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[ CAS No. 68-41-7 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 68-41-7
Chemical Structure| 68-41-7
Structure of 68-41-7 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 68-41-7 ]

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Product Details of [ 68-41-7 ]

CAS No. :68-41-7 MDL No. :MFCD00005353
Formula : C3H6N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :DYDCUQKUCUHJBH-UWTATZPHSA-N
M.W : 102.09 Pubchem ID :6234
Synonyms :
α-Cycloserine;RO-1-9213;Oxamycin;Orientomycin;68-41-7;Seromycin;Cycloserine;NSC 154851;NSC 76029;(R)-Cycloserine;(+)-Cycloserine;D-Cycloserine
Chemical Name :(R)-4-Aminoisoxazolidin-3-one

Calculated chemistry of [ 68-41-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.67
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 25.13
TPSA : 64.35 ?2

Pharmacokinetics

GI absorption : Low
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) : -7.99 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.53
Log Po/w (XLOGP3) : -1.51
Log Po/w (WLOGP) : -2.01
Log Po/w (MLOGP) : -1.68
Log Po/w (SILICOS-IT) : -0.44
Consensus Log Po/w : -1.02

Druglikeness

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

Water Solubility

Log S (ESOL) : 0.48
Solubility : 307.0 mg/ml ; 3.01 mol/l
Class : Highly soluble
Log S (Ali) : 0.66
Solubility : 471.0 mg/ml ; 4.62 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : 0.27
Solubility : 192.0 mg/ml ; 1.88 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.73

Safety of [ 68-41-7 ]

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 [ 68-41-7 ]

* 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.

  • Downstream synthetic route of [ 68-41-7 ]

[ 68-41-7 ] Synthesis Path-Downstream   1~1

  • 1
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  • C9H8FN2O3Pol [ No CAS ]
  • C10H10FN2O3Pol [ No CAS ]
  • C11H12FN2O3Pol [ No CAS ]
  • C14H10FN2O3Pol [ No CAS ]
  • C11H8FN4O3Pol [ No CAS ]
  • C12H8FN4O3Pol [ No CAS ]
  • C13H10FN2O4Pol [ No CAS ]
  • C15H12FN2O3Pol [ No CAS ]
  • C14H11FN3O3Pol [ No CAS ]
  • C13H14FN2O3Pol [ No CAS ]
  • C13H10FN2O3PolS [ No CAS ]
  • C13H16FN2O4Pol [ No CAS ]
  • C13H14FN2O4Pol [ No CAS ]
  • C16H14FN2O4Pol [ No CAS ]
  • C11H9FN3O5Pol [ No CAS ]
  • C15H11ClFN2O3Pol [ No CAS ]
  • C17H17FN3O3Pol [ No CAS ]
  • C14H17FN3O3Pol [ No CAS ]
  • C14H17FN3O4Pol [ No CAS ]
  • C15H19FN3O3Pol [ No CAS ]
  • C16H12FN2O5Pol [ No CAS ]
  • C18H13FN3O3Pol [ No CAS ]
  • C15H17FN3O4Pol [ No CAS ]
  • C16H22FN4O3Pol [ No CAS ]
YieldReaction ConditionsOperation in experiment
A library of compounds in which R4 was various groups having the formula [CONHR ?] was prepared by the process described above using 4-fluoro-3-nitrobenzoic acid, as follows: [72] Aldehyde resin was mixed with a primary amine (R17-NH2) in [DICHLOROETHANE] (DCE), triethylorthoformate (TEOF), and DMF (containing [1%] acetic acid) in a 1: 1: 1 ratio. After shaken overnight, sodium triacetoxyborohydride (20 eq. ) dissolved in DMF was added (Abdel-Magid, A. F. , et al., Tetrahedron Lett, 3 1: 5595-5598 (1990) ). After the mixture was shaken at room temperature overnight, the resin was filtered and washed with DMF (3 x 5 mL), [MEOH] [(3 X 5] mL), DMF [(3 X 5] mL), [MEOH] [(3 X 5] mL), and [CH2CL2] [(3 X 5] mL). The resin was washed twice with 5 mL DMF containing [1%] Hunig's base. To the filtered resin was added a mixture of 4-fluoro-3-nitrobenzoic acid (FNBA, 10 eq. ) and diisopropylcarbodiimide (DIC, 5 eq. ) in 2: 1 DMF : DCM. After shaking at room temperature overnight, the resin was filtered and washed with DMF (3 x 5 mL) and [CH2C12] (3 x 5 mL). [73] The resin was shaken with a primary amine [(R2-NH2)] in DMF for 8 hrs, filtered, and washed with DMF (6 x 5 mL), [MEOH] [(3 X 5] mL), and CH2C12 (3 x 5 mL). The aryl nitro group was reduced by the addition of tin (II) chloride dihydrate (20 eq. , >2 M) and N-methyl morpholine (NMM, 20 eq. ) in N-methyl pyrrolidinone (NMP). After shaken at room temperature overnight, the resin was filtered and washed with NMP (3 x 5 mL), [MEOH] (3 x 5 mL), and [CH2CI2 (3 X 5] mL). The resulting resin was shaken at room temperature with cyanogen bromide (5 eq. ) overnight, filtered, and washed with CH2Cl2 (3 x 5 mL), [MEOH] (3 x 5 mL), and CH2CI2 (3 x 5 mL). To produce a free amine, the resin was shaken for 30 min. in CHCl2 with the addition of sodium methoxide in methanol, filtered, and washed with CH2Cl2 [(4 X 5] mL). [[74]] In the final diversification step, the resin was heated at 500 C in DMF with a mono- substituted epoxide [[RLCH (-CH2O-)].] After shaking for 2 to 4 days the resin was filtered and washed with DMF (5 x 5 mL), [MEOH] [(3 X 5] mL), and CH2Cl2 (3 x 5 mL). T he resin-bound benzimidazole was cleaved from the solid-support by treatment with TFA: [CH2C12] (2: 3) for 1 hour at room temperature.
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(S)-4-Aminoisoxazolidin-3-one

Reason: Optical isomers

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