[ CAS No. 6287-86-1 ] {[proInfo.proName]}

Name: 6287-86-1|Ethyl 4-formylbenzoate|95%
Brand: Ambeed
SKU: A100912
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Quality Control of [ 6287-86-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 6287-86-1 ]

SDS Specification

Alternatived Products of [ 6287-86-1 ]

Product Details of [ 6287-86-1 ]

CAS No. :	6287-86-1	MDL No. :	MFCD00460463
Formula :	C₁₀H₁₀O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BHYVHYPBRYOMGC-UHFFFAOYSA-N
M.W :	178.19	Pubchem ID :	80498
Synonyms :

Calculated chemistry of [ 6287-86-1 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.2
Num. rotatable bonds :	4
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	47.92
TPSA :	43.37 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.97 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.97
Log Po/w (XLOGP3) :	2.0
Log Po/w (WLOGP) :	1.68
Log Po/w (MLOGP) :	1.59
Log Po/w (SILICOS-IT) :	2.21
Consensus Log Po/w :	1.89

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.28
Solubility :	0.93 mg/ml ; 0.00522 mol/l
Class :	Soluble
Log S (Ali) :	-2.54
Solubility :	0.517 mg/ml ; 0.0029 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.83
Solubility :	0.267 mg/ml ; 0.0015 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.31

Safety of [ 6287-86-1 ]

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 [ 6287-86-1 ]

* 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 [ 6287-86-1 ]
Downstream synthetic route of [ 6287-86-1 ]

[ 6287-86-1 ] Synthesis Path-Upstream 1~3

1
[ 27332-37-2 ]
[ 34046-43-0 ]
[ 93-89-0 ]
[ 6287-86-1 ]
[ 101-97-3 ]
[ 141-05-9 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 1993, vol. 41, # 12, p. 2187 - 2189

2
[ 6287-86-1 ]
[ 71441-28-6 ]

Reference： [1] Chem.Abstr., 1979, vol. 91, # 140631,

3
[ 6287-86-1 ]
[ 19675-63-9 ]

Reference： [1] Justus Liebigs Annalen der Chemie, 1885, vol. 231, p. 363

[ 6287-86-1 ] Synthesis Path-Downstream 1~68

1
[ 7153-22-2 ]
[ 6287-86-1 ]

Reference： [1]Organic and Biomolecular Chemistry,2018,vol. 16,p. 6600 - 6605
[2]Chemische Berichte,1938,vol. 71,p. 335,338

2
[ 6287-86-1 ]
[ 713-57-5 ]

Reference： [1]Chemische Berichte,1912,vol. 45,p. 1586
[2]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,1992,vol. 31,p. 46 - 48
[3]Journal of the Indian Chemical Society,1998,vol. 75,p. 439 - 442

3
[ 64-17-5 ]
[ 619-66-9 ]
[ 6287-86-1 ]

Yield	Reaction Conditions	Operation in experiment
90%	With graphene oxide; at 100℃; for 24h;	General procedure: A mixture of acid (0.2 mmol), alcohol (0.6 mmol) and GO (50 wt%, calculated with the mass of acid) in ethyl alcohol or DCE (1 mL) was placed in a test tube equipped with a magnetic stirring bar. The mixture was stirred at 100 C for 24 h. After the reaction was finished, filtered the GO, solvent was removed, and the residue was separated by column chromatography to give the pure sample.
83.1%	With sulfuric acid; for 18h;Heating / reflux;	A starting material of the compound (4), 4-ethoxycarbonylbenzaldehyde, was synthesized according to the description in the reference, K. Ogawa, J. Dy, and Y. Kobuke, Journal of Porphyrins and Phthalocyanine 9, 735-744 (2005). The details are described below. First, terephthalaldehydic acid (5.5 g, 36.6 mmol), strong sulfuric acid (0.91 mL), and ethanol (166.6 mL) were added to a 300-mL recovery flask and then were heated to be refluxed for 18 hours. Then this was returned to room temperature and then the organic solvent was distilled away. Thereafter, this was dissolved in ethyl acetate (100 mL). Then it was washed with saturated sodium bicarbonate (200 mL×2), a saturated saline solution (200 mL×2), and distilled water (200 mL×2), and then was dried with anhydrous sodium sulfate. Thus enrichment and drying were carried out (5.42 g, 83.1%). The instrumental analysis data of this product is indicated below.4-ethoxycarbonylbenzaldehyde1H-NMR (270 MHz, CDCl3), delta 10.10 (s, 1H, -CHO), 8.15 (d, 2H, J=8.1 Hz), 7.94 (d, 2 h, J=8.1 Hz), 4.42 (q, 2H, J=3.5 Hz, -CH2-), 1.42 (t, 2H, J=3.5 Hz, -CH3)

