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[ CAS No. 20439-47-8 ] {[proInfo.proName]}

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Chemical Structure| 20439-47-8
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Product Details of [ 20439-47-8 ]

CAS No. :20439-47-8 MDL No. :MFCD00062985
Formula : C6H14N2 Boiling Point : -
Linear Structure Formula :(NH2CH)2(C4H8) InChI Key :SSJXIUAHEKJCMH-PHDIDXHHSA-N
M.W : 114.19 Pubchem ID :43806
Synonyms :

Calculated chemistry of [ 20439-47-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 34.26
TPSA : 52.04 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.22 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.49
Log Po/w (XLOGP3) : -0.32
Log Po/w (WLOGP) : 0.21
Log Po/w (MLOGP) : 0.21
Log Po/w (SILICOS-IT) : 0.15
Consensus Log Po/w : 0.35

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.35
Solubility : 51.4 mg/ml ; 0.45 mol/l
Class : Very soluble
Log S (Ali) : -0.31
Solubility : 55.7 mg/ml ; 0.488 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.31
Solubility : 55.8 mg/ml ; 0.489 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.81

Safety of [ 20439-47-8 ]

Signal Word:Danger Class:8
Precautionary Statements:P210-P261-P264-P271-P280-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P312-P363-P370+P378-P403+P233-P403+P235-P405-P501 UN#:2735
Hazard Statements:H227-H303-H314-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 20439-47-8 ]

* 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 [ 20439-47-8 ]
  • Downstream synthetic route of [ 20439-47-8 ]

