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[ CAS No. 34637-22-4 ] {[proInfo.proName]}

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Chemical Structure| 34637-22-4
Chemical Structure| 34637-22-4
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Product Details of [ 34637-22-4 ]

CAS No. :34637-22-4 MDL No. :MFCD01321351
Formula : C11H15NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :WXQCFKYWSKKNKY-UHFFFAOYSA-N
M.W : 209.24 Pubchem ID :562256
Synonyms :

Calculated chemistry of [ 34637-22-4 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.36
Num. rotatable bonds : 7
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 56.27
TPSA : 58.56 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.79 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.2
Log Po/w (XLOGP3) : 1.11
Log Po/w (WLOGP) : 1.14
Log Po/w (MLOGP) : 1.25
Log Po/w (SILICOS-IT) : 1.38
Consensus Log Po/w : 1.42

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.67
Solubility : 4.47 mg/ml ; 0.0214 mol/l
Class : Very soluble
Log S (Ali) : -1.93
Solubility : 2.44 mg/ml ; 0.0117 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.19
Solubility : 0.135 mg/ml ; 0.000647 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.06

Safety of [ 34637-22-4 ]

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 [ 34637-22-4 ]

* 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 [ 34637-22-4 ]
  • Downstream synthetic route of [ 34637-22-4 ]