Reference： [1]Synlett,2017,vol. 28,p. 981 - 985
[2]Patent: US2007/224529,2007,A1 .Location in patent: Page/Page column 23
[3]Justus Liebigs Annalen der Chemie,1885,vol. 231,p. 363
[4]Journal of Heterocyclic Chemistry,1971,vol. 8,p. 105 - 110
[5]Chemical and pharmaceutical bulletin,1984,vol. 32,p. 5044 - 5047
[6]RSC Advances,2014,vol. 4,p. 60342 - 60348
[7]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 1896 - 1908

4
[ 542-02-9 ]
[ 6287-86-1 ]
[ 139979-27-4 ]

Yield	Reaction Conditions	Operation in experiment
15%	With formic acid for 57h; Heating;

Reference： [1]Hasegawa; Yanagisawa; Okui; Sato; Hosaka; Chin; Mitsuhashi [Chemical and Pharmaceutical Bulletin, 1991, vol. 39, # 12, p. 3180 - 3182]

5
[ 201230-82-2 ]
[ 348-06-1 ]
[ 93-89-0 ]
[ 6287-86-1 ]

Reference： [1]Journal of Organometallic Chemistry,1984,vol. 270,p. 283 - 288

6
[ 6287-86-1 ]
[ 92788-07-3 ]
[ 88579-35-5 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 12 By the procedure of Example 1, from [1-(4,4-dimethyl-6-thiochromanyl)ethyl]triphenylphosphonium bromide and 4-ethoxycarbonylbenzaldehyde there is obtained ethyl p-[(E)-2-(4,4-dimethyl-6-thiochromanyl)propenyl]benzoate. The phosphonium salt used as the starting material can be prepared starting from 4,4-dimethylthiochromane by the method described in paragraphs 2 through 4 of Example 1.
	With n-butyllithium; In ethanol; hexane;	Ethyl (E)-p-[2-(4,4-Dimethylthiochroman-6-yl)propenyl]benzoate or Ethyl (E)-4-[2-(3,4-dihydro-4,4-dimethyl-2H-1-benzothiopyran-6-yl)-1-propenyl]benzoate (X=S) A solution of n-butyllithium in hexane (1.55M, 1.3 mL, 2.01 mmol) was added dropwise under N2 to a stirred suspension of the phosphonium salt 13 (1.1 g, 2.01 mmol) in dry ether (30 mL). The resulting dark red mixture was stirred for 5 minutes. A solution of the freshly distilled aldehyde 6 (9.40 g, 2.25 mmol) in dry ether (15 mL) was then added all at once. The mixture became creamy yellow and then cream-colored, and a large amount of off-white solid precipitated. After stirring at room temperature for 36 hours, the mixture was filtered. The solid was washed with ether (50 mL). The combined filtrates were concentrated to give a yellow oil which was dissolved in warm 95% ethanol (50 mL). The resulting solution was filtered and then concentrated to 10 mL. After cooling slowly to room temperature, the resulting solid was filtered and washed with cold 95% ethanol. After drying in the air, 0.30 g (40.7 %) of the compound (X=S) was obtained as a white solid: mp 92-93 C.; IR (KBr) 1710-1725 cm-1 (C=O); 1 H NMR (DCCl3) delta1.38 [s, 6H, (CH3)2 ], 1.41 [t, 3H, OCH2 CH3 ], 1.96-2.02 [m, 2H, SCH2 CH2 ], 2.28 [s, 3H, CH=C--CH3 ], 3.04-3.09 [m, 2H, SCH2 ], 4.4 [q, 2H, OCH2 ], 6.82 [s, 1H, C=CH], 7.11 [d, 1H, J=9 Hz, H(8)], 7.21-7.28 [m, 1H, H(7)], 7.44 [d, 2H, Ar--H], 7.54 [s, 1H, H(5)], 8.07 [d, 2H, Ar--H]; Mass spectral data for C23 H26 O 2 S: m/e (M+) theoretical 366.1653; Found: 366.1650.

