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Chemical Structure| 6072-57-7
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Product Details of [ 6072-57-7 ]

CAS No. :6072-57-7 MDL No. :MFCD00156725
Formula : C10H10O Boiling Point : -
Linear Structure Formula :- InChI Key :XVTQSYKCADSUHN-UHFFFAOYSA-N
M.W : 146.19 Pubchem ID :259560
Synonyms :

Safety of [ 6072-57-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 6072-57-7 ]

* 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 [ 6072-57-7 ]

[ 6072-57-7 ] Synthesis Path-Downstream   1~92

  • 1
  • [ 6072-57-7 ]
  • [ 66248-98-4 ]
YieldReaction ConditionsOperation in experiment
69% With sulfuric acid; potassium nitrate In sulfuric acid; ethyl acetate at 0℃; 3 <Preparation of 3-methyl-6-nitro-2,3-dihydro-1-H-inden-1-one> As presented in the following reaction formula, a solution of potassium nitrate (KNO2; 6.2 g, 0.06 mol) in sulfuric acid (30 mL) was added dropwise at 0°C to a mixture of 3-methyl-2,3-dihydro-1H-inden-1-one (9.0 g, 0.06 mol) in sulfuric acid (H2SO4; 40 mL). Then, the mixture was stirred at 0°C until the completion of reaction. The mixture obtained after the reaction was added to ice water and filtered. The cake was washed with water and purified by silica gel (100 g) column chromatography (product of Merck Co., Ltd.) using an eluent of pentane (PE): ethyl acetate (10:1 (by volume)) to give 3-methyl-6-nitro-2,3-dihydro-1-H-inden-1-one (8 g, yield: 69%) as a yellow solid.
69% With sulfuric acid; potassium nitrate at 0℃; 3 Preparation of 3-methyl-6-nitro-2,3-dihydro-1-H-inden-1-one As presented in the following reaction formula, a solution of potassium nitrate (KNO2; 6.2 g, 0.06 mol) in sulfuric acid (30 mL) was added dropwise at 0° C. to a mixture of 3-methyl-2,3-dihydro-1H-inden-1-one (9.0 g, 0.06 mol) in sulfuric acid ic (H2SO4; 40 mL). Then, the mixture was stirred at 0° C. until the completion of reaction. The mixture obtained after the reaction was added to ice water and filtered. The cake was washed with water and purified by silica gel (100 g) column chromatography (product of Merck Co., Ltd.) using an eluent of pentane (PE):ethyl acetate (10:1 (by volume)) to give 3-methyl-6-nitro-2,3-dihydro-1-H-inden-1-one (8 g, yield: 69%) as a yellow solid.
With nitric acid at 15℃;
  • 3
  • [ 772-17-8 ]
  • [ 6072-57-7 ]
YieldReaction ConditionsOperation in experiment
88% With terbium(III) trifluoromethanesulfonate In chlorobenzene at 250℃; for 4h;
72% In PPA 68 4(S)-Methyl-1,2,3,4-tetrahydro-2(1H)-quinolinone In the same way, cyclization of 3R-(-)-phenylbutyric acid (14.9 g) in 149 g polyphosphoric acid gave, after distillation, pure 3R-methyl-l-indanone (9.52 g, 72%, [α]25 D - 16.7° (c=1, acetone)).
With sulfuric acid at 20℃;
With PPA; Polyphosphoric acid (PPA) at 70℃; for 2h;
With aluminium trichloride; phosphorus pentachloride 1.) benzene, reflux, 0.5 h; 2.) reflux, 20 min; Yield given. Multistep reaction;
With methanesulfonic acid at 110 - 115℃; for 3h; Yield given;
With phosphoric acid at 110℃;
Multi-step reaction with 2 steps 1: PCl3 2: 90 percent / AlCl3 / nitromethane / 3 h
Multi-step reaction with 2 steps 1: 100 percent / SOCl2 / 3 h / 80 °C 2: 89 percent / AlCl3 / benzene / 1.5 h / Heating
In thionyl chloride; water; benzene 1 Production of 3-Methylindan-1-One Example 1 Production of 3-Methylindan-1-One 3-phenylbutyric acid (26.1 g, 0.159 mole) is reacted at 25° C. in one portion with thionyl chloride (28.4 g, 17.3 ml, 0.24 mole). The reaction mixture is heated for 4 hours under reflux and stirred for 15 hours at 25° C. The excess thionyl chloride is distilled off from the reaction mixture (b.p.: 79° C.). The orange-brown oil that is obtained is dissolved in 100 ml of benzene and cooled to 0° C. AlCl3 is then added in portions (21.0 g, 0.159 mole). The reaction mixture is stirred for 30 minutes at 25° C. and then heated for 1.5 hours under reflux. After the end of the reaction, the mixture is poured onto 400 ml of iced water and acidified with concentrated hydrochloric acid to pH=1. The organic phase is now separated in a separating funnel, the aqueous phase is extracted once with 30 ml of benzene, and the combined organic phases are dried over Na2SO4. The volatile constituents are removed in a rotary evaporator (40° C., 240 mbar) and the residue is distilled under an oil pump vacuum at 78° C. A yellow liquid is obtained. Yield: 21.0 g (0.144 mole, 90% of theory referred to 3-phenylbutyric acid).
Multi-step reaction with 2 steps 1: thionyl chloride / 2 h / Reflux 2: aluminum (III) chloride / toluene / 0 °C / Reflux
Multi-step reaction with 2 steps 1: thionyl chloride / 2 h / Reflux 2: aluminum (III) chloride / toluene / 0.5 h / 0 °C
Stage #1: 3-phenylbutyric acid With thionyl chloride; N,N-dimethyl-formamide for 2h; Reflux; Stage #2: With aluminum (III) chloride In dichloromethane at 20℃;

  • 4
  • [ 6072-57-7 ]
  • [ 767-58-8 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; amalgamated zinc
With hydrogen In ethanol
  • 6
  • [ 6072-57-7 ]
  • [ 123-11-5 ]
  • [ 5706-39-8 ]
YieldReaction ConditionsOperation in experiment
82% With sodium hydroxide In ethanol; water at 20℃; for 2h; Reflux;
With methanol; acetic anhydride at 0℃;
With hydrogenchloride; acetic anhydride In methanol
  • 7
  • [ 6072-57-7 ]
  • [ 22339-44-2 ]
YieldReaction ConditionsOperation in experiment
94% With lithium aluminium tetrahydride
94% With methanol; sodium tetrahydroborate at 0℃; for 1h; General Procedure B for the Synthesis of 1-(2-Fluoro-Ethyl)-3-(Substituted-Indan-1-yl)-Ureas: Indanone was dissolved in ether and cooled to 0° C., a solution NaBH4 (1.0 eq) in MeOH was slowly added. The reaction mixture was stirred for 1 hour and then quenched with saturated NH4Cl. The resulting mixture was extracted with Et2O (3×50 mL), and the combined organic extracts was washed with H2O (3×50 mL), brine (1×50 mL), dried over MgSO4 and concentrated. Purification by column chromatography using hexane:EtOAc (4:1) as eluant gave the pure indanol. The indanol was then dissolved in toluene and cooled to 0° C., diphenylphosphoryl azide (1.5 eq) was added. The resulting mixture was stirred for a few minutes and DBU (1.5 eq) was added slowly. After stirring the reaction mixture overnight, it was diluted with toluene and washed with H2O (3×50 mL), brine (1×50 mL), dried over MgSO4 and concentrated. Purification by column chromatography using hexane:EtOAc (4:1) as eluant gave the desired azido compound. This azido compound was then dissolved in THF:H2O (3:1), Ph3P (1.1 eq) was added, followed by KOH (1.0 eq). The resulting mixture was stirred overnight. The reaction mixture was then diluted with H2O and slowly acidified with HCl and the aqueous layer was washed with Et2O (3×50 mL). The aqueous layer was then basified with NaOH (pH 14) and extracted with Et2O (3×50 mL). The combined organic extracts were washed with H2O (1×25 mL), brine (1×25 mL), dried over K2CO3 and concentrated to give the desired indan amine. The final fluoroethyl ureas were thus obtained according to the protocol described in General Procedure A. This method may be adapted to other cycloalkyl-aryl fused rings systems using starting materials such as those shown below.Synthesis of 1-(2-fluoroethyl)-3-(3-methylindan-1-yl)ureaThe title compound was generated from commercially available 3-methyl-1-indanone according to the general procedure B. The intermediates 3-methyl-1-indanol, 1-azido-3-methylindan and 3-methylindan-1-ylamine were isolated and characterized.3-Methyl-1-indanoli: 4.77 g (94%) of the title indanol was obtained from 3-methyl-1-indanone (5.00 g, 34.20 mmol) according to the protocol described in general procedure B. Spectroscopic data: 1H NMR (300 MHz, CDCl3) δ 1.3 (d, 3H, J=6.7 Hz), 1.41-1.52 (m, 1H), 1.9 (br s, 1H), 2.68-2.80 (m, 1H), 2.98-3.11 (m, 1H), 5.2 (t, 1H, J=7.3 Hz), 7.19-7.31 (m, 3H), 7.35-7.41 (m, 1H).
With lithium aluminium tetrahydride
With sodium tetrahydroborate In tetrahydrofuran; methanol at 0 - 20℃;
100 % Spectr. With ammonium hydroxide; titanium(III) chloride In methanol at 20 - 25℃; for 0.0833333h;
Stage #1: 3-methylindanone With sodium tetrahydroborate In methanol at 0℃; for 1h; Stage #2: With water; ammonium chloride In methanol C Example C; Method C: Procedure for the preparation of:; Sodium borohydride (1.3 g, 34.36 mmol, 1.0 eq) was added to a cooled (0 0C) solution of 3-methyl-2,3-dihydro-lH-inden-l-one (Intermediate 7) (5.0 g, 34.2 mmol) in MeOH. The reaction mixture was stirred for 1 hour after which it was quenched with saturated NH4Cl. The resulting mixture was extracted with Et2O (3x 50 mL), and the combined organic extracts was washed with H2O (3x 50 mL), brine (Ix 50 mL), dried over MgSO4 and concentrated to give 3-methyl-2,3-dihydro-lH- inden-1-ol (Intermediate 8) which was purified by column chromatography using hexane:EtOAc (4: 1) as eluant.

