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CAS No. :13070-45-6 MDL No. :MFCD06662245
Formula : C13H15NO Boiling Point : -
Linear Structure Formula :- InChI Key :LJUKCUCBMZNDOR-UHFFFAOYSA-N
M.W : 201.26 Pubchem ID :10798130
Synonyms :

Safety of [ 13070-45-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H317 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 13070-45-6 ]

* 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 [ 13070-45-6 ]

[ 13070-45-6 ] Synthesis Path-Downstream   1~101

  • 1
  • [ 93-59-4 ]
  • [ 13070-45-6 ]
  • 6-methoxy-1,2,3,4-tetrahydro-carbazol-4a-yl hydroperoxide [ No CAS ]
  • 2
  • [ 13070-45-6 ]
  • [ 71-43-2 ]
  • 6-methoxy-1,2,3,4-tetrahydro-carbazol-4a-yl hydroperoxide [ No CAS ]
  • 3
  • [ 13070-45-6 ]
  • [ 18992-85-3 ]
YieldReaction ConditionsOperation in experiment
92% With copper(II) choride dihydrate; In dimethyl sulfoxide; at 100℃; for 7h; General procedure: A mixture of starting compound (2.69 mmol), CuCl2.2H2O (10 mol %) in DMSO (5 mL) stirred at 100 C. The reaction progress was monitored by thin layer chromatography (PMA was used for stain solution). The reaction mixture was poured into ice cold water. The crude product was purified by column chromatography using ethyl acetate and petroleum ether as eluent to afford carbazoles.
53% With palladium 10% on activated carbon; In water; for 48h;Reflux; To a solution of compound 6 (0.409 g, 2.03 mmol) in p-cymene and H2O (5 mL, 4:1) 10 % Pd/C (0.206 g) was added and the mixture heated under reflux for 48 h. After cooling it was filtered over Celite and washed with boiling EtOAc. The filtrate was evaporated to dryness, and the product was obtained as an oil. Yield: 0.210 g (1.07 mmol, 53 %). 1H NMR (300 MHz, CDCl3): delta 8.04 (d, 1H ,J = 8.1 Hz, H-5), 7.57 (d, 1H, J = 2.4 Hz, H-4), 7.41-7.40 (m, 2H, H-7 and H-8), 7.34 (d, 1H, J = 8.7 Hz, H-1), 7.24-7.20 (m, 1H, H-6), 7.07 (dd, 1H, J = 9.0 and 2.4 Hz, H-2), 3.94 (s, 3H, OCH3) ppm. NH was not observed.
  • 6
  • [ 13070-45-6 ]
  • 6-methoxy-1,2,3,4-tetrahydro-carbazol-4a-yl hydroperoxide [ No CAS ]
  • 7
  • [ 13070-45-6 ]
  • (6-methoxy-1,2,3,4-tetrahydro-9H-carbazol-9-yl)(phenyl)methanone [ No CAS ]
  • 10
  • [ 13070-45-6 ]
  • [ 407-25-0 ]
  • [ 83696-92-8 ]
  • 11
  • [ 13070-45-6 ]
  • [ 75457-24-8 ]
  • 13
  • [ 108-94-1 ]
  • [ 3471-32-7 ]
  • [ 13070-45-6 ]
YieldReaction ConditionsOperation in experiment
85% With Amberlite IR 120; In ethanol; at 80℃; for 10h; General procedure: A mixture of the carbonyl compound (5, 1.0 mmol), arylhydrazine (6, 1.2 mmol), and the solid acid (7, Amberlite, 1.5 g, obtained from Aldrich Chemical Co.) was refluxed in absolute ethanol (10 ml) for 8 h. The reaction was monitored by thin-layer chromatography(TLC), and upon completion the mixture was cooled to room temperature, the catalyst filtered off, and the product was washed thoroughly with ethylacetate (30 ml). The combined organics were washed with water, dried (Na2SO4), and concentrated in vacuo. The resulting residue was chromatographed on a silicagel column eluting with ethylacetate-hexane mixtures to obtain the purified indole (8). This was fully characterized by infrared, 400-MHz 1H NMR, high-resolution mass spectrometry, and melting point (solids).
