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[ CAS No. 49606-99-7 ] {[proInfo.proName]}

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Chemical Structure| 49606-99-7
Chemical Structure| 49606-99-7
Structure of 49606-99-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 49606-99-7 ]

CAS No. :49606-99-7 MDL No. :MFCD06659116
Formula : C5H9NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :BUSBCPMSNBMUMT-BYPYZUCNSA-N
M.W : 115.13 Pubchem ID :1501944
Synonyms :

Calculated chemistry of [ 49606-99-7 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.8
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 28.51
TPSA : 63.32 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) : -8.79 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.83
Log Po/w (XLOGP3) : -2.52
Log Po/w (WLOGP) : -0.25
Log Po/w (MLOGP) : -2.59
Log Po/w (SILICOS-IT) : -0.24
Consensus Log Po/w : -0.95

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : 1.17
Solubility : 1690.0 mg/ml ; 14.6 mol/l
Class : Highly soluble
Log S (Ali) : 1.73
Solubility : 6240.0 mg/ml ; 54.2 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : 0.51
Solubility : 375.0 mg/ml ; 3.26 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.33

Safety of [ 49606-99-7 ]

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 [ 49606-99-7 ]

* 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 [ 49606-99-7 ]
  • Downstream synthetic route of [ 49606-99-7 ]