  • 8
  • [ 6072-57-7 ]
  • [ 59-88-1 ]
  • [ 133505-09-6 ]
YieldReaction ConditionsOperation in experiment
43% With hydrogenchloride In acetic acid for 75h; Heating;
  • 10
  • [ 6072-57-7 ]
  • 4-methyl-chroman-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid In 1,2-dichloro-ethane
40% With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; regioselective reaction;
With toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid In dichloromethane for 24h;
  • 11
  • [ 6072-57-7 ]
  • 2-Hydroxyimino-3-methyl-1-indanon [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With hydrogenchloride; n-Butyl nitrite In methanol at 0℃; for 8h;
  • 12
  • [ 6072-57-7 ]
  • cis-3-methyl-2,3-dihydro-1H-inden-1-ol [ No CAS ]
  • 3-methyl-2,3-dihydro-1H-inden-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With methanol; sodium tetrahydroborate at 0 - 20℃; Inert atmosphere;
1: 22% 2: 74% With ammonium hydroxide; titanium(III) chloride In methanol at 0 - 20℃; for 0.0833333h;
With sodium tetrahydroborate In isopropyl alcohol at 25℃; for 2h; sev. α- and β-alkyl substituted indanones, respectively;
With sodium tetrahydroborate In isopropyl alcohol at 25℃; for 2h;

  • 13
  • [ 6072-57-7 ]
  • [ 77077-81-7 ]
YieldReaction ConditionsOperation in experiment
57% With n-Butyl nitrite; sodium methylate In diethyl ether at 0℃; for 14h;
  • 14
  • [ 772-17-8 ]
  • [ 6072-57-7 ]
  • 3-phenylbutanoic anhydride [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 15% 2: 62% With trifluoromethylsulfonic anhydride; Triphenylphosphine oxide In 1,2-dichloro-ethane at 25℃; for 4h;
  • 15
  • [ 51552-98-8 ]
  • [ 6072-57-7 ]
YieldReaction ConditionsOperation in experiment
90% With aluminium trichloride In nitromethane for 3h;
89% With aluminium trichloride In benzene for 1.5h; Heating;
60% With aluminum (III) chloride In toluene at 0℃; Reflux; 3 <Preparation of 3-methyl-2,3-dihydro-1H-inden-1-one> As presented in the following reaction formula, a mixture of 3-phenylbutanoic acid (30 g, 0.18 mol) in thionyl chloride (SOCl2; 100 mL) was refluxed under heating for 2 hours, and then the thionyl chloride was removed. Toluene (200 mL) and aluminum chloride (AlCl3; 24 g, 0.18 mol) were added to the resulting mixture at 0°C, and the reaction mixture was stirred at 0°C for 0.5 hours, followed by refluxing under heating. After the completion of reaction, the mixture was treated with ice water and then extracted twice with 200 mL of dichloromethane (DCM). The combined organic phase was washed with water (100 mL) and saturated brine (100 mL), and dried and concentrated with magnesium sulfate to give a crude product. The crude product was purified by gel column chromatography (using 100 g of silica gel (product of Merck Co., Ltd.)) using an eluent of pentane (PE): ethyl acetate (20:1 (by volume)) to give 3-methyl-2,3-dihydro-1H-inden-1-one (16 g, yield: 60%) as a brown oil.
With aluminum (III) chloride In benzene for 1.5h; Heating / reflux; 11.T Starting from (+/-)-3-Phenylbutyric acid (118-1) and using the scheme outlined, tether T118 was prepared as a mixture of stereoisomers at the (*) carbon atom, although that at the other chiral center is controlled by that of the lactate ester. Treatment of 118-1 with thionyl chloride followed by intramolecular Freidel-Crafts acylation gave 118-2 (Smonou, I.; Orfanopoulos, M. Synth. Commun. 1990, 20, 1387-1397; Stephan, E. et. al. Tetrahedron: Asy. 1994, 5, 41-44). Baeyer-Villager reaction of 118-2 with urea hydrogen peroxide (UHP) proceeded to give racemic 118-3 (Caron, S.; Do, N. D.; Sieser, J. E. Tetrahedron Lett. 2000, 41, 2299-2302). Opening of the lactone with ammonia, LAH reduction of the amide and protection of the resulting amine gave 118-5. Mitsunobu reaction with (S)-methyl lactate and lithium borohydride reduction of the product completed the construction of Boc-T118.1H NMR (300 MHz, CDCl3): δ 7.16 (m, 2H), 6.92 (m, 2H), 4.54 (m, 1H), 3.68 (m, 2H), 3.30 (m, 2H), 2.78 (m, 1H), 2.67 (s, br, 1H), 1.67 (m, 2H), 1.44, 1.43 (s, 9H), 1.27 (m, 6H)MS: 324 (M+H)+ Use of (R)-methyl lactate in the second step provides the diastereomeric tethers, T118b/d. In order to obtain one isomer at the * carbon atom, use of an enantiomeric coumarin corresponding to 118-3 is required. This can be accessed using the method shown for the synthesis of 118-10 (Arp, F. O.; Fu, G. C. J. Am. Chem. Soc. 2005, 127, 10482-10483).
16 g With aluminum (III) chloride In toluene at 0℃; for 0.5h; 3 Preparation of 3-methyl-2,3-dihydro-1H-inden-1-one As presented in the following reaction formula, a mixture of 3-phenylbutanoic acid (30 g, 0.18 mol) in thionyl chloride (SOCl2; 100 mL) was refluxed under heating for 2 hours, and then the thionyl chloride was removed. Toluene (200 mL) and aluminum chloride (AlCl3; 24 g, 0.18 mol) were added to the resulting mixture at 0° C., and the reaction mixture was stirred at 0° C. for 0.5 hours, followed by refluxing under heating. After the completion of reaction, the mixture was treated with ice water and then extracted twice with 200 mL of dichloromethane (DCM). The combined organic phase was washed with water (100 mL) and saturated brine (100 mL), and dried and concentrated with magnesium sulfate to give a crude product. The crude product was purified by gel column chromatography (using 100 g of silica gel (product of Merck Co., Ltd.)) using an eluent of pentane (PE):ethyl acetate (20:1 (by volume)) to give 3-methyl-2,3-dihydro-1H-inden-1-one (16 g, yield: 60%) as a brown oil.

  • 16
  • [ 6072-57-7 ]
  • [ 100-52-7 ]
  • [ 118485-40-8 ]
YieldReaction ConditionsOperation in experiment
52% With sodium hydroxide In ethanol; water at 0 - 5℃; for 0.25h;
  • 17
  • [ 6072-57-7 ]
  • [ 90-02-8 ]
  • 10-methyl-10H-benzo<b>indeno<2,1-e>pyrylium perchlorate [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With perchloric acid; acetic anhydride In diethyl ether for 2h; Ambient temperature;
  • 18
  • [ 6072-57-7 ]
  • [ 2231-57-4 ]
  • [ 128884-37-7 ]
YieldReaction ConditionsOperation in experiment
73% With acetic acid In ethanol for 2h; Ambient temperature;
  • 19
  • [ 6072-57-7 ]
  • [ 616-38-6 ]
  • [ 66130-38-9 ]
YieldReaction ConditionsOperation in experiment
85% With sodium hydride In benzene at 80℃; for 4h;
With sodium hydride 1.) benzene, 62-64 deg C, 2 h; 2.) benzene, 70 deg C, 3 h; Yield given. Multistep reaction;
  • 20
  • (3-Methyl-indan-1-yl)-methanol [ No CAS ]
  • [ 6072-57-7 ]
YieldReaction ConditionsOperation in experiment
52% With silica gel; pyridinium chlorochromate In dichloromethane at 25℃; for 10h;
  • 21
  • [ 6072-57-7 ]
  • [ 107-96-0 ]
  • [ 87240-78-6 ]
YieldReaction ConditionsOperation in experiment
70% With toluene-4-sulfonic acid In benzene for 16h; Heating;
  • 22
  • [ 939-52-6 ]
  • [ 6072-57-7 ]
YieldReaction ConditionsOperation in experiment
70% In neat (no solvent) at 90℃; for 1h;
  • 23
  • [ 6072-57-7 ]
  • [ 105-58-8 ]
  • [ 53204-62-9 ]
YieldReaction ConditionsOperation in experiment
75% With sodium hydride In benzene for 3h; Heating;
  • 24
  • [ 3724-65-0 ]
  • [ 71-43-2 ]
  • [ 6072-57-7 ]
YieldReaction ConditionsOperation in experiment
95% With aluminum (III) chloride at 80℃; for 4h; Inert atmosphere; The caged compound represented by the above formula (3) was synthesized. More specifically, first, crotonic acid represented by the formula (4) (manufactured by Wako Pure Chemical Industries, Ltd., 2.03 g, 23.6 mmol) and aluminum chloride (manufactured by Tokyo Chemical Industry Co., Ltd., 9.42 g). 15 mL of a dry benzene solution (70.8 mmol) was heated and stirred at 80 ° C. for 4 hours under a nitrogen atmosphere. Then, it was cooled to room temperature, added to ice water and extracted with methylene chloride, the organic layer was dried over sodium sulfate, filtered and the solvent was distilled off. Then, the crude product is purified by using silica gel chromatography (hexane: ethyl acetate (volume ratio) = 10: 1) to obtain 3-methyl-2,3-dihydro represented by the formula (5). -1H-inden-1-one (3.26 g, yield: 95%) was obtained.