[ 20439-47-8 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 20439-47-8 ]
  • [ 68737-65-5 ]
Reference: [1] Canadian Journal of Chemistry, 2004, vol. 82, # 2, p. 145 - 161
[2] Journal of the American Chemical Society, 2005, vol. 127, # 22, p. 8044 - 8049
[3] Tetrahedron Letters, 2005, vol. 46, # 11, p. 1921 - 1925
[4] Tetrahedron Letters, 2003, vol. 44, # 9, p. 1971 - 1974
[5] Tetrahedron Letters, 2002, vol. 43, # 45, p. 8059 - 8062
[6] Tetrahedron, 1996, vol. 52, # 44, p. 13837 - 13866
[7] Helvetica Chimica Acta, 1988, vol. 71, p. 1999 - 2021
[8] Journal of the American Chemical Society, 1984, vol. 106, # 19, p. 5754 - 5756
[9] Bulletin of the Chemical Society of Japan, 1980, vol. 53, # 8, p. 2275 - 2280
[10] Journal of Organic Chemistry, 1992, vol. 57, # 4, p. 1224 - 1231
[11] Tetrahedron: Asymmetry, 1990, vol. 1, # 7, p. 437 - 440
[12] Synthetic Communications, 2011, vol. 41, # 24, p. 3627 - 3634
  • 2
  • [ 20439-47-8 ]
  • [ 541-41-3 ]
  • [ 68737-65-5 ]
Reference: [1] Chinese Chemical Letters, 2011, vol. 22, # 2, p. 155 - 158
  • 3
  • [ 20439-47-8 ]
  • [ 74-88-4 ]
  • [ 68737-65-5 ]
Reference: [1] Tetrahedron Letters, 2005, vol. 46, # 11, p. 1921 - 1925
  • 4
  • [ 1121-22-8 ]
  • [ 20439-47-8 ]
  • [ 21436-03-3 ]
Reference: [1] Tetrahedron Asymmetry, 2003, vol. 14, # 18, p. 2763 - 2769
[2] Journal of the American Chemical Society, 2012, vol. 134, # 30, p. 12758 - 12773
[3] CrystEngComm, 2012, vol. 14, # 24, p. 8708 - 8713
[4] Tetrahedron Asymmetry, 2017, vol. 28, # 3, p. 454 - 459
  • 5
  • [ 1121-22-8 ]
  • [ 108-59-8 ]
  • [ 20439-47-8 ]
  • [ 21436-03-3 ]
  • [ 186144-56-9 ]
Reference: [1] Organic Letters, 2005, vol. 7, # 18, p. 4045 - 4048
  • 6
  • [ 1121-22-8 ]
  • [ 108-59-8 ]
  • [ 20439-47-8 ]
  • [ 21436-03-3 ]
  • [ 186144-56-9 ]
Reference: [1] Chemical Communications, 1996, # 21, p. 2471 - 2472
  • 7
  • [ 694-83-7 ]
  • [ 20439-47-8 ]
  • [ 21436-03-3 ]
Reference: [1] Tetrahedron Asymmetry, 2003, vol. 14, # 21, p. 3297 - 3300
  • 8
  • [ 694-83-7 ]
  • [ 20439-47-8 ]
  • [ 1436-59-5 ]
  • [ 21436-03-3 ]
Reference: [1] Tetrahedron Asymmetry, 2008, vol. 19, # 13, p. 1600 - 1607
  • 9
  • [ 20439-47-8 ]
  • [ 124-63-0 ]
  • [ 122833-58-3 ]
Reference: [1] Journal of Medicinal Chemistry, 2009, vol. 52, # 3, p. 840 - 851
[2] Tetrahedron, 1992, vol. 48, # 27, p. 5691 - 5700
[3] Tetrahedron Letters, 1995, vol. 36, # 13, p. 2219 - 2222
  • 10
  • [ 37942-07-7 ]
  • [ 20439-47-8 ]
  • [ 135616-40-9 ]
Reference: [1] Macromolecules, 2003, vol. 36, # 10, p. 3498 - 3504
[2] Macromolecules, 2004, vol. 37, # 20, p. 7469 - 7476
[3] Helvetica Chimica Acta, 2002, vol. 85, # 10, p. 3301 - 3312
[4] Tetrahedron, 2004, vol. 60, # 46 SPEC. ISS., p. 10461 - 10468
[5] Dalton Transactions, 2006, # 25, p. 3134 - 3140
  • 11
  • [ 37942-07-7 ]
  • [ 20439-47-8 ]
  • [ 360784-94-7 ]
  • [ 135616-40-9 ]
  • [ 886055-61-4 ]
Reference: [1] Journal of Catalysis, 2004, vol. 221, # 1, p. 77 - 84
  • 12
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  • [ 146504-07-6 ]
YieldReaction ConditionsOperation in experiment
94% at 20℃; for 5 h; (R, R) -cyclohexanediamine (5.70 g, 50.0 mmol) was dissolved in 1,4-dioxane (110.0 mL) A solution of BOC-anhydride (1.09 g, 5.0 mmol) in 1,4-dioxane (35.0 mL) was slowly added dropwise with stirring at room temperature, After completion of the dropwise addition, the reaction was stirred for 5 hours. The solvent was removed by flash evaporation, and the resulting residue was added to water (55 mL). The insoluble matter was removed by filtration and the filtrate was extracted with dichloromethane (3 x 55 mL). The organic phases were combined and washed with water to separate the organic phase, Dried in magnesium, filtered, concentrated by rotary distillation, purified by silica gel column chromatography, The product was shown as a yellow solid 1 (1.00 g, 94percent yield).
81.5% at 0 - 20℃; for 24 h; Inert atmosphere Under an atmosphere of Ar, a solution of di-tert-butyl dicarbonate (Boc2O, 4.37g, 0.02 mol) in CH2Cl2 (50 mL) was added dropwise to the solution of(1R,2R)-cyclohexane-1,2-diamine (6.85 g, 0.06 mol) in CH2Cl2 (60 mL) over a periodof 30 min at 0 oC. Then the reaction mixture was warmed to room temperature andwas stirred an additional 24 h. Water (30 mL) and CH2Cl2 (25 mL) were added todissolve the white precipitate. The organic phase was separated and concentratedunder reduced pressure. The residue was dissolved in ether (50 mL) and water (80mL). HCl (4 M) was sued to acidify the mixture to pH 5, and the aqueous wascollected. The aqueous was alkalified to pH 11 with NaOH (4 M) and extracted withEtOAc (5 X 50 mL). The organic phase was then dried and concentrated to yield theintermediate 1 (3.49 g, 81.5percent yield).
