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[ CAS No. 130931-83-8 ] {[proInfo.proName]}

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Chemical Structure| 130931-83-8
Chemical Structure| 130931-83-8
Structure of 130931-83-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 130931-83-8 ]

CAS No. :130931-83-8 MDL No. :MFCD00211275
Formula : C6H7NO Boiling Point : -
Linear Structure Formula :- InChI Key :DDUFYKNOXPZZIW-CRCLSJGQSA-N
M.W : 109.13 Pubchem ID :11789150
Synonyms :

Calculated chemistry of [ 130931-83-8 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.5
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 33.17
TPSA : 29.1 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) : -6.92 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.21
Log Po/w (XLOGP3) : 0.07
Log Po/w (WLOGP) : -0.32
Log Po/w (MLOGP) : 0.37
Log Po/w (SILICOS-IT) : 0.73
Consensus Log Po/w : 0.41

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.56
Solubility : 30.0 mg/ml ; 0.275 mol/l
Class : Very soluble
Log S (Ali) : -0.23
Solubility : 63.5 mg/ml ; 0.582 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.49
Solubility : 35.6 mg/ml ; 0.326 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 4.12

Safety of [ 130931-83-8 ]

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 [ 130931-83-8 ]

* 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 [ 130931-83-8 ]

[ 130931-83-8 ] Synthesis Path-Downstream   1~8

  • 2
  • [ 49805-30-3 ]
  • [ 151907-80-1 ]
YieldReaction ConditionsOperation in experiment
103 (1R,4S)-(+)-4-Aminocyclopent-2-en-1-carboxylic Acid Hydrochloride (113, Scheme 13) EXAMPLE 103 (1R,4S)-(+)-4-Aminocyclopent-2-en-1-carboxylic Acid Hydrochloride (113, Scheme 13) It was prepared from (+)-(1S,4R)-2-azabicyclo[2.2.1]hept-5-en-3-one (110, 4.9 g) according to the method used for compound 112.
  • 4
  • [ 34619-03-9 ]
  • [ 49805-30-3 ]
  • [ 168960-18-7 ]
YieldReaction ConditionsOperation in experiment
88% The first filtrate of Example 2 containing (-)-(1S, 4R-amino-2-cycopentene-1-methanol was cooled in anice-acetone bath and treated with di-tert-butyl dicarbonate (199.42 g, 0.9265 mol, Aldrich). The mixture was concentrated under vacuum to a volume of 300 mL, and added to the second filtrate of Example 2 that had meanwhile been cooled in an ice-acetone bath. The mixture was allowed to stir and warm to room temperature over the course of 18 hours, during which time gas evolved and a clear solution formed. This solution was combined with the last filtrate of Example 2 which had been evaporated under vacuum to a mixture of oil and solids. The resulting solution was evaporated under vacuum to an oil. The oil was partitioned between ethyl acetate (300 mL) and phosphate buffer (100 mL of 1.5 molar potassium dihydrogen phosphate adjusted to pH 7.0 with 50% sodium hydlroxide-water). The phases were separated, the aqueous phase was reextracted twice with ethyl acetate (200 mL). The organic phases were dried over sodium sulfate and filtered through silica gel (50 g.). The solvent was removed under vacuum to give an oil (220.78 g), which was taken up in hexanes (300 mL). A minimum amount of ethyl acetate (about 50 mL) was added in order to dissolve the oil, and the solution was set to crystallize over the course of three days. The crystals were filtered off, washed with 20% ethyl acetate/hexanes, and dried by suction to a constantweight (156.1 g, 0.732 mol, 82.6% of theory) of the title compound; m.p. 73-73.7 C.; 1 H-NMR (DMSO-d6) 5: 6.72 (d, J=7.9 Hz, 1H, NH), 5.80 and 5.60 (two m, 2H, CHCH), 4.59 (t, J=5.2 Hz, 1H, OH), 4.45 (m, 1H, CHN), 3.35 (m, overlapping H2O, CH2O), 2.60 (m, 1H, CH), 2.30 (m, 1H, ½ CH2), 1.40 (s, 9H, C(CH3)3), 1.2 (m, 1H, ½CH2); [alpha]20589-2.78, [alpha]20578-2.84, [alpha]20546-3.6, [alpha]20436-3.39, [alpha]20365-0.95 (c=5.07, methanol); Cl-MS (CH4) 214 (M+1); TLC (silica, 10% methanol-chloroform, iodine visualization), Rf=0.51. Anal. Calcd. for C11H19O13N: C, 61.95; H, 8.98, N, 6.57. Found: C, 61.87; H, 8.96; N, 6.59. An additional 10.14 g of crystalline material was recovered from the mother liquor by crystallization and chromatography, bringing the total yield to 166.24 g (0.780 mol, 87.9% of theory from the lactam starting material of Example 1). It was also found convenient to prepare the title compound directly from 2-azabicyclo [2.2.1] hept-S-en-3-one, either racemic or the (-) enantiomer, as follows. (-)2-Azabicyclo [2.2.1] hept-S-en-3-one (6.00 g, 55.0 mmol) in anhydroustetrahydrofuran (30 mL) was warmed to 34 C. and stirred while methanesulfonic acid (3.6 mL, 55 mmol) and water (0.99 mL, 55 mmol) were added dropwise over 10 minutes. An exotherm of 10 C. was observed within 5 minutes and a crystalline solid began to precipitate. The mixture was refluxed (oil bath at 74 C.) for 2.5 hours. The mixture was cooled to -10 C. and a solution of lithium aluminum hydride (1.0 M intetrahydrofuran, 100 mL) added. The first 15 mL was added over 10 minutes and an exotherm of 7 C. noted. The remaining 85 mL was added rapidly