Reference： [1]Journal of Medicinal Chemistry,1985,vol. 28,p. 116 - 124
[2]Patent: US4678793,1987,A
[3]Patent: US4826984,1989,A

7
[ 6287-86-1 ]
[ 95693-77-9 ]
[ 95674-62-7 ]

Reference： [1]Journal of Medicinal Chemistry,1985,vol. 28,p. 914 - 921

8
[ 6287-86-1 ]
[ 119999-20-1 ]

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 1504 - 1517
[2]Journal of Medicinal Chemistry,1984,vol. 27,p. 1516 - 1531

9
[ 64-17-5 ]
[ 1571-08-0 ]
[ 6287-86-1 ]

Reference： [1]Green Chemistry,2018,vol. 20,p. 2465 - 2471
[2]Helvetica Chimica Acta,1993,vol. 76,p. 2757 - 2774

10
[ 6287-86-1 ]
[ 123-38-6 ]
[ 77837-68-4 ]

Reference： [1]Russian Chemical Bulletin,1993,vol. 42,p. 2039 - 2042
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1993,p. 2126 - 2129

11
[ 26496-94-6 ]
[ 6287-86-1 ]

Reference： [1]Tetrahedron Letters,2000,vol. 41,p. 5423 - 5425
[2]Tetrahedron Letters,1998,vol. 39,p. 1981 - 1984
[3]Chemistry Letters,2005,vol. 34,p. 194 - 195
[4]European Journal of Organic Chemistry,2014,vol. 2014,p. 3402 - 3410

12
[ 201230-82-2 ]
[ 51934-41-9 ]
[ 6287-86-1 ]

Reference： [1]European Journal of Organic Chemistry,1999,p. 1471 - 1473

13
[ 6287-86-1 ]
air [ No CAS ]
[ 713-57-5 ]

Reference： [1]Chemische Berichte,1912,vol. 45,p. 1586

14
[ 6287-86-1 ]
[ 603-81-6 ]
[ 313279-01-5 ]

Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 4084 - 4097

15
[ 6287-86-1 ]
[ 6232-12-8 ]
C₂₀H₂₁NO₄ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 1183 - 1192

16
[ 6287-86-1 ]
[ 15852-63-8 ]

Yield	Reaction Conditions	Operation in experiment
46%	With sodium tetrahydroborate; In ethanol; at 0 - 20℃; for 5h;	A mixture of 4-formylbenzoic acid (1.00 g, 6.66 mmol), bromoethane (1.09 g, 9.99 mmol), and K2CO3 (1.10 g, 7.99 mmol) in acetonitrile (30 mL) was refluxed for 6 h. After evaporation of the solvent, 4-formylbenzoic acid ethyl ester was extracted with ether (30 EPO <DP n="60"/>mL), and the organic solution was washed with 1 N NaOH aqueous solution (20 mL) and water (30 mL), dried over Na2SO4, and concentrated to give the ethyl ester product (0.65 g, 55%). Without further purification, to a solution of the ester was added sodium borohydride (NaBH4; 0.05 g, 3.65 mmol) in ethanol (20 mL) at 0 C. After stirring for 5 h at room temperature, the product was extracted with ether (30 mL), and the ether solution was washed with water (30 mL), dried over Na2SO4, and concentrated. The residue was purified by using column chromatography on silica gel eluting with hexane and ethyl acetate (3:1) to give 4- hydroxymethylbenzoic acid ethyl ester (0.30 g, 46%) as an oil. [0196] To a solution of 4-(3-adamantan-l-yl-ureido)butyric acid 822 (1.23 g, 0.83 mmol), DMAP (0.05 g, 0.42 mmol), and the above alcohol (0.15 g, 0.83 mmol) in methylene chloride (30 mL) was added EDCI (0.16 g, 0.83 mmol) at room temperature. After stirring for 12 h, the reaction mixture was washed with 1 N NaOH aqueous solution (15 mL) and water (30 mL), and the organic layer was dried over Na2SO4 and concentrated. Then the residue was purified by column chromatography on silica gel eluting hexane and ethyl acetate (5: 1) to provide 849 (0.28 g, 75%) as a white solid: 1H NMR (CDCl3) 1.40 (3H, t, J = 6.9 Hz), 1.66- 1.68 (6H, m), 1.84 (2H, quint, J = 6.9 Hz), 1.94-1.96 (6H, m), 2.05-2.07 (3H, m), 2.44 (2H, t, J = 6.9 Hz), 3.17 (2H, q, J = 6.9 Hz), 4.02 (IH, s), 4.17 (IH, s), 4.38 (2H, q, J = 6.9 Hz), 5.17 (2H, s), 7.40 (2H, d, J = 7.8 Hz), 8.00 (2H, d, J = 7.8 Hz); LC-MS (ESI) m/z calcd for C25H34N2O5 [M + H]+ 443.25, found [M + H]+ 443.25; mp 96-99 C. Anal. (C25H34N2O5) C, H, N.