[ 34637-22-4 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 34637-22-4 ]
  • [ 2304-94-1 ]
  • [ 65564-05-8 ]
YieldReaction ConditionsOperation in experiment
11.5 μmol With chloroperoxidase from C. fumago; dihydrogen peroxide In aq. acetate buffer for 24 h; Enzymatic reaction General procedure: N-Cbz-3-aminopropanol (-OH), N-Cbz-3-aminopropanal (-CHO), and N-Cbz-3-aminopropanoic acid (-COOH) were incu-bated at maximum concentration (38, 17, and 11 mM, respectively)in 5 mL of 100 mM sodium acetate buffer (pH 5.0). The reaction wasallowed to take place under orbital agitation in a MultiThermTMdevice overnight for 19 h. Peroxide was continuously added to thereactor at 3 mM h−1
Reference: [1] Process Biochemistry, 2016, vol. 51, # 9, p. 1204 - 1211
  • 2
  • [ 75-91-2 ]
  • [ 34637-22-4 ]
  • [ 2304-94-1 ]
  • [ 65564-05-8 ]
YieldReaction ConditionsOperation in experiment
16.1 μmol With chloroperoxidase from C. fumago In aq. acetate buffer for 7 h; Enzymatic reaction General procedure: N-Cbz-3-aminopropanol (-OH), N-Cbz-3-aminopropanal (-CHO), and N-Cbz-3-aminopropanoic acid (-COOH) were incu-bated at maximum concentration (38, 17, and 11 mM, respectively)in 5 mL of 100 mM sodium acetate buffer (pH 5.0). The reaction wasallowed to take place under orbital agitation in a MultiThermTMdevice overnight for 19 h. Peroxide was continuously added to thereactor at 3 mM h−1
Reference: [1] Process Biochemistry, 2016, vol. 51, # 9, p. 1204 - 1211
  • 3
  • [ 34637-22-4 ]
  • [ 2304-94-1 ]
Reference: [1] Process Biochemistry, 2016, vol. 51, # 9, p. 1204 - 1211
  • 4
  • [ 34637-22-4 ]
  • [ 2304-94-1 ]
Reference: [1] RSC Advances, 2015, vol. 5, # 85, p. 69819 - 69828
  • 5
  • [ 34637-22-4 ]
  • [ 65564-05-8 ]
YieldReaction ConditionsOperation in experiment
60% With pyridinium chlorochromate In dichloromethaneInert atmosphere PCC (8.75g, 40.6mmol, 1.7 equiv.) and Celite© (9g) were stirred in CH2Cl2 (50mL) for 5min whereupon alcohol 7 (5.0g, 24mmol) dissolved in CH2Cl2 (30mL) was added. After 4h the reaction was diluted with Et2O (100mL) and passed through a short pad of layered silica and Celite©. The remaining solids were suspended in CH2Cl2 (25mL) and precipitated with Et2O (50mL) and this mixture passed through the same pad. This process was repeated a further three times and the filtrate evaporated under reduced pressure to give a yellow oil (5.0g). Column chromatography (40percent EtOAc in PE) gave 8 as a colourless viscous oil (3.0g, 14.5mmol) in 60percent yield. (0012) Rf 0.4 (50percent EtOAc in petrol, PMA); δH 2.75 (2H, t, J 5.7Hz, CH2), 3.49 (2H, apparent q, J 6.0Hz, CH2), 5.09 (2H, s, CH2), 5.15 (1H, br s, HN), 7.30–7.39 (5H, m, Ar), 9.81 (1H, s, CHO); δC 34.6, 44.2, 66.9, 128.2, 128.3, 128.7, 136.5, 165.4, 201.3; vmax 3445, 1704, 1645cm−1.
20.2% With triethylamine In dimethyl sulfoxide at 0℃; for 1 h; To a solution of benzyl (3-hydroxypropyl)carbamate (1.0 g, 4.8 mmol) in DMSO (5 mL) was added Et3N (2.4 g, 24.0 mmol) and sulfur trioxide-pyridine complex (2.3 g, 14.4 mmol) at 0°C and the mixture was stirred at the same temperature for 1 h. The mixture wasthen diluted with DCM (20 mL), which was washed with 10percent Cu504 solution, saturated citric acid solution and brine (30 mL each). The organic layer was dried over Na2504, concentrated and the residue was purified by silica-gel column to give benzyl (3-oxopropyl)carbamate (200 mg, 20.2percent yield) as a white solid.
Reference: [1] Tetrahedron Letters, 2001, vol. 42, # 2, p. 183 - 185
[2] European Journal of Organic Chemistry, 2012, # 17, p. 3270 - 3277
[3] Tetrahedron, 1997, vol. 53, # 37, p. 12391 - 12404
[4] Tetrahedron Letters, 1987, vol. 28, # 33, p. 3827 - 3830
[5] Synlett, 2017, vol. 28, # 13, p. 1554 - 1557
[6] Journal of Medicinal Chemistry, 1992, vol. 35, # 23, p. 4264 - 4269
