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[ CAS No. 4049-33-6 ] {[proInfo.proName]}

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Chemical Structure| 4049-33-6
Chemical Structure| 4049-33-6
Structure of 4049-33-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 4049-33-6 ]

CAS No. :4049-33-6 MDL No. :MFCD00069790
Formula : C13H18O9 Boiling Point : -
Linear Structure Formula :- InChI Key :MJOQJPYNENPSSS-XQHKEYJVSA-N
M.W : 318.28 Pubchem ID :2817255
Synonyms :

Calculated chemistry of [ 4049-33-6 ]

Physicochemical Properties

Num. heavy atoms : 22
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.69
Num. rotatable bonds : 8
Num. H-bond acceptors : 9.0
Num. H-bond donors : 0.0
Molar Refractivity : 68.72
TPSA : 114.43 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) : -8.4 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.83
Log Po/w (XLOGP3) : -0.23
Log Po/w (WLOGP) : -0.3
Log Po/w (MLOGP) : -0.16
Log Po/w (SILICOS-IT) : -0.04
Consensus Log Po/w : 0.42

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.14
Solubility : 23.0 mg/ml ; 0.0724 mol/l
Class : Very soluble
Log S (Ali) : -1.72
Solubility : 6.13 mg/ml ; 0.0193 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.37
Solubility : 135.0 mg/ml ; 0.424 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 4.34

Safety of [ 4049-33-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 4049-33-6 ]

* 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 [ 4049-33-6 ]
  • Downstream synthetic route of [ 4049-33-6 ]

[ 4049-33-6 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 4049-33-6 ]
  • [ 3068-31-3 ]
YieldReaction ConditionsOperation in experiment
80% With hydrogen bromide; acetic acid In dichloromethane for 4.5 h; Inert atmosphere A solution of 13.2 g (0.162 mol) HBr in 30percent acetic acid was added at –5°C under argon to a solution of 17.1 g (0.054 mol) of compound 1 in 100 mL of anhydrous dichloromethane. The reaction mixture was stirred at 5°C for 1.5 h and then an additional 3 h at 20°C. Reaction progress was monitored by TLC, eluent ethyl acetate–hexane, 1 : 1. When the reaction was complete, the mixture was cooled to 0°C and diluted with cold dichloromethane, after which pieces of frozen 5percent solution of NaHCO3 were added. The aqueous layer was washed with 3 portions of cold dichloromethane, the combined extracts were dried with anhydrous MgSO4 and concentrated at a reduced pressure. Compound 2 readily decomposed on storage and on column chromatography on silica gel and, therefore, it was used in the subsequent reaction without additional purification. An analytical sample of bromide 2 was prepared by recrystallizaition from ethyl acetate–hexane, 2 : 3. Yield 80percent, mp 102–103°C (mp 101–102°C [50]), Rf 0.67 (ethyl acetate–hexane, 1 : 1). 1H NMR spectrum (CDCl3), δ, ppm (J, Hz): 2.03 s, 2.04 s, 2.06 s (9H, acetyl groups), 3.58 d.d (1H, H5 , J4,5a = 8.7, J5,5b = 12.0), 4.17 d.d (1H, H5b, J4,5b = 5.0, J5b,5a = 12.0), 4.96 d.d.d (1H, H4, J4,5 = 8.6, J4,5b = 5.2), 5.04 t (1H, H2, J2,3 = 7.9), 5.18 t (1H, H3, J3,4 = 7.9), 5.34 d (1H, H1, J1,2 = 4.2). 13C NMR spectrum (CDCl3), δC, ppm: 20.70, 20.73, 20.76 [C(O)OCH3], 65.74 (C5), 68.25 (C4), 69.15 (C3), 72.03 (C2), 80.60 (C1), 169.62, 169.79, 169. 88 [C(O)OCH3]. Mass spectrum (MALDI TOF), m/z: 340.12 [M + H]+ (calculated for C11H16BrO7: 340.09).
Reference: [1] Journal of Organic Chemistry, 1999, vol. 64, # 11, p. 3987 - 3995
[2] Beilstein Journal of Organic Chemistry, 2010, vol. 6, p. 699 - 703
[3] Heteroatom Chemistry, 2008, vol. 19, # 2, p. 199 - 206
[4] Russian Journal of General Chemistry, 2017, vol. 87, # 3, p. 456 - 462[5] Zh. Obshch. Khim., 2017, vol. 87, # 3, p. 450 - 456,7
[6] Carbohydrate Research, 1986, vol. 151, p. 225 - 232
[7] Journal of the American Chemical Society, 1999, vol. 121, # 29, p. 6911 - 6918
[8] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 1, p. 272 - 275
[9] Journal of Organic Chemistry, 2009, vol. 74, # 14, p. 5071 - 5074
[10] Carbohydrate Research, 2012, vol. 349, p. 12 - 23
[11] Steroids, 2014, vol. 80, p. 71 - 79
[12] Journal of Medicinal Chemistry, 2018, vol. 61, # 7, p. 2937 - 2948
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