82% With aluminium trichloride for 4h; Heating;
81% With aluminum (III) chloride for 5h; Reflux;
With aluminium trichloride
With aluminum (III) chloride Inert atmosphere;

  • 25
  • [ 107-93-7 ]
  • [ 71-43-2 ]
  • [ 6072-57-7 ]
YieldReaction ConditionsOperation in experiment
77% With aluminium trichloride for 17h; Heating;
74% With aluminum (III) chloride for 7h; Reflux; 7.1 Step 1: Preparation of 3-methyl-indan-1-one Step 1: Preparation of 3-methyl-indan-1-one [0246] crotonic acid (20 g, 0.232 moles) in benzene (147 ml) was added AlCl3 (93 g, 0.748 moles) and the mixture was refluxed for 7 hours. Completion of the reaction was monitored by HPLC & GC. Excess benzene was distilled off and the reaction mixture was poured slowly into ice cold HCl. The organic compound was extracted with ethylacetate. The organic phase was washed thoroughly with water, dried, and evaporated under vacuum. The resultant oil was purified by high vacuum distillation (90-94° C. at 2 mm) giving 25 g (74%) of 99.2% pure 3-methyl-indan-1-one.
71%
66% With HUSY-zeolite at 130℃;
62% With H-USY zeolite at 130℃; for 20h;
44% With trifluorormethanesulfonic acid In dichloromethane at 0 - 20℃; Inert atmosphere;

  • 26
  • [ 6072-57-7 ]
  • [ 22303-81-7 ]
YieldReaction ConditionsOperation in experiment
(i) AcOH, Pb3O4, (ii) (pyrolysis); Multistep reaction;
Stage #1: 3-methylindanone With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In benzene at 80℃; Inert atmosphere; Sealed tube; Stage #2: With triethylamine In dichloromethane at 0 - 23℃; for 0.5h; Inert atmosphere; Sealed tube;
  • 27
  • [ 6072-57-7 ]
  • [ 104-87-0 ]
  • [ 5706-35-4 ]
YieldReaction ConditionsOperation in experiment
69% With sodium hydroxide In ethanol; water at 20℃; for 2h; Reflux;
With hydrogenchloride; acetic anhydride In methanol
  • 28
  • [ 6072-57-7 ]
  • [ 104-88-1 ]
  • [ 5706-36-5 ]
YieldReaction ConditionsOperation in experiment
72% With sodium hydroxide In ethanol; water at 20℃; for 2h; Reflux;
With hydrogenchloride; acetic anhydride In methanol
  • 29
  • [ 6072-57-7 ]
  • [ 100-52-7 ]
  • [ 5706-41-2 ]
YieldReaction ConditionsOperation in experiment
73% With sodium hydroxide In ethanol; water for 2h; Reflux;
With hydrogenchloride; acetic anhydride In methanol
  • 30
  • [ 6072-57-7 ]
  • [ 74-88-4 ]
  • trans-1,3-dimethylindan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With magnesium In diethyl ether for 19h; Heating;
  • 31
  • trans-chrotonyl chloride [ No CAS ]
  • [ 71-43-2 ]
  • [ 6072-57-7 ]
YieldReaction ConditionsOperation in experiment
88% With aluminium trichloride Heating;
79% Stage #1: trans-chrotonyl chloride; benzene With aluminium trichloride In 1,2-dichloro-benzene at 20℃; for 5h; Stage #2: In 1,2-dichloro-benzene at 185℃; for 0.333333h; microwave irradiation;
  • 32
  • [ 107-10-8 ]
  • [ 6072-57-7 ]
  • (3-methylindan-1-ylidene)propylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With titanium tetrachloride In diethyl ether at -35 - 20℃;
  • 33
  • [ 6072-57-7 ]
  • [ 74-89-5 ]
  • methyl(3-methylindan-1-ylidene)amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With titanium tetrachloride In diethyl ether at -35 - 20℃;
  • 34
  • [ 201230-82-2 ]
  • [ 61161-21-5 ]
  • [ 6072-57-7 ]
YieldReaction ConditionsOperation in experiment
100% With pyridine; palladium diacetate; tetrabutyl-ammonium chloride In N,N-dimethyl-formamide at 100℃; for 12h;
  • 35
  • [ 6072-57-7 ]
  • (+/-)-2-iodo-c-3-methylindan-1-one [ No CAS ]
  • (+/-)-2-iodo-t-3-methylindan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With iodine; Selectfluor In methanol at 22℃; for 24h; Title compound not separated from byproducts;
  • 36
  • [ 799804-35-6 ]
  • [ 6072-57-7 ]
YieldReaction ConditionsOperation in experiment
42% With 1-methyl-1H-imidazole In dichloromethane Irradiation;
  • 37
  • [ 7073-70-3 ]
  • [ 6072-57-7 ]
YieldReaction ConditionsOperation in experiment
62% With tetrabutyl-ammonium chloride; tri tert-butylphosphoniumtetrafluoroborate In 1,4-dioxane at 150℃; for 0.666667h; microwave irradiation;
  • 38
  • [ 23417-79-0 ]
  • [ 6072-57-7 ]
YieldReaction ConditionsOperation in experiment
100% With hydrogen In diethyl ether; 1,2-dichloro-ethane at 20℃; for 1h;
97% With (bicyclo[2.2.1]hepta-2,5-diene)(1,2-bis(diphenylphosphanyl)ethane)rhodium(I) perchlorate; hydrogen In dichloromethane at 23℃; for 2h;
With silver hexafluoroantimonate; chloro(1,5-cyclooctadiene)rhodium(I) dimer; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,4-dioxane at 100℃; for 16h; Inert atmosphere; Sealed tube;
  • 39
  • [ 98-82-8 ]
  • trans-chrotonyl chloride [ No CAS ]
  • 5-isopropyl-3-methyl-1-indanone [ No CAS ]
  • [ 6072-57-7 ]
YieldReaction ConditionsOperation in experiment
Stage #1: Isopropylbenzene; trans-chrotonyl chloride With aluminium trichloride In 1,2-dichloro-benzene at 20℃; for 5h; Stage #2: In 1,2-dichloro-benzene at 185℃; for 0.333333h; microwave irradiation;
  • 40
  • [ 253185-04-5 ]
  • trans-chrotonyl chloride [ No CAS ]
  • [ 6072-57-7 ]
YieldReaction ConditionsOperation in experiment
78% Stage #1: tert-butylbenzene; trans-chrotonyl chloride With aluminium trichloride In 1,2-dichloro-benzene at 20℃; for 5h; Stage #2: In 1,2-dichloro-benzene at 185℃; for 0.333333h; microwave irradiation;
  • 41
  • [ 6072-57-7 ]
  • [ 5470-11-1 ]
  • [ 30696-24-3 ]
YieldReaction ConditionsOperation in experiment
95% With sodium hydroxide In methanol; water at 80℃; for 2h; 14.a To a solution of 3-methylindan-1-one (221 mg, 1.51 mmol) and hydroxylamine hydrochloride (295 mg, 4.25 mmol) in MeOH (4.00 mL) was added a solution of NaOH (200 mg, 5.00 mmol) in H2O (2.00 mL) and the mixture was stirred at 80° C. for 2 h. The cooled reaction was concentrated in vacuo to remove most of the MeOH, and the residue was partitioned between DCM and H2O. The organic layer was concentrated in vacuo to afford the title compound as a waxy solid (232 mg, 95%). LC/MS: Rt=1.51 min, ES+ 162 (AA standard).