[ 49606-99-7 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 281191-43-3 ]
  • [ 49606-99-7 ]
YieldReaction ConditionsOperation in experiment
4.75 g With formic acid; palladium 10% on activated carbon In tetrahydrofuran; water 16.8 g of (S)-phenylethyl-(S)-cyclopropyl glycine obtained in the previous step, 200 mL of THE, 100 mL of water, and 4.76 g of Pd/C having a concentration of 10percent were mixed, then 17 mL of formic acid was added, then stir was performed overnight. After reacting, filtering was performed to remove a catalyst to obtain a filtrate, the filtrate was concentrated, and then methanol was added, then concentration was performed over again, operate repeatedly for several times, and vacuum drying was performed to obtain 4.75 g of a solid product.
Reference: [1] Patent: WO2005/107464, 2005, A2, . Location in patent: Page/Page column 25
[2] Patent: US2016/319312, 2016, A1, . Location in patent: Paragraph 0096-0097
  • 2
  • [ 56512-18-6 ]
  • [ 49606-99-7 ]
Reference: [1] Organic Process Research and Development, 2012, vol. 16, # 3, p. 464 - 469
  • 3
  • [ 155976-13-9 ]
  • [ 49606-99-7 ]
Reference: [1] Advanced Synthesis and Catalysis, 2006, vol. 348, # 9, p. 1071 - 1078
  • 4
  • [ 121703-92-2 ]
  • [ 49606-99-7 ]
  • [ 49607-01-4 ]
  • [ 121703-92-2 ]
  • [ 121786-35-4 ]
Reference: [1] Journal of the American Chemical Society, 1989, vol. 111, # 16, p. 6354 - 6364
[2] Journal of the American Chemical Society, 1989, vol. 111, # 16, p. 6354 - 6364
  • 5
  • [ 936097-37-9 ]
  • [ 49606-99-7 ]
Reference: [1] Advanced Synthesis and Catalysis, 2006, vol. 348, # 9, p. 1071 - 1078
  • 6
  • [ 15785-26-9 ]
  • [ 49606-99-7 ]
Reference: [1] Advanced Synthesis and Catalysis, 2006, vol. 348, # 9, p. 1071 - 1078
  • 7
  • [ 768356-83-8 ]
  • [ 49606-99-7 ]
Reference: [1] Advanced Synthesis and Catalysis, 2006, vol. 348, # 9, p. 1071 - 1078
  • 8
  • [ 638207-62-2 ]
  • [ 49606-99-7 ]
Reference: [1] Advanced Synthesis and Catalysis, 2006, vol. 348, # 9, p. 1071 - 1078
  • 9
  • [ 638207-64-4 ]
  • [ 49606-99-7 ]
Reference: [1] Advanced Synthesis and Catalysis, 2006, vol. 348, # 9, p. 1071 - 1078
  • 10
  • [ 121703-92-2 ]
  • [ 49606-99-7 ]
  • [ 121786-35-4 ]
Reference: [1] Journal of the American Chemical Society, 1989, vol. 111, # 16, p. 6354 - 6364
  • 11
  • [ 765-43-5 ]
  • [ 49606-99-7 ]
Reference: [1] Organic Process Research and Development, 2012, vol. 16, # 3, p. 464 - 469
[2] Patent: US2016/319312, 2016, A1,
  • 12
  • [ 24424-99-5 ]
  • [ 49606-99-7 ]
  • [ 155976-13-9 ]
Reference: [1] Organic Process Research and Development, 2012, vol. 16, # 3, p. 464 - 469
  • 13
  • [ 67-56-1 ]
  • [ 49606-99-7 ]
  • [ 138326-68-8 ]
YieldReaction ConditionsOperation in experiment
62% at 0 - 20℃; for 4 h; Heating / reflux To a 0° C. solution of thionyl chloride (7.6 mL, 104 mmol) in anhydrous methanol (750 mL) was added (S)-cyclopropylglycine (10.0 g, 86.9 mmol, Eastman Chemical Company, Kingsport, Tenn.). The reaction mixture was allowed to warm to room temperature and then refluxed for 4 hrs, then cooled to room temperature and concentrated in vacuo to give a crude solid. The solids were washed with acetone to give 8.94 g of the product as a white solid. Yield: 62percent, MS: 130 (M+H+), mp=134.0-135.9° C.
62% With thionyl chloride In methanol at 0 - 20℃; for 4 h; Heating / reflux To a 0° C. solution of thionyl chloride (7.6 mL, 104 mmol) in anhydrous methanol (750 mL) was added (S)-cyclopropylglycine (10.0 g, 86.9 mmol, Eastman Chemical Company, Kingsport, Tenn.).
The reaction mixture was allowed to warm to room temperature and then refluxed for 4 hrs, then cooled to room temperature and concentrated in vacuo to give a crude solid.
The solids were washed with acetone to give 8.94 g of (S)-cyclopropylglycine methyl ester HCl as a white solid. Yield: 62percent, MS: 130 (M+H+), mp=134.0-135.9° C.
Reference: [1] Patent: US2004/77646, 2004, A1, . Location in patent: Page 88
[2] Patent: US2004/248949, 2004, A1, . Location in patent: Page 33
[3] Journal of the American Chemical Society, 2015, vol. 137, # 5, p. 2042 - 2046
[4] Patent: US2018/110824, 2018, A1, . Location in patent: Paragraph 0642; 0643; 0644
  • 14
  • [ 49606-99-7 ]
  • [ 75-36-5 ]
  • [ 138326-68-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2011, vol. 54, # 24, p. 8305 - 8320
  • 15
  • [ 28920-43-6 ]
  • [ 49606-99-7 ]
  • [ 1212257-18-5 ]
YieldReaction ConditionsOperation in experiment
84% With sodium carbonate In 1,4-dioxane; water at 0 - 25℃; for 8.17 h; (5)-2-((((9/ -fluoren-9-yl)methoxy)carbonyl)amino)-2-cyclopropylacetic acid (43a): To a stirred solution of Na2C03 (2.3 g) in water (34 mL) was added (2C12); FT-IR (neat) 2669, 2335, 2159, 2106, 1785, 1689, 1550, 1489, 1463, 1433, 1369, 1296, 1253, 1172, 1128, 1001 cm"1; NMR: (CDCI3, 600 MHz) δ = 7.76 (d, 2 H, J = 7.2 Hz), 7.60-7.59 (m, 2 H), 7.41-7.39 (m, 2 H), 7.32-7.30 (m, 2 H), 5.36 (d, 1 H, J = 6), 4.45-4.39 (m, 2 H), 4.24-4.21 (m, 1 H), 3.83-3.81 (m, 1 H), 1.14-1.13 (m, 1 H), 0.65-0.46 (m, 5 H) ppm. 13C NMR: (CDCI3, 150 MHz) δ = 176.6, 156.2, 143.9, 143.8, 141.4, 127.9, 127.2, 125.2, 125.1, 120.1, 67.3, 57.4, 47.3, 13.9, 3.4 ppm; HRMS calcd for C20H19NO4 [ +Na+] 360.1206 found 360.1193.
Reference: [1] Journal of the American Chemical Society, 2016, vol. 138, # 5, p. 1698 - 1708
[2] Patent: WO2016/138288, 2016, A1, . Location in patent: Page/Page column 124
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