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[ CAS No. 1219810-16-8 ] {[proInfo.proName]}

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Chemical Structure| 1219810-16-8
Chemical Structure| 1219810-16-8
Structure of 1219810-16-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1219810-16-8 ]

CAS No. :1219810-16-8 MDL No. :MFCD30187526
Formula : C23H21ClN2O5 Boiling Point : -
Linear Structure Formula :- InChI Key :TXJZRSRTYPUYRW-NQIIRXRSSA-N
M.W : 440.88 Pubchem ID :1750826
Synonyms :
(1S,3R)-RSL3

Calculated chemistry of [ 1219810-16-8 ]

Physicochemical Properties

Num. heavy atoms : 31
Num. arom. heavy atoms : 15
Fraction Csp3 : 0.26
Num. rotatable bonds : 7
Num. H-bond acceptors : 5.0
Num. H-bond donors : 1.0
Molar Refractivity : 119.01
TPSA : 88.7 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.48 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.01
Log Po/w (XLOGP3) : 3.54
Log Po/w (WLOGP) : 2.5
Log Po/w (MLOGP) : 2.35
Log Po/w (SILICOS-IT) : 3.95
Consensus Log Po/w : 3.07

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.7
Solubility : 0.0088 mg/ml ; 0.00002 mol/l
Class : Moderately soluble
Log S (Ali) : -5.09
Solubility : 0.00361 mg/ml ; 0.00000818 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -6.51
Solubility : 0.000136 mg/ml ; 0.000000308 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 2.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 3.89

Safety of [ 1219810-16-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1219810-16-8 ]

* 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.

  • Downstream synthetic route of [ 1219810-16-8 ]