  • 42
  • [ 40138-16-7 ]
  • [ 6072-57-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Pd(PPh3)4; aq. Na2CO3 / toluene; methanol / 80 °C 2: 97 percent / [Rh(dppe)(NBD)]ClO4; H2 / CH2Cl2 / 2 h / 23 °C
  • 43
  • [ 6072-57-7 ]
  • 3-[3-Methyl-indan-(1Z)-ylidenemethyl]-pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: NaBH4 / methanol; tetrahydrofuran / 0 - 20 °C 2: benzene / 12 h / Heating 3: K2CO3; 18-crown-6 / CH2Cl2 / 12 h / Heating
  • 44
  • [ 6072-57-7 ]
  • 3-[3-Methyl-indan-(1E)-ylidenemethyl]-pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: NaBH4 / methanol; tetrahydrofuran / 0 - 20 °C 2: benzene / 12 h / Heating 3: K2CO3; 18-crown-6 / CH2Cl2 / 12 h / Heating
  • 45
  • [ 6072-57-7 ]
  • (3-methyl-indan-1-yl)-triphenyl-phosphonium; bromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: NaBH4 / methanol; tetrahydrofuran / 0 - 20 °C 2: benzene / 12 h / Heating
  • 46
  • [ 799804-42-5 ]
  • [ 6072-57-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: n-BuLi / diethyl ether; hexane / 0.5 h / -78 °C 1.2: 41 percent / diethyl ether; hexane / 1.5 h / 20 °C 2.1: 31 percent / N-methylimidazole / Irradiation
Multi-step reaction with 2 steps 1.1: n-BuLi / diethyl ether; hexane / 0.5 h / -78 °C 1.2: 41 percent / diethyl ether; hexane / 1.5 h / 20 °C 2.1: 24 percent / Irradiation
Multi-step reaction with 2 steps 1.1: n-BuLi / diethyl ether; hexane / 0.5 h / -78 °C 1.2: 41 percent / diethyl ether; hexane / 1.5 h / 20 °C 2.1: 42 percent / N-methylimidazole / CH2Cl2 / Irradiation
  • 47
  • [ 6072-57-7 ]
  • 4,5-dimethoxy-12-methyl-1,2,3,12-tetrahydroindeno[1,2-b]pyrido[4,3,2-de]quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: PPTS / toluene / 24 h / Heating 2: aq. HCl / 4 h / Heating
  • 48
  • [ 6072-57-7 ]
  • [ 80070-43-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triethylamine / dimethylformamide / Heating; 2-4 h 2: HOF*CH3CN, NaF / CHCl3; acetonitrile; H2O / 3-4 min 3: CrO3, H(1+) / acetone / 0.17 h
Multi-step reaction with 2 steps 1: alcoholic hydrochloric acid 2: concentrated hydrochloric acid; formaldehyde
  • 49
  • [ 6072-57-7 ]
  • trans-1,3-dimethyl-indane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 89 percent / magnesium / diethyl ether / 19 h / Heating 2: ethanol / Raney nickel/Celite / 2 h / Heating
  • 50
  • [ 6072-57-7 ]
  • (+/-)-iso-trans-trikentrin B [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 13 steps 1: 89 percent / magnesium / diethyl ether / 19 h / Heating 2: ethanol / Raney nickel/Celite / 2 h / Heating 3: 70 percent / 1.) aluminium trichloride / CH2Cl2 / 1.) 50 min; 2.) 2 deg C, then room temp., 15 h 4: 95 percent / sodium borohydride / methanol / 0 deg C -> room temp. 50 min 5: 37 percent / 1.) t-butyllithium, carbon tetrabromide / pentane; heptane / 1.) 0 deg C, then reflux, 1 h 6: 95 percent / 4-dimethylaminopyridine, ethyldiisopropylamine / 17 h / Ambient temperature; 1.) 0 deg C 7: 65 percent / 1.) butyllithium / heptane; hexane / 1.) -78 deg C, 10 min; 2.) -78 deg C -> room temp. 8: 54 percent / sodium / ethanol / -15 - -10 deg C, 5.5 h, then -> room temp., 1 h 9: 79 percent / toluene / 2 h / 135 °C 10: 51 percent / diisobutylaluminium hydride / toluene / -74 deg C, then -41 deg C, 1 h, then room temp., 75 min. 11: 65 percent / manganese dioxude / CH2Cl2 / 6.5 h / Heating 12: 64 percent / bis(triphenylphossphine)(carbonyl)rhodium(I)chloride, 1,3-bis(diphenylphosphino)propane / 1,3,5-trimethyl-benzene / 0.5 h / 180 - 200 °C 13: 1.) dimethylboron bromide; 2.) triethylamine / 1.) CH2Cl2, -78 deg C, 4 min; 2.) CH2Cl2, 78 deg C, 5 min
  • 51
  • [ 6072-57-7 ]
  • 1-((1R,3R)-1,3-Dimethyl-indan-5-yl)-butan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 89 percent / magnesium / diethyl ether / 19 h / Heating 2: ethanol / Raney nickel/Celite / 2 h / Heating 3: 70 percent / 1.) aluminium trichloride / CH2Cl2 / 1.) 50 min; 2.) 2 deg C, then room temp., 15 h 4: 95 percent / sodium borohydride / methanol / 0 deg C -> room temp. 50 min
  • 52
  • [ 6072-57-7 ]
  • 1-((1R,3R)-1,3-Dimethyl-indan-5-yl)-butan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 89 percent / magnesium / diethyl ether / 19 h / Heating 2: ethanol / Raney nickel/Celite / 2 h / Heating 3: 70 percent / 1.) aluminium trichloride / CH2Cl2 / 1.) 50 min; 2.) 2 deg C, then room temp., 15 h
  • 53
  • [ 6072-57-7 ]
  • 1-((1R,3R)-6-Bromo-1,3-dimethyl-indan-5-yl)-butan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 89 percent / magnesium / diethyl ether / 19 h / Heating 2: ethanol / Raney nickel/Celite / 2 h / Heating 3: 70 percent / 1.) aluminium trichloride / CH2Cl2 / 1.) 50 min; 2.) 2 deg C, then room temp., 15 h 4: 95 percent / sodium borohydride / methanol / 0 deg C -> room temp. 50 min 5: 37 percent / 1.) t-butyllithium, carbon tetrabromide / pentane; heptane / 1.) 0 deg C, then reflux, 1 h
  • 54
  • [ 6072-57-7 ]
  • (1R,3R)-5-Bromo-6-(1-methoxymethoxy-butyl)-1,3-dimethyl-indan [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 89 percent / magnesium / diethyl ether / 19 h / Heating 2: ethanol / Raney nickel/Celite / 2 h / Heating 3: 70 percent / 1.) aluminium trichloride / CH2Cl2 / 1.) 50 min; 2.) 2 deg C, then room temp., 15 h 4: 95 percent / sodium borohydride / methanol / 0 deg C -> room temp. 50 min 5: 37 percent / 1.) t-butyllithium, carbon tetrabromide / pentane; heptane / 1.) 0 deg C, then reflux, 1 h 6: 95 percent / 4-dimethylaminopyridine, ethyldiisopropylamine / 17 h / Ambient temperature; 1.) 0 deg C
  • 55
  • [ 6072-57-7 ]
  • (6R,8R)-4-(1-Methoxymethoxy-butyl)-6,8-dimethyl-1,6,7,8-tetrahydro-cyclopenta[g]indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 12 steps 1: 89 percent / magnesium / diethyl ether / 19 h / Heating 2: ethanol / Raney nickel/Celite / 2 h / Heating 3: 70 percent / 1.) aluminium trichloride / CH2Cl2 / 1.) 50 min; 2.) 2 deg C, then room temp., 15 h 4: 95 percent / sodium borohydride / methanol / 0 deg C -> room temp. 50 min 5: 37 percent / 1.) t-butyllithium, carbon tetrabromide / pentane; heptane / 1.) 0 deg C, then reflux, 1 h 6: 95 percent / 4-dimethylaminopyridine, ethyldiisopropylamine / 17 h / Ambient temperature; 1.) 0 deg C 7: 65 percent / 1.) butyllithium / heptane; hexane / 1.) -78 deg C, 10 min; 2.) -78 deg C -> room temp. 8: 54 percent / sodium / ethanol / -15 - -10 deg C, 5.5 h, then -> room temp., 1 h 9: 79 percent / toluene / 2 h / 135 °C 10: 51 percent / diisobutylaluminium hydride / toluene / -74 deg C, then -41 deg C, 1 h, then room temp., 75 min. 11: 65 percent / manganese dioxude / CH2Cl2 / 6.5 h / Heating 12: 64 percent / bis(triphenylphossphine)(carbonyl)rhodium(I)chloride, 1,3-bis(diphenylphosphino)propane / 1,3,5-trimethyl-benzene / 0.5 h / 180 - 200 °C
  • 56
  • [ 6072-57-7 ]
  • (1R,3R)-6-(1-Methoxymethoxy-butyl)-1,3-dimethyl-indan-5-carbaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: 89 percent / magnesium / diethyl ether / 19 h / Heating 2: ethanol / Raney nickel/Celite / 2 h / Heating 3: 70 percent / 1.) aluminium trichloride / CH2Cl2 / 1.) 50 min; 2.) 2 deg C, then room temp., 15 h 4: 95 percent / sodium borohydride / methanol / 0 deg C -> room temp. 50 min 5: 37 percent / 1.) t-butyllithium, carbon tetrabromide / pentane; heptane / 1.) 0 deg C, then reflux, 1 h 6: 95 percent / 4-dimethylaminopyridine, ethyldiisopropylamine / 17 h / Ambient temperature; 1.) 0 deg C 7: 65 percent / 1.) butyllithium / heptane; hexane / 1.) -78 deg C, 10 min; 2.) -78 deg C -> room temp.
  • 57
  • [ 6072-57-7 ]
  • [(6R,8R)-4-(1-Methoxymethoxy-butyl)-6,8-dimethyl-1,6,7,8-tetrahydro-cyclopenta[g]indol-2-yl]-methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1: 89 percent / magnesium / diethyl ether / 19 h / Heating 2: ethanol / Raney nickel/Celite / 2 h / Heating 3: 70 percent / 1.) aluminium trichloride / CH2Cl2 / 1.) 50 min; 2.) 2 deg C, then room temp., 15 h 4: 95 percent / sodium borohydride / methanol / 0 deg C -> room temp. 50 min 5: 37 percent / 1.) t-butyllithium, carbon tetrabromide / pentane; heptane / 1.) 0 deg C, then reflux, 1 h 6: 95 percent / 4-dimethylaminopyridine, ethyldiisopropylamine / 17 h / Ambient temperature; 1.) 0 deg C 7: 65 percent / 1.) butyllithium / heptane; hexane / 1.) -78 deg C, 10 min; 2.) -78 deg C -> room temp. 8: 54 percent / sodium / ethanol / -15 - -10 deg C, 5.5 h, then -> room temp., 1 h 9: 79 percent / toluene / 2 h / 135 °C 10: 51 percent / diisobutylaluminium hydride / toluene / -74 deg C, then -41 deg C, 1 h, then room temp., 75 min.
