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Chemical Structure| 83-34-1 Chemical Structure| 83-34-1
Chemical Structure| 83-34-1

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Skatole (3-methylindole) is a heterocyclic compound naturally found in the feces of vertebrates and some plants. It is produced by gut bacteria and regulates intestinal epithelial cell function through activation of the aryl hydrocarbon receptor and p38.

Synonyms: 3-Methylindole; 3-Methyl-1H-indole; Scatole

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Product Details of Skatole

CAS No. :83-34-1
Formula : C9H9N
M.W : 131.17
SMILES Code : C2=C(C1=CC=CC=C1[NH]2)C
Synonyms :
3-Methylindole; 3-Methyl-1H-indole; Scatole
MDL No. :MFCD00005627
InChI Key :ZFRKQXVRDFCRJG-UHFFFAOYSA-N
Pubchem ID :6736

Safety of Skatole

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of Skatole

* 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 [ 83-34-1 ]

[ 83-34-1 ] Synthesis Path-Downstream   1~26

  • 1
  • [ 83-34-1 ]
  • [ 66365-41-1 ]
  • [ 13006-59-2 ]
  • 4
  • [ 83-34-1 ]
  • [ 700-06-1 ]
  • [ 78440-76-3 ]
  • [ 70423-69-7 ]
  • 5
  • [ 83-34-1 ]
  • [ 700-06-1 ]
  • 6
  • [ 5234-26-4 ]
  • [ 18107-18-1 ]
  • [ 83-34-1 ]
  • N-(2-(prop-1-yn-1-yl)phenyl)acetamide [ No CAS ]
  • 7
  • [ 83-34-1 ]
  • [ 26638-43-7 ]
  • 2-(3-methyl-indole-1-sulfonyl)-benzoic acid methyl ester [ No CAS ]
  • 8
  • [ 83-34-1 ]
  • [ 700-06-1 ]
  • [ 70423-69-7 ]
  • 9
  • [ 700-06-1 ]
  • [ 16640-68-9 ]
  • [ 83-34-1 ]
  • [ 4414-76-0 ]
  • [ 21777-18-4 ]
  • 10
  • [ 83-34-1 ]
  • [ 13006-59-2 ]
  • 11
  • [ 83-34-1 ]
  • 3-methyl-indole-carboxylic acid-(2) [ No CAS ]
  • [ 13006-59-2 ]
  • 12
  • [ 83-34-1 ]
  • nickel [ No CAS ]
  • [ 90725-50-1 ]
  • 13
  • [ 83-34-1 ]
  • nickel [ No CAS ]
  • [ 13006-59-2 ]
  • 14
  • [ 700-06-1 ]
  • [ 83-34-1 ]
  • 15
  • [ 83-34-1 ]
  • [ 97-08-5 ]
  • 1-(4-chloro-3-nitrophenylsulfonyl)-3-methyl-1H-indole [ No CAS ]
  • 2-(4-chloro-3-nitrophenylsulfinyl)-3-methyl-1H-indole [ No CAS ]
  • 2-(4-chloro-3-nitrophenylsulfonyl)-3-methyl-1H-indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
20% With zinc(II) oxide; In neat (no solvent); at 80℃; for 2h; General procedure: Indole (8.54 mmol), phenylsulfonyl chloride (10.25 mmol) and oxide fine powder (25.62 mmol) were blended and the mixture was stirred for the period indicated (TLC) at 80 C. After reaction, the crude mixture was washed with acetone or dichloromethane and filtered through celite. The concentrated filtrate was flash chromatographied (hexane/ethyl acetate 3/1, 5/1 or 1/3) on silica gel, obtaining the desired product. When indoles 1a, 1b, 1j and 1l andsulfonyl chlorides 2f, 2h, 2j, 2k were used, the correspondent 2- or 3-sulfinylindole 6 or 7 was also isolated.
  • 16
  • [ 83-34-1 ]
  • [ 97-08-5 ]