with no further exotherm noted. The mixture was brought to reflux over 30 minutes and reflux continued for 18hours. The mixture was cooled to 25 C.and sodium fluoride (25.2 g, 0.600 mole) was added and, after stirring for 30 minutes water (5.3 mL) was added dropwise over 10 minutes to the cooled (0 C.) mixture. The mixture was stirred for 30 minutes at 25 C. and di-tert-butyl dicarbonate (12.6 mL, 55.0 mmol) was added. This mixture was stirred for 16 hours, filtered, and the cake triturated with ethyl acetate (2×50 mL). The combined filteratewash was washed with water (20 mL), dried (Na2SO4), evaporated, and the residual syrup crystallized from ethyl acetate:hexanes/1:2 (30 mL) to give title compound as white crystals (10.32 g, 88%), identical in properties to the above-described samp
  • 5
  • [ 130931-83-8 ]
  • [ 130931-85-0 ]
YieldReaction ConditionsOperation in experiment
90% With hydrogenchloride In water for 2h; Reflux;
  • 6
  • [ 49805-30-3 ]
  • [ 79200-56-9 ]
  • [ 130931-83-8 ]
  • (-)-(1S, 4R)-4-amino-2-cyclopentene-1-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 99 % ee 2: 50 % ee With water; lipase B from Candida antarctica In isopropyl alcohol at 60℃; for 0.5h; Enzymatic reaction; General procedure: In a typical small-scale experiment, to the racemic substrate (0.05M solution) in i-Pr2O (1mL) CAL-B (30mg), H2O (0.5equiv) and then benzylamine (1equiv) were added. The mixture was shaken (167rpm) at 60°C. The progress of the reaction was followed by taking samples from the reaction mixtures and analyzing them by a GC method on a Chrompack Chirasil-Dex CB column [140°C for 25min→190°C (temperature rise 20°Cmin-1; 140kPa; retention times (min), (1S,4R)-1: 5.84 (antipode: 5.66)], (1R,4S)-2: 7.47 (antipode: 7.11)]. The ee values for the product γ-amino acids [after pre-column derivatization16 with CH2N2 (Caution derivatization with CH2N2 should be performed under a well-ventillating hood)] were determined by a GC method [120°C for 25min→160°C (temperature rise 10°Cmin-1; 140kPa; retention times (min), (1S,4R)-6: 27.38 (antipode: 27.84)], (1R,3S)-8: 28.74 (antipode: 28.98)].
  • 7
  • [ 24424-99-5 ]
  • [ 130931-83-8 ]
  • [ 702666-72-6 ]
YieldReaction ConditionsOperation in experiment
55.9% 1. Preparation of tert-butyl (1S, 4R)-2-azabicyclo[2.2.1]heptan-5-en-2-carboxylate (1S, 4R)-2-azabicyclo[2.2.1]heptan-5-en-3-one (3.0 g, 27.5 mmol) was dissolved in THF (80 mL), and LiAlH4 (1.36 g, 35.8 mmol) was added at 0 C. The reaction solution reacted at 25 C for 3 hrs, and then reacted at an elevated temperature of 60 C for 4 hrs. Then, water (2 mL) was added at 0 C to quench the reaction. The reaction solution was filtered through celite, the filter cake was washed with ethyl acetate (50 mL), and the filtrate was concentrated to 50 mL. Boc2O (9.0 g, 41.2 mmol) was added to the concentrated filtrate, and the mixture solution reacted at 25 C for 16 hrs. The reaction solution was concentrated, and purified by silica-gel column chromatography (petroleum ether : ethyl acetate = 10:1) to obtain the product (3.0 mg, two-step yield: 55.9%).
  • 8
  • [ 49805-30-3 ]
  • [ 79200-56-9 ]
  • [ 130931-83-8 ]
  • cis-4-amino-cyclopent-2-ene-1-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With (+) γ-lactamase immobilized on epoxy graphene oxide carrier In aq. phosphate buffer at 80℃; Enzymatic reaction; Analysis of enzyme activity and enzyme protein concentration One (+) γ-lactamase activity unit (U) was defined as the amount of enzyme capable of hydrolyzing 1 mol of (+) -lactam per minute under assay conditions. For the free enzyme, 0.5 g of (rac)-γ-lactam was added to 10 ml of crude enzyme solution (pH 8.0); for the immobilized enzyme, 0.1 g of (rac)-γ-lactam and 0.1 g immobilized enzyme were added to 10 mL of phosphate buffer (pH 8.0). These mixtures were taken in 50-ml conical flasks to perform enzymatic reactions at 50°C for 1 h, at which point the amount of hydrolyzed (+) γ-lactam was calculated. The products were extracted by adding isopycnic ethyl acetate (1:1 mL). The ethyl acetate extract (10 L) was applied to a chiral HPLC (LC-20A, Shimadzu Corporation, Kyoto, Japan) equipped with a Daicel AS-Hchiral column (Daicel Corporation, Tokyo, Japan) and eluted with a mobile phase consisting of 90% acetonitrile and 10% isopropyl alcohol (v/v). The ultraviolet (UV) absorbance of the eluted γ-lactam was measured at 230 nm. Ethyl acetate, (+) -lactam, and (-) -lactam had retention times of 5.3, 9.7, and 11.7 min, respectively, at a total flow rate of 0.6 ml/min. The amount of hydrolyzed (+) γ-lactam was calculated with reference to the HPLC diagram usingthe following equation (Eq. (1)): Hydrolytic amount (mol) = A1 -A2/2A1×M, (1) where A1 is the area ratio of (-) γ-lactam, A2 is the area ratio of (+)-lactam, and M (mol) is the total amount of substrate initially added. The crude (+) γ-lactamase protein concentration (g/mL) was determined using bovine serum albumin as a reference, as described by Bradford [14].
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