  • 58
  • [ 6072-57-7 ]
  • (6R,8R)-4-(1-Methoxymethoxy-butyl)-6,8-dimethyl-1,6,7,8-tetrahydro-cyclopenta[g]indole-2-carbaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 11 steps 1: 89 percent / magnesium / diethyl ether / 19 h / Heating 2: ethanol / Raney nickel/Celite / 2 h / Heating 3: 70 percent / 1.) aluminium trichloride / CH2Cl2 / 1.) 50 min; 2.) 2 deg C, then room temp., 15 h 4: 95 percent / sodium borohydride / methanol / 0 deg C -> room temp. 50 min 5: 37 percent / 1.) t-butyllithium, carbon tetrabromide / pentane; heptane / 1.) 0 deg C, then reflux, 1 h 6: 95 percent / 4-dimethylaminopyridine, ethyldiisopropylamine / 17 h / Ambient temperature; 1.) 0 deg C 7: 65 percent / 1.) butyllithium / heptane; hexane / 1.) -78 deg C, 10 min; 2.) -78 deg C -> room temp. 8: 54 percent / sodium / ethanol / -15 - -10 deg C, 5.5 h, then -> room temp., 1 h 9: 79 percent / toluene / 2 h / 135 °C 10: 51 percent / diisobutylaluminium hydride / toluene / -74 deg C, then -41 deg C, 1 h, then room temp., 75 min. 11: 65 percent / manganese dioxude / CH2Cl2 / 6.5 h / Heating
  • 59
  • [ 6072-57-7 ]
  • (6R,8R)-4-(1-Methoxymethoxy-butyl)-6,8-dimethyl-1,6,7,8-tetrahydro-cyclopenta[g]indole-2-carboxylic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1: 89 percent / magnesium / diethyl ether / 19 h / Heating 2: ethanol / Raney nickel/Celite / 2 h / Heating 3: 70 percent / 1.) aluminium trichloride / CH2Cl2 / 1.) 50 min; 2.) 2 deg C, then room temp., 15 h 4: 95 percent / sodium borohydride / methanol / 0 deg C -> room temp. 50 min 5: 37 percent / 1.) t-butyllithium, carbon tetrabromide / pentane; heptane / 1.) 0 deg C, then reflux, 1 h 6: 95 percent / 4-dimethylaminopyridine, ethyldiisopropylamine / 17 h / Ambient temperature; 1.) 0 deg C 7: 65 percent / 1.) butyllithium / heptane; hexane / 1.) -78 deg C, 10 min; 2.) -78 deg C -> room temp. 8: 54 percent / sodium / ethanol / -15 - -10 deg C, 5.5 h, then -> room temp., 1 h 9: 79 percent / toluene / 2 h / 135 °C
  • 60
  • [ 6072-57-7 ]
  • (E)-2-Azido-3-[(1R,3R)-6-(1-methoxymethoxy-butyl)-1,3-dimethyl-indan-5-yl]-acrylic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: 89 percent / magnesium / diethyl ether / 19 h / Heating 2: ethanol / Raney nickel/Celite / 2 h / Heating 3: 70 percent / 1.) aluminium trichloride / CH2Cl2 / 1.) 50 min; 2.) 2 deg C, then room temp., 15 h 4: 95 percent / sodium borohydride / methanol / 0 deg C -> room temp. 50 min 5: 37 percent / 1.) t-butyllithium, carbon tetrabromide / pentane; heptane / 1.) 0 deg C, then reflux, 1 h 6: 95 percent / 4-dimethylaminopyridine, ethyldiisopropylamine / 17 h / Ambient temperature; 1.) 0 deg C 7: 65 percent / 1.) butyllithium / heptane; hexane / 1.) -78 deg C, 10 min; 2.) -78 deg C -> room temp. 8: 54 percent / sodium / ethanol / -15 - -10 deg C, 5.5 h, then -> room temp., 1 h
  • 61
  • [ 6072-57-7 ]
  • [ 119971-34-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 2.5 h / 180 - 190 °C 2: POCl3 / 0.08 h / Ambient temperature 3: 15 percent / 2-ethoxy-ethanol / 14 h / Heating
  • 62
  • [ 6072-57-7 ]
  • (1R,S,1'R,S)-1,1'-Dimethyl-2,2'-spirobiindane, proximal [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1: 75 percent / NaH / benzene / 3 h / Heating 2: 81 percent / NaOC2H5 / ethanol / Heating 3: 93 percent / LiAlH4 / diethyl ether / 2 h / Heating 4: 88 percent / H2, conc. HCl / 10percent Pd-C / 48 h 5: NaOCH3 / methanol / Ambient temperature; overnight 6: 83 percent / CrO3, aq. H2SO4 / acetone / 1 h / Ambient temperature 7: 48 percent / CrO3, aq. H2SO4 / acetone / Ambient temperature 8: 1) PCl5, 2) SnCl4 / 1) benzene, 2 h, r.t.; 15 min reflux, 2) benzene, 20 h, r.t. 9: 76 percent / 2 h / Heating 10: H2 / Pd-C / methanol / overnight
Multi-step reaction with 9 steps 1: 75 percent / NaH / benzene / 3 h / Heating 2: 81 percent / NaOC2H5 / ethanol / Heating 3: 93 percent / LiAlH4 / diethyl ether / 2 h / Heating 4: 88 percent / H2, conc. HCl / 10percent Pd-C / 48 h 5: NaOCH3 / methanol / Ambient temperature; overnight 6: 14 percent / CrO3, aq. H2SO4 / acetone / 1 h / Ambient temperature 7: 1) PCl5, 2) SnCl4 / 1) benzene, 2 h, r.t.; 15 min reflux, 2) benzene, 20 h, r.t. 8: 76 percent / 2 h / Heating 9: H2 / Pd-C / methanol / overnight
  • 63
  • [ 6072-57-7 ]
  • (1R,S,1'S,R)-1,1'-Dimethyl-2,2'-spirobiindane, medial [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1: 75 percent / NaH / benzene / 3 h / Heating 2: 81 percent / NaOC2H5 / ethanol / Heating 3: 93 percent / LiAlH4 / diethyl ether / 2 h / Heating 4: 88 percent / H2, conc. HCl / 10percent Pd-C / 48 h 5: NaOCH3 / methanol / Ambient temperature; overnight 6: 83 percent / CrO3, aq. H2SO4 / acetone / 1 h / Ambient temperature 7: 48 percent / CrO3, aq. H2SO4 / acetone / Ambient temperature 8: 1) PCl5, 2) SnCl4 / 1) benzene, 2 h, r.t.; 15 min reflux, 2) benzene, 20 h, r.t. 9: 76 percent / 2 h / Heating 10: H2 / Pd-C / methanol / overnight
Multi-step reaction with 9 steps 1: 75 percent / NaH / benzene / 3 h / Heating 2: 81 percent / NaOC2H5 / ethanol / Heating 3: 93 percent / LiAlH4 / diethyl ether / 2 h / Heating 4: 88 percent / H2, conc. HCl / 10percent Pd-C / 48 h 5: NaOCH3 / methanol / Ambient temperature; overnight 6: 14 percent / CrO3, aq. H2SO4 / acetone / 1 h / Ambient temperature 7: 1) PCl5, 2) SnCl4 / 1) benzene, 2 h, r.t.; 15 min reflux, 2) benzene, 20 h, r.t. 8: 76 percent / 2 h / Heating 9: H2 / Pd-C / methanol / overnight
  • 64
  • [ 6072-57-7 ]
  • 1'r-Methyl-2,2'-spirobiindan-1c-on [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: 75 percent / NaH / benzene / 3 h / Heating 2: 81 percent / NaOC2H5 / ethanol / Heating 3: 93 percent / LiAlH4 / diethyl ether / 2 h / Heating 4: 88 percent / H2, conc. HCl / 10percent Pd-C / 48 h 5: NaOCH3 / methanol / Ambient temperature; overnight 6: 83 percent / CrO3, aq. H2SO4 / acetone / 1 h / Ambient temperature 7: 48 percent / CrO3, aq. H2SO4 / acetone / Ambient temperature 8: 1) PCl5, 2) SnCl4 / 1) benzene, 2 h, r.t.; 15 min reflux, 2) benzene, 20 h, r.t.
Multi-step reaction with 7 steps 1: 75 percent / NaH / benzene / 3 h / Heating 2: 81 percent / NaOC2H5 / ethanol / Heating 3: 93 percent / LiAlH4 / diethyl ether / 2 h / Heating 4: 88 percent / H2, conc. HCl / 10percent Pd-C / 48 h 5: NaOCH3 / methanol / Ambient temperature; overnight 6: 14 percent / CrO3, aq. H2SO4 / acetone / 1 h / Ambient temperature 7: 1) PCl5, 2) SnCl4 / 1) benzene, 2 h, r.t.; 15 min reflux, 2) benzene, 20 h, r.t.