78%
Stage #1: With hydrogenchloride In methanol; water at 20℃; for 0.5 h; Cooling with ice
Stage #2: at 20℃; for 1 h;
22.4 g (0.1 mol) of 1R, 2R-cyclohexanediamine was dissolved in 200 mL of a methanol solution,Placed in 500mL single-necked flask at room temperature and stirring constantly;The amount of cylinder to take 5.17mol / L of methanol 19.4mL placed in a constant pressure funnel;Hydrochloric acid under ice bath slowly dropping to a single-necked flask;Dropwise.Remove the ice bath,The reaction at room temperature for 30 minutes.Weigh 38.28g (0.176mol) (Boc) 2O dissolved in 100mL of methanol,Placed in a constant pressure funnel,Slowly added to a single-necked flask,Dropwise.1 hour at room temperature,Spin dry,Obtained as a white solid;The white solid was dissolved in water,Ether extraction,Take the water phase;Adjust the pH to 10,CH2Cl2 extraction,Take the organic phase,Spin dry,CH2Cl2 / PE recrystallization,Got white crystals,Yield 78percent.
78%
Stage #1: With hydrogenchloride In methanol at 20℃; for 0.5 h; Cooling with ice
Stage #2: at 20℃; for 1 h;
he 22.4g (0.1 µM) 1R, 2R - cyclohexyl diamine dissolved in 200 ml of methanol solution, under the normal temperature condition is placed in the 500 ml of shan Jingping and continuously stirring; graduated cylinder quantity taking 5.17 mol/L hydrochloric acid methanol 19.4 ml is placed in the constant pressure funnel; ice bath slowly dropping hydrochloric acid methanol under the condition applied to the bottle-neck; then completing, removed ice, the reaction at room temperature 30 minutes. Weighing 38.28g (0.176 µM) (Boc)2O dissolved in 100 ml methanol, is placed in the constant pressure funnel, slowly to the shan Jingping, then completing, the reaction at room temperature 1 hour, turns on lathe does, to obtain white solid; the white solid soluble in water, ether, takes the aqueous phase; adjusting the pH to 10, CH2Cl2Extraction, takes organically phase, turns on lathe does, CH2Cl2Recrystallization/PE, to obtain white crystal, yield 78percent.
72%
Stage #1: With hydrogenchloride In methanol at 0 - 20℃; for 0.25 h;
Stage #2: at 20℃; for 1 h;
This compound is known but not fully characterised. A solution of 3.0 cm3 of HCl in MeOH (3M) was stirred at 0 °C for 15 min. Then, to this solution, was carefullyadded (R,R)-1,2-diaminocyclohexane (0.5 g, 4.36 mmol) at 0 °C. The mixture was stirred for 15 min at r.t. before adding water (1.0 cm3) and stirring for another 0.5 h.To the solution, (Boc)2O (0.95 g, 8.76 mmol) in 4.0 cm3 of MeOH was added at r.t.for 10 min, and the resultant solution was stirred for 1 h. The mixture was concentrated in vacuo. Unreacted diamine was removed by diethyl ether (30 cm3 x 2).The residue was dissolved in DCM (20 cm3), treated with 2 N NaOH solution (15cm3). The product in the organic layer was washed with of brine (20 cm3) dried overanhydrous MgSO4, and concentrated in vacuo to yield a mono-Boc product 15 as awhite solid, (0.68 g, 3.18 mmol, 72percent). Mp 109-112 °C; [α]D25 = -1.2, (c 0.1, CHCl3);νmax(neat) 2929, 1691, 1545, 1317, 1240, 1040, 1016, 965, 850 and 759 cm−1; δH (400MHz, CDCl3) 4.46 (1H, br s, NH), 3.14-3.12 (1H, m, CH), 2.32 (1H, td, J 5.6, 10.1,CH), 2.04-1.98 (2H, m, CH2), 1.72-1.69 (2H, m, CH2), 1.45 (9H, s, t-butyl), 1.37 (2H,br s, NH2), 1.29-1.07 (4H, m, 2 x CH2); δC (100 MHz,CDCl3) 156.49 (C=O), 57.69(C), 55.63 (CH), 55.01, (CH), 35.20 (CH2), 32.86 (CH2), 28.36 (3 x CH3), 25.15(CH2), 25.04 (CH2). m/z (ESI) 215.2 [M+H]+. HRMS found (ESI) 215.1751(C11H23N2O2 [M+H]+ requires 215.1754, error= 1.6 ppm).
70%
Stage #1: With hydrogenchloride In methanol for 2 h;
Stage #2: for 3 h;
The 800 mL of methanol containing 16.53 g (0.453 mol) ofdry HCl was added dropwise to the solution of 51.78 g (0.453mol) of trans-(1R,2R)-()-1,2-diaminocyclohexane in 80 mLof methanol for 2 h. After adding 50 mL of water, 98.97 g(0.453 mol) of di-t-butyl dicarbonate was added by portions for1 h. The mixture was stirred for 2 h, and then methanol wasremoved. The residue was rinsed with 900 mL of ether and theinsoluble matter was filtered off and dried. The crude productwas dissolved in 800 mL of water and then extracted with amixture of 500 mL of CH2Cl2 and 340 mL of 2 M NaOH. Theorganic layer was retained and treated with MgSO4 and the solvent evaporated. Recrystallization from 900 mL of ligroingave 67.87 g (70percent) of trans-(1R,2R)-1-Boc-amino-2-aminocyclohexane. IR (KBr, cm1): 1695 (νC=O urethane), 1554(δN-H amide II).

