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[ CAS No. 75885-58-4 ] {[proInfo.proName]}

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Chemical Structure| 75885-58-4
Chemical Structure| 75885-58-4
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Product Details of [ 75885-58-4 ]

CAS No. :75885-58-4 MDL No. :MFCD00216614
Formula : C6H11NO Boiling Point : No data available
Linear Structure Formula :- InChI Key :YBZQRYWKYBZZNT-SCSAIBSYSA-N
M.W : 113.16 Pubchem ID :10197657
Synonyms :

Calculated chemistry of [ 75885-58-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.83
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 31.49
TPSA : 43.09 ?2

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) : 1.36
Log Po/w (XLOGP3) : 0.43
Log Po/w (WLOGP) : 0.52
Log Po/w (MLOGP) : 0.47
Log Po/w (SILICOS-IT) : 0.65
Consensus Log Po/w : 0.68

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.75
Solubility : 20.3 mg/ml ; 0.179 mol/l
Class : Very soluble
Log S (Ali) : -0.9
Solubility : 14.2 mg/ml ; 0.125 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.77
Solubility : 19.0 mg/ml ; 0.168 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.2

Safety of [ 75885-58-4 ]

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

Application In Synthesis of [ 75885-58-4 ]

* 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 [ 75885-58-4 ]