  • 65
  • [ 6072-57-7 ]
  • C19H20O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1: 75 percent / NaH / benzene / 3 h / Heating 2: 81 percent / NaOC2H5 / ethanol / Heating 3: 93 percent / LiAlH4 / diethyl ether / 2 h / Heating 4: 88 percent / H2, conc. HCl / 10percent Pd-C / 48 h 5: NaOCH3 / methanol / Ambient temperature; overnight 6: 83 percent / CrO3, aq. H2SO4 / acetone / 1 h / Ambient temperature 7: 48 percent / CrO3, aq. H2SO4 / acetone / Ambient temperature 8: 1) PCl5, 2) SnCl4 / 1) benzene, 2 h, r.t.; 15 min reflux, 2) benzene, 20 h, r.t. 9: Heating
Multi-step reaction with 8 steps 1: 75 percent / NaH / benzene / 3 h / Heating 2: 81 percent / NaOC2H5 / ethanol / Heating 3: 93 percent / LiAlH4 / diethyl ether / 2 h / Heating 4: 88 percent / H2, conc. HCl / 10percent Pd-C / 48 h 5: NaOCH3 / methanol / Ambient temperature; overnight 6: 14 percent / CrO3, aq. H2SO4 / acetone / 1 h / Ambient temperature 7: 1) PCl5, 2) SnCl4 / 1) benzene, 2 h, r.t.; 15 min reflux, 2) benzene, 20 h, r.t. 8: Heating
  • 66
  • [ 6072-57-7 ]
  • C19H20O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1: 75 percent / NaH / benzene / 3 h / Heating 2: 81 percent / NaOC2H5 / ethanol / Heating 3: 93 percent / LiAlH4 / diethyl ether / 2 h / Heating 4: 88 percent / H2, conc. HCl / 10percent Pd-C / 48 h 5: NaOCH3 / methanol / Ambient temperature; overnight 6: 83 percent / CrO3, aq. H2SO4 / acetone / 1 h / Ambient temperature 7: 48 percent / CrO3, aq. H2SO4 / acetone / Ambient temperature 8: 1) PCl5, 2) SnCl4 / 1) benzene, 2 h, r.t.; 15 min reflux, 2) benzene, 20 h, r.t. 9: 76 percent / 2 h / Heating
Multi-step reaction with 8 steps 1: 75 percent / NaH / benzene / 3 h / Heating 2: 81 percent / NaOC2H5 / ethanol / Heating 3: 93 percent / LiAlH4 / diethyl ether / 2 h / Heating 4: 88 percent / H2, conc. HCl / 10percent Pd-C / 48 h 5: NaOCH3 / methanol / Ambient temperature; overnight 6: 14 percent / CrO3, aq. H2SO4 / acetone / 1 h / Ambient temperature 7: 1) PCl5, 2) SnCl4 / 1) benzene, 2 h, r.t.; 15 min reflux, 2) benzene, 20 h, r.t. 8: 76 percent / 2 h / Heating
  • 67
  • [ 6072-57-7 ]
  • 2t-Benzyl-1r-methyl-2c-indancarbonsaeure [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: 75 percent / NaH / benzene / 3 h / Heating 2: 81 percent / NaOC2H5 / ethanol / Heating 3: 93 percent / LiAlH4 / diethyl ether / 2 h / Heating 4: 88 percent / H2, conc. HCl / 10percent Pd-C / 48 h 5: NaOCH3 / methanol / Ambient temperature; overnight 6: 83 percent / CrO3, aq. H2SO4 / acetone / 1 h / Ambient temperature 7: 48 percent / CrO3, aq. H2SO4 / acetone / Ambient temperature
Multi-step reaction with 6 steps 1: 75 percent / NaH / benzene / 3 h / Heating 2: 81 percent / NaOC2H5 / ethanol / Heating 3: 93 percent / LiAlH4 / diethyl ether / 2 h / Heating 4: 88 percent / H2, conc. HCl / 10percent Pd-C / 48 h 5: NaOCH3 / methanol / Ambient temperature; overnight 6: 14 percent / CrO3, aq. H2SO4 / acetone / 1 h / Ambient temperature
  • 68
  • [ 917-64-6 ]
  • [ 6072-57-7 ]
  • [ 7439-95-4 ]
  • [ 74-88-4 ]
  • [ 2177-48-2 ]
YieldReaction ConditionsOperation in experiment
In diethyl ether; water 3 Production of 1,3-Dimethylindene Example 3 Production of 1,3-Dimethylindene For this, the 3-methylindan-1-one produced in Example 1 (21.0 g, 0.144 mole) was dissolved in 20 ml of diethyl ether and added dropwise to a solution of methylmagnesium iodide in diethyl ether (the Grignard solution is prepared by adding methyl iodide (25.4 g, 11.3 ml, 0.18 mole) dropwise to a suspension of magnesium powder (4.4 g, 0.18 mole) in 40 ml of diethyl ether). After boiling for 2 hours under reflux the reaction mixture is poured onto 100 ml of iced water. The mixture is acidified with 5 N hydrochloric acid until the precipitated magnesium salts have dissolved. The aqueous and organic phases are separated and the aqueous phase is extracted twice with in each case 50 ml of diethyl ether. The combined organic phases are washed with 30 ml of each of a saturated NaHCO3 solution, water and then with saturated NaCl solution. The organic phase is next freed from all volatile constituents in a rotary evaporator (40° C., 1013 mbar) and the residue is taken up in 120 ml of benzene.
  • 69
  • [ 110-89-4 ]
  • [ 59-48-3 ]
  • [ 6072-57-7 ]
  • 3-(3-methylindan-1-ylidene)-1,3-dihydroindol-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride 1 3-(3-Methylindan-1-ylidene)-1,3-dihydroindol-2-one EXAMPLE 1 3-(3-Methylindan-1-ylidene)-1,3-dihydroindol-2-one A mixture of 0.5 g of 3-methyl-1-indanone, 1.37 g oxindole and 5 ml piperidine in 3 ml of dimethylforamide was heated in a sealed tube at 130° C. overnight to yield a reddish-brown suspension. The mixture was added to 1N hydrochloric acid solution and extracted with ethyl acetate. The organic layer was washed with brine, dried with magnesium sulfate and concentrated. Chromatography afforded 120 mg of 3-(3-methylindan-1-ylidene)-1,3-dihydroindol-2-one as an orange solid. 1H-NMR (360 MHz, DMSO-d6) δ: 10.54 (s, 1H, NH), 9.43 (d, J=9.7 Hz, 1H, Ar-H), 7.58 (d, J=9.36 Hz, 1H, Ar-H), 7.46 (d, J=4.68 Hz, 2H, Ar-H), 7.3 (m, 1H, Ar-H), 7.19 (m, J=9.0 and 9.7 Hz, 1H, Ar-H), 6.99 (m, J=9.0 and 9.36 Hz, 1H, Ar-H), 6.83(m, J=9.0 and 1.08 Hz, 1H, Ar-H), 3.61 (dd, J=9.0 and 21.9 HZ 1H, 1*CH2CH), 3.43 (m, 1H, CHCH3), 2.86 (dd, J=4.3 and 21.9 Hz, 1H, 1*CH2CH), 1.35 (d, J=8.6 Hz, 3H, CH3). MS (m/z (relative intensity %, ion)): found 262.0 (100, [M+1]+); calc. 261.3.
  • 70
  • [ 6072-57-7 ]
  • [ 616-34-2 ]
  • methyl N-(2,3-dihydro-3-methyl-1H-inden-1-yl)glycine [ No CAS ]
YieldReaction ConditionsOperation in experiment
19 parts (54.1%) With sodium formate In thiophene; methanol; water 33.a EXAMPLE 33 a) A mixture of 21 parts of 2,3-dihydro-3-methyl-1H-inden-1-one, 25 parts of methyl 2-aminoacetate, 2 parts of a solution of thiophene in methanol 4%, 25 parts of sodium formate and 480 parts of methanol is hydrogenated in a Parr-apparatus and at 50° C. with 5 parts of palladium-on-charcoal catalyst 10%. The reaction mixture is evaporated. The residue is taken up in water and 1,1'-oxybisethane is added. The separated organic layer is extracted with a hydrochloric acid solution 10%. The aqueous layer is made alkaline and the product is extracted with 1,1'-oxybisethane. The combined extracts are dried, filtered and evaporated, yielding 19 parts (54.1%) of methyl N-(2,3-dihydro-3-methyl-1H-inden-1-yl)glycine as a residue.
  • 71
  • [ 6072-57-7 ]
  • [ 6000-59-5 ]
  • [ 141741-37-9 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid In 1,4-dioxane; water 16.1 Step 1 Step 1 1-Methyl-3-oxo-2-indenylidene acetic acid A mixture of 3-methylindan-1-one (J.C.S. Chem. Comm. 1973, 636) (2.0 g, 13.7 mmol), glyoxylicacid hydrate (12.6 g, 137 mmol), dioxane (96 mL) and sulfuric acid (8.2 mL) was stirred at 95° C. for 45 minutes. Water (100 mL) was added, and the dioxane evaporated. The residual aqueous suspension was diluted with water and filtered to afford the title compound as a yellow solid.