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 2110 - 2122
[2]Patent: WO2006/45119,2006,A2 .Location in patent: Page/Page column 58-59

17
[ 74-96-4 ]
[ 619-66-9 ]
[ 6287-86-1 ]

Yield	Reaction Conditions	Operation in experiment
98%	With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 15h;sealed tube;	A mixture of 4-carboxybenzaldehyde (15A) (0.255 g, 1.69 mmol), bromoethane (0.25 mL, 3.33 mmol) and potassium carbonate (0.446 g, 3.23 mmol) in DMF (2.5 mL) was heated to 100 C in a sealed tube and allowed to stir at this temperature for about 15 hours. The reaction was cooled to room temperature and the solvent removed in vacuo. Ether was added to the residue and the organics were washed sequentially with dilute NaOH, water and brine, then dried over MgSO4, filtered and concentrated in vacuo to provide compound 15B (0.290 g, 98%) which was used without further purification.
73%	With potassium carbonate; In N,N-dimethyl-formamide; at 70℃; for 12h;	General procedure: To a mixture of 4-formylbenzoic acid (1.5 g, 0.01 mol) and potassium carbonate (2.76 g, 0.02 mol) in dry N,N-dimethylformamide (30 mL), the corresponding n-alkyl bromide was added. The solution was maintained at 70 C under magnetic stirring for 12 h. The solvent was evaporated under reduced pressure and the product was separated by solvent extraction (dichloromethane/water, 50:10 mL). The organic phase was dried with anhydrous sodium sulfate and evaporated under reduced pressure furnishing yellowish liquids for compounds 5a-d and a white solid for 5e. Compounds 5a-d were purified by distillation leading to the formation of colorless products and compound 5e was purified flash chromatography in silica gel (hexane/ethyl acetate; 95:05, Rf 0.3).Compound 5a (73% yield); IR (NaCl, cm-1): nu 2975, 2837, 2732, 1721, 1709, 1275, 1102, 764; 1H NMR (250 MHz, CDCl3, TMS) delta (ppm): 10.10 (s, 1H), 8.20 (d, 2H, J = 8.2 Hz), 7.95 (d, 2H, J = 8.5 Hz), 4.42 (q, 2H, J = 7.0 Hz), 1.42 (t, 2H, J = 7.2 Hz); EI-MS, m/z 178 [M]+, 149 [HO2C-C6H4-CO]+, 133 [OC-C6H4-CHO]+. Compound 5b (75% yield); IR (NaCl, cm-1): nu 2976, 2879, 2734, 1721, 1708, 1272, 1104, 762; 1H NMR (250 MHz, CDCl3, TMS) delta (ppm): 10.07 (s, 1H), 8.20 (d, 2H, J = 8.5 Hz), 7.95 (d, 2H, J = 8.2 Hz), 4.32 (t, 2H, J = 6.7 Hz), 1.82 (h, 2H, J = 7.2 Hz), 1.04 (t, 3H, J = 7.5 Hz); EI-MS, m/z 192 [M]+, 151 [H2O2C-C6H4-CHO]+, 133 [OC-C6H4-CHO]+. Compound 5c (82% yield); IR (NaCl, cm-1): nu 2957, 2879, 2734, 1722, 1709, 1282, 1106, 759; 1H NMR (250 MHz, CDCl3, TMS) delta (ppm): 10.10 (s, 1H), 8.20 (d, 2H, J = 8.3 Hz), 7.95 (d, 2H, J = 8.4 Hz), 4.36 (t, 2H, J = 6.7 Hz), 1.78 (p, 2H, J = 7.2 Hz), 1.50 (h, 2H, J = 7.3 Hz), 0.98 (t, 3H, J = 7.3 Hz); EI-MS, m/z 205 [M-H]+, 151 [H2O2C-C6H4-CHO]+, 133 [OC-C6H4-CHO]+. Compound 5d (80% yield); IR (NaCl, cm-1): nu 2963, 