82% With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; In ethyl acetate; at 110℃; for 0.166667h;Microwave irradiation; Sealed vessel; General procedure: T3P (50% in EtOAc) (0.55-0.68 mmol) was added to a mixture of hydrazine (59 mg, 0.55 mmol) and ketone/aldehyde (0.55 mmol) in a microwave vial. The reaction volume was then made up to 0.5 mL with EtOAc and the vessel was sealed under air. The mixture was heated under microwave irradiation (Biotage Initiator) at 100-150 C for 5-15 min. The solvent was evaporated under reduced pressure and the oily residue was purified by filtration through a plug of silica gel (eluent: isohexane/EtOAc, 8:2) to yield the desired indole or tetrahydrocarbazole. When the reaction was conducted on a 5 mmol scale the product (3a) was purified by precipitation from acetone/water.
71% With acetic acid; for 4.5h;Reflux; To a solution of cyclohexanone (0.30 mL, 2.86 mmol) in glacial acetic acid (1 mL), methyl 4-methoxyphenyl hydrazine (0.501 g, 2.87 mmol) was added over 1 h. The mixture was refluxed for 3.5 h and left stirring until reaching room temperature. It was then cooled in ice for 20 min and then 75 % (v/v) aqueous MeOH (4 mL) was added. The solid formed was filtered and washed with 12 mL of the same aqueous methanol to give a beige solid. Yield: 0.409 g (2.03 mmol, 71 %). mp 93-95 C. 1H NMR (300 MHz, CDCl3): delta 7.56 (sbr, 1H, NH), 7.18 (d, 1H, J = 9.0 Hz, H-1), 6.93 (d, 1H, J = 2.4 Hz, H-4), 6.77 (dd, 1H, J = 8.7 and 2.4 Hz, H-2), 3.86 (s, 3H, OCH3), 2.72-2.68 (m, 4H, H-6 and H-7), 1.90-1.89 (m, 4H, H-5 and H-8) ppm. 13C NMR (75.4 MHz, CDCl3): delta 153.84 (C-3), 153.06 (C-8a), 130.68 (C-9a), 128.17 (C-4a), 110.90 (C-1), 110.50 (C-2), 110.02 (C-4b), 100.23 (C-4), 55.95 (OCH3), 23.33 (C-6 or C-7), 23.18 (C-5 and C-8), 20.94 (C-6 or C-7) ppm. Anal. calcd for C13H15NO: C, 77.91; H, 7.223; N, 6.983 %; found: C, 77.58; H, 7.51; N, 6.96 %.
With hydrogenchloride; In water; at 50 - 60℃; for 5h; General procedure: Substituted phenyl hydrazine (14 mmol) was solved in the mixture of concentrated hydrochloric acid and water (50 mL, 1:20) and then ketone (16.8 mmol) was added dropwise at rt. After that, the mixture was stirred for more than 5 h at 50-60 . When the reaction cooled to rt, some rice shape solids appeared in the system. The mixture was filtered and the solid was washed with enough water until neutral.T he crude product was recrystallized in hexane to afford 1k-1q in 72-95% yield.

  • 16
  • [ 13070-45-6 ]
  • [ 106-89-8 ]
  • [ 123063-72-9 ]
  • 17
  • [ 13070-45-6 ]
  • [ 5809-23-4 ]
  • 3-(Diethylamino)-8,9,10,11-tetrahydrospiro<<1>benzopyrano<3,2-b>carbazole-13(7H),1'(3'H)-isobenzofuran>-3'-one [ No CAS ]
  • 18
  • [ 13070-45-6 ]
  • [ 75-08-1 ]
  • 6-ethylthio-1,2,3,4-tetrahydrocarbazole [ No CAS ]
  • 20
  • [ 13070-45-6 ]
  • lead oxide [ No CAS ]
  • [ 18992-85-3 ]
YieldReaction ConditionsOperation in experiment
78% With 4-(dimethylamino)-1-pentylpyridin-1-ium fluoride; zinc(II) chloride; In ethanol; at 78 - 80℃;Inert atmosphere; General procedure: In a general procedure, an oven dried round bottomed flask was charged with corresponding phenyl hydrazine hydrochloride (1 mmol, 1 equiv.) and ethanol (3 mL). To the resulting solution corresponding 43uinolone43one/methyl cyclohxanone (1 mmol, 1 equiv.) and 4-(dimethylamino)-1-pentylpyridin-1-ium fluoride (2) [or (II)] (0.2 mmol, 0.2 equiv.) was added at room temperature and mixture was heated at reflux (78-80 C.) under nitrogen atmosphere. The consumption of starting material was monitored by thin layered chromatography by using eluents ethyl acetate/hexane (3:7). The crude reaction mixture was directly purified by silica gel column chromatography by using eluents in gradient eluents EtOAc/Hexane (1:9 to 1:1) to get the corresponding pure products (6a-h) in different yields.
