[ CAS No. 2058-74-4 ] {[proInfo.proName]}

Name: 2058-74-4|1-Methylindoline-2,3-dione|98%
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Quality Control of [ 2058-74-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 2058-74-4 ]

Product Details of [ 2058-74-4 ]

CAS No. :	2058-74-4	MDL No. :	MFCD00005812
Formula :	C₉H₇NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VCYBVWFTGAZHGH-UHFFFAOYSA-N
M.W :	161.16	Pubchem ID :	16358
Synonyms :	N-Methylisatin	Chemical Name :	1-Methylindoline-2,3-dione

Calculated chemistry of [ 2058-74-4 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.11
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	47.06
TPSA :	37.38 Å²

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) :	-6.87 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.34
Log Po/w (XLOGP3) :	0.58
Log Po/w (WLOGP) :	0.46
Log Po/w (MLOGP) :	0.49
Log Po/w (SILICOS-IT) :	1.4
Consensus Log Po/w :	0.85

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.57
Solubility :	4.29 mg/ml ; 0.0266 mol/l
Class :	Very soluble
Log S (Ali) :	-0.94
Solubility :	18.6 mg/ml ; 0.115 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.44
Solubility :	0.588 mg/ml ; 0.00365 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.47

Safety of [ 2058-74-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H317-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 2058-74-4 ]

* 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.

Upstream synthesis route of [ 2058-74-4 ]
Downstream synthetic route of [ 2058-74-4 ]

[ 2058-74-4 ] Synthesis Path-Upstream 1~6

1
[ 59-48-3 ]
[ 2058-74-4 ]
[ 97207-47-1 ]

Yield	Reaction Conditions	Operation in experiment
86%	With zirconium(IV) chloride In ethanolReflux	General procedure: A mixture of isatins (1, 1.0 mmol), indolin-2-ones (2, 1.0 mmol) and ZrCl4 (23 mg, 0.1 mmol) was heated in anhydrous ethanol (5 mL) under reflux. After the disappearance of the reactants (8–12 h, monitored by TLC), the mixture was slowly cooled to room temperature. The red solids precipitated and were collected by filtration, then washed by a small amount of anhydrous ethanol to deliver pure compounds 3.

Reference： [1] Tetrahedron Letters, 2016, vol. 57, # 52, p. 5856 - 5858
[2] Bulletin de la Societe Chimique de France, 1914, vol. <4> 15, p. 335[3] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1913, vol. 156, p. 1385

2
[ 2058-74-4 ]
[ 61-70-1 ]

Yield	Reaction Conditions	Operation in experiment
47%	for 3 h; Reflux	General procedure: Isatin (0.1 mol, 14.7 g) was dissolved in DMF (60 mL) and finely ground anhydrous K2CO3 (0.15 mol,20.7 g) was added under stirring. RX (0.15 mol) was added dropwise and mixture was heated at 60–70°C for 3 h (as alkylation reagent RX were used Me2SO4, EtI, n-PrBr, AmBr, BnCl, PMBCl,respectively). After cooling to room temperature mixture was poured into ice water (200 mL).Precipitated orange solid was filtereted, washed with water and recrystallized from ethanol (95percent) togive N-alkylated isatins as red crystalls in 37–92percent yield. The purity of obtained compounds weredetermined by melting points, which corresponded to those published in the literature (ref. 2–4).N-Substituted isatin (10 mmol) was mixed with 16 M N2H4·H2O (15 mL). The suspension was heatedat reflux 3 h (caution: rapid gas evolution), then it was cooled to room temperature, diluted with waterS4(40 mL) and extracted with EtOAc (3 x 25 mL). Organic phase was washed with water (25 mL), brine (25 mL), then it was dried over Na2SO4 and evaporated under reduced pressure to give the desired product. The latter was recrystallized from hexane and small amount of EtOAc to give N-substituted indolin-2-one as yellow solid in 47–96percent yield. The purity of obtained compounds were determined by melting points and 1H NMR spectra data, which corresponded to those published in the literature (ref. 5,6).N-Substituted indolin-2-one (2 mmol) were dissolved in dry DMF (5 mL) and NaH (60percent dispersion in mineral oil, 6 mmol, 240 mg) was portionwise added carefully at a temperature of –15 °C. When the rapid evolution of H2 stops, the mixture allowed to stir for 10 min. Then solution of 1,2-dibromoethane (508 mg, 2.7 mmol) in dry DMF (3 mL) was added to the mixture. The latter was warmed to room temperature and stirred overnight. Then it was cooled with ice, diluted with water (20 mL) and extracted with PhMe (2 x 15 mL). Organic phase was washed with water (2 x 15 mL), brine (15 mL) and then it was dried over Na2SO4. Evaporation under reduced pressure gave the desired product. The latter was washed with hexane to remove mineral oil or purified by flash column chromatography (eluent: hexane/CH2Cl2). The spiro[cyclopropane-1,3'-indolin]-2'-ones 1 are yellow solids, except N-amyl substituted spiro[cyclopropane-1,3'-indolin]-2'-one, which is brown liquid. The purity of obtained compounds were determined by 1H NMR spectra data. Corresponding cyclopropanes were previously known in the literature (ref. 7–11).

