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[ CAS No. 29841-69-8 ] {[proInfo.proName]}

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Chemical Structure| 29841-69-8
Chemical Structure| 29841-69-8
Structure of 29841-69-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 29841-69-8 ]

CAS No. :29841-69-8 MDL No. :MFCD00082751
Formula : C14H16N2 Boiling Point : -
Linear Structure Formula :- InChI Key :PONXTPCRRASWKW-KBPBESRZSA-N
M.W : 212.29 Pubchem ID :6931238
Synonyms :

Calculated chemistry of [ 29841-69-8 ]

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) : 2.11
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 : 1.97

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 [ 29841-69-8 ]

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 [ 29841-69-8 ]

* 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 [ 29841-69-8 ]
  • Downstream synthetic route of [ 29841-69-8 ]

[ 29841-69-8 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 358-23-6 ]
  • [ 29841-69-8 ]
  • [ 121788-77-0 ]
Reference: [1] Tetrahedron: Asymmetry, 1995, vol. 6, # 1, p. 3 - 6
[2] Organic Syntheses, 1993, vol. 71, p. 30 - 30
  • 2
  • [ 29841-69-8 ]
  • [ 98-59-9 ]
  • [ 167316-27-0 ]
YieldReaction ConditionsOperation in experiment
88% With sodium hydroxide In dichloromethane at 0 - 5℃; for 3 h; Inert atmosphere Synthesis of Compound 2009: To a 2-L, three-neck, round-bottom flask equipped with a temperature probe, magnetic stir bar, nitrogen inlet, and addition funnel were added (lS,2S)-(-)-l,2-diphenylethylenediamine (20 g, 0.094 mol) and dichloromethane (160 mL). The mixture was cooled to 0-3 0C and a 1 M solution of sodium hydroxide (160 mL) was added dropwise while maintaining the temperature below 5 0C. To this mixture was added a solution of toluenesulfonyl chloride (17.9 g, 0.094 mol) in dichloromethane (320 mL) dropwise over a 2-h period. The biphasic mixture was stirred at 0-5 0C for an additional 1 h and the reaction was deemed complete by TLC (50percent EtO Ac/heptane, UV). Phases were separated and the organic phase was washed with water (2 x 320 mL) and brine (320 mL), dried over sodium sulfate and concentrated to a crude solid. The solid was dissolved in toluene (200 mL) at 70-80 0C and heptane (300 mL) was added portionwise while maintaining this temperature. The resulting slurry was cooled and stirred at 20-25 0C for 1 h and then cooled and stirred at 0-5 0C for 10 min. The solids were filtered and washed with a 50percent solution of toluene in heptane (3 x 1 bed volume) to give compound 2009 (30.24 g, 88percent) as a white powder.
82.3% With sodium hydroxide In dichloromethane; water at 0 - 20℃; for 3 h; The procedure is the same as in Example 1,Except that (1S, 2S) -1,2-diphenylethylenediamine (3.0 g, 14.1 mmol)Added to 50mLDCM,After stirring and dissolving,A 15 mL aqueous solution of 2N NaOH was added,Cooling to 0 ,A solution of p-toluenesulfonyl chloride (2.65 g, 14.1 mmol)In dichloromethane (30 mL)After maintaining the reaction at 0 ° C for 1 hour,The temperature was raised to room temperature for 2 hours,HPLC detection reaction ended.The reaction solution was poured into saturated sodium chloride solution (30 mL)Stir for 10 minutes,After stratification,The aqueous phase was extracted once with DCM (30 mL)Combine organic phase,dry,The dichloromethane was removed by distillation under reduced pressure,Get crude.Recrystallization from petroleum ether / ethyl acetate system gave yellow solid Compound I (4.48 g, 82.3percent)
Reference: [1] Organic and Biomolecular Chemistry, 2011, vol. 9, # 7, p. 2505 - 2511
[2] Journal of Organic Chemistry, 2004, vol. 69, # 4, p. 1283 - 1289
[3] Patent: WO2010/120719, 2010, A1, . Location in patent: Page/Page column 194; 196-197
[4] Patent: CN106496099, 2017, A, . Location in patent: Paragraph 0033; 0034; 0035; 0048; 0049
[5] Organic Syntheses, 2005, vol. 82, p. 10 - 17
[6] European Journal of Organic Chemistry, 1999, # 9, p. 2315 - 2321
[7] Tetrahedron Asymmetry, 1997, vol. 8, # 13, p. 2101 - 2108
[8] European Journal of Organic Chemistry, 2000, # 12, p. 2247 - 2252
[9] Patent: EP1174426, 2002, A1, . Location in patent: Page 36
[10] Chemistry - A European Journal, 2008, vol. 14, # 25, p. 7687 - 7698
  • 3
  • [ 29841-69-8 ]
  • [ 98-59-9 ]
  • [ 170709-41-8 ]
  • [ 167316-27-0 ]
Reference: [1] Patent: EP1375477, 2004, A2, . Location in patent: Page/Page column 7-8
[2] Patent: EP1375477, 2004, A2, . Location in patent: Page/Page column 8
[3] Patent: US2005/59842, 2005, A1, . Location in patent: Page/Page column 5
[4] Patent: US2005/59842, 2005, A1, . Location in patent: Page/Page column 5
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