  • 22
  • (+-)-2-<4-methoxy-anilino>-cyclohexanone [ No CAS ]
  • [ 13070-45-6 ]
  • 23
  • [ 108-94-1 ]
  • 4-methoxy-phenylhydrazine hydrochloride [ No CAS ]
  • [ 13070-45-6 ]
  • 24
  • cyclohexanone-<4-methoxy-phenylhydrazone> [ No CAS ]
  • [ 13070-45-6 ]
  • 25
  • [ 108-94-1 ]
  • [ 380383-75-5 ]
  • [ 13070-45-6 ]
  • 26
  • [ 13070-45-6 ]
  • 9-methoxy-3,4,5,6-tetrahydro-1<i>H</i>-benzo[<i>b</i>]azonine-2,7-dione [ No CAS ]
  • 27
  • [ 1056477-06-5 ]
  • [ 104-94-9 ]
  • [ 13070-45-6 ]
  • 28
  • [ 19501-58-7 ]
  • [ 1122-60-7 ]
  • [ 13070-45-6 ]
  • 30
  • [ 13070-45-6 ]
  • [ 475273-53-1 ]
  • 31
  • [ 13070-45-6 ]
  • 9<i>H</i>,9'<i>H</i>-[2,4']bicarbazolyl-3,3'-diol [ No CAS ]
  • 32
  • [ 13070-45-6 ]
  • (S)-(-)-9H,9'H-[4,4']bicarbazole-3,3'-diol [ No CAS ]
  • 33
  • [ 13070-45-6 ]
  • Carbonic acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester 3'-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxycarbonyloxy)-9H,9'H-[4,4']bicarbazolyl-3-yl ester [ No CAS ]
  • 34
  • [ 13070-45-6 ]
  • Carbonic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 3'-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxycarbonyloxy)-9H,9'H-[4,4']bicarbazolyl-3-yl ester [ No CAS ]
  • 35
  • [ 13070-45-6 ]
  • [ 13314-77-7 ]
  • 36
  • [ 13070-45-6 ]
  • 6-ethylthio-1,2,3,4-tetrahydro-9-methylcarbazole [ No CAS ]
  • 37
  • [ 108-94-1 ]
  • [ 13070-45-6 ]
  • 38
  • [ 5345-54-0 ]
  • [ 13070-45-6 ]
  • 39
  • [ 13070-45-6 ]
  • 1-Diethylamino-3-(6-methoxy-1,2,3,4-tetrahydro-carbazol-9-yl)-propan-2-ol; compound with (E)-but-2-enedioic acid [ No CAS ]
  • 40
  • [ 13070-45-6 ]
  • 1-(6-Methoxy-1,2,3,4-tetrahydro-carbazol-9-yl)-3-piperidin-1-yl-propan-2-ol; compound with (E)-but-2-enedioic acid [ No CAS ]
  • 41
  • [ 13070-45-6 ]
  • 1-(6-Methoxy-1,2,3,4-tetrahydro-carbazol-9-yl)-3-morpholin-4-yl-propan-2-ol; compound with (E)-but-2-enedioic acid [ No CAS ]
  • 42
  • [ 13070-45-6 ]
  • [ 120400-60-4 ]
  • 44
  • [ 104-94-9 ]
  • optically inactive bis-<2-chloro-propyl>-<2>naphthyl-amine [ No CAS ]
  • [ 13070-45-6 ]
  • 49
  • [ 13070-45-6 ]
  • [ 108839-93-6 ]
  • 50
  • [ 19501-58-7 ]
  • [ 108-94-1 ]
  • [ 13070-45-6 ]
YieldReaction ConditionsOperation in experiment
97% With 1,3,5-trichloro-2,4,6-triazine; In ethanol; at 80℃; for 2h; General procedure: A mixture ofphenyl hydrazines.HCl (1 mmol), ketones (1 mmol) andTCT (0.1 mmol) in distilled ethanol was heated to 80 C. After 2 h the startingmaterial was absent as monitored by TLC. The reaction mixture was cooled toambient temperature and diluted with water. The product was extracted intoethyl acetate (5x3 mL). The combined organiclayer was dried over anhydrous Na2SO4 and concentrated toresidue. Thus obtained residue was purified by column chromatography (gradientof 5-10 % EtOAc in Petroleum ether) to yield indole ortetrahydrocarbazole or tetrahydrocarboline derivatives (3a-3x).