Reference： [1] Synthetic Communications, 1994, vol. 24, # 20, p. 2835 - 2841
[2] Journal of Organic Chemistry, 2005, vol. 70, # 5, p. 1828 - 1834
[3] Tetrahedron Letters, 2018, vol. 59, # 37, p. 3409 - 3412
[4] Heterocycles, 1996, vol. 43, # 1, p. 7 - 10
[5] Patent: US2006/30609, 2006, A1, . Location in patent: Page/Page column 9
[6] Patent: US2006/229348, 2006, A1, . Location in patent: Page/Page column 9
[7] Tetrahedron, 2011, vol. 67, # 5, p. 982 - 989
[8] J.Shinshu Univ., 1951, vol. 1, p. 1,4
[9] Organic Letters, 2015, vol. 17, # 6, p. 1373 - 1376
[10] Organic Letters, 2016, vol. 18, # 20, p. 5232 - 5235
[11] European Journal of Medicinal Chemistry, 2017, vol. 126, p. 1071 - 1082
[12] Journal of Organic Chemistry, 2018, vol. 83, # 15, p. 7622 - 7632
[13] Journal of Fluorine Chemistry, 2018, vol. 215, p. 44 - 51

3
[ 2058-74-4 ]
[ 61-70-1 ]
[ 67-64-1 ]

Reference： [1] Heterocycles, 1996, vol. 43, # 1, p. 7 - 10

4
[ 2058-74-4 ]
[ 61-70-1 ]
[ 3335-86-2 ]

Reference： [1] Tetrahedron, 2014, vol. 70, # 51, p. 9668 - 9675
[2] Heterocycles, 1996, vol. 43, # 1, p. 7 - 10

5
[ 2058-74-4 ]
[ 60434-13-1 ]

Reference： [1] Organic and Biomolecular Chemistry, 2013, vol. 11, # 42, p. 7372 - 7386
[2] Journal of the Brazilian Chemical Society, 2011, vol. 22, # 2, p. 257 - 263

6
[ 932-96-7 ]
[ 15249-31-7 ]
[ 2058-74-4 ]
[ 108726-52-9 ]
[ 26772-93-0 ]
[ 15950-17-1 ]

Reference： [1] Advanced Synthesis and Catalysis, 2018, vol. 360, # 17, p. 3391 - 3400

[ 2058-74-4 ] Synthesis Path-Downstream 1~88

1
[ 2058-74-4 ]
[ 2058-72-2 ]

Reference： [1]Monatshefte fur Chemie,1913,vol. 34,p. 783
[2]Chemische Berichte,1914,vol. 47,p. 358
[3]Pharmazie,1983,vol. 38,p. 585 - 586
[4]Chemical Communications,2018,vol. 54,p. 10590 - 10593

2
[ 2058-74-4 ]
[ 143-33-9 ]
[ 517-21-5 ]
[ 35103-99-2 ]

Reference： [1]Journal of the Chemical Society, Section D: Chemical Communications,1971,p. 1614

3
[ 2058-74-4 ]
[ 369-32-4 ]
[ 128316-89-2 ]

Reference： [1]Heterocycles,1990,vol. 31,p. 473 - 477

4
[ 2058-74-4 ]
[ 151-50-8 ]
[ 517-21-5 ]
[ 35103-99-2 ]

Reference： [1]Pharmazie,1983,vol. 38,p. 585 - 586

5
[ 2058-74-4 ]
[ 7732-18-5 ]
[ 7726-95-6 ]
[ 2058-72-2 ]

Reference： [1]Monatshefte fur Chemie,1913,vol. 34,p. 783

6
[ 2058-74-4 ]
[ 7726-95-6 ]
[ 64-19-7 ]
[ 2058-72-2 ]

Reference： [1]Chemische Berichte,1914,vol. 47,p. 363

7
[ 75833-63-5 ]
[ 2058-74-4 ]

Reference： [1]Organic Preparations and Procedures International,2001,vol. 33,p. 615 - 619

8
[ 40299-87-4 ]
[ 2058-74-4 ]
1-methyl-3'-(morpholin-4-ylcarbonyl)spiro[indole-3,2'-oxiran]-2(1H)-one [ No CAS ]
1-methyl-3'-(morpholin-4-ylcarbonyl)spiro[indole-3,2'-oxiran]-2(1H)-one [ No CAS ]

Reference： [1]Organic Letters,2007,vol. 9,p. 1745 - 1748

9
[ 2058-74-4 ]
[ 2532-74-3 ]

Reference： [1]Tetrahedron,2002,vol. 58,p. 8399 - 8412

10
[ 26340-49-8 ]
[ 2058-74-4 ]

Reference： [1]Organic Preparations and Procedures International,2001,vol. 33,p. 615 - 619

11
C₂₉H₃₁FN₃O₄Pol [ No CAS ]
[ 2058-74-4 ]
[ 84145-28-8 ]
C₄₅H₄₄F₂N₅O₅Pol [ No CAS ]