[ 1219810-16-8 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 171596-53-5 ]
  • [ 79-04-9 ]
  • [ 1219810-16-8 ]
YieldReaction ConditionsOperation in experiment
60% With sodium hydrogencarbonate In chloroform at 0 - 20℃; for 4h; 3 Synthesis of cis-, fraϖs-(3S)- and (3R)-methyl-1-(1 ,3-benzodioxol-5yl)-2- (chloroacetyl)-2,3,4,9-tetrahydro-1H-^-carboline-3-carboxilatesCompound 27[0351] Chloroacetyl chloride (0.096 mol) was slowly added to a cooled-on-ice, stirred solution of 4a or 4b (0.04 mol) and NaHCθ3 (0.048 mol) in dry chloroform (200 ml_). The reaction mixture was allowed to warm to room temperature and stirred for four hours. Dichloromethane (200 ml_) was added to the reaction mixture. The resulting solution was washed with NaHCθ3, washed with a saturated solution of NaCI, dried with MgSO4, and concentrated. The solid residue was triturated with ether, filtered off, and washed with small amount of methanol to yield the product. [0352] Cis-, trans- (3R)-methyl-1-(1 ,3-benzodioxol-5yl)-2-(chloroacetyl)-2,3,4,9-tetrahydro-1 H-yβ-carboline-3-carboxilate: yield 60 %, M.p. 273-275°C. NMR1H {δ, ppm, DMSO-d6, 500 MHz): 2.86 (3H, s, OCH3); 3.11-3.50 (2H, m, CH2CI); 3.83 (3H, s, OCH3); 4.38 (1 H, d, ArCH2, JHH = 14 Hz); 4.77 (1 H, d, ArCH2, JHH = 14 Hz); 5.19 (1 H, d, ArCH, JHH = 2.5 Hz); 6.91 (1 H, s, Ar); 7.01-7.08 (2H, dt, Ar, JHH = 25 Hz, 3 Hz); 7.23-7.53 (3H, m, Ar); 7.85 (2H, d, Ar, JHH = 4 Hz); 10.82 (1 H, s, NH). NMR13C (δ, ppm, DMSO-d6, 125.76 MHz): 21.01(s), 42.78(s), 51.09(s), 51.39(s), 51.99(s), 52.48(S), 106.34(s), 111.10 (s), 118.02(s), 118.67 (s), 121.56(s), 125.79(s), 128.72(d), 128.90(s), 136.36(s), 144.50(s), 165.82(s), I66.87(s), 169.97(s). "V2 440(M+).[0353] Cis-, trans- (3S)-methyl-1-(1 ,3-benzodioxol-5yl)-2-(chloroacetyl)-2,3,4,9-tetrahydro-1 H-0-carboline-3-carboxilate: yield 45 %, M.p. 272-273°C. NMR1H (<5, ppm, DMSO-d6, 500 MHz): 2.84 (1 H, s, OCH3); 3.12-3.49 (2H, m, CH2CI); 3.82 (3H, s, OCH3); 4.48 (1 H, d, ArCH2, JHH = 14Hz); 4.86 (1 H, d, ArCH2, JHH = 14 Hz); 5.23 (1 H, d, ArCH, JHH = 2.5 Hz); 6.91 (1 H1 s, Ar); 7.03-7.10 (2H, dt, Ar, JHH = 25 Hz, 3 Hz); 7.21-7.54 (3H1 m, Ar); 7.84 (2H, d, Ar, JHH = 4 Hz); 10.92 (1 H, s, NH). NMR13C (δ, ppm, DMSO-d6, 125.76 MHz): 21.07(s), 43.08(s), 51.15 (s), 51.50 (s), 52.13(s), 52.53 (s), 106.50(s), 111.25 (s), 118.10(s), 118.69 (s), 121.62(s), 125.87(s), 128.77(d), 128.95 (s), 136.43 (s), 144.69 (s), 165.92(s), 166.97(s), 170.09(s). m/z 440(M+).
With sodium hydrogencarbonate In chloroform at 0 - 20℃; for 4h; [0894] To a solution of AA-3 (4.50 g, 12.35 mmol, 1.00 eq) and NaHCO3 (1.25 g, 14.82 mmol, 576.40 μL, 1.20 eq) in CHCl3 (50.00 mL) was added slowly 2-chloroacetyl chloride (3.35 g, 29.64 mmol, 2.36 mL, 2.40 eq) at 0°C. The mixture was stirred at 20°C. for 4 h to give a black mixture. The completion of reaction was detected by TLC. The reaction mixture was diluted with DCM (20 mL), washed with a saturated solution of NaHCO3 and brine (10 mL each) in sequence. The organic layer was dried over Na2SO4, concentrated under reduced pressure. The product was purified by column chromatography (SiO2, Petroleum ether/Ethyl acetate=10/1 to 4:1) to give K601 . LC-MS (m/z): 441.1 [M+H]+. 1H NMR (400 MHz, DMSO, T=80°C.) δ 10.80 (s, 1H), 7.88-7.86 (m, 2H), 7.60-7.58 (m, 2H), 7.47 (d, J=7.5 Hz, 1H), 7.26 (d, J=8.0 Hz, 1H), 7.06-7.02 (m, 1H), 7.01-6.96 (m, 1H), 6.19 (s, 1H), 5.27 (s, 1H), 4.60 (d, J=13.8 Hz, 1H), 4.27-4.24 (m, 1H), 3.82 (s, 3H), 3.54 (s, 3H), 3.49-3.48 (m, 1H), 3.36-3.32 (m, 1H).
  • 2
  • [ CAS Unavailable ]
  • [ 1219810-16-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: trifluoroacetic acid / benzene / 3 h / 20 °C / Heating / reflux; Molecular sieve 1.2: pH 8 2.1: sodium hydrogencarbonate / chloroform / 4 h / 0 - 20 °C
  • 3
  • [ 14907-27-8 ]
  • [ 1219810-16-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: triethylamine / benzene / 1 h / 20 °C 2.1: trifluoroacetic acid / benzene / 1 h / Heating / reflux; Molecular sieve 3.1: trifluoroacetic acid / benzene / 3 h / 20 °C / Heating / reflux; Molecular sieve 3.2: pH 8 4.1: sodium hydrogencarbonate / chloroform / 4 h / 0 - 20 °C
Multi-step reaction with 2 steps 1.1: triethylamine / toluene / 18 h / 20 °C 1.2: 4 h / 120 °C / Molecular sieve 2.1: sodium hydrogencarbonate / chloroform / 4 h / 0 - 20 °C
  • 4
  • [ 153-94-6 ]
  • [ 1219810-16-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: thionyl chloride / 6 h / 0 - 40 °C 2.1: triethylamine / benzene / 1 h / 20 °C 3.1: trifluoroacetic acid / benzene / 1 h / Heating / reflux; Molecular sieve 4.1: trifluoroacetic acid / benzene / 3 h / 20 °C / Heating / reflux; Molecular sieve 4.2: pH 8 5.1: sodium hydrogencarbonate / chloroform / 4 h / 0 - 20 °C
  • 5
  • [ 22032-65-1 ]
  • [ 1219810-16-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: trifluoroacetic acid / benzene / 1 h / Heating / reflux; Molecular sieve 2.1: trifluoroacetic acid / benzene / 3 h / 20 °C / Heating / reflux; Molecular sieve 2.2: pH 8 3.1: sodium hydrogencarbonate / chloroform / 4 h / 0 - 20 °C
  • 6
  • [ 1571-08-0 ]
  • [ 1219810-16-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: triethylamine / toluene / 18 h / 20 °C 1.2: 4 h / 120 °C / Molecular sieve 2.1: sodium hydrogencarbonate / chloroform / 4 h / 0 - 20 °C
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