  • 72
  • [ 6072-57-7 ]
  • [ 105-56-6 ]
  • [ 918972-39-1 ]
YieldReaction ConditionsOperation in experiment
49% With morpholine; sulfur; acetic acid In ethanol
  • 73
  • [ 6072-57-7 ]
  • [ 75-26-3 ]
  • [ 941-97-9 ]
YieldReaction ConditionsOperation in experiment
Stage #1: isopropyl bromide With magnesium In diethyl ether for 1h; Stage #2: 3-methylindanone In diethyl ether at 20℃; for 48h; Stage #3: With hydrogenchloride In methanol Further stages.;
  • 74
  • [ 6072-57-7 ]
  • [ 100-58-3 ]
  • [ 22360-62-9 ]
YieldReaction ConditionsOperation in experiment
74% Stage #1: 3-methylindanone; phenylmagnesium bromide In tetrahydrofuran; diethyl ether at 20℃; for 6h; Inert atmosphere; Stage #2: With sulfuric acid In tetrahydrofuran; diethyl ether at 20℃; for 3h;
  • 75
  • cis-2,3-dihydro-N-methoxy-3-methyl-1H-inden-1-amine [ No CAS ]
  • [ 100-58-3 ]
  • [ 6072-57-7 ]
  • trans-1,2,3,4-tetrahydro-4-methyl-2-phenylquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 33% 2: 11% In diethyl ether at 20℃; for 0.25h; Inert atmosphere;
  • 76
  • [ 6072-57-7 ]
  • [ 593-56-6 ]
  • C11H13NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium acetate In methanol at 20℃; for 5h; Inert atmosphere;
  • 77
  • [ 6072-57-7 ]
  • [ 30696-28-7 ]
YieldReaction ConditionsOperation in experiment
57% With sodium azide; phosphoric acid at 50℃; Preparation of 4-methyl-3,4-dihydro-lH-quinolin-2-one: Preparation of 4-methyl-3,4-dihydro-lH-quinolin-2-one: to 2 mL of polyphosphoric acid was added 3-methylindan-l-one (500 mg, 3.42 mmol, 1 eq) and stirred with mechanical stirrer for 10 minutes. Sodium azide (234 mg, 3.59 mmol, 1.05 eq) was added in portions while stirring for 20 minutes. The mixture was heated at 50 °C while stirring overnight. Small portion of ice-cold water was added to the reaction mixture and stirred until all polyphosphoric acid dissolved. Mixture was then poured onto 20 mL of water/ice and pH made basic with 2N NaOH. Extracted with 2x20 mL EtO AC. Organic layer was washed with water and concentrated in vacuo. Crude product was purified by flash chromatography in the solvent system EtO Ac-heptane, 0- 35% EtO Ac. Purest fractions were combined and solvent evaporated to give 313 mg of 4-methyl-3,4-dihydro-lH-quinolin-2-one as white solid (yield 57%). MS: m/z (M+H)+ 162 1H NMR (300 MHz, DMSO- 6) δ 10.07 (s, 1H), 7.25 - 7.07 (m, 2H),) 6.93 (td, J = 1.5, 1.3 Hz, 1H), 6.85 (dd, J= 7.8, 1.2 Hz, 1H), 3.11 - 2.97 (m, 1H), 2.57 (dd, J = 16.0, 5.9 Hz, 1H), 2.22 (dd, J= 15.9, 7.1 Hz, 1H), 1.17 (d, J= 6.9 Hz, 3H). 2 0
43% Stage #1: 3-methylindanone for 0.166667h; Stage #2: With sodium azide at 50℃; K.1.a Method K-1; Example K-1; 4-({(3S,R4S,f?)-4-methyl-2-oxo-1 -r2-(tϖfluoromethyl)benzyl1-1 ,2,3,4-tetrahvdroquinolin-3-vl)methyl)benzoic acid; Preparation of K-1 -a; 4-methyl-3,4-dihvdroquinolin-2(1 /-/)-one; To 130 g of polyphosphoric acid was added 3-methylindan-1 -one (9.82g, 67.2 mmol) and stirred with mechanical stirrer for 10 minutes. Sodium azide (4.58 g, 70.5 mmol) was added in portions while stirring for 20 minutes. The mixture was heated in 50 0C oil bath while stirring overnight. The reaction mixture was cooled down and mixed with 600 ml of ice water and sonicated until all the polyphosphoric acid dissolves. This mixture was extracted by CH2CI2 3 times, totally -700 ml. The CH2CI2 phase was washed with brine once, dried with sodium sulfate. After silica gel chromatography eluting with 0 - 50% hexane/EtOAc gradient 4.66 g of product was obtained (43% yield). 1H NMR (400 MHz, DMSO-c/6) δ ppm 1.17 (d, J=6.8Hz, 3 H) 2.22(dd, J=6.8 Hz, 16.2Hz, 1 H) 2.58(dd, J=5.8 Hz, 15.9Hz, 1 H) 2.95 - 3.13 (m, 1 H) 6.81 -6.88 (m, 1 H) 6.89-6.98 (m, 1 H) 7.08-7.16 (m, 1 H) 7.18 (d, J=7.3 Hz, 1 H) 10.07 (s, 1 H). LRMS (M+H)+: 162.2.
  • 78
  • [ 6072-57-7 ]
  • [ 1100-88-5 ]
  • [ 1354727-76-6 ]
YieldReaction ConditionsOperation in experiment
69% General procedure: To a suspension of benzyltriphenylphosphonium bromide (1.63 g, 3.76 mmol) in THF (40 mL) was dropwise added n-BuLi (2.35 mL, 1.6 M in hexanes). After the system was stirred at room temperature for 2 h, indanone (7a, 0.25 g, 1.89 mmol) or its derivative (8a-17a, 1.89 mmol) in THF (10 mL) was added. The reaction mixture was stirred at reflux for 24 h, then, cooled to room temperature, quenched with water (20 mL), and extracted with n-hexane (3 × 30 mL). The organic layers were combined, washed with water, dried (Na2SO4) and filtered. The filtrate was concentrated under reduced pressure. The residue was purified with silica gel column chromatography (n-hexane) to give the corresponding products (7b-17b).
  • 79
  • [ 1379674-96-0 ]
  • [ 6072-57-7 ]
YieldReaction ConditionsOperation in experiment
37% With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I); silver(I) triflimide In 1,2-dichloro-ethane at 25℃; for 12h; Inert atmosphere;
  • 80
  • [ 2564-83-2 ]
  • [ 6072-57-7 ]
  • 3-methyl-2-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)-1-indanone [ No CAS ]
  • 3-methyl-2-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)-1-indanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With 2,6-di-tert-butyl-pyridine; 2-chloro-1,3,2-benzodioxaborole In dichloromethane at 0 - 20℃; for 3h; stereoselective reaction;
  • 81
  • [ 10487-71-5 ]
  • [ 71-43-2 ]
  • [ 6072-57-7 ]
  • [ 1533-20-6 ]
YieldReaction ConditionsOperation in experiment
1: 35 %Spectr. 2: 12 %Spectr. With aluminum (III) chloride at 25 - 30℃; for 3.3h; General procedure for the AlCl3-promoted tandem Friedel-Crafts acylation and alkylation of arenes with 2-alkenoyl chlorides To a stirring mixture of anhydrous aluminum chloride (2.0 g, 15 mmol) and arene (15 mL for the reaction under refluxing, 25 mL for the reaction at RT) was added a solution of 2-alkenoyl chloride (10 mmol) in the same arene (8 mL) dropwise during 3 h at 25-30 ◦C (RT) or under refluxing. After addition, the resulting mixture was kept stirring for 20 min and then allowed to cool to the room temperature. It was poured into 150 mL of 1 mol/L HCl to decompose AlCl3 complex. After phase separation, the aqueous phase was extracted with ethyl acetate (3× 50 mL). After dried over Na2SO4 and evaporation of the solvents, the residue was purified on silica gel column with a mixture of petroleum ether (60-90 ◦C) and ethyl acetate (10:1, v/v) as eluent to afford the desired product. 1,3-Diphenylbutan-1-one (2b) [22] Colorless oil, 1H NMR (400 MHz, CDCl3): δ 1.34 (d, J = 6.9 Hz, 3H, CH3), 3.19 (dd, J = 8.3, 16.4 Hz, 1H in CH2), 3.30 (dd, J = 5.7, 16.4 Hz, 1H in CH2), 3.49-3.62 (m, 1H, CH), 7.18-7.35 (m, 5H, ArH), 7.42-7.50 (m, 2H, ArH), 7.52-7.60 (m, 1H, ArH), 7.93-7.97 (m, 2H, ArH).
1: 21 %Spectr. 2: 39 %Spectr. With aluminum (III) chloride at 25 - 30℃; for 3.63333h; General procedure for the AlCl3-promoted tandem Friedel-Crafts acylation and alkylation of arenes with 2-alkenoyl chlorides To a stirring mixture of anhydrous aluminum chloride (2.0 g, 15 mmol) and arene (15 mL for the reaction under refluxing, 25 mL for the reaction at RT) was added a solution of 2-alkenoyl chloride (10 mmol) in the same arene (8 mL) dropwise during 3 h at 25-30 ◦C (RT) or under refluxing. After addition, the resulting mixture was kept stirring for 20 min and then allowed to cool to the room temperature. It was poured into 150 mL of 1 mol/L HCl to decompose AlCl3 complex. After phase separation, the aqueous phase was extracted with ethyl acetate (3× 50 mL). After dried over Na2SO4 and evaporation of the solvents, the residue was purified on silica gel column with a mixture of petroleum ether (60-90 ◦C) and ethyl acetate (10:1, v/v) as eluent to afford the desired product. 1,3-Diphenylbutan-1-one (2b) [22] Colorless oil, 1H NMR (400 MHz, CDCl3): δ 1.34 (d, J = 6.9 Hz, 3H, CH3), 3.19 (dd, J = 8.3, 16.4 Hz, 1H in CH2), 3.30 (dd, J = 5.7, 16.4 Hz, 1H in CH2), 3.49-3.62 (m, 1H, CH), 7.18-7.35 (m, 5H, ArH), 7.42-7.50 (m, 2H, ArH), 7.52-7.60 (m, 1H, ArH), 7.93-7.97 (m, 2H, ArH).
  • 82
  • [ 6072-57-7 ]
  • [ 947-57-9 ]
  • dimethyl (1SR,4RS,5RS,6RS)-exo-5-((2′SR, 3′RS)-3′-methyl-1′-indanon-2′-yl)bicyclo[2.2.1]hept-2-ene-bis-endo-5,6-dicarboxylate [ No CAS ]
  • dimethyl exo-5-(3′-methyl-1′-indanon-2′-yl)bicyclo[2.2.1]hept-2-ene-endo-5-exo-6-dicarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 26% 2: 20% Stage #1: 3-methylindanone With lithium diisopropyl amide In tetrahydrofuran at -5 - 0℃; Inert atmosphere; Stage #2: dimethyl bicyclo[2.2.1]hept-2,5-diene-2,3-dicarboxylate In tetrahydrofuran at 20℃; Inert atmosphere;
  • 83
  • [ 6072-57-7 ]
  • [ 108-95-2 ]
  • [ 1572177-23-1 ]
YieldReaction ConditionsOperation in experiment
10 g With hydrogenchloride; 3-mercaptopropionic acid at 20 - 35℃; for 10.5h; 7.2 Step 2: Preparation of 4,4′-(3-methyl-2,2,3-trihydro-1H-indene-1,1-diyl)diphenol Step 2: Preparation of 4,4′-(3-methyl-2,2,3-trihydro-1H-indene-1,1-diyl)diphenol [0248] 3-methyl-indan-1-one (20 g, 0.136 moles), phenol (128 g, 1.36 moles) and 3-MPA (2.528 g, 3 wt % with regard to the reaction mixture). The reaction mixture was initially stirred at room temperature and dry HCl was bubbled through the mixture. After 0.5 hour, HCl bubbling was stopped, the bath temperature was gradually increased to 35° C. and the reaction mixture was continually stirred at that temperature for 10 hours. After completion of 10 hours, 100 ml of toluene was added to the reddish brown viscous mass and the resultant mixture was washed with water (2×50 ml), saturated NaHCO3 (2×50 ml), water, and then dried over anhydrous Na2SO4. The remaining solvent was then removed under vacuum. The residue obtained was subjected to vacuum distillation (50° C. at 1 mm) to remove excess (unreacted) phenol. A dark brown residue was obtained after distilling excess phenol. The residue was dissolved in 20% NaOH (200 ml). The insolubles were filtered off and the resultant filtrate was acidified with dilute HCl. A solid precipitated from the reaction mixture, which was filtered and washed thoroughly with water until chloride free. The solid was then dried to provide 25 g of a solid. The solid was suspended in toluene (50 ml) and the resultant mixture was heated to reflux for 1 hour. After 1 hour, the mixture was cooled to room temperature and stirred for another 4 hours. A solid precipitated, was filtered, washed with hot toluene (1 wt/vol.), and dried to provide 10 g of the desired product, 4,4′-(3-methyl-2,2,3-trihydro-1H-indene-1,1-diyl)diphenol, with purity of 99.25%. MP=165.75° C. 1H NMR (DMSO-d6, 300 MHz): δ 9.2 (s, 2H, Ar-OH), δ 7.3-7.1 (m, 3H, Ar-H), δ 7.0-6.8 (m, 5H, Ar-H), δ 6.7-6.6 (m, 4H, Ar-H), δ 3.0-2.8 (m, 2H, -CH2), δ 2.2-2.1 (m, 1H, -CH2).