95% With 4-methylbenzenesulfonic acid-based ionic liquid supported on silica gel; In ethanol; at 20℃; for 4h; General procedure: To a solution of phenylhydrazine (10 mmol) and ketone or aldehyde (10 mmol) in ethanol (15 mL) was added catalyst IL-SO3H-SiO2 (1.2 g). The mixture was allowed to stirringat room temperature for a period time specified in Table 2.The reaction was monitored by TLC and GC. After completionof the reaction, the catalyst was recovered by filtration.Evaporation of the solvent under reduced pressuregave the crude product. Further purification was achievedby flash column chromatography on a silica gel to give thedesired product. The recovered catalyst was dried andreused for the next run. Spectroscopic data for selectedproducts is as follows.
89% With acetic acid; for 8h;Reflux; General procedure: A substituted phenyl hydrazine. HCl (4.61 mmol) was added to the mixture of cyclohexanone (4.61 mmol) and acetic acid (15 ml) portion wise for 30 min. The mixture was then refluxed for 8 h and progress of reaction was monitored by thin layer chromatography. The reaction mixture was cooled and poured into crushed ice. The solid product was separated, filtered, dried and recrystallized from the methanol solvent.
79% With acetic acid; at 80℃; for 1h; EXAMPLE 16; Methyl 2,3,4,9-tetrahvdro-lff-carbazol-6-vI ether [Compound 161; 4-Methoxyhydrazine hydrochloride (1.746 g, 0.01 mol) was suspended in acetic acid (10 mL) and heated to 8O0C, with stirring. Cyclohexanone (1.00 g, 0.01 mol) was added dropwise, with stirring. The reaction mixture was heated for 1 hour, cooled to room temperature and then kept in the fridge overnight. The colour of the reaction mixture changed to dark-brown. The solid material was filtered and washed with a small amount of acetic acid. More material was recovered from the filtrate. The combined solids were dried under reduced pressure to give an off-white crystalline material (1.596 g, 79%), mpl08-110C [Clark, D.W.; Jackson, A.H.; Prasitrhoan, N. and Shannon, P.V.R., J.Chem.Soc.Perkin Trans.II, 1982, 909-916, mp94-96C], RF=0.50 (ethyl acetate/n-hexane 1A). IR (KBr): 3389, 2915, 2845, 1622, 1589, 1482, 1434, 1218, 1134, 1028, 826, 798 cm.-1 1H NMR (DMSO-d6): 1O.39(1H, s), 7.11(1H, d, J=8.7Hz), EPO <DP n="29"/>6.81(1H5 d5 J=2.4Hz), 6.62(1H, dd, J=2.4 & 8.6Hz)5 3.73(3H5 s), 2.67(2H, t, J=5.4Hz), 2.57(1H5 1, J=5.8Hz), 1.82-1.77(4H5 m).