2852, 1721, 1279, 1110, 726; 1H NMR (250 MHz, CDCl3, TMS) delta (ppm): 10.10 (s, 1H), 8.20 (d, 2H, J = 8.3 Hz), 7.95 (d, 2H, J = 8.5 Hz), 4.36 (t, 2H, J = 6.7 Hz), 1.79 (p, 2H, J = 6.7 Hz), 1.29-1.48 (m, 12H), 0.88 (t, 3H, J = 6.5 Hz); EI-MS, m/z 262[M]+, 151 [H2O2C-C6H4-CHO]+, 133 [OC-C6H4-CHO]+. Compound 5e (isolated as a white solid, mp 52 C, in 61% yield); IR (KBr, cm-1): nu 2960, 2916, 2854, 1724, 1282, 1124, 753; 1H NMR (250 MHz, CDCl3, TMS) delta (ppm): 10.10 (s, 1H), 8.20 (d, 2H, J = 8.3 Hz), 7.95 (d, 2H, J = 8.4 Hz), 4.35 (t, 2H, J = 6.7 Hz), 1.78 (p, 2H, J = 6.9 Hz), 1.25-1.47 (m, 26H), 0.88 (t, 3H, J = 6.3 Hz); EI-HRMS, calculated for C24H38O3m/z 374.2821, found: m/z 374.2845 [M]+, 151.0409 [H2O2C-C6H4-CHO]+ (calcd 151.0395), 133.0285 [OC-C6H4-CHO]+ (calcd 133.0290).
55%	With potassium carbonate; In acetonitrile; for 6h;Heating / reflux;	A mixture of 4-formylbenzoic acid (1.00 g, 6.66 mmol), bromoethane (1.09 g, 9.99 mmol), and K2CO3 (1.10 g, 7.99 mmol) in acetonitrile (30 mL) was refluxed for 6 h. After evaporation of the solvent, 4-formylbenzoic acid ethyl ester was extracted with ether (30 EPO <DP n="60"/>mL), and the organic solution was washed with 1 N NaOH aqueous solution (20 mL) and water (30 mL), dried over Na2SO4, and concentrated to give the ethyl ester product (0.65 g, 55%). Without further purification, to a solution of the ester was added sodium borohydride (NaBH4; 0.05 g, 3.65 mmol) in ethanol (20 mL) at 0 C. After stirring for 5 h at room temperature, the product was extracted with ether (30 mL), and the ether solution was washed with water (30 mL), dried over Na2SO4, and concentrated. The residue was purified by using column chromatography on silica gel eluting with hexane and ethyl acetate (3:1) to give 4- hydroxymethylbenzoic acid ethyl ester (0.30 g, 46%) as an oil. [0196] To a solution of 4-(3-adamantan-l-yl-ureido)butyric acid 822 (1.23 g, 0.83 mmol), DMAP (0.05 g, 0.42 mmol), and the above alcohol (0.15 g, 0.83 mmol) in methylene chloride (30 mL) was added EDCI (0.16 g, 0.83 mmol) at room temperature. After stirring for 12 h, the reaction mixture was washed with 1 N NaOH aqueous solution (15 mL) and water (30 mL), and the organic layer was dried over Na2SO4 and concentrated. Then the residue was purified by column chromatography on silica gel eluting hexane and ethyl acetate (5: 1) to provide 849 (0.28 g, 75%) as a white solid: 1H NMR (CDCl3) 1.40 (3H, t, J = 6.9 Hz), 1.66- 1.68 (6H, m), 1.84 (2H, quint, J = 6.9 Hz), 1.94-1.96 (6H, m), 2.05-2.07 (3H, m), 2.44 (2H, t, J = 6.9 Hz), 3.17 (2H, q, J = 6.9 Hz), 4.02 (IH, s), 4.17 (IH, s), 4.38 (2H, q, J = 6.9 Hz), 5.17 (2H, s), 7.40 (2H, d, J = 7.8 Hz), 8.00 (2H, d, J = 7.8 Hz); LC-MS (ESI) m/z calcd for C25H34N2O5 [M + H]+ 443.25, found [M + H]+ 443.25; mp 96-99 C. Anal. (C25H34N2O5) C, H, N.

