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[ CAS No. 1115-59-9 ] {[proInfo.proName]}

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Chemical Structure| 1115-59-9
Chemical Structure| 1115-59-9
Structure of 1115-59-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1115-59-9 ]

CAS No. :1115-59-9 MDL No. :MFCD00063662
Formula : C5H12ClNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :JCXLZWMDXJFOOI-WCCKRBBISA-N
M.W :153.61 Pubchem ID :2724356
Synonyms :
H-Ala-OEt.HCl

Calculated chemistry of [ 1115-59-9 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.8
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 37.11
TPSA : 52.32 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) : -6.68 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 0.78
Log Po/w (WLOGP) : 0.7
Log Po/w (MLOGP) : 0.39
Log Po/w (SILICOS-IT) : -0.22
Consensus Log Po/w : 0.33

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.09
Solubility : 12.6 mg/ml ; 0.0821 mol/l
Class : Very soluble
Log S (Ali) : -1.46
Solubility : 5.33 mg/ml ; 0.0347 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.39
Solubility : 63.3 mg/ml ; 0.412 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.58

Safety of [ 1115-59-9 ]

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 [ 1115-59-9 ]

* 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 [ 1115-59-9 ]
  • Downstream synthetic route of [ 1115-59-9 ]

[ 1115-59-9 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 15761-38-3 ]
  • [ 1115-59-9 ]
  • [ 27317-69-7 ]
Reference: [1] Patent: US5162307, 1992, A,
  • 2
  • [ 64-17-5 ]
  • [ 56-41-7 ]
  • [ 1115-59-9 ]
YieldReaction ConditionsOperation in experiment
80% at -5 - 78℃; for 1.5 h; Reflux General procedure: A mixture of alanine (3.56 g, 0.04 mol) in ethanol (30 mL), with thionyl chloride (3.6 mL) dropwise added at -5 °C, was refluxed in ethanol at 78 °C under stirring within 1.5 h. Subsequently, the solution was distilled in vacuum to afford Alanine ethyl ester hydrochloride 2a in >80percent yield. The physical constants of 2a-2l are identical with the corresponding data in reference [24].
Reference: [1] Chemical Communications, 2011, vol. 47, # 26, p. 7347 - 7349
[2] Dalton Transactions, 2015, vol. 44, # 3, p. 1170 - 1177
[3] Tetrahedron, 1999, vol. 55, # 11, p. 3337 - 3354
[4] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 8, p. 1942 - 1944
[5] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1994, # 7, p. 1455 - 1462
[6] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 12, p. 1197 - 1201
[7] European Journal of Inorganic Chemistry, 2003, # 11, p. 2113 - 2122
[8] Journal of the Chemical Society, Faraday Transactions 1: Physical Chemistry in Condensed Phases, 1980, vol. 76, p. 915 - 922
[9] Journal of the Indian Chemical Society, 2001, vol. 78, # 3, p. 137 - 141
[10] European Journal of Medicinal Chemistry, 2011, vol. 46, # 1, p. 11 - 20
[11] Tetrahedron, 2008, vol. 64, # 7, p. 1301 - 1308
[12] Chemistry of Natural Compounds, 1994, vol. 30, # 2, p. 238 - 244[13] Khimiya Prirodnykh Soedinenii, 1994, # 2, p. 261 - 268
[14] Tetrahedron, 1990, vol. 46, # 15, p. 5325 - 5332
[15] Journal of Organometallic Chemistry, 1981, vol. 221, # 2, p. 203 - 222
[16] Helvetica Chimica Acta, 1995, vol. 78, p. 109 - 121
[17] Tetrahedron, 2007, vol. 63, # 14, p. 3031 - 3041
[18] Advanced Synthesis and Catalysis, 2012, vol. 354, # 2-3, p. 295 - 300
[19] Green Chemistry, 2012, vol. 14, # 5, p. 1350 - 1356
[20] Chemistry of Natural Compounds, 2012, vol. 48, # 2, p. 194 - 197
[21] Tetrahedron, 2012, vol. 68, # 49, p. 10218 - 10229,12
[22] Tetrahedron, 2012, vol. 68, # 49, p. 10218 - 10229
[23] Nucleosides, Nucleotides and Nucleic Acids, 2013, vol. 32, # 4, p. 161 - 173
[24] Patent: US2016/264611, 2016, A1, . Location in patent: Paragraph 0222; 0223; 0224
[25] International Journal of Pharmaceutics, 2018, vol. 546, # 1-2, p. 31 - 38
  • 3
  • [ 56-41-7 ]
  • [ 1115-59-9 ]
Reference: [1] Patent: US5801249, 1998, A,
  • 4
  • [ 51814-53-0 ]
  • [ 1115-59-9 ]
Reference: [1] European Journal of Medicinal Chemistry, 2009, vol. 44, # 9, p. 3765 - 3770
  • 5
  • [ 1115-59-9 ]
  • [ 100-58-3 ]
  • [ 78603-91-5 ]
Reference: [1] Tetrahedron Asymmetry, 1999, vol. 10, # 3, p. 411 - 427
  • 6
  • [ 108-86-1 ]
  • [ 1115-59-9 ]
  • [ 78603-91-5 ]
Reference: [1] Journal of Physical Organic Chemistry, 1995, vol. 8, p. 159 - 170
  • 7
  • [ 1115-59-9 ]
  • [ 78603-91-5 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1994, # 7, p. 1455 - 1462
[2] Collection of Czechoslovak Chemical Communications, 1968, vol. 33, p. 1911 - 1916
  • 8
  • [ 1115-59-9 ]
  • [ 61275-22-7 ]
YieldReaction ConditionsOperation in experiment
2.2 g
Stage #1: With methylamine In ethanol for 97 h;
Stage #2: With sodium hydrogencarbonate; potassium carbonate In water
Stage #3: With hydrogenchloride In diethyl ether for 0.166667 h;
l-Alanine ethyl ester hydrochloride (8.1 g, 52.4 mmol) was stirred in an ethanolic methylamine solution (36 mL, 289 mmol) for 97 h then evaporated. The residue was taken up in potassium carbonate (4 M, 30 mL) and sodium bicarbonate (saturated, 20 mL) then extracted with chloroform (5.x.25 mL), which was dried over sodium carbonate and evaporated to yield crude l-Alanine N-methylamide, a red oil (3.62 g, 35.5 mmol, 68percent). A solution of the free amine (1.9 g, 18.5 mmol) in diethyl ether (200 mL) was treated with hydrogen chloride gas for 10 min before the product was removed by filtration and washed with diethyl ether to yield the hydrochloride salt, a clear crystalline solid (2.2 g, 16.0 mmol, 86percent). This was further purified by recrystallisation from ethanol and hexane; mp 213-215 °C; [α]D25 19.6 (c 0.1, CH3OH); νmax (NaCl disk)/cm-1 3408, 1674, 1514, 1417, 1275, 1169; δH (400 MHz, D2O) 3.85 (1H, q, J 7.1, CH), 2.60 (3H, s, NCH3), 1.32 (3H, d, J 7.1, CCH3); δC (100 MHz, D2O) 174.1 (C), 51.2 (CH), 28.5 (CH3), 19.2 (CH3).
Reference: [1] Tetrahedron, 2011, vol. 67, # 23, p. 4263 - 4267
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