[ 75885-58-4 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 78834-75-0 ]
  • [ 75885-58-4 ]
  • [ 877758-94-6 ]
YieldReaction ConditionsOperation in experiment
l-bromo-5-chloropentane (29 lg, 1.57 mol) was reacted with diethyl oxalate (206.5g) through Grignard reaction to obtain <strong>[78834-75-0]ethyl 7-chloro-2-oxo-heptanoate</strong> (3) and the compound (3) was reacted with (S)-2,2-dimethylcyclopropanecarboxamide to obtain ethyl (Z)-7-chloro-2-((S)-2,2-dimethylcyclopropanecarboxamido)-2-heptanoate (237g, 0.79 mol). The above-described step was performed by the procedure according to the procedure disclosed in EP 48301 (Bl).
36.4 g With toluene-4-sulfonic acid; In water; toluene;Reflux; 25.0 g of <strong>[78834-75-0]ethyl 7-chloro-2-oxoheptanoate</strong> obtained in Example 1 (GC normalized content 98.3%, external standard content 98.5%),(+) - S-2,2-dimethylcyclopropanecarboxamide and 0.15 g of p-toluenesulfonic acid were added to 125 ml of toluene, and the mixture was heated under reflux to azeotropize toluene with water to carry out the reaction.After completion of the reaction, the reaction mixture was cooled to room temperature, and the reaction solution was washed three times with 10% dilute hydrochloric acid (100 ml x 3) and 10% sodium hydrogen sulfite solution (100 ml x 3). After the washing, the toluene layer was separated and dried over anhydrous sodium sulfate. Filtered and concentrated under reduced pressure recovered toluene to give 36.4g of brown viscous liquid, the product will not be isolated directly used in the next step.
With toluene-4-sulfonic acid; In toluene; at 130℃; for 10h; 247.8 g of <strong>[78834-75-0]ethyl 7-chloro-2-oxoheptanoate</strong>,135.6 g of S - (+) 2,2-dimethylcyclopropylcarboxamidewith1.6 g of p-toluenesulfonic acid at 130 C1200ml toluene refluxed for 10 hours;After the reaction is completed, the toluene is concentrated and recovered;To the concentrate is added 600 ml of ethanol and 720 g of 10% sodium hydroxide solution,HPLC monitoring of the reaction process,At 45 ~ 50 for 10 hours;Then add t-butyl ether three times,Each 1000ml, discard the organic layer,Add concentrated hydrochloric acid,Adjust the pH to 3 ~ 3.5, add ethyl acetate three times,Each time 1000ml,Discard the water layer,Add anhydrous sodium sulfate drying,Concentration under reduced pressure gave (Z) -7-chloro-2- [(S) -2,2-dimethylcyclopropylcarboxamido] -2-heptenoic acid viscous liquid. Under reflux, 200 g of the above concentrate was added to 600 ml of dioxane,Then add 1260ml cyclohexane, stir,Let stand for 12 hours at room temperature, filtered,Drying in vacuo gave (Z) -7-chloro-2- [(S) -2,2-dimethylcyclopropylcarboxamido] -2-heptenoic acid as a solid; After controlling the temperature to be less than or equal to 10 DEG C, purging with nitrogen, 105.3 g of L-cysteine hydrochloride monohydrate was added, the mixture was stirred for 0.5 hours, warmed to 55-60 DEG C, the reaction was monitored by HPLC, the reaction was completed in 8 hours, Cooled to room temperature, washed three times with dichloromethane,Each 600ml, discard the organic layer,One volume of water was added to the reaction solution,Concentrated hydrochloric acid to adjust the pH to 2.5 to 3.0,Four times with dichloromethane,Each 800ml, discard the organic layer,That is included[R- [R *, S * (Z)]] - 7 - [(2-Amino-2- carboxyethyl) thio]2 - [[(2,2-dimethylcyclopropyl) carbonyl] amino] -2-heptenoic acid.
  • 2
  • [ 78834-75-0 ]
  • [ 75885-58-4 ]
  • [ 877758-94-6 ]
  • [ 1022895-93-7 ]
YieldReaction ConditionsOperation in experiment
Ref. Ex. 1; Preparation of Ethyl (Z)-7-chloro-((S)-2,2-dimethylcyclopropanecarboxamido)-2-heptenoate (2); As described in European Patent No. 48301, 250 g of <strong>[78834-75-0]ethyl 7-chloro-2-oxoheptanoate</strong> and 141 g of (S)-2,2-dimethyl cyclopropanecarboxamid were reacted and concentrated. In result, 372.4 g of ethyl (Z)-7-chloro-((S)-2,2-dimethylcyclopropanecarboxamido)-2-hepnoate (2) containing, by gas chromatography assay, 10.5% of ethyl (E)-7-chloro-((S)-2,2-dimethylcyclopropanecarboxamido)-2-heptenoate (3) was obtained.
  • 3
  • [ 1022895-93-7 ]
  • [ 78834-75-0 ]
  • [ 75885-58-4 ]
YieldReaction ConditionsOperation in experiment
Ex. 1; Preparation of (Z)-7-chloro-((S)-2,2-dimethylcyclopropanecarboxamido)-2-heptenoic acid (1); 200 g (0.66 mol) of ethyl (Z)-7-chloro-((S)-2,2-dimethylcyclopropanecarboxamido)-2-heptenoate (2) obtained from the Ref. Ex. 1 was dissolved in 600 ml of dichloromethane. 126 g of 4-toluenesulfonic acid was added to the mixture and stirred at 20° C. When a (mol) ratio of the ethyl (Z)-7-chloro-((S)-2,2-dimethylcyclopropanecarboxamido)-2-heptenoate (2) to the ethyl (E)-7-chloro-((S)-2,2-dimethylcyclopropanecarboxamido)-2-heptenoate (3) was about 200:1 according to gas chromatography assay, the pH of the mixture was adjusted to 8-9 by adding 0.5N caustic soda solution, and an organic phase was isolated. The isolated organic phase was concentrated under reduced pressure and provided to 1,000 ml of acetonitrile. Next, 1,420 ml (0.925 mole) of 0.65N caustic soda solution was added and stirred at room temperature until ethyl (Z)-7-chloro-((S)-2,2-dimethylcyclopropanecarboxamido)-2-heptenoate (2) was completely reacted. Most of acetonitrile was evaporated under reduced pressure, and an aqueous phase was washed with 270 ml of dichloromethane. The pH of the aqueous phase was adjusted to 3.5 by adding hydrochloric acid and extracted from 670 ml of dichloromethane. Meanwhile, the organic phase was provided into 70 g of anhydrous magnesium sulfate, stirred, filtered and concentrated under reduced pressure. The residual was crystallized from a mixed solvent of ethyl acetate and n-hexane (about 1:4), filtered and dried in hot air at 40° C. for 10 hours to produce 101.4 g of the target compound, (Z)-7-chloro-((S)-2,2-dimethylcyclopropanecarboxamido)-2-heptenoic acid (1).HPLC(C18, 40percent aqueous acetonitrile solution) purity: 99.1percent, (Z)/(E)=910H1 nmr (CDCl3, 500 MHz) ppm: 0.82-0.84 (dd, 1H), 1.15-1.23 (s, 7H), 1.43-1.46 (dd, 1H), 1.61-1.67 (m, 2H), 1.78-1.83 (m, 2H), 2.19-2.23 (m, 2H), 3.53-3.56 (t, 2H), 6.77-6.79 (t, 1H), 6.99 (s, 1H)
