[ CAS No. 22955-77-7 ] {[proInfo.proName]}

Name: 22955-77-7|Methyl 1-oxo-2,3-dihydro-1H-indene-2-carboxylate|95%
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SKU: A257742
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Quality Control of [ 22955-77-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 22955-77-7 ]

Product Details of [ 22955-77-7 ]

CAS No. :	22955-77-7	MDL No. :	MFCD00667641
Formula :	C₁₁H₁₀O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YBKCOFSJGXNOKP-UHFFFAOYSA-N
M.W :	190.20	Pubchem ID :	312866
Synonyms :

Calculated chemistry of [ 22955-77-7 ] Expand+

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.27
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	50.39
TPSA :	43.37 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.19 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.75
Log Po/w (XLOGP3) :	1.79
Log Po/w (WLOGP) :	1.21
Log Po/w (MLOGP) :	1.22
Log Po/w (SILICOS-IT) :	2.19
Consensus Log Po/w :	1.63

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.33
Solubility :	0.885 mg/ml ; 0.00466 mol/l
Class :	Soluble
Log S (Ali) :	-2.32
Solubility :	0.911 mg/ml ; 0.00479 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.96
Solubility :	0.207 mg/ml ; 0.00109 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.18

Safety of [ 22955-77-7 ]

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

Application In Synthesis of [ 22955-77-7 ]

* 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.

Upstream synthesis route of [ 22955-77-7 ]
Downstream synthetic route of [ 22955-77-7 ]

[ 22955-77-7 ] Synthesis Path-Upstream 1~14

1
[ 34288-40-9 ]
[ 22955-77-7 ]

Yield	Reaction Conditions	Operation in experiment
85%	With Stryker's reagent In toluene at 25℃; for 20 h; Inert atmosphere	General procedure: A 3.0'10^-2 M solution of the ortho-substituted cinnamic esters (n mmol) in toluene and recently prepared Stryker's reagent (n/2 mmol), were mixed together and stirred at room temperature or 0°C for corresponding time. The reaction was quenched with saturated ammonium chloride solution. The mixture was stirred for 1 h. During this period a white precipitate was formed. The reaction mixture was filtered and the residue was washed with ethyl acetate. The organic phase was separated and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried with MgSO₄ and the solvent was removed under vacuum. The residue was purified by column chromatography on silica gel. The yields are shown in tables 1 and 2.

Reference： [1] Tetrahedron Letters, 2011, vol. 52, # 41, p. 5371 - 5374

2
[ 83-33-0 ]
[ 616-38-6 ]
[ 22955-77-7 ]

Reference： [1] Chemistry - A European Journal, 2017, vol. 23, # 54, p. 13309 - 13313
[2] European Journal of Organic Chemistry, 2016, vol. 2016, # 5, p. 918 - 920
[3] Advanced Synthesis and Catalysis, 2018, vol. 360, # 15, p. 2869 - 2878
[4] Tetrahedron, 2002, vol. 58, # 21, p. 4225 - 4236
[5] Organic letters, 2000, vol. 2, # 20, p. 3083 - 3086
[6] Organic Letters, 2015, vol. 17, # 12, p. 3070 - 3073
[7] Advanced Synthesis and Catalysis, 2016, vol. 358, # 12, p. 1934 - 1941
[8] Chemical Communications (Cambridge, United Kingdom), 2018, vol. 54, # 82, p. 11602 - 11605
[9] European Journal of Organic Chemistry, 2004, # 12, p. 2707 - 2714
[10] Chemistry - A European Journal, 2010, vol. 16, # 31, p. 9457 - 9461
[11] Advanced Synthesis and Catalysis, 2013, vol. 355, # 8, p. 1631 - 1639
[12] Organic Letters, 2013, vol. 15, # 13, p. 3246 - 3249
[13] Chemical Communications, 2014, vol. 50, # 58, p. 7870 - 7873
[14] Chemical Communications, 2009, # 26, p. 3925 - 3927
[15] Organic and Biomolecular Chemistry, 2014, vol. 12, # 28, p. 5071 - 5076
[16] Chemistry Letters, 2014, vol. 43, # 1, p. 137 - 139
[17] Journal of Organic Chemistry, 1970, vol. 35, p. 647 - 651
[18] Bulletin de la Societe Chimique de France, 1982, vol. 2, # 3-4, p. 116 - 124
[19] Patent: US1705, 1998, H1,
[20] Chemical Communications, 2008, # 21, p. 2474 - 2476
[21] Chemistry - A European Journal, 2008, vol. 14, # 32, p. 9864 - 9867
[22] Chemical Communications, 2013, vol. 49, # 33, p. 3470 - 3472
[23] Angewandte Chemie - International Edition, 2013, vol. 52, # 49, p. 12860 - 12864[24] Angew. Chem., 2013, vol. 125, # 49, p. 13098 - 13102
[25] Journal of the American Chemical Society, 2015, vol. 137, # 17, p. 5678 - 5681
[26] Synlett, 2015, vol. 26, # 12, p. 1725 - 1731
[27] Journal of Medicinal Chemistry, 2015, vol. 58, # 11, p. 4738 - 4748
[28] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 20, p. 4576 - 4579
[29] Chemistry - A European Journal, 2017, vol. 23, # 8, p. 1775 - 1778
[30] Journal of Organic Chemistry, 2017, vol. 82, # 1, p. 701 - 708
[31] Organic and Biomolecular Chemistry, 2017, vol. 15, # 37, p. 7753 - 7757
[32] Journal of Fluorine Chemistry, 2017, vol. 204, p. 23 - 30
[33] Synthesis (Germany), 2016, vol. 48, # 9, p. 1359 - 1370
[34] Chinese Journal of Chemistry, 2017, vol. 35, # 11, p. 1665 - 1668
[35] Organic Letters, 2018, vol. 20, # 7, p. 1875 - 1879

3
[ 25040-17-9 ]
[ 22955-77-7 ]

Yield	Reaction Conditions	Operation in experiment
66%	With sodium hydride In tetrahydrofuran; oil for 1 h; Reflux	A solution of methyl 2-[3-(methyloxy)-3-oxopropyl]benzoate (3.77g, 16.98mmol, Description 1 ) in dry THF (75 ml) under argon was stirred during the addition of sodium hydride (2.04g of 60percent suspension in oil, 50.9mmol) over 2 minutes. The mixture was then slowly heated to reflux. After 1 hour at reflux a thick paste had formed. This was cooled to room temperature and treated dropwise with water (1 ml) added over 5 minutes. The resulting slurry was acidified with 5M hydrochloric acid (20ml) and extracted twice with ethyl acetate. The combined organics were dried over MgSO₄ and evaporated to afford an oil which was chromatographed on silica gel (7Og). Elution with 0-50percent ethyl acetate in pentane gave methyl 1-oxo-2,3-dihydro-1 H-indene-2-carboxylate as a yellow oil (2.14g, 66percent), which solidified on standing. ¹H-NMR (400MHz, CDCI₃): δ 7.79 (1 H, d, J = 7.6 Hz), 7.63 (1 H, dd, J = 7.6 and 7.6 Hz), 7.50 (1 H, d, J = 7.6 Hz), 7.42 (1 H, dd, J = 7.6 and 7.6 Hz), 3.80 (3H, s), 3.75 (1 H, m), 3.60 (1 H, m), 3.40 (1 H, m).