Reference： [1]Patent: WO2008/130584,2008,A1 .Location in patent: Page/Page column 145
[2]Carbohydrate Research,2012,vol. 353,p. 69 - 78
[3]Patent: WO2006/45119,2006,A2 .Location in patent: Page/Page column 58-59
[4]Chemical Communications,2012,vol. 48,p. 5512 - 5514
[5]Journal of Medicinal Chemistry,2004,vol. 47,p. 2110 - 2122

18
[ 6287-86-1 ]
[ 60-24-2 ]
4-[1,3]oxathiolan-2-yl-benzoic acid ethyl ester [ No CAS ]

Reference： [1]Journal of Chemical Research,2004,p. 389 - 391
[2]Australian Journal of Chemistry,2005,vol. 58,p. 607 - 610

19
[ 15852-63-8 ]
[ 6287-86-1 ]

Yield	Reaction Conditions	Operation in experiment
71%	With manganese dioxide; In tetrachloromethane; hexane;	STAGE C: ETHYL 4-FORMYLBENZOATE 24.1 g (0.277 mmol) of manganese dioxide are added with stirring and at room temperature to a solution of 2.5 g (13.9 mmol) of ethyl 4-(hydroxymethyl)benzoate in an n-hexane/carbon tetrachloride (50 ml: 30 ml) mixture. After half an hour of stirring, the reaction is complete. After filtration of the reaction medium and removal of the solvents under vacuum, 1.76 g of a yellow oil which gives a single spot in TLC are obtained. A crystallization in isopropyl ether yields a white solid. Overall yield: 71% Melting point: 157 C.

Reference： [1]Organic Process Research and Development,1998,vol. 2,p. 261 - 269
[2]Tetrahedron,2006,vol. 62,p. 556 - 562
[3]Synthetic Communications,2008,vol. 38,p. 3107 - 3111
[4]Patent: US4975455,1990,A
[5]Zeitschrift fur Physikalische Chemie,2011,vol. 225,p. 249 - 263
[6]Journal of Molecular Liquids,2010,vol. 155,p. 85 - 90

20
[ 5798-75-4 ]
[ 201230-82-2 ]
[ 6287-86-1 ]

