
  • 2
  • [ 54664-52-7 ]
  • [ 1073-67-2 ]
  • [ 17422-33-2 ]
  • [ 52537-00-5 ]
  • [ 54664-55-0 ]
Reference: [1] Journal of the American Chemical Society, 1981, vol. 103, # 6, p. 1525 - 1533
  • 3
  • [ 90685-58-8 ]
  • [ 54664-55-0 ]
YieldReaction ConditionsOperation in experiment
93% at 120℃; for 3 h; 6,7-Dihydro-5H-cyclopenta[b]pyridine 1-oxide (2.5 g, 18 mmol) was mixed with phosphoryl chloride (20 mL, 200 mmol). The reaction mixture was stirred at 120° C. for 3 h. The excess POCl3 was removed under reduced pressure. The residue was diluted in 80 mL of EtOAc and neutralized with Na2CO3 solution. After filtration, the aqueous layer was extracted with EtOAc twice. The combined organic extracts were dried, filtered and concentrated under reduced pressure to give the sub-title compound (2.6 g, 93percent). LCMS calc. for C8H9ClN (M+H)+: m/z=154.2. Found: 154.3
93% at 120℃; for 3 h; 6,7-Dihydro-5H-cyclopenta[b]pyridine 1-oxide (2.5 g, 18 mmol) was mixed with POCl3 (20 mL). The reaction mixture was stirred at 120° C. for 3 h. The excess POCl3 was removed under reduced pressure. The residue was diluted in EtOAc (80 mL) and neutralized with aq. Na2CO3. After filtration, the aqueous layer was extracted with EtOAc twice. The combined organic layers were dried, filtered and concentrated under reduced pressure to give the sub-title compound (2.6 g, 93percent). LCMS calc. for C8H9ClN (M+H)+: m/z=154.0. Found: 154.3.
93% at 120℃; for 3 h; 6,7-Dihydro-5H-cyclopenta[Z>]pyridine 1-oxide (2.5 g, 18 mmol) was mixed with POCh (20 mL). The reaction mixture was stirred at 120 °C for 3 h. The excess POCh was removed under reduced pressure. The residue was dissolved in EtOAc (80 mL) and neutralized with aq. Na2C03. After filtration, the aqueous layer was extracted with EtOAc twice. The combined organic layers were dried, filtered and concentrated under reduced pressure to give the sub-title compound (2.6 g, 93percent). LCMS calc. for CsHoClN (M+H)+: m/z = 154.0. Found: 154.3.
91%
Stage #1: With lithium chloride In acetonitrile at 20℃; for 0.166667 h;
Stage #2: With trichlorophosphate In water; acetonitrile at 20 - 80℃;
Stage #3: With sodium carbonate In water; acetonitrile at 20℃; for 0.666667 h;
b- :1.) .Preparation of .mtermediate.b A solution of 49.5g intermediate a (0.366mol), 15.5g lithiumchloride (LiCl) (leq) and 495mL acetonitrile (lOmL/g) was prepared and stirred for 10 minutes at ambient temperature. 102mL phosphoroxychloride (POCI3) (3eq) was added dropwise to the reaction mixture. The reaction mixture was heated to 800C and stirred for one night. The reaction mixture was cooled to 450C and 75OmL H2O (15mL/g) was added dropwise, while keeping the temperature between 400C and 500C, over lhour. The reaction mixture was cooled to ambient temperature and stirred for 2 hours at ambient temperature. 213g Na2CO3 (5.5eq) was added and stirred for 30 minutes at ambient temperature. Further Na2CO3 was added and stirring for 10 minutes at ambient temperature. 75OmL dsopropylether (DIPE) (15mL/g) was added and 50OmL H2O (lOmL/g). The mixture was stirred for 10 minutes at ambient temperature. The reaction mixture was filtered over dicalite. The layers were separated. The organic layer was dried with MgSO4. MgSO4 was filtered off. The filtrate was concentrated under reduced pressure. Yield: 5 Ig (91percent) (brown oil) of intermediate b.

Reference: [1] Patent: US2014/200216, 2014, A1, . Location in patent: Paragraph 0532; 0533
[2] Patent: US2014/200227, 2014, A1, . Location in patent: Paragraph 0641; 0642
[3] Patent: WO2016/196244, 2016, A1, . Location in patent: Page/Page column 195
[4] Patent: WO2009/19274, 2009, A1, . Location in patent: Page/Page column 32
[5] Advanced Synthesis and Catalysis, 2007, vol. 349, # 14-15, p. 2345 - 2352
[6] Patent: WO2016/168098, 2016, A1, . Location in patent: Page/Page column 38
  • 4
  • [ 533-37-9 ]
  • [ 54664-55-0 ]
Reference: [1] Patent: US2014/200216, 2014, A1,
[2] Patent: US2014/200227, 2014, A1,
[3] Patent: WO2016/168098, 2016, A1,
[4] Patent: WO2016/196244, 2016, A1,
  • 5
  • [ 54664-52-7 ]
  • [ 1073-67-2 ]
  • [ 17422-33-2 ]
  • [ 52537-00-5 ]
  • [ 54664-55-0 ]
Reference: [1] Journal of the American Chemical Society, 1981, vol. 103, # 6, p. 1525 - 1533
  • 6
  • [ 54664-52-7 ]
  • [ 1073-67-2 ]
  • [ 54664-55-0 ]
  • [ 76653-03-7 ]
Reference: [1] Journal of the American Chemical Society, 1981, vol. 103, # 6, p. 1525 - 1533
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 54664-55-0 ]

Chlorides

Chemical Structure| 611-35-8

[ 611-35-8 ]

4-Chloroquinoline

Similarity: 0.85

Chemical Structure| 86-98-6

[ 86-98-6 ]

4,7-Dichloroquinoline

Similarity: 0.84

Chemical Structure| 1998216-32-2

[ 1998216-32-2 ]

4-Chloro-3-cyclopropylpyridine hydrochloride

Similarity: 0.83

Chemical Structure| 126053-15-4

[ 126053-15-4 ]

4-Chloro-6,7-dihydro-5H-cyclopenta[b]pyridin-7-ol

Similarity: 0.83

Chemical Structure| 98420-91-8

[ 98420-91-8 ]

4-Chloro-2-isopropylpyridine

Similarity: 0.83

Related Parent Nucleus of
[ 54664-55-0 ]

Other Aromatic Heterocycles

Chemical Structure| 126053-15-4

[ 126053-15-4 ]

4-Chloro-6,7-dihydro-5H-cyclopenta[b]pyridin-7-ol

Similarity: 0.83

Chemical Structure| 230-07-9

[ 230-07-9 ]

4,7-Phenanthroline

Similarity: 0.72

Chemical Structure| 945666-87-5

[ 945666-87-5 ]

4-Chloro-6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl acetate

Similarity: 0.68

Chemical Structure| 15679-03-5

[ 15679-03-5 ]

6-Chlorophenanthridine

Similarity: 0.66

Chemical Structure| 1187930-42-2

[ 1187930-42-2 ]

6,7-Dihydro-5H-cyclopenta[b]pyridin-7-amine hydrochloride

Similarity: 0.66