Reference： [1] Patent: WO2010/57865, 2010, A1, . Location in patent: Page/Page column 23-24

4
[ 124-38-9 ]
[ 83-33-0 ]
[ 74-88-4 ]
[ 22955-77-7 ]

Reference： [1] Green Chemistry, 2011, vol. 13, # 2, p. 376 - 383

5
[ 36919-03-6 ]
[ 83-33-0 ]
[ 22955-77-7 ]

Reference： [1] Organic Letters, 2013, vol. 15, # 2, p. 370 - 373

6
[ 83-33-0 ]
[ 22955-77-7 ]

Reference： [1] Chemical & Pharmaceutical Bulletin, 1988, vol. 36, # 1, p. 401 - 404
[2] Patent: US6211212, 2001, B1,

7
[ 63600-27-1 ]
[ 25040-17-9 ]
[ 22955-77-7 ]

Reference： [1] Journal of Organic Chemistry, 2012, vol. 77, # 20, p. 9374 - 9378

8
[ 67-56-1 ]
[ 61402-25-3 ]
[ 22955-77-7 ]

Reference： [1] Chemical & Pharmaceutical Bulletin, 1988, vol. 36, # 1, p. 401 - 404

9
[ 6742-26-3 ]
[ 22955-77-7 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1993, # 4, p. 405 - 410

10
[ 18454-53-0 ]
[ 22955-77-7 ]

Reference： [1] Tetrahedron Letters, 2011, vol. 52, # 41, p. 5371 - 5374

11
[ 135-19-3 ]
[ 22955-77-7 ]

Reference： [1] Tetrahedron Letters, 2011, vol. 52, # 41, p. 5371 - 5374

12
[ 103-26-4 ]
[ 22955-77-7 ]

Reference： [1] Chemical Communications, 2013, vol. 49, # 33, p. 3470 - 3472

13
[ 103-25-3 ]
[ 22955-77-7 ]

Reference： [1] Chemical Communications, 2013, vol. 49, # 33, p. 3470 - 3472

14
[ 186581-53-3 ]
[ 100188-67-8 ]
[ 22955-77-7 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1993, # 4, p. 405 - 410

[ 22955-77-7 ] Synthesis Path-Downstream 1~33

1
[ 22955-77-7 ]
[ 4254-32-4 ]

Reference： [1]Monatshefte fur Chemie,1989,vol. 120,p. 623 - 642

2
[ 83-33-0 ]
[ 616-38-6 ]
[ 22955-77-7 ]

Yield	Reaction Conditions	Operation in experiment
83%	With sodium hydride; In tetrahydrofuran; mineral oil; for 2h;Reflux; Inert atmosphere;	A solution of 1-indanone 8 (2.00 g, 15.1 mmol) in THF (16.0 mL) was added dropwise to a stirred suspension of dimethyl carbonate (6.37 mL, 76.0 mmol) in THF (32.0 mL) containing sodium hydride 60% in oil (1.27 g, 31.8 mmol) under nitrogen atmosphere. The reaction mixture was heated to reflux for 2 h. Once completion, the reaction mixture was acidified with 1 M HCl (15 mL), and then extracted with Et2O (20mL × 2). The combined organic layers were washed with brine (20 mL), dried over sodium sulfate and filtered. The filtrate was concentrated, and purified by MPLC (0% to 30% EtOAc/hexanes) to give 9 as a yellow oil (2.38 g, 83% yield). The product was isolated as a mixture of keto and enol tautomer (ratio 6:1 by 1H NMR). 1H NMR (400 MHz, CDCl3), keto tautomer: delta 7.78 (d, J = 7.7 Hz, 1H), 7.63 (td, J = 7.5 Hz, 1.0 Hz, 1H), 7.50 (d, J = 7.7 Hz, 1H), 7.40 (t, J = 7.1 Hz, 1H), 3.79 (s, 3H), 3.74 (dd, J = 8.3, 4.1 Hz, 1H), 3.57 (dd, J = 17.3, 4.0 Hz, 1H), 3.38 (dd, J = 17.3, 8.3 Hz, 1H); enol tautomer: delta 10.37 (brs, 1H), 7.63-7.67 (m, 1H), 7.45-7.49 (m, 1H), 7.42 (td, J = 7.3, 1.5 Hz, 1H), 7.35-7.37 (m, 1H), 3.86 (s, 3H), 3.52 (s, 2H).
75%	With sodium hydride; In tetrahydrofuran; mineral oil;Reflux; Inert atmosphere;	General procedure: In a round-bottomed flask NaH 60% in grease (3 eq.) was placed. Then, it wasdissolved in dry THF (0.2 mL/mmol NaH) while stirring under argon atmosphere,forming a white suspension. Next, dimethyl carbonate (3 eq.) was added (methyl 1Himidazole-1-carboxylate in case 1i) to the suspension and the corresponding ketone (1eq.) was dissolved with dry THF (1 mL/mol ketone) in an addition funnel. The ketonesolution was added to the reaction mixture dropwise in a period of 3-5 minutes. Thereaction mixture was heated to reflux until total conversion of the reagent was observedby TLC (3-5 h). Afterwards, 1 M HCl was added to the mixture until pH = 2-3. Theaqueous mixture was then extracted with dichloromethane. The organic fraction wasdried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. Finally, the product was purified by column chromatography on silica-gel whennecessary.
	With hydrogenchloride; sodium methylate; In water; toluene;	EXAMPLE 4 2-Carbomethoxy-1-Indanone Solid sodium methoxide (1.0 g, 18.5 mmol) was added to 30 mL of toluene. The mixture was stirred and heated to 96 C. To this hot mixture was added a solution of 1.8 g (13.6 mmol) of 1-indanone in 9.1 mL of DMC. The indanone solution was added at a rate sufficient to permit removal of methanol formed in the reaction as its azeotrope with either DMC or toluene (distillation head temperature was 64 C.). Upon completion of the addition, the mixture was cooled and a solution of 1.25 mL of concentrated HCl in 4 mL water was added. The phases were separated and the toluene phase was washed with water and the solvent removed by evaporation yielding 2.22 g. 1 H NMR: delta3.38, (dd,1H), (J=8, 17 Hz), delta3.58, (dd,1H) (J=4,17 Hz), delta3.75, (dd,1H) (J=4,8 Hz), delta3.80, (s,3H), delta7.40, (t,1H), delta7.51,(d,1H), delta7.64,(t,1H), delta7.79,(d,1H).

	With sodium hydride; In tetrahydrofuran; mineral oil; at 60℃; for 1h;Inert atmosphere; Sealed tube;	NaH (60% suspension in mineral oil, 2.86g, 71.5mmol) and THF(40 mL) were added into aflame-dried round-bottom flask equipped with a stir bar under argon atmosphere. Then dimethylcarbonate (14.4 mL, 171.6 mmol) was added, and the mixture was warmed to 60 oC. A solution of1-indanone (3.78 g, 28.6 mmol) in THF (40 mL) was added dropwise into the flask over 1 h. Themixture was refluxed until complete conversion by TLC. After cooled to room temperature, it wasquenched by 2 M HCl (60 mL). The mixture was extracted with DCM. The combined organicphases were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified byflash column chromatography (petroleum ether /EtOAc = 5/1) to afford the desired compound.
	With potassium tert-butylate; sodium hydride; at 20℃; for 1h;Inert atmosphere;	General procedure: In an ice bath, anhydrous dimethyl carbonate (30 mL) was added to a mixture of 95% NaH (3.03 g, 120 mmol) and potassiumtert-butoxide (4.2 g, 37.5 mmol). And then, a solution of indenone (30 mmol) in anhydrous dimethyl carbonate (70 mL) was added dropwise under argon. The mixture was stirred at room temperature for 1 h and adjusted pH to 2-3 with diluted HCl. The organic layers were collected and washed with brine (2 × 100 mL), dried over MgSO4, filtered and concentrated in vacuum to obtain the corresponding crude compounds 2a-g. The crude products were used in the next reaction without further purification.
	With sodium hydride; In tetrahydrofuran; mineral oil;Inert atmosphere; Reflux;	General procedure: Procedure C: A solution of ketone (10 mmol) in dry THF (10 mL) was added dropwise to a stirred mixture of dimethyl carbonate (4.2 mL, 50 mmol) and NaH (60% in mineral oil, 0.80 g, 20 mmol) in dry THF (15 mL) under a nitrogen atmosphere. The mixture was heated at reflux overnight, cooled to room temperature, acidified with 1.0 M aqueous HCl solution, and extracted with Et2O (3 × 10 mL). The combined organic layers were dried over anhydrous Na2SO4 and concentrated to dryness under reduced pressure. The crude product was purified by column chromatography on silica gel using a mixture of petroleum ether / ethyl acetate = 10 : 1 or 2 : 1 (v / v) as eluents to give the desired product.
	With sodium hydride; In tetrahydrofuran; mineral oil; at 60℃;Inert atmosphere; Reflux;	General procedure: NaH (60% suspension in mineral oil, 2.86 g, 71.5mmol) and THF (40 mL) were added into a flame-dried round-bottom flask equipped with a stir bar under argon atmosphere. Then dimethyl carbonate (14.4 mL, 171.6 mmol) was added, and the mixture was warmed to 60 oC. A solution of 1-indanone (3.78 g, 28.6 mmol) in THF (40 mL) was added dropwise into the flask over 1 h. The mixture was refluxed until TLC indicated the total consumption of the 1-indanone. After cooled to room temperature, it was quenched by 2 M HCl (60 mL). The mixture was extracted with DCM. The combined organic phases were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography (petroleum ether /EtOAc = 5/1) to afford the desired compound.

Reference： [1]Chemistry - A European Journal,2017,vol. 23,p. 13309 - 13313
[2]European Journal of Organic Chemistry,2016,vol. 2016,p. 918 - 920
[3]Advanced Synthesis and Catalysis,2020,vol. 362,p. 242 - 247
[4]Advanced Synthesis and Catalysis,2018,vol. 360,p. 2869 - 2878
[5]Tetrahedron,2002,vol. 58,p. 4225 - 4236
[6]Organic letters,2000,vol. 2,p. 3083 - 3086
[7]Organic Letters,2015,vol. 17,p. 3070 - 3073
[8]Bulletin of the Korean Chemical Society,2019,vol. 40,p. 262 - 269
[9]Advanced Synthesis and Catalysis,2016,vol. 358,p. 1934 - 1941
[10]Molecules,2019,vol. 24
[11]Chemical Communications,2018,vol. 54,p. 11602 - 11605
[12]European Journal of Organic Chemistry,2004,p. 2707 - 2714
[13]Chemistry - A European Journal,2010,vol. 16,p. 9457 - 9461
[14]Advanced Synthesis and Catalysis,2013,vol. 355,p. 1631 - 1639
[15]Organic Letters,2013,vol. 15,p. 3246 - 3249
[16]Chemical Communications,2014,vol. 50,p. 7870 - 7873
[17]Chemical Communications,2009,p. 3925 - 3927
[18]Chemistry - A European Journal,2019
[19]Organic and Biomolecular Chemistry,2014,vol. 12,p. 5071 - 5076
[20]Chemistry Letters,2014,vol. 43,p. 137 - 139
[21]Journal of Organic Chemistry,1970,vol. 35,p. 647 - 651
[22]Bulletin de la Societe Chimique de France,1982,vol. 2,p. 116 - 124
[23]Patent: US1705,1998,H1
[24]Chemical Communications,2008,p. 2474 - 2476
[25]Chemistry - A European Journal,2008,vol. 14,p. 9864 - 9867
[26]Chemical Communications,2013,vol. 49,p. 3470 - 3472
[27]Angewandte Chemie - International Edition,2013,vol. 52,p. 12860 - 12864
Angew. Chem.,2013,vol. 125,p. 13098 - 13102
[28]Journal of the American Chemical Society,2015,vol. 137,p. 5678 - 5681
[29]Synlett,2015,vol. 26,p. 1725 - 1731
[30]Journal of Medicinal Chemistry,2015,vol. 58,p. 4738 - 4748
[31]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 4576 - 4579
[32]Chemistry - A European Journal,2017,vol. 23,p. 1775 - 1778
[33]Journal of Organic Chemistry,2017,vol. 82,p. 701 - 708
[34]Organic and Biomolecular Chemistry,2017,vol. 15,p. 7753 - 7757
[35]Journal of Fluorine Chemistry,2017,vol. 204,p. 23 - 30
[36]Synthesis,2016,vol. 48,p. 1359 - 1370
[37]Chinese Journal of Chemistry,2017,vol. 35,p. 1665 - 1668
[38]Organic Letters,2018,vol. 20,p. 1875 - 1879
[39]Chemistry - A European Journal,2019,vol. 25,p. 8214 - 8218
[40]MedChemComm,2019,vol. 10,p. 1027 - 1036
[41]Organic Letters,2019,vol. 21,p. 6025 - 6028
[42]Organic Letters,2020,vol. 22,p. 5561 - 5566

3
[ 22955-77-7 ]
[ 123-73-9 ]
methyl 1-oxo-2-(4-oxobutan-2-yl)-2,3-dihydro-1H-indene-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With st-DNA; In aq. buffer; at 20℃; for 168h;pH 6.5;	General procedure: To a solution of st-DNA (2.5 mL of a 2.0 mg mL-1 solution of st-DNA dissolved in 20 mM MOPS buffer, pH 6.5, and prepared 24 h in advance) were added 0.1 mmol of beta-ketoesther 4 and 1.0 mmol of the corresponding electrophile 2. The reaction was allowed to continue for the indicated time in Table 2 at rt, while mixing continuously by a stirring shaker. The product was isolated by extraction with CH2Cl2 (2 × 5.0 mL). After drying (Na2SO4) and removal of the solvent, the crude product was analyzed by 1H NMR spectroscopy and was purified by flash chromatography.

Reference： [1]Synlett,2001,p. 715 - 717
[2]Synthetic Communications,2004,vol. 34,p. 1515 - 1533
[3]Catalysis Communications,2014,vol. 44,p. 10 - 14

4
[ 22955-77-7 ]
[ 75-65-0 ]
[ 375349-06-7 ]

Yield	Reaction Conditions	Operation in experiment
68%	With zinc(II) oxide; In toluene; at 140℃;	General procedure: In a round-bottomed flask, the corresponding 1-indanone(1 eq.), ZnO (0.2 eq.) and the corresponding alcohol (10 equivalents) were dissolved in toluene(5 mL/mol 1-indanone). The reaction mixture was heated up to 140 C under a distillation setup untiltotal conversion of the 1-indanone was observed by TLC (from 6 to 8 h). If necessary, more toluene wasadded. Afterwards, the reaction mixture was filtered through Celite and the solvent was removedunder reduced pressure. The product obtained was purified by column chromatography on silica-gel.Pentan-3-yl 1-oxo-2,3-dihydro-1H-indene-2-carboxylate (2b): Following the general procedure, 1.00 g(5.26 mmol, 1 eq) of 1a was allowed to react with 3-pentanol (52.7 mmol, 10 eq.) and ZnO (0.09 g,1.06 mmol, 0.2 eq.) in 6 mL of toluene for 5 h. After purification by column chromatography onsilica-.gel (hexanes (95): AcOEt (5)) a brown oil was obtained in 90% yield (1.17 g).
	With di(n-butyl)tin oxide; In toluene;Reflux; Inert atmosphere; Sealed tube;	General procedure: Methyl 1-indanone-2-carboxylate (1.00 g, 5.26 mmol), the alcohol (10 mL) and dibutyl tinoxide (131 mg, 0.526mmol) were dissolved into toluene. The mixture was then refluxed untilcompletion of the reaction, and then cooled to room temperature. After concentrated in vacuo, theresidue was purified by flash column chromatography (petroleum ether /EtOAc = 5/1) to afford thedesired compound.
	With di(n-butyl)tin oxide; In toluene; mineral oil;Reflux;	General procedure: Methyl 1-indanone-2-carboxylate (1.00 g, 5.26 mmol), the alcohol (10 mL) and dibutyl tin oxide (131 mg, 0.526mmol) were dissolved into toluene. The mixture was then refluxed until completion of the reaction, and then cooled to room temperature. After concentrated in vacuo, the residue was purified by flash column chromatography (petroleum ether /EtOAc = 5/1) to afford the desired compound.

Reference： [1]Chemical Communications,2009,p. 3925 - 3927
[2]Molecules,2019,vol. 24
[3]Tetrahedron,2003,vol. 59,p. 7307 - 7313
[4]Journal of the American Chemical Society,2007,vol. 129,p. 5772 - 5778
[5]Chemical Communications,2007,p. 3921 - 3923
[6]Angewandte Chemie - International Edition,2010,vol. 49,p. 568 - 571
[7]Chemical Communications,2013,vol. 49,p. 3470 - 3472
[8]Journal of the American Chemical Society,2015,vol. 137,p. 5678 - 5681
[9]Synlett,2015,vol. 26,p. 1725 - 1731
[10]Green Chemistry,2016,vol. 18,p. 5493 - 5499
[11]Chemistry - A European Journal,2017,vol. 23,p. 1775 - 1778
[12]Synthesis,2016,vol. 48,p. 1359 - 1370
[13]Chemistry - A European Journal,2019,vol. 25,p. 8214 - 8218
[14]Organic Letters,2019,vol. 21,p. 6025 - 6028
[15]Organic Letters,2020,vol. 22,p. 5561 - 5566

5
[ 22955-77-7 ]
[ 107-02-8 ]
[ 51686-56-7 ]

Yield	Reaction Conditions	Operation in experiment
82%	With st-DNA; In aq. buffer; at 20℃; for 24h;pH 6.5;	General procedure: To a solution of st-DNA (2.5 mL of a 2.0 mg mL-1 solution of st-DNA dissolved in 20 mM MOPS buffer, pH 6.5, and prepared 24 h in advance) were added 0.1 mmol of beta-ketoesther 4 and 1.0 mmol of the corresponding electrophile 2. The reaction was allowed to continue for the indicated time in Table 2 at rt, while mixing continuously by a stirring shaker. The product was isolated by extraction with CH2Cl2 (2 × 5.0 mL). After drying (Na2SO4) and removal of the solvent, the crude product was analyzed by 1H NMR spectroscopy and was purified by flash chromatography.

Reference： [1]Catalysis Communications,2014,vol. 44,p. 10 - 14
[2]Chemistry Letters,2006,vol. 35,p. 926 - 927
[3]Synthetic Communications,2004,vol. 34,p. 1515 - 1533

7
[ 22955-77-7 ]
[ 933-99-3 ]
C₁₉H₁₆O₅ [ No CAS ]

Reference： [1]Organic Letters,2007,vol. 9,p. 4901 - 4904
[2]Tetrahedron,2010,vol. 66,p. 6399 - 6410

8
[ 22955-77-7 ]
[ 1040235-31-1 ]

Yield	Reaction Conditions	Operation in experiment
96%		General procedure: To a solution of 1,3-dicarbonyl compound 1a, 1b or 1c (0.26 mmol, 1equiv) in MeCN (3 mL) was added TMSCl (1.04 mmol, 4 equiv). After the reaction mixture was stirred at r.t. for 10 min, PhI(OAc)2 (0.26mmol, 1 equiv) was added. The mixture was stirred at r.t. and monitored by TLC. After the starting material was no longer detected (TLC), the reaction mixture was poured into ice-water (10 mL). The mixture was extracted with CH2Cl2 and the combined organic phases were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash column chromatography to afford compound 4a, 4b or 4c.
99%Chromat.	With N-chloro-succinimide; O,O-bis(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl) hydrazine-1,2-bis(carbothioate); In methanol; at 25℃; for 0.166667h;	General procedure: Fluorous hydrazine-1,2-bis(carbothioate) C1 (0.042 g,0.05 mmol) with NCS (0.013 g, 1.2 mmol) was added inMeOH (3 mL) was stirred at 25 C for 10 min. Thenketone 1 (1 mmol) was added and the resulting mixturewas stirred at 25 C for 1 h. After the reaction completed,the mixture was concentrated and then loaded onto a FluoroFlash silica gel cartridge (5 g), eluted by 80 %methanol at first for non-fluorous components. Then driedover Na2SO4 and evaporated for GC analysis. Ether was then added onto the fluorous gel column to wash out thefluorous hydrazine-1,2-bis(carbothioate) C1. After removalthe ether, compound C1 was dried in vacuo at 40 C for8 h and could be directly used in the next run.

Reference： [1]Tetrahedron Asymmetry,2010,vol. 21,p. 247 - 253
[2]Chirality,2011,vol. 23,p. 272 - 276
[3]Advanced Synthesis and Catalysis,2010,vol. 352,p. 3329 - 3338
[4]Organic and biomolecular chemistry,2020,vol. 18,p. 1769 - 1779
[5]Synthesis,2016,vol. 48,p. 1359 - 1370
[6]Tetrahedron Letters,2008,vol. 49,p. 3802 - 3804
[7]European Journal of Organic Chemistry,2016,vol. 2016,p. 5937 - 5940
[8]Catalysis Letters,2016,vol. 146,p. 570 - 574

9
[ 22955-77-7 ]
[ 51737-05-4 ]

Yield	Reaction Conditions	Operation in experiment
82%	With Cumene hydroperoxide; tetrabutylammomium bromide; In water; at 60℃; for 12h;Green chemistry;	General procedure: The reaction was conducted with b-keto esters (0.1 mmol), CHP(0.2 mmol), TBABr (0.005 mmol) and H2O (2 mL) in a test tube. Thenthe tube was stirred at 60 C in open air for 12e24 h. After the reactionwascompleted (confirmed by TLC analysis), the mixture wasdiluted with EtOAc (20 mL), washed with water (10 mL), dried overanhydrous Na2SO4, filtered, and concentrated in vacuo. The residuewas purified by flash chromatography (silica gel; petroleum ether/ethyl acetate 20:1 to 2:1) to afford the desired products 2a-2r.
63%	With bis(4-fluorophenyl)disulfide; In N,N-dimethyl-formamide; for 8h;Irradiation;	Add 2,3-dihydro-1-oxo-1H-indene-2-carboxylic acid methyl ester to 4 mL of DMF solution (Formula II, where R1, R2, R3 is H, R4 is Me, 0.0190 g, 0.1 mmol) and p-fluorodiphenyl disulfide (0.00127g, 0.005mmol), 10W blue light for 8 hours to form methyl 2,3-dihydro-2-hydroxy-1-oxo-1H-indene-2-carboxylate The yield was 63%.
	With tert.-butylhydroperoxide; Cinchonin; In toluene; at 20℃; for 24h;Inert atmosphere;	General procedure: Toluene (60 mL) was added to a mixture of crude compound 2 (30 mmol) and cinchonine (886 mg, 3.0 mmol) under an atmosphere of argon, 65% tert-butyl hydroperoxide (5.1 mL, 33 mmol) was added to the mixture via a syringe. The mixture was then stirred at room temperaturefor 24 h, and condensed in vacuo for column chromatography (petroleum ether/ethylacetate) to give the desired products 3a-g.

Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 5447 - 5453
[2]Tetrahedron Asymmetry,2010,vol. 21,p. 2675 - 2680
[3]Organic Letters,2013,vol. 15,p. 3106 - 3109
[4]European Journal of Organic Chemistry,2010,p. 7020 - 7026
[5]Tetrahedron,2019,vol. 75,p. 3856 - 3863
[6]Patent: CN108558665,2018,A .Location in patent: Paragraph 0029; 0030
[7]Chemical Communications,2019,vol. 55,p. 13008 - 13011
[8]Journal of the American Chemical Society,2009,vol. 131,p. 4562 - 4563
[9]Tetrahedron,2015,vol. 71,p. 85 - 90
[10]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 4576 - 4579

10
[ 22955-77-7 ]
(2S)-methyl 2-hydroxy-1-oxo-2,3-dihydro-1H-indene-2-carboxylate [ No CAS ]

Reference： [1]Organic Letters,2013,vol. 15,p. 3106 - 3109
[2]Organic Letters,2017,vol. 19,p. 448 - 451
[3]Advanced Synthesis and Catalysis,2016,vol. 358,p. 737 - 745
[4]Patent: CN105152958,2017,B .Location in patent: Paragraph 0063; 0064
[5]Advanced Synthesis and Catalysis,2020,vol. 362,p. 2976 - 2983
[6]Journal of the American Chemical Society,2009,vol. 131,p. 4562 - 4563

11
[ 7341-96-0 ]
[ 22955-77-7 ]
[ 1199942-01-2 ]

Reference： [1]Synlett,2009,p. 2643 - 2646

12
[ 768-95-6 ]
[ 22955-77-7 ]
1-oxo-indan-2-carboxylic acid adamantan-1-yl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With zinc(II) oxide; In toluene; at 140℃;	General procedure: In a round-bottomed flask, the corresponding 1-indanone(1 eq.), ZnO (0.2 eq.) and the corresponding alcohol (10 equivalents) were dissolved in toluene(5 mL/mol 1-indanone). The reaction mixture was heated up to 140 C under a distillation setup untiltotal conversion of the 1-indanone was observed by TLC (from 6 to 8 h). If necessary, more toluene wasadded. Afterwards, the reaction mixture was filtered through Celite and the solvent was removedunder reduced pressure. The product obtained was purified by column chromatography on silica-gel.Pentan-3-yl 1-oxo-2,3-dihydro-1H-indene-2-carboxylate (2b): Following the general procedure, 1.00 g(5.26 mmol, 1 eq) of 1a was allowed to react with 3-pentanol (52.7 mmol, 10 eq.) and ZnO (0.09 g,1.06 mmol, 0.2 eq.) in 6 mL of toluene for 5 h. After purification by column chromatography onsilica-.gel (hexanes (95): AcOEt (5)) a brown oil was obtained in 90% yield (1.17 g).

Reference： [1]Molecules,2019,vol. 24
[2]European Journal of Organic Chemistry,2010,p. 6525 - 6530
[3]Chemical Communications,2014,vol. 50,p. 7870 - 7873
[4]Journal of Organic Chemistry,2010,vol. 75,p. 3085 - 3096
[5]Advanced Synthesis and Catalysis,2013,vol. 355,p. 1631 - 1639
[6]Chemical Communications,2013,vol. 49,p. 3470 - 3472
[7]Organic and Biomolecular Chemistry,2014,vol. 12,p. 5071 - 5076
[8]Green Chemistry,2016,vol. 18,p. 5493 - 5499
[9]Chemistry - A European Journal,2017,vol. 23,p. 1775 - 1778
[10]Journal of Organic Chemistry,2017,vol. 82,p. 701 - 708
[11]Organic Letters,2019,vol. 21,p. 6025 - 6028

13
[ 22955-77-7 ]
[ 181934-29-2 ]
[ 1252671-60-5 ]

Yield	Reaction Conditions	Operation in experiment
98%	Stage #1: methyl 1-oxo-2,3-dihydro-1H-indene-2-carboxylate; 1-[(trimethylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one In tetrahydrofuran at -78℃; for 0.0833333h; Inert atmosphere; Stage #2: With N,N,N-tributylbutan-1-aminium fluoride In tetrahydrofuran at -78℃; for 1.5h; Inert atmosphere;
98%	Stage #1: methyl 1-oxo-2,3-dihydro-1H-indene-2-carboxylate; 1-[(trimethylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one In tetrahydrofuran at -78℃; for 0.0833333h; Inert atmosphere; Stage #2: With N,N,N-tributylbutan-1-aminium fluoride In tetrahydrofuran at -78℃; for 1.5h;
62%	With N,N,N-tributylbutan-1-aminium fluoride In tetrahydrofuran at -78℃; for 1.5h; Inert atmosphere;

Reference： [1]Gonzalez, Davinia Fernandez; Brand, Jonathan P.; Waser, Jerome [Chemistry - A European Journal, 2010, vol. 16, # 31, p. 9457 - 9461]
[2]Fernandez Gonzalez, Davinia; Brand, Jonathan P.; Mondiere, Regis; Waser, Jerome [Advanced Synthesis and Catalysis, 2013, vol. 355, # 8, p. 1631 - 1639]
[3]Miura, Tomoya; Moritani, Shunsuke; Murakami, Masahiro; Shiratori, Yota [Chemical Communications, 2022, vol. 58, # 16, p. 2710 - 2713]

14
[ 22955-77-7 ]
[ 4873-09-0 ]
[ 1263197-71-2 ]

Reference： [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 9753 - 9756

15
[ 22955-77-7 ]
[ 7115-91-5 ]
[ 1380601-37-5 ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: methyl 1-indanone-2-carboxylate With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20 - 60℃; for 0.5h; Stage #2: 2-ethoxycarbonylbenzyl bromide In N,N-dimethyl-formamide; mineral oil at 60℃;

Reference： [1]Taniguchi, Tohru; Monde, Kenji [Journal of the American Chemical Society, 2012, vol. 134, # 8, p. 3695 - 3698]

16
[ 22955-77-7 ]
[ 105935-24-8 ]
methyl 2-(2-(tert-butoxycarbonyl)-3,3,3-trifluoropropyl)-2,3-dihydro-1-oxo-1H-indene-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With cinchonine In dichloromethane at -80℃; for 24h; Inert atmosphere; optical yield given as %de; stereoselective reaction;

Reference： [1]Ogawa, Shinichi; Yasui, Hiroyuki; Tokunaga, Etsuko; Nakamura, Shuichi; Shibata, Norio [Chemistry Letters, 2009, vol. 38, # 10, p. 1006 - 1007]

17
[ 36919-03-6 ]
[ 83-33-0 ]
[ 22955-77-7 ]

Yield	Reaction Conditions	Operation in experiment
94%	With dmap; magnesium bromide ethyl etherate; N-ethyl-N,N-diisopropylamine In dichloromethane for 68h; Inert atmosphere; Reflux;

Reference： [1]Hale, Karl J.; Grabski, Milosz; Flasz, Jakub T. [Organic Letters, 2013, vol. 15, # 2, p. 370 - 373]

18
[ 22955-77-7 ]
[ 1443454-26-9 ]

Yield	Reaction Conditions	Operation in experiment
96%	With trimethylsilylazide; urea hydrogen peroxide adduct; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine hydroiodide; In acetonitrile; at 20℃; for 1h;Green chemistry;	To a stirred solution of beta-dicarbonyl compound 1a (19.0 mg, 0.100 mmol) in acetonitrile (1.0 mL) was added TBD·HI (2.7 mg, 0.01 mmol), TMSN3 (14.5 mL, 0.11mmol) and UHP (11.3 mg, 0.12 mmol) at ambient temperature. After stirring for 1 hour at this temperature, the reaction was quenched with a 10% aqueous solution of Na2S2O3. The aqueous layer was extracted with ethyl acetate (x2) and the combined organic layer was washed with brine and then dried over MgSO4. After removing solvent under reduced pressure, the residue was purified by flash column chromatography (n-hexane/ethylacetate = 5:1) to afford alpha-azido-beta-dicarbonyl compound 2a (22.2 mg, 96% yield). NMR data correspond to the reportedvalues.7c (Detail of the reaction conditions was shown in Table 2).

Reference： [1]European Journal of Organic Chemistry,2016,vol. 2016,p. 447 - 452
[2]Tetrahedron,2016,vol. 72,p. 5350 - 5354
[3]Organic Letters,2013,vol. 15,p. 3246 - 3249
[4]Organic Letters,2018,vol. 20,p. 1875 - 1879

19
[ 22955-77-7 ]
[ 102-96-5 ]
methyl 2-(2-nitro-1-phenylethyl)-1-oxo-2,3-dihydro-1H-indene-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With st-DNA; In aq. buffer; at 20℃; for 24h;pH 6.5;	General procedure: To a solution of st-DNA (2.5 mL of a 2.0 mg mL-1 solution of st-DNA dissolved in 20 mM MOPS buffer, pH 6.5, and prepared 24 h in advance) were added 0.1 mmol of beta-ketoesther 4 and 1.0 mmol of the corresponding electrophile 2. The reaction was allowed to continue for the indicated time in Table 2 at rt, while mixing continuously by a stirring shaker. The product was isolated by extraction with CH2Cl2 (2 × 5.0 mL). After drying (Na2SO4) and removal of the solvent, the crude product was analyzed by 1H NMR spectroscopy and was purified by flash chromatography.
	With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-((S)-1-methylpyrrolidin-2-yl)(phenyl)methyl)thiourea; In tert-butyl methyl ether; at -15℃; for 8h;Inert atmosphere;	General procedure: To a stirred solution of 1c (3.45mg, 0.0075mmol, 5mol%) and nitroalkene 9a (0.15mmol) in MTBE (1.5mL), substituted 1,3-dicarbonyl 12 (0.17mmol) was added under argon. The solution was stirred at the mentioned temperature for 8-12h. After the reaction was completed (monitored by TLC), the resulting mixture was concentrated under reduced pressure and the residue was purified through column chromatography on silica gel.

Reference： [1]Catalysis Communications,2014,vol. 44,p. 10 - 14
[2]Tetrahedron Asymmetry,2014,vol. 25,p. 568 - 577

20
[ 22955-77-7 ]
[ 2043-21-2 ]
[ 1486549-05-6 ]

Yield	Reaction Conditions	Operation in experiment
42%	With st-DNA In aq. buffer at 20℃; for 72h;	5 2.3. General procedure for the synthesis of compound 6 (Table 2) General procedure: To a solution of st-DNA (2.5 mL of a 2.0 mg mL-1 solution of st-DNA dissolved in 20 mM MOPS buffer, pH 6.5, and prepared 24 h in advance) were added 0.1 mmol of β-ketoesther 4 and 1.0 mmol of the corresponding electrophile 2. The reaction was allowed to continue for the indicated time in Table 2 at rt, while mixing continuously by a stirring shaker. The product was isolated by extraction with CH2Cl2 (2 × 5.0 mL). After drying (Na2SO4) and removal of the solvent, the crude product was analyzed by 1H NMR spectroscopy and was purified by flash chromatography.

Reference： [1]Izquierdo, Cristina; Luis-Barrera, Javier; Fraile, Alberto; Alemán, José [Catalysis Communications, 2014, vol. 44, p. 10 - 14]

21
[ 22955-77-7 ]
[ 172876-96-9 ]
methyl 2-cyano-1-oxo-2,3-dihydro-1H-indene-2-carboxylate [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2015,vol. 13,p. 365 - 368

22
[ 22955-77-7 ]
[ 63160-12-3 ]
(S,S)-3-phenyl-2-tosyl-1,2-oxaziridine [ No CAS ]
(R,R)-3-phenyl-2-tosyl-1,2-oxaziridine [ No CAS ]
(2S)-methyl 2-hydroxy-1-oxo-2,3-dihydro-1H-indene-2-carboxylate [ No CAS ]
(R)-2-hydroxy-1-oxo-2,3-dihydro-1H-indene-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 3602 - 3605

23
[ 22955-77-7 ]
[ 63160-12-3 ]
[ 63160-12-3 ]
[ 165523-69-3 ]
(2S)-methyl 2-hydroxy-1-oxo-2,3-dihydro-1H-indene-2-carboxylate [ No CAS ]
(R)-2-hydroxy-1-oxo-2,3-dihydro-1H-indene-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 3602 - 3605
[2]Organic Letters,2016,vol. 18,p. 3602 - 3605
[3]Organic Letters,2016,vol. 18,p. 3602 - 3605

24
[ 770-71-8 ]
[ 22955-77-7 ]
(adamantan-1-yl)methyl-1,1-dicyano-6-oxo-1a,6-dihydrocyclopropa[a]indene-6a(1H)-carboxylate [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 6176 - 6179

25
[ 770-71-8 ]
[ 22955-77-7 ]
adamantan-1-ylmethyl 1-oxo-2,3-dihydro-1H-indene-2-carboxylate [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 6176 - 6179

26
[ 22955-77-7 ]
[ 172876-96-9 ]
(-)-methyl-2-cyano-1-oxo-2,3-dihydro-1H-indene-2-carboxylate [ No CAS ]
methyl-2-cyano-1-oxo-2,3-dihydro-1H-indene-2-carboxylate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 701 - 708

27
[ 22955-77-7 ]
[ 69454-42-8 ]

Reference： [1]Organic Letters,2018,vol. 20,p. 1875 - 1879

28
[ 22955-77-7 ]
[ 27126-76-7 ]
methyl 1-oxo-2-(tosyloxy)-2,3-dihydro-1H-indene-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	In acetonitrile at 20℃; for 4h;	General procedure of α-sulfonyloxylation (3a-k) General procedure: In a round-bottom flask, hypervalent iodine 2 (0.9 mmol) and acetoacetate 1 (0.5 mmol) were dissolved in CH3CN (1.5 mL). The reaction mixture was stirred at room temperature for 4h and the solvent was removed under reduced pressure. The products were isolated by column chromatography of the residue on silica gel to give the corresponding products 3a-k.

Reference： [1]Liu, Ruojuan; Wang, Junzheng; Hu, Wen; Zhang, Xiaohui; Xiong, Yan [Synthetic Communications, 2018, vol. 48, # 15, p. 1957 - 1965]

29
[ 934-00-9 ]
[ 22955-77-7 ]
C₁₈H₁₆O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With oxygen In water; <i>tert</i>-butyl alcohol at 50℃; for 24h; Green chemistry; regioselective reaction;

Reference： [1]Maeno, Zen; Yamamoto, Masanobu; Mitsudome, Takato; Mizugaki, Tomoo; Jitsukawa, Koichiro [Catalysis science and technology, 2018, vol. 8, # 21, p. 5401 - 5405]

30
[ 22955-77-7 ]
[ 10420-89-0 ]
methyl 3-((1-(naphthalen-1-yl)ethyl)amino)-1H-indene-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	With zinc diacetate In methanol Inert atmosphere; Reflux;	3.2. Synthesis of Chiral Enamine (General Procedure) General procedure: Amine (2.2 mmol, 1.5 equiv) was added to a solution of β-ketoester (1.47 mmol) and zinc acetate(0.29 mmol, 20 mol%) in methanol under nitrogen atmosphere, the reaction mixture was refluxed for16-64 h. After the reaction, the mixture was concentrated under reduced pressure, and the residue waspurified by column chromatography (with ethyl acetate: hexane mixtures as eluent).Methyl 5-methyl-3-((1-phenylethyl)amino)-1H-indene-2-carboxylate (2a). Following the general procedurethe reaction mixture was stirred at 50 C for 53 h. After the reaction was complete, the mixture wasworked up as described. Brown solid (35%, 156.6 mg

Reference： [1]Gondo, Satoshi; Matsubara, Okiya; Chachignon, Hélène; Sumii, Yuji; Cahard, Dominique; Shibata, Norio [Molecules, 2019, vol. 24, # 2]

31
[ 584-02-1 ]
[ 22955-77-7 ]
pentan-3-yl 1-oxo-2,3-dihydro-1H-indene-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.17 g	With zinc(II) oxide In toluene at 140℃; for 5h;	General transesterification procedure: General procedure: In a round-bottomed flask, the corresponding 1-indanone(1 eq.), ZnO (0.2 eq.) and the corresponding alcohol (10 equivalents) were dissolved in toluene(5 mL/mol 1-indanone). The reaction mixture was heated up to 140 °C under a distillation setup untiltotal conversion of the 1-indanone was observed by TLC (from 6 to 8 h). If necessary, more toluene wasadded. Afterwards, the reaction mixture was filtered through Celite and the solvent was removedunder reduced pressure. The product obtained was purified by column chromatography on silica-gel.Pentan-3-yl 1-oxo-2,3-dihydro-1H-indene-2-carboxylate (2b): Following the general procedure, 1.00 g(5.26 mmol, 1 eq) of 1a was allowed to react with 3-pentanol (52.7 mmol, 10 eq.) and ZnO (0.09 g,1.06 mmol, 0.2 eq.) in 6 mL of toluene for 5 h. After purification by column chromatography onsilica-.gel (hexanes (95): AcOEt (5)) a brown oil was obtained in 90% yield (1.17 g). IR (ATR) ν =2968, 1711 (C=O), 1608, 1572, 1207, 1092 cm1; 1H-NMR (360 MHz [D]CDCl3, 298 K, TMS) δ = 10.50(bs, 0.08H, OH, enol), 7.79 (d, 3J(H,H) = 7.5 Hz, 1H, ArH), 7.64 (t, 3J(H,H) = 7.1 Hz, 1H, ArH), 7.52 (d,3J(H,H) = 7.5 Hz, 1H, ArH), 7.50-7.44 (m, 0.17H, ArH, enol), 7.41 (3J(H,H), J = 7.5 Hz, 1H, ArH), 4.98 (quint,3J(H,H) = 6.1 Hz, 0.16H, OCH, enol), 4.86 (quint, 3J(H,H) = 6.3 Hz, 1H, OCH,), 3.74 (dd, 3J(H,H) = 4.2 Hz,3J(H,H) = 8.7 Hz, 1H, CH2CH), 3.59 (d, 3J(H,H) = 4.2 Hz, 0.42H, CH2C, enol), 3.55 (d, 3J(H,H) = 3.7 Hz,1H, CH2CH), 3.40 (dd, 3J(H,H) = 8.3 Hz, J = 17.5 Hz, 1H, CH2CH), 1.70 (m, 1H, CH2CH3, enol), 1.65(m, 4H, CH2CH3), 1.02-0.86 ppm (m, 7.36, CH2CH3); 13C-NMR (101 MHz, [D]CDCl3, 298 K, TMS) δ = 199.6, 169.0, 153.6, 143.1, 137.0, 135.3, 135.2, 129.1, 127.7, 126.7, 126.5, 124.6, 124.6, 120.6, 102.7, 78.3,76.4, 53.6, 32.52, 30.3, 26.6, 26.4, 9.6, 9.4 ppm; HRMS (ESI): (M + Na)+ Calcd for C15H18O3Na 269.1148;found 269.1144.
	With zinc(II) oxide In toluene at 140℃; for 6h;

Reference： [1]Granados, Albert; Sarró, Pau; Vallribera, Adelina [Molecules, 2019, vol. 24, # 6]
[2]Granados, Albert; Rivilla, Iván; Cossío, Fernando P.; Vallribera, Adelina [Chemistry - A European Journal, 2019, vol. 25, # 35, p. 8214 - 8218]

32
[ 22955-77-7 ]
[ 115262-00-5 ]
[ 1280126-16-0 ]
methyl 2-difluoromethyl-1-oxo-2,3-dihydro-1H-indene-2-carboxylate [ No CAS ]
methyl 2-difluoromethyl-1-oxo-2,3-dihydro-1H-indene-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43 % ee	With (1S,2R,4S,5R)-1-(3,5-dibromobenzyl)-2-((S)-hydroxy(2-(4-(trifluoromethyl)phenyl)quinolin-4-yl)methyl)-5-vinylquinuclidin-1-ium bromide; potassium carbonate In chloroform; toluene at -20℃; for 12h; Overall yield = 56 percent; enantioselective reaction;

Reference： [1]Wang, Yakun; Wang, Shuaifei; Qiu, Peiyong; Fang, Lizhen; Wang, Ke; Zhang, Yawei; Zhang, Conghui; Zhao, Ting [Organic and Biomolecular Chemistry, 2021, vol. 19, # 21, p. 4788 - 4795]

33
[ 18292-38-1 ]
[ 22955-77-7 ]
C₁₅H₁₆O₃ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2022,vol. 144,p. 495 - 502

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• 1,4-Addition of an Amine to a Conjugated Enone • 1,4-Additions of Organometallic Reagents • Acetal Formation • Acid-Catalyzed α -Halogenation of Ketones • Acyl Group Substitution • Add Hydrogen Cyanide to Aldehydes and Ketones to Produce Alcohols • Alcohol Syntheses from Aldehydes, Ketones and Organometallics • Alcohols Convert Acyl Chlorides into Esters • Alcoholysis of Anhydrides • Aldehydes and Ketones Form Hemiacetals Reversibly • Aldehydes May Made by Terminal Alkynes Though Hydroboration-oxidation • Aldol Addition • Aldol Condensation • Alkenes React with Ozone to Produce Carbonyl Compounds • Alkylation of Aldehydes or Ketones • Alkylation of Enolate Ions • Amines Convert Esters into Amides • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Base-Catalyzed Hydration of α,β -Unsaturated Aldehydes and Ketones • Baylis-Hillman Reaction • Benzylic Oxidation • Birch Reduction • Birch Reduction of Benzene • Blanc Chloromethylation • Bouveault-Blanc Reduction • Bucherer-Bergs Reaction • Catalytic Hydrogenation • Claisen Condensations Produce β-Dicarbonyl Compounds • Claisen Condensations Produce β-Dicarbonyl Compounds • Clemmensen Reduction • Complete Benzylic Oxidations of Alkyl Chains • Complete Benzylic Oxidations of Alkyl Chains • Complex Metal Hydride Reductions • Conjugated Enone Takes Part in 1,4-Additions • Conversion of Amino with Nitro • Convert Esters into Aldehydes Using a Milder Reducing Agent • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Cyanohydrins can be Convert to Carbonyl Compounds under Basic Conditions • Decarboxylation of 3-Ketoacids Yields Ketones • Decarboxylation of Substituted Propanedioic • Deoxygenation of the Carbonyl Group • Deprotection of Cbz-Amino Acids • Deprotonation of a Carbonyl Compound at the α -Carbon • Deprotonation of Methylbenzene • Diorganocuprates Convert Acyl Chlorides into Ketones • Directing Electron-Donating Effects of Alkyl • Dithioacetal Formation • Electrophilic Chloromethylation of Polystyrene • Enamines Can Be Used to Prepare Alkylated Aldehydes • Enol-Keto Equilibration • Enolate Ions Are Protonated to Form ketones • Ester Cleavage • Ester Hydrolysis • Exclusive 1,4-Addition of a Lithium Organocuprate • Fischer Indole Synthesis • Friedel-Crafts Alkylation of Benzene with Acyl Chlorides • Friedel-Crafts Alkylation of Benzene with Carboxylic Anhydrides • Friedel-Crafts Alkylation Using Alkenes • Friedel-Crafts Alkylations of Benzene Using Alkenes • Friedel-Crafts Alkylations Using Alcohols • Friedel-Crafts Reaction • Furan Hydrolyzes to Dicarbonyl Compounds • Geminal Diols and Acetals Can Be Hydrolyzed to Carbonyl Compounds • Grignard Reaction • Grignard Reagents Transform Esters into Alcohols • Groups that Withdraw Electrons Inductively Are Deactivating and Meta Directing • Halogenation of Benzene • Hantzsch Pyridine Synthesis • Hemiaminal Formation from Amines and Aldehydes or Ketones • Hemiaminal Formation from Amines and Aldehydes or Ketones • Henry Nitroaldol Reaction • HIO4 Oxidatively Degrades Vicinal Diols to Give Carbonyl Derivatives • Horner-Wadsworth-Emmons Reaction • Hydration of the Carbonyl Group • Hydride Reductions • Hydride Reductions of Aldehydes and Ketones to Alcohols • Hydride Reductions of Aldehydes and Ketones to Alcohols • Hydrogenation by Palladium on Carbon Gives the Saturated Carbonyl Compound • Hydrogenation to Cyclohexane • Hydrogenolysis of Benzyl Ether • Hydrolysis of Imines to Aldehydes and Ketones • Imine Formation from Amines and Aldehydes or Ketones • Isomerization of β, γ -Unsaturated Carbonyl Compounds • Ketone Synthesis from Nitriles • Ketones Undergo Mixed Claisen Reactions to Form β-Dicarbonyl Compounds • Lawesson's Reagent • Leuckart-Wallach Reaction • Lithium Organocuprate may Add to the α ,β -Unsaturated Carbonyl Function in 1,4-Fashion • Mannich Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mercury Ions Catalyze Alkynes to Ketones • Michael Addition • Nitration of Benzene • Nucleophilic Aromatic Substitution • Nucleophilic Aromatic Substitution with Amine • Oxidation of Alcohols to Carbonyl Compounds • Oxidation of Alkyl-substituted Benzenes Gives Aromatic Ketones • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Phenylhydrazone and Phenylosazone Formation • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Preparation of Amines • Prins Reaction • Pyrroles, Furans, and Thiophenes are Prepared from γ-Dicarbonyl Compounds • Reactions of Aldehydes and Ketones • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions with Organometallic Reagents • Reduction of an Ester to an Alcohol • Reduction of an Ester to an Aldehyde • Reductive Amination • Reductive Amination • Reductive Removal of a Diazonium Group • Reformatsky Reaction • Reverse Sulfonation——Hydrolysis • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • Stobbe Condensation • Strecker Synthesis • Sulfonation of Benzene • Tebbe Olefination • The Acylium Ion Attack Benzene to Form Phenyl Ketones • The Claisen Rearrangement • The Cycloaddition of Dienes to Alkenes Gives Cyclohexenes • The Nitro Group Conver to the Amino Function • The Reaction of Alkynyl Anions with Carbonyl Derivatives • The Wittig Reaction • Thiazolium Salt Catalysis in Aldehyde Coupling • Thiazolium Salts Catalyze Aldehyde Coupling • Thiazolium Salts Catalyze Aldehyde Coupling • Transesterification • Ugi Reaction • Use 1,3-dithiane to Prepare of α-Hydroxyketones • Vilsmeier-Haack Reaction • Wittig Reaction • Wolff-Kishner Reduction

Historical Records

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[ 22955-77-7 ]

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 22955-77-7 ] {[proInfo.proName]}

Quality Control of [ 22955-77-7 ]

Related Doc. of [ 22955-77-7 ]

Product Details of [ 22955-77-7 ]

Calculated chemistry of [ 22955-77-7 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 22955-77-7 ]

Application In Synthesis of [ 22955-77-7 ]

[ 22955-77-7 ] Synthesis Path-Upstream 1~14

[ 22955-77-7 ] Synthesis Path-Downstream 1~33

Technical Information

Related Functional Groups of [ 22955-77-7 ]

Aryls

Esters

Ketones

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 22955-77-7 ]