  • 51
  • [ 13070-45-6 ]
  • [ 35466-83-2 ]
  • [ 1029578-16-2 ]
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  • [ 108-85-0 ]
  • [ 459-64-3 ]
  • [ 13070-45-6 ]
  • 53
  • [ 1279722-91-6 ]
  • [ 13070-45-6 ]
  • 54
  • [ 1279722-99-4 ]
  • [ 13070-45-6 ]
  • 55
  • [ 1279722-88-1 ]
  • [ 13070-45-6 ]
  • 56
  • [ 1332747-76-8 ]
  • [ 13070-45-6 ]
  • 58
  • [ 32338-02-6 ]
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  • [ 13070-45-6 ]
  • [ 78-94-4 ]
  • [ 1379786-41-0 ]
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  • [ 13070-45-6 ]
  • [ 24424-99-5 ]
  • [ 1415566-48-1 ]
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  • [ 24424-99-5 ]
  • [ 1415566-43-6 ]
  • 64
  • [ 13070-45-6 ]
  • [ 1029578-16-2 ]
  • 65
  • [ 13070-45-6 ]
  • [ 2937-50-0 ]
  • [ 1424130-76-6 ]
  • 67
  • [ 13070-45-6 ]
  • (-)-(4aS,9aS)-5-methoxy-2,3,4,4a,9,9a-hexahydro-1H-carbazole [ No CAS ]
  • (4aR,9aR)-5-methoxy-2,3,4,4a,9,9a-hexahydro-1H-carbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
With palladium(II) trifluoroacetate; 5,5'-decamethylenedioxy-2,2'-bis(diphenylphosphino)biphenyl; (1S)-10-camphorsulfonic acid; hydrogen; In dichloromethane; at 35℃; under 45004.5 Torr; for 24h;Autoclave; General procedure: (S)-C10-BridgePHOS (2.0mg, 2.4mol%) and Pd(OCOCF3)2 (0.8mg, 2mol%) were placed into an oven dried flask under a nitrogen atmosphere, and degassed fresh dry acetone (2mL) was added. The mixture was stirred at room temperature for 1h. Then acetone was removed under vacuum and a solvent system of CH2Cl2/TFE (1/1, 1mL) was added to the mixture to afford the catalyst solution. The substrate 1 (0.15mmol) and additive (1equiv) were placed in a reaction tube under nitrogen and the above catalyst solution was added to the tube. The mixture was then degassed and transferred to a stainless steel autoclave in a glove box. After exchanging the gas three times, the hydrogenation was carried out at 35C under 60bar H2. After several hours, the reaction mixture was concentrated under reduced pressure. After alkalization with saturated NaHCO3, the percentage conversion of product was determined by 1H NMR analysis of the crude product. The organic residue was purified by flash chromatography with ethyl acetate/petrol ether (1:50) to give pure product 2. Enantiomeric excess was determined using a Daicel Chiralcel column with hexane/i-propyl alcohol as the eluant.
  • 68
  • [ 286-20-4 ]
  • [ 104-94-9 ]
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  • [ 13070-45-6 ]
  • [ 79-44-7 ]
  • [ 1548776-62-0 ]
  • 70
  • [ 13070-45-6 ]
  • [ 1548775-66-1 ]
  • 71
  • [ 13070-45-6 ]
  • [ 152547-42-7 ]
  • (R)-2-((6-methoxy-1,2,3,4-tetrahydro-4aH-carbazol-4a-yl)methyl)-4-oxo-4H-pyran-3-yl methanesulfonate [ No CAS ]
  • 72
  • [ 13070-45-6 ]
  • [ 152547-42-7 ]
  • C19H19NO4 [ No CAS ]
  • 73
  • [ 108-94-1 ]
  • [ 29242-84-0 ]
  • [ 13070-45-6 ]
  • 74
  • [ 13070-45-6 ]
  • (E)-ethyl 3-(3-hydroxy-9H-carbazol-9-yl)acrylate [ No CAS ]
  • 75
  • [ 13070-45-6 ]
  • 3-methoxy-9H-carbazole-9-carbaldehyde [ No CAS ]
  • 76
  • [ 13070-45-6 ]
  • 3-hydroxy-9H-carbazole-9-carbaldehyde [ No CAS ]
  • 77
  • [ 13070-45-6 ]
  • 3-iodo-6-methoxy-9H-carbazole [ No CAS ]
  • 78
  • [ 13070-45-6 ]
  • 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]propen-1-one [ No CAS ]