Yield	Reaction Conditions	Operation in experiment
	With N,N,N,N,-tetramethylethylenediamine; hydrogen;(9-methylfluoren-9-yl)dicyclohexylphosphine; palladium diacetate; In toluene; at 115℃; under 18751.9 Torr; for 20h;Autoclave;Product distribution / selectivity;	(ii) Reductive carbonylation of ethyl 4-bromobenzoate using different phosphonium salts 0.0025 mmol Pd(OAc)2, 0.0075 mmol ligand (phosphonium salts) and 0.385 mmol TMEDA were diluted in toluene to a total volume of 10 ml. 0.5 mmol of ethyl 4-bromobenzoate was introduced directly in the autoclaves, and then 1 ml of the catalyst solution was added to the autoclave. After purging with synthesis gas (CO/H2 1:1), the pressure was set to 25 bar CO/H2 and the autoclave was stirred while warming up to 115C. The reactions were hold at 115C for 20h. After cooling down and releasing the pressure the raw mixtures were filtered through a short path of Al2O3 and the conversion was determined via GC.
	With N,N,N,N,-tetramethylethylenediamine; hydrogen;9-(octadecylfluoren-9-yl)dicyclohexylphosphine; palladium diacetate; In toluene; at 115℃; under 18751.9 Torr; for 20h;Autoclave;Product distribution / selectivity;	(ii) Reductive carbonylation of ethyl 4-bromobenzoate using different phosphonium salts 0.0025 mmol Pd(OAc)2, 0.0075 mmol ligand (phosphonium salts) and 0.385 mmol TMEDA were diluted in toluene to a total volume of 10 ml. 0.5 mmol of ethyl 4-bromobenzoate was introduced directly in the autoclaves, and then 1 ml of the catalyst solution was added to the autoclave. After purging with synthesis gas (CO/H2 1:1), the pressure was set to 25 bar CO/H2 and the autoclave was stirred while warming up to 115C. The reactions were hold at 115C for 20h. After cooling down and releasing the pressure the raw mixtures were filtered through a short path of Al2O3 and the conversion was determined via GC.
	With N,N,N,N,-tetramethylethylenediamine; hydrogen;9-(methylfluoren-9-yl)diisopropylphosphine; palladium diacetate; In toluene; at 115℃; under 18751.9 Torr; for 20h;Autoclave;Product distribution / selectivity;	(ii) Reductive carbonylation of ethyl 4-bromobenzoate using different phosphonium salts 0.0025 mmol Pd(OAc)2, 0.0075 mmol ligand (phosphonium salts) and 0.385 mmol TMEDA were diluted in toluene to a total volume of 10 ml. 0.5 mmol of ethyl 4-bromobenzoate was introduced directly in the autoclaves, and then 1 ml of the catalyst solution was added to the autoclave. After purging with synthesis gas (CO/H2 1:1), the pressure was set to 25 bar CO/H2 and the autoclave was stirred while warming up to 115C. The reactions were hold at 115C for 20h. After cooling down and releasing the pressure the raw mixtures were filtered through a short path of Al2O3 and the conversion was determined via GC.

	With N,N,N,N,-tetramethylethylenediamine; hydrogen;9-(ethylfluoren-9-yl)diisopropylphosphine; palladium diacetate; In toluene; at 115℃; under 18751.9 Torr; for 20h;Autoclave;Product distribution / selectivity;	(ii) Reductive carbonylation of ethyl 4-bromobenzoate using different phosphonium salts 0.0025 mmol Pd(OAc)2, 0.0075 mmol ligand (phosphonium salts) and 0.385 mmol TMEDA were diluted in toluene to a total volume of 10 ml. 0.5 mmol of ethyl 4-bromobenzoate was introduced directly in the autoclaves, and then 1 ml of the catalyst solution was added to the autoclave. After purging with synthesis gas (CO/H2 1:1), the pressure was set to 25 bar CO/H2 and the autoclave was stirred while warming up to 115C. The reactions were hold at 115C for 20h. After cooling down and releasing the pressure the raw mixtures were filtered through a short path of Al2O3 and the conversion was determined via GC.
	With N,N,N,N,-tetramethylethylenediamine; hydrogen;9-(ethylfluoren-9-yl)dicyclohexylphosphine; palladium diacetate; In toluene; at 115℃; under 18751.9 Torr; for 20h;Autoclave;Product distribution / selectivity;	(ii) Reductive carbonylation of ethyl 4-bromobenzoate using different phosphonium salts 0.0025 mmol Pd(OAc)2, 0.0075 mmol ligand (phosphonium salts) and 0.385 mmol TMEDA were diluted in toluene to a total volume of 10 ml. 0.5 mmol of ethyl 4-bromobenzoate was introduced directly in the autoclaves, and then 1 ml of the catalyst solution was added to the autoclave. After purging with synthesis gas (CO/H2 1:1), the pressure was set to 25 bar CO/H2 and the autoclave was stirred while warming up to 115C. The reactions were hold at 115C for 20h. After cooling down and releasing the pressure the raw mixtures were filtered through a short path of Al2O3 and the conversion was determined via GC.
	With N,N,N,N,-tetramethylethylenediamine; hydrogen;9-iPrFluPