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[ CAS No. 35132-20-8 ] {[proInfo.proName]}

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Chemical Structure| 35132-20-8
Chemical Structure| 35132-20-8
Structure of 35132-20-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 35132-20-8 ]

CAS No. :35132-20-8 MDL No. :MFCD00082769
Formula : C14H16N2 Boiling Point : -
Linear Structure Formula :- InChI Key :PONXTPCRRASWKW-ZIAGYGMSSA-N
M.W : 212.29 Pubchem ID :2724998
Synonyms :
(+)-1,2-Diphenylethylenediamine;(+)-Stilbenediamine
Chemical Name :(1R,2R)-1,2-Diphenylethane-1,2-diamine

Calculated chemistry of [ 35132-20-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.14
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 66.12
TPSA : 52.04 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.6 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.75
Log Po/w (XLOGP3) : 1.4
Log Po/w (WLOGP) : 1.74
Log Po/w (MLOGP) : 2.41
Log Po/w (SILICOS-IT) : 2.17
Consensus Log Po/w : 1.89

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.4
Solubility : 0.855 mg/ml ; 0.00403 mol/l
Class : Soluble
Log S (Ali) : -2.1
Solubility : 1.7 mg/ml ; 0.008 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.3
Solubility : 0.0106 mg/ml ; 0.0000501 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.98

Safety of [ 35132-20-8 ]

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 [ 35132-20-8 ]

* 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.

  • Upstream synthesis route of [ 35132-20-8 ]
  • Downstream synthetic route of [ 35132-20-8 ]

[ 35132-20-8 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 35132-20-8 ]
  • [ 98-59-9 ]
  • [ 144222-34-4 ]
YieldReaction ConditionsOperation in experiment
75% at 0℃; for 1.5 h; (1)(R, R) -1,2-diphenyl-ethylenediamine (20 mmol, available from Kling 24650) was dissolvedIn dichloromethane (30 mL)At 0 ° CWill be dissolved in dichloroethane (30mL)Of p-methylphenyl sulfonyl chloride(20 mmol, available from Kling 283322)Drip into it (30min drip finished),Continue to react at 0 ° C for 1 h, then rotary evaporator under reduced pressure,The solid was separated and purified by column chromatography (eluent dichloromethane / methanol 10: 1 by volume)Thus, 15 mmol of a chiral diamine represented by the formula (R, R) - (3-1-1-1)The yield is 75percent
75% at 0℃; for 1.5 h; (1) (R,R)-1,2-diphenyl-ethylenediamine (20 mmol,Purchased from Valinway Technology Corporation No. 24694) dissolved in dichloromethane (30 mL),And p-methylphenylsulfonyl chloride dissolved in dichloroethane (30 mL) at 0°C(20 mmol, purchased from the JV of Schering Technology, Inc. 283322) was added dropwise (completed within 30 min), and the reaction was continued at 0 °C for 1 h. The mixture was then evaporated under reduced pressure and the solid was purified by column chromatography.(The eluent was a 10:1 volume ratio of dichloromethane/methanol) to give 15 mmolThe chiral diamine represented by (R,R)-(3-1-1-1) has a yield of 75percent.
75% at 0℃; for 1.5 h; (1) Dissolving (R,R)-1,2-diphenyl-ethylenediamine (20 mmol, available from Valinway Technology Corporation No. 24694)p-Methylphenylsulfonyl chloride (20 mmol, from Schering-Plant Technology, Inc. 283322 grade) dissolved in dichloroethane (30 mL) was added dropwise to dichloromethane (30 mL) in dichloromethane (30 mL). After 30 minutes, the reaction was continued at 0°C for 1 hour, and then the mixture was evaporated under reduced pressure. The solid was purified by column chromatography (eluent: 10:1 dichloromethane/methanol) to give 15 mmol. The chiral diamine of the formula (R,R)-(3-1-1-1) has a yield of 75percent.
65% With triethylamine In tetrahydrofuran at 0℃; for 12 h; General procedure: Catalysts 1a–1d were similarly prepared. Catalyst 1a was prepared as follows: (1R,2R)-(+)-(1,2)-DPEN (0.50g,2.40mmol) and Et3N (1mL) were dispersed into 20mL anhydrous tetrahydrofuran (THF). A solution of p-TsCl (0.45g, 2.40mmol) in 5 mL anhydrousTHF was added to the aforementioned solution. The reaction mixture was stirred vigorously at 0° C for 12 h and then evaporated to generate the crude product. The crude was purified by column chromatography on silica gel (200–300 mesh, PE=EtOAc1:1).

Reference: [1] Tetrahedron Letters, 2008, vol. 49, # 27, p. 4289 - 4291
[2] European Journal of Organic Chemistry, 2000, # 12, p. 2247 - 2252
[3] Tetrahedron Asymmetry, 2009, vol. 20, # 6-8, p. 910 - 920
[4] Molecules, 2010, vol. 15, # 4, p. 2551 - 2563
[5] Patent: CN107286089, 2017, A, . Location in patent: Paragraph 0078; 0148-0149
[6] Patent: CN104610256, 2017, B, . Location in patent: Paragraph 0138
[7] Patent: CN105111208, 2018, B, . Location in patent: Paragraph 0137
[8] Journal of Organic Chemistry, 2008, vol. 73, # 13, p. 4903 - 4906
[9] Synthetic Communications, 2015, vol. 45, # 10, p. 1248 - 1258
[10] Journal of Organic Chemistry, 2009, vol. 74, # 9, p. 3350 - 3355
[11] Journal of Organometallic Chemistry, 2009, vol. 694, # 13, p. 2092 - 2095
[12] Tetrahedron Asymmetry, 2007, vol. 18, # 9, p. 1124 - 1128
[13] Chemical Communications, 2010, vol. 46, # 25, p. 4589 - 4591
  • 2
  • [ 421-83-0 ]
  • [ 35132-20-8 ]
  • [ 121788-73-6 ]
Reference: [1] Advanced Synthesis and Catalysis, 2005, vol. 347, # 1, p. 61 - 77
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