  • 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]-3-(6-methoxy-1,2,3,4-tetrahydrocarbazol-9-yl)propan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With hydroquinone; cesium fluoride; In N,N-dimethyl-formamide; at 120 - 140℃; for 4h; General procedure: A stirred solution of acrylate 9 (1 mmol), cycloalkaneindole 10a,b, 11a-j, 12a,b, or 13a,b, (1 mmol), CsF (0.1 g), and hydroquinone (0.02 g) in DMF (1.5 mL) was heated at 120-140C for 4 h. The solvent was removed in vacuo (3 Torr), the residue was extracted with dichloromethane, the solvent was removed in vacuo. Column chromatography of the residue (silica gel (60 mesh), elution with methanol-chloroform, 1 : 10) afforded target compounds. This procedure was applied for the synthesis of the following compounds: 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]-3-(2,3dihydro-1H-cyclopenta[b]indol-4-yl)propan-1-one hydrochloride (14a), 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]-3-(7-methyl-2,3-dihydro-1H-cyclopenta[b]indol-4-yl)propan-1-one (14b), 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]-3-(1,2,3,4-tetrahydrocarbazol-9-yl)propan-1-one (15a), 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]-3-(6-methyl-1,2,3,4-tetrahydrocarbazol-9-yl)propan-1-one (15b), 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]-3-(6-fluoro-1,2,3,4-tetrahydrocarbazol-9-yl)propan-1-one (15c), 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]-3-(6-methoxy-1,2,3,4-tetrahydrocarbazol-9-yl)propan-1-one (15d), 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]-3-(6-trifluoromethoxy-1,2,3,4-tetrahydrocarbazol-9-yl)propan-1-one (15e), 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]-3-(3-methyl-1,2,3,4-tetrahydrocarbazol-9-yl)propan-1-one (15f), 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]-3-(3,6-dimethyl-1,2,3,4-tetrahydrocarbazol-9-yl)propan-1-one (15g), 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]-3-(6-fluoro-3-methyl-1,2,3,4-tetrahydrocarbazol-9-yl)propan-1-one (15h), 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]-3-(3-methyl-6-methoxy-1,2,3,4-tetrahydrocarbazol-9-yl)propan-1-one (15i), 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]-3-(3methyl-6-trifluoromethoxy-1,2,3,4-tetrahydrocarbazol-9-yl)propan-1-one (15j), 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]-3-(7,8,9,10-tetrahydro-6H-cyclohepta[b]indol-4-yl)propan-1-one (16a), 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]-3-(2-methyl-7,8,9,10-tetrahydro-6H-cyclohepta[b]indol-4-yl)propan-1-one (16b), 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]-3-(6,7,8,9,10,11-hexahydrocycloocta[b]indol-5-yl)propan-1-one (17a), 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]-3-(2-methyl-6,7,8,9,10,11-hexahydrocycloocta[b]indol-5-yl)propan-1-one (17b).
  • 79
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  • 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]propen-1-one [ No CAS ]
  • 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]-3-(6-methoxy-1,2,3,4-tetrahydrocarbazol-9-yl)propan-1-one dihydrochloride [ No CAS ]
  • 80
  • [ 13070-45-6 ]
  • [ 150-76-5 ]
  • (±)-2,9-dimethoxy-6H-5a,10b-butanobenzofuro[2,3-b]indole [ No CAS ]
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  • [ 303-38-8 ]
  • C20H19NO5 [ No CAS ]
  • 83
  • 4-methoxyphenylhydrazine hydrochloric acid salt [ No CAS ]
  • [ 108-94-1 ]
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  • 84
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  • [ 81112-28-9 ]
  • C17H21NO [ No CAS ]
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  • [ 17345-61-8 ]
  • C20H18N2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% With tert.-butylhydroperoxide; methanesulfonic acid; iron(II) phthalocyanine; acetic acid; In acetonitrile; for 0.0833333h;Cooling with ice; Dissolve 93 mg of S11 in acetonitrile.Add 135 mg of 3,4-dihydroxybenzonitrile and add 7 mg of iron phthalocyanine under ice bath.30 mg of acetic acid, 4.8 mg of methanesulfonic acid and 135 mg of tert-butyl hydroperoxide, After stirring the reaction for 5 minutes under the same conditions,After monitoring the reaction, it was diluted with 20 mL of ethyl acetate and extracted with 20 mL of H2O.The combined organic layer Wash with 20 mL of saturated brine.Dry with anhydrous Na2SO4, filter and spin dry. Purified with silica gel column, eluent PE/ EtOAc = 8:1,188 mg of compound 11,The reaction yield was 56%;The product was a light yellow oil at room temperature.Physical state: light yellow oil; melting point: 138.5-139.4 C
  • 86
  • [ 99-50-3 ]
  • [ 13070-45-6 ]
  • C20H19NO5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% With tert.-butylhydroperoxide; methanesulfonic acid; iron(II) phthalocyanine; acetic acid; In acetonitrile; for 0.0833333h;Cooling with ice; Dissolve 101 mg of S2 in acetonitrile.Add 154 mg of 3,4-dihydroxybenzoic acid,Add 7 mg under ice bath Iron phthalocyanine, 30 mg of acetic acid,4.8 mg of methanesulfonic acid and 135 mg of tert-butyl hydroperoxide. The reaction system is under the same conditions After stirring for 5 minutes, after monitoring the reaction, it was diluted with 20 mL of ethyl acetate and extracted with 20 mL of H2O, then combined. The organic layer was washed with 20 mL of saturated brine, dried over anhydrous Na2SO4, filtered and evaporated. Silica gel chromatography The crude product was purified (PE/EtOAc = 2:1).Obtaining 101 mg of compound 2,The reaction yield is 57%.The product was a white solid at room temperature.Physical state: white solid; melting point: 149.6-151.9 C
  • 87
  • [ 13070-45-6 ]
  • [ 4289-20-7 ]
  • 6-methoxy-9-((2E,4E)-5-phenylpenta-2,4-dien-1-yl)-2,3,4,9-tetrahydro-1H-carbazole [ No CAS ]
  • 6-methoxy-9-(5-phenylpenta-2,4-dien-1-yl)-2,3,4,9-tetrahydro-1H-carbazole [ No CAS ]
  • 89
  • [ 13070-45-6 ]
  • 2-(6-methoxy-9-methyl-2,3,4,9-tetrahydro-1H-carbazol-4-yl)isoindoline-1,3-dione [ No CAS ]
  • 90
  • [ 13070-45-6 ]
  • [ 86451-26-5 ]
  • 2-(6-methoxy-2,3,4,9-tetrahydro-1H-carbazol-4-yl)isoindoline-1,3-dione [ No CAS ]
  • 91
  • [ 13070-45-6 ]
  • [ 17345-61-8 ]
  • 9-methoxy-6H-5a,10b-butanobenzo[5,6][1,4]dioxino[2,3-b]indole-2-carbonitrile [ No CAS ]
  • 92
  • [ 99-50-3 ]
  • [ 13070-45-6 ]
  • 9-methoxy-6H-5a,10b-butanobenzo[5,6][1,4]dioxino[2,3-b]indole-2-carboxylic acid [ No CAS ]
  • 93
  • [ 13070-45-6 ]
  • [ 98-88-4 ]
  • (6-methoxy-1,2,3,4-tetrahydro-9H-carbazol-9-yl)(phenyl)methanone [ No CAS ]
  • 94
  • [ 13070-45-6 ]
  • [ 98-88-4 ]
  • (3,8-dimethoxy-10H-4b,9b-butanobenzofuro[3,2-b]indol-10-yl)(phenyl)methanone [ No CAS ]
  • (2,9-dimethoxy-6H-5a,10b-butanobenzofuro[2,3-b]indol-6-yl)(phenyl)methanone [ No CAS ]
  • 95
  • [ 13070-45-6 ]
  • [ 7250-67-1 ]
  • 6‑methoxy‑9‑(2‑(pyrrolidin‑1‑yl)ethyl)‑2,3,4,9‑tetrahydro‑1H‑carbazole [ No CAS ]
  • 96
  • [ 13070-45-6 ]
  • [ 2008-75-5 ]
  • 6‑methoxy‑9‑(2‑(piperidin‑1‑yl)ethyl)‑2,3,4,9‑tetrahydro‑1H‑carbazole [ No CAS ]
  • 97
  • [ 13070-45-6 ]
  • [ 3647-69-6 ]
  • 4‑(2‑(6‑methoxy‑1,2,3,4‑tetrahydro‑9H‑carbazol‑9‑yl)ethyl)morpholine [ No CAS ]
  • 98
  • [ 13070-45-6 ]
  • [ 106-51-4 ]
  • (5aS,10bR)-9-methoxy-6H-5a,10b-butanobenzofuro[2,3-b]indol-2-ol [ No CAS ]
  • (5aR,10bS)-9-methoxy-6H-5a,10b-butanobenzofuro[2,3-b]indol-2-ol [ No CAS ]
  • 99
  • [ 108-94-1 ]
  • [ 501-58-6 ]
  • [ 13070-45-6 ]
YieldReaction ConditionsOperation in experiment
60% With 4,4'-bipyridine; 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane In benzene-d6 at 100℃; for 24h; Inert atmosphere; Glovebox;
  • 100
  • [ 108-94-1 ]
  • [ 2396-60-3 ]
  • [ 942-01-8 ]
  • [ 13070-45-6 ]
YieldReaction ConditionsOperation in experiment
1: 47% 2: 29% With 4,4'-bipyridine; 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane In benzene-d6 at 100℃; for 24h; Inert atmosphere; Glovebox;
  • 101
  • [ 13070-45-6 ]
  • [ 3449-49-8 ]
YieldReaction ConditionsOperation in experiment
With orthoperiodic acid In methanol at 20℃;
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