  • 2-(4-chloro-3-nitrophenylsulfinyl)-3-methyl-1H-indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% With zinc(II) oxide; In neat (no solvent); at 80℃; General procedure: Indole (8.54 mmol), phenylsulfonyl chloride (10.25 mmol) and oxide fine powder (25.62 mmol) were blended and the mixture was stirred for the period indicated (TLC) at 80 C. After reaction, the crude mixture was washed with acetone or dichloromethane and filtered through celite. The concentrated filtrate was flash chromatographied (hexane/ethyl acetate 3/1, 5/1 or 1/3) on silica gel, obtaining the desired product. When indoles 1a, 1b, 1j and 1l andsulfonyl chlorides 2f, 2h, 2j, 2k were used, the correspondent 2- or 3-sulfinylindole 6 or 7 was also isolated.
  • 17
  • [ 83-34-1 ]
  • [ 802919-90-0 ]
  • [ 1609470-43-0 ]
  • 18
  • [ 83-34-1 ]
  • [ 521-73-3 ]
  • 4-hydroxy-4-(3-methyl-1H-indol-2-yl)-1,3(2H,4H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% General procedure: A heterogeneous mixture of <strong>[521-73-3]isoquinoline-1,3,4-trione</strong>(17.5 mg, 0.1 mmol), indole (14.0 mg, 0.12 mmol) and alginic acid (1.76 mg,0.01 mmol, purchased from Sigma Aldrich) in H2O (0.2 mL) was stirred for 24 h(monitored by TLC). Afterwards, the reaction mixture was concentrated under reduced pressure to leave the crude residue which was purified by column chromatography over silica-gel using ethyl acetate/hexane as a mixture of solvent to give the pure compound 3aa in75% yield (21.9 mg) as a white solid.4-Hydroxy-4-(1H-indol-3-yl)isoquinoline-1,3(2H,4H)-dione (3aa): yield 75%; mp:188-190 C; Rf = 0.25 (EtOAc/hexane = 1:3); 1H NMR (400 MHz, acetone-d6) d10.24 (br s, 1H, NH), 10.10 (br s, 1H, NH), 8.14 (d, J = 7.8 Hz, 1H), 7.89 (d,J = 7.8 Hz, 1H), 7.76-7.79 (m, 2H), 7.59-7.63 (m, 1H), 7.36 (d, J = 8.2 Hz, 1H),7.06-7.10 (m, 1H), 6.96-7.00 (m, 1H), 6.65-6.66 (m, 1H), 5.66 (br s, 1H, OH); 13CNMR (100 MHz, acetone-d6) d 175.0 (CO), 164.7 (CO), 144.3, 138.0, 134.7,129.2, 128.2, 127.9, 125.8, 125.8, 124.8, 122.6, 122.4, 121.7, 120.1, 112.4, 74.7(C-4, quaternary); HRMS (ESI) m/z calcd For C17H12N2O3 [M+Na]+: 315.0897.Found 315.0953.
  • 19
  • [ 67-56-1 ]
  • [ 700-06-1 ]
  • [ 83-34-1 ]
  • 20
  • [ 52562-19-3 ]
  • [ 83-34-1 ]
YieldReaction ConditionsOperation in experiment
54% With dipotassium peroxodisulfate; iron(II) fluoride; triethylamine; In tetrahydrofuran; at 70℃; for 16h; General procedure: To a solution of the 2-vinylaniline (0.3 mmol) and catalyst FeF2 (0.03 mmol, 2.8 mg) in THF (3 mL) was added K2S2O8 (0.9 mmol, 0.2433 g) and Et3N (0.15 mmol, 21 μL), open to the air. The mixture was stirred at 70 C for 16 h, then diluted with water (10 mL) and extracted with CH2Cl2 (3 × 10 mL). The combined organic extracts were washed with brine and dried with Na2SO4, filtered and concentrated under vacuum (eluted with EtOAc/hexane 1:20 to 1:5) to give the corresponding product.
  • 21
  • [ 83-34-1 ]
  • [ 1074-40-4 ]
  • C14H12ClN3O [ No CAS ]
  • 22
  • [ 83-34-1 ]
  • [ 1593-60-8 ]
  • [ 1622221-71-9 ]
  • 23
  • [ 83-34-1 ]
  • [ 4498-72-0 ]
  • 24
  • [ 83-34-1 ]
  • [ 101906-05-2 ]
  • 1-(3-methyl-1H-indol-2-yl)-2-(4-(trifluoromethyl)phenyl)ethane-1,2-dione [ No CAS ]
  • 25
  • [ 83-34-1 ]
  • [ 101906-05-2 ]
  • 1-(3-methyl-1H-indol-1-yl)-2-(4-(trifluoromethyl)phenyl)ethane-1,2-dione [ No CAS ]
  • 26
  • [ 83-34-1 ]
  • [ 34595-26-1 ]
  • 16-methyl-1,3,4,16b-tetrahydro-2H,10H-benzo[5,6]pyrido[2',1':3,4][1,4]diazepino[1,2-a]indole [ No CAS ]
 

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