  • 84
  • [ 6072-57-7 ]
  • [ 625126-76-3 ]
  • ((1S,3R)-1-isopropyl-3-((3-methyl-2,3-dihydro-1H-inden-1-yl)amino)cyclopentyl)(7-(trifluoromethyl)-3,4-dihydroisoquinolin-2(1H)-yl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
41% With titanium(IV) isopropylate In tetrahydrofuran at 20℃; for 48h; Inert atmosphere; 4.1.5. General procedure for the synthesis of compounds 8, 14-16 and 36-40 General procedure: In a 5 mL glass tube, amine 6 (1 equiv) dissolved in 1 mL of dry THF, and the corresponding indanone (1.2 equiv) dissolved in 1 mL of dry THF were loaded. Mixture was flushed with nitrogen gas and the tube was capped. Through the septa Ti(O-i-Pr)4 (3 equiv) was added and the reaction mixture was stirred for 48 h at room temperature.Then the tube was decapped and NaBH4 (5 equiv) and 0.5 mL of absolute EtOH were added, and stirred for 16 h. The reaction mixture was quenched with H2O and resulting inorganic precipitate was filtered off and washed with DCM. The filtrate was extracted with DCM/H2O. The organic layer was dried with MgSO4 and evaporated. The product was purified by column chromatography (40% ethyl acetate in DCM).
  • 85
  • [ 6072-57-7 ]
  • [ 146796-60-3 ]
YieldReaction ConditionsOperation in experiment
73% With triphenylphosphine hydrobromide In dimethyl sulfoxide at 50℃; for 23h; Inert atmosphere; Then, in 22 mL of a DMSO solution of triphosphonium bromide (manufactured by Wako Pure Chemical Industries, Ltd., 2.53 g, 7.38 mmol), 3-methyl-2,3-dihydro-1H-indene-indicated by the formula (5) was used. 1-one (0.5 mL, 3.68 mmol) was added, and the mixture was heated with stirring at 50 ° C. for 23 hours under a nitrogen atmosphere. Then, the mixture was cooled to room temperature, added to saturated aqueous ammonium chloride solution and extracted with ethyl acetate, the organic layer was dried over sodium carbonate, filtered, and the solvent was evaporated. Then, the crude product is purified using silica gel chromatography (hexane: ethyl acetate (volume ratio) = 30: 1) to give 2-bromo-3-methyl-1H represented by the formula (6). -Inden-1-one (599 mg, yield: 73%) was obtained.
52% With triphenylphosphine hydrobromide; dimethyl sulfoxide at 50℃; for 18h; Inert atmosphere; chemoselective reaction;
43% With triphenylphosphine hydrobromide In dimethyl sulfoxide at 50℃; for 18h;
  • 86
  • [ 6072-57-7 ]
  • [ 115262-01-6 ]
  • 2-fluoro-4-methylnaphthalen-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% Stage #1: 3-methylindanone; [bromo(difluoro)methyl]-trimethyl-silane With tetrabutylammomium bromide In toluene at 110℃; for 7h; Sealed tube; Stage #2: With tetrabutyl ammonium fluoride In toluene at 20℃; for 2h;
  • 87
  • [ 6072-57-7 ]
  • [ 4229-44-1 ]
  • C11H13NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% In neat (no solvent) at 125℃; for 0.583333h; Microwave irradiation;
  • 88
  • [ 6072-57-7 ]
  • [ 361389-86-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydroxide / methanol; water / 2 h / 80 °C 2: hydrogen / palladium 10% on activated carbon / methanol
  • 89
  • [ 6072-57-7 ]
  • [ 70079-42-4 ]
  • [ 30696-28-7 ]
YieldReaction ConditionsOperation in experiment
1: 41% 2: 31% With sodium azide; methanesulfonic acid at 0℃; for 3h; Inert atmosphere; Heating; 3.2.1. Synthesis of substituted 3,4-dihydro-2(1H)-quinolinones 3a-c and 3,4-dihydro-1(2H)-isoquinolinones 4a-c General procedure: To a solution of 2,3-dihydro-3-substituted-1H-inden-1-one 2a-c (8.21 mmol) in methanesulfonic acid (15 mL), sodium azide (12.31 mmol) was added at 0 °C. Then the reaction mixture was warmed to 15-32 °C and stirred further for next 3 h. Then the reaction mixture was poured into ice and extracted with ethyl acetate (300 mL). The organic layer was washed with brine solution, dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to afford crude product which was subjected to column chromatography over silica gel (100-200 mesh), eluted with ethyl acetate in hexane afforded 3a-c and 4a-c with 38-46% and 13-31% of yields, respectively.
  • 90
  • [ 6072-57-7 ]
  • [ 74-85-1 ]
  • 5-methyl-8,9-dihydro-5H-benzo[7]annulen-7(6H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
32% With 3-methylpyridin-2-ylamine; chlorobis(ethylene)rhodium(I) dimer; water; toluene-4-sulfonic acid In tetrahydrofuran at 150℃; for 72h; chemoselective reaction;
  • 91
  • [ 6072-57-7 ]
  • [ 74-85-1 ]
  • [ 69379-34-6 ]
  • 5-methyl-8,9-dihydro-5H-benzo[7]annulen-7(6H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 24 %Spectr. 2: 8 %Spectr. With 2-aminopyridine; chlorobis(ethylene)rhodium(I) dimer; water; toluene-4-sulfonic acid; 1,3-bis(2,4,6-trimethylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene In tetrahydrofuran at 150℃; for 72h; chemoselective reaction;
  • 92
  • [ 6072-57-7 ]
  • 5-(4-amino-5-(trifluoromethyl)pyrrolo[2,1-f][1,2,4]triazin-7-yl)-N-((3R,4S)-4-fluoropyrrolidin-3-yl)-2-methoxynicotinamide [ No CAS ]
  • 5-(4-amino-5-(trifluoromethyl)pyrrolo[2,1-f][1,2,4]triazin-7-yl)-N-((3R,4S)-4-fluoro-1-(3-methyl-2,3-dihydro-1H-inden-1-yl)pyrrolidin-3-yl)-2-methoxynicotinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
49% With acetic acid; bis(pinacol)diborane In methanol at 50℃; 1353 Example 1353: 5-(4-Amino-5-(trifluoromethyl)pyrrolo[2,1-f][1,2,4]triazin-7-yl)- N-((3R,4S)-4-fluoro-1-(3-methyl-2,3-dihydro-1H-inden-1-yl)pyrrolidin-3-yl)-2- methoxynicotinamide In a 1 dram vial were combined 5-(4-amino-5-(trifluoromethyl)pyrrolo[2,1- f][1,2,4]triazin-7-yl)-N-((3R,4S)-4-fluoropyrrolidin-3-yl)-2-methoxynicotinamide (20 mg, 0.046 mmol) with 3-methylindan-1-one (16.64 mg, 0.114 mmol, 2.5 eq.) in a mixture of MeOH (0.300 mL) and AcOH (0.075 mL). To the mixture was added borane-2- picoline complex (19.48 mg, 0.182 mmol, 4 eq.) The mixture was heated to 50 oC and stirred ON. The crude mixture was filtered and purified via preparative LC/MS with the following conditions: Column = XBridge C18, 200 mm x 19 mm, 5-μm particles; Mobile Phase A = 5:95 acetonitrile:water with 10-mM ammonium acetate; Mobile Phase B = 95:5 acetonitrile:water with 10-mM ammonium acetate; Gradient = 39-79% B over 25 minutes, then a 4-minute hold at 100% B; Flow Rate = 20 mL/min; Column Temperature = 25 oC. Fractions containing the desired product were combined and dried via centrifugal evaporation to give the desired product (12.7 mg, 49% yield) as a mixture of two diastereomers. (1445) MS ESI m/z 570.2 (M+H)+ (1446) 1H NMR (500 MHz, DMSO-d6) δ 8.80 (br s, 1H), 8.74 (br d, J=6.4 Hz, 1H), 8.68 (br s, 1H), 8.04 (s, 1H), 7.50 - 7.40 (m, 2H), 7.40 - 7.26 (m, 3H), 5.43 (br s, 0.5H), 5.36 - 5.30 (m, 0.5H), 5.05 - 4.93 (m, 1H), 4.87 - 4.67 (m, 1H), 4.43 - 4.34 (m, 1H), 3.99 (br s, 3H), 3.77 - 3.57 (m, 2H), 3.48 - 3.31 (m, 1H), 3.17 - 3.09 (m, 1H), 2.72 (m, 1H), 1.65 - 1.53 (m, 1H), 1.34 - 1.27 (m, 3H).
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