Ex. 2; Preparation of (Z)-7-chloro-((S)-2,2-dimethylcyclopropanecarboxamido)-2-heptenoic acid (1); 100 g (0.33 mol) of ethyl (Z)-7-chloro-((S)-2,2-dimethylcyclopropanecarboxamido)-2-heptenoate (2) obtained from the Ref. Ex. 1 was dissolved in 300 ml of toluene. 47 g of methyl sulfonic acid was added to the mixture and stirred at 30° C. When a (mol) ratio of the ethyl (Z)-7-chloro-((S)-2,2-dimethylcyclopropanecarboxamido)-2-heptenoate (2) to the ethyl (E)-7-chloro-((S)-2,2-dimethylcyclopropanecarboxamido)-2-heptenoate (3) was about 120:1 according to gas chromatography assay, the reaction was ended, and the mixture was stirred. The pH of the mixture was adjusted to 8-9 by adding 0.5N caustic soda solution, and an organic phase was isolated. The isolated organic phase was concentrated under reduced pressure and provided to 300 ml of ethanol. Next, 380 ml (0.46 mole) of 1.2N caustic soda solution was added and stirred at room temperature until ethyl (Z)-7-chloro-((S)-2,2-dimethylcyclopropanecarboxamido)-2-heptenoate (2) was completely reacted. Most of ethanol was evaporated under reduced pressure, and an aqueous phase was washed with 150 ml of dichloromethane. The pH of the aqueous phase was adjusted to 3.5 by adding 35percent hydrochloric acid and extracted from 1,500 ml of isoprophyl ether. Meanwhile, the organic phase was provided into 100 g of anhydrous magnesium sulfate, stirred, filtered and concentrated under reduced pressure. The filtrate was crystallized, filtered and dried in hot air at 40° C. for 10 hours to produce 50.5 g of the target compound, (Z)-7-chloro-((S)-2,2-dimethylcyclopropanecarboxamido)-2-heptenoic acid (1).HPLC(C18, 40percent aqueous acetonitrile solution) purity: 99.3percent, (Z)/(E)=540H1 nmr (CDCl3, 500 MHz) ppm: 0.82-0.84 (dd, 1H), 1.15-1.23 (s, 7H), 1.43-1.46 (dd, 1H), 1.61-1.67 (m, 2H), 1.78-1.83 (m, 2H), 2.19-2.23 (m, 2H), 3.53-3.56 (t, 2H), 6.77-6.79 (t, 1H), 6.99 (s, 1H)
  • 4
  • [ 78834-75-0 ]
  • [ 75885-58-4 ]
  • [ 1022895-92-6 ]
YieldReaction ConditionsOperation in experiment
With toluene-4-sulfonic acid; In toluene; for 20h;Heating / reflux; EXAMPLE 1 Preparation of 7-chloro-2-[[(1S)-2,2-dimethyl cyclopropane]carboxamide]-2-heptenoic Acid (II) (Starting Material) To the solution of S-2,2-dimethylcylopropyl carboxamide (100 gm) in toluene (500) was added Ethyl-7-chloro-2-oxo-heptanoate (270 gm) and p-toluene sulphonic acid (1.5 gm). The resulted solution was refluxed for 20 hrs azeotropically. The resulted mass was cooled to 5-10 C. and added the solution of sodium hydroxide (140 gm) in water 500 ml and the resulted two-layered solution was stirred for 8 hrs at 25-30 C. up to the complete disappearance of ester. The toluene layer was separated and the aqueous layer was washed with toluene. The pH of the aqueous layer was adjusted to 4.0 to 4.5 and extracted with toluene (1 lt). The toluene layer containing 7-chloro-2-[[(1S)-2,2-dimethyl cyclopropane]carboxamide]-2-heptenoic acid was washed with water and used as such for the next step. The ratio of Z and E isomer 90:10% was obtained.
  • 5
  • [ 78834-75-0 ]
  • [ 75885-58-4 ]
  • [ 877674-77-6 ]
  • (E)-7-chloro-2[[(1S)-2,2-dimethyl cyclopropane]carboxamide]-2-heptenoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 1Preparation of 7-chloro-2-[[(1S)-2,2-dimethyl cyclopropane]carboxamide]-2-heptenoic acid (II) (starting material):To the solution of S-2, 2-dimethylcylopropyl carboxamide (100gm) in toluene (500) was added Ethyl-7-chloro-2-oxo-heptanoate (270gm) and p-toluene sulphonic acid (1.5gm).The resulted solution was refluxed for 20hrs azeotropically.The resulted mass was cooled to 5-10°C and added the solution of sodium hydroxide (140gm) in water 500 ml and the resulted two-layered solution was stirred for 8hrs at 25-30°C up to the complete disappearance of ester.The toluene layer was separated and the aqueous layer was washed with toluene.The pH of the aqueous layer was adjusted to 4.0 to 4.5 and extracted with toluene (1 lt).The toluene layer containing 7-chloro-2-[[(1S)-2,2-dimethyl cyclopropane]carboxamide]-2-heptenoic acid was washed with water and used as such for the next step.The ratio of Z and E isomer 90:10percent was obtained.
  • 6
  • [ 78834-75-0 ]
  • [ 75885-58-4 ]
  • (Z)-7-[(2R)-(2-amino-2-carboxyethyl)thio][(1S)-2,2-dimethylcyclopropanecarboxamido]-2-heptenoic acid sodium salt [ No CAS ]
  • 7
  • [ 78834-75-0 ]
  • [ 75885-58-4 ]
  • 7-chloro-2-[[(1S)-2,2-dimethylcyclopropane]carboxamide]-2-heptenoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With toluene-4-sulfonic acid; In toluene; at 110℃; for 24h; 25 g of <strong>[78834-75-0]ethyl 7-chlorooxoheptanoate</strong>,13.68 g of (s)-2,2-dimethylcyclopropanecarboxamide and 0.14 g of p-tolueneSulfonic acid dissolved in toluene solution, the temperature of 110 ° C under the conditions of water reflux reaction 24h, After completion of the condensation, the reaction mixture was washed with dilute hydrochloric acid and saturated aqueous solution of sodium hydrogen sulfite, respectively, and then concentrated to recover toluene. The viscous material in ethanol 20ml and 50percent sodium hydroxide aqueous solution 25ml hydrolysis reaction 12h,The pH was then adjusted to 3.0 to 4.0 with concentrated hydrochloric acid, and extracted three times with 30 ml of ethyl acetate and concentrated to give 31.2 g of a viscous material.
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