Reference: [1] Journal of the Chemical Society, Dalton Transactions, 2001, # 14, p. 2188 - 2198
[2] Patent: CN105017172, 2017, B, . Location in patent: Paragraph 0043; 0044
[3] European Journal of Organic Chemistry, 2018, vol. 2018, # 1, p. 99 - 103
[4] Journal of the American Chemical Society, 2011, vol. 133, # 37, p. 14704 - 14709
[5] Organic and Biomolecular Chemistry, 2018, vol. 16, # 35, p. 6423 - 6429
[6] Angewandte Chemie - International Edition, 2015, vol. 54, # 41, p. 11971 - 11977[7] Angew. Chem., 2015, vol. 127, p. 12139 - 12145,7
[8] Tetrahedron Letters, 2009, vol. 50, # 19, p. 2228 - 2231
[9] Tetrahedron Letters, 2014, vol. 55, # 27, p. 3697 - 3700
[10] Synthetic Communications, 2007, vol. 37, # 5, p. 737 - 742
[11] Patent: CN106543233, 2017, A, . Location in patent: Paragraph 0037; 0038
[12] Patent: CN106543234, 2017, A, . Location in patent: Paragraph 0035; 0036
[13] Tetrahedron Letters, 2000, vol. 41, # 46, p. 8999 - 9003
[14] Tetrahedron Letters, 2013, vol. 54, # 32, p. 4250 - 4253
[15] Angewandte Chemie - International Edition, 2012, vol. 51, # 2, p. 394 - 398
[16] Angewandte Chemie - International Edition, 2017, vol. 56, # 15, p. 4272 - 4276[17] Angew. Chem., 2017, vol. 129, p. 4336 - 4340,5
[18] Bulletin of the Chemical Society of Japan, 2017, vol. 90, # 3, p. 312 - 321
[19] Chemistry - A European Journal, 1997, vol. 3, # 6, p. 912 - 919
[20] European Journal of Medicinal Chemistry, 2012, vol. 55, p. 297 - 306
[21] Tetrahedron Letters, 2013, vol. 54, # 47, p. 6358 - 6362
  • 13
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Reference: [1] Synlett, 2017, vol. 28, # 11, p. 1278 - 1281
  • 14
  • [ 20439-47-8 ]
  • [ 80994-44-1 ]
  • [ 146504-07-6 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1999, vol. 36, # 2, p. 381 - 388
  • 15
  • [ 34619-03-9 ]
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  • [ 146504-07-6 ]
Reference: [1] Tetrahedron Asymmetry, 2014, vol. 25, # 15, p. 1091 - 1094
  • 16
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  • [ 144-62-7 ]
  • [ 61825-94-3 ]
YieldReaction ConditionsOperation in experiment
20% With silver(l) oxide In water at 90 - 100℃; for 10 - 12 h; A mixture of 50 g of potassium tetrachloroplatinate (0.12 mol), trans-l-1,2-diamino cyclohexane, 13.74 g (0.12 mol), 25.15 g of silver oxide (0.10 mol) and 13.66 g of oxalic acid dihydrate (0.10 mol) were heated together in 3 liters of DM water at 90-100° C. for 10-12 h. The reaction mixture was cooled to 50° C. filtered through celite. The filtrate was treated with 0.5 g of potassium iodide at 30° C. for 10-12 h in dark. Then again filtered through celite. The filtrate was treated with activated carbon to remove colour. Removal of 2.8 liters of water at 60° C. under vacuum produces oxaliplatin as a white crystalline solid (10 g, 20percent).
Reference: [1] Patent: US2008/207935, 2008, A1, . Location in patent: Page/Page column 7
  • 17
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  • [ 6147-53-1 ]
  • [ 176763-62-5 ]
Reference: [1] Journal of Molecular Catalysis A: Chemical, 1997, vol. 116, # 3, p. 375 - 384
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