[7] Chemistry - A European Journal, 2003, vol. 9, # 20, p. 4887 - 4899
[8] Journal of Organic Chemistry, 2003, vol. 68, # 19, p. 7479 - 7484
[9] Tetrahedron, 2000, vol. 56, # 16, p. 2449 - 2460
[10] Chemical Communications, 2015, vol. 51, # 34, p. 7360 - 7363
[11] Tetrahedron, 2017, vol. 73, # 31, p. 4545 - 4548
[12] Heterocycles, 1989, vol. 28, # 1, p. 477 - 480
[13] Journal of Medicinal Chemistry, 2002, vol. 45, # 23, p. 5098 - 5111
[14] Patent: WO2017/84630, 2017, A1, . Location in patent: Paragraph 001141
[15] Tetrahedron, 1991, vol. 47, # 24, p. 4089 - 4100
[16] Tetrahedron Letters, 1993, vol. 34, # 34, p. 5385 - 5388
[17] Canadian Journal of Chemistry, 1995, vol. 73, # 12, p. 2111 - 2118
[18] Tetrahedron, 1997, vol. 53, # 25, p. 8421 - 8438
[19] Bioorganic and Medicinal Chemistry, 1997, vol. 5, # 11, p. 2089 - 2094
[20] Tetrahedron Letters, 1998, vol. 39, # 5-6, p. 443 - 446
[21] Tetrahedron Letters, 1987, vol. 28, # 33, p. 3827 - 3830
[22] Journal of the American Chemical Society, 1999, vol. 121, # 49, p. 11356 - 11368
[23] Journal of the American Chemical Society, 2005, vol. 127, # 8, p. 2396 - 2397
[24] Chemistry - A European Journal, 2006, vol. 12, # 31, p. 8056 - 8066
[25] Patent: US2007/260057, 2007, A1, . Location in patent: Page/Page column 13
[26] Advanced Synthesis and Catalysis, 2016, vol. 358, # 3, p. 380 - 385
[27] Patent: WO2016/106241, 2016, A1, . Location in patent: Paragraph 00181; 00191; 00192; 00193
[28] Patent: WO2017/156071, 2017, A1, . Location in patent: Paragraph 00397
  • 6
  • [ 34637-22-4 ]
  • [ 65564-05-8 ]
Reference: [1] European Journal of Organic Chemistry, 2015, vol. 2015, # 7, p. 1433 - 1436
  • 7
  • [ 34637-22-4 ]
  • [ 65564-05-8 ]
Reference: [1] European Journal of Organic Chemistry, 2015, vol. 2015, # 7, p. 1433 - 1436
  • 8
  • [ 34637-22-4 ]
  • [ 2304-94-1 ]
  • [ 65564-05-8 ]
YieldReaction ConditionsOperation in experiment
11.5 μmol With chloroperoxidase from C. fumago; dihydrogen peroxide In aq. acetate buffer for 24 h; Enzymatic reaction General procedure: N-Cbz-3-aminopropanol (-OH), N-Cbz-3-aminopropanal (-CHO), and N-Cbz-3-aminopropanoic acid (-COOH) were incu-bated at maximum concentration (38, 17, and 11 mM, respectively)in 5 mL of 100 mM sodium acetate buffer (pH 5.0). The reaction wasallowed to take place under orbital agitation in a MultiThermTMdevice overnight for 19 h. Peroxide was continuously added to thereactor at 3 mM h−1
Reference: [1] Process Biochemistry, 2016, vol. 51, # 9, p. 1204 - 1211
  • 9
  • [ 75-91-2 ]
  • [ 34637-22-4 ]
  • [ 2304-94-1 ]
  • [ 65564-05-8 ]
YieldReaction ConditionsOperation in experiment
16.1 μmol With chloroperoxidase from C. fumago In aq. acetate buffer for 7 h; Enzymatic reaction General procedure: N-Cbz-3-aminopropanol (-OH), N-Cbz-3-aminopropanal (-CHO), and N-Cbz-3-aminopropanoic acid (-COOH) were incu-bated at maximum concentration (38, 17, and 11 mM, respectively)in 5 mL of 100 mM sodium acetate buffer (pH 5.0). The reaction wasallowed to take place under orbital agitation in a MultiThermTMdevice overnight for 19 h. Peroxide was continuously added to thereactor at 3 mM h−1
Reference: [1] Process Biochemistry, 2016, vol. 51, # 9, p. 1204 - 1211
  • 10
  • [ 34637-22-4 ]
  • [ 921-26-6 ]
  • [ 108549-23-1 ]
  • [ 145471-95-0 ]
Reference: [1] Carbohydrate Research, 1992, vol. 230, # 1, p. 63 - 78
  • 11
  • [ 34637-22-4 ]
  • [ 921-26-6 ]
  • [ 100-51-6 ]
  • [ 108549-23-1 ]
  • [ 145471-95-0 ]
Reference: [1] Carbohydrate Research, 1992, vol. 230, # 1, p. 63 - 78
  • 12
  • [ 34637-22-4 ]
  • [ 39945-54-5 ]
Reference: [1] Nature Chemistry, 2011, vol. 3, # 2, p. 140 - 145
[2] Organic and Biomolecular Chemistry, 2010, vol. 8, # 12, p. 2829 - 2839
[3] Organic Letters, 2012, vol. 14, # 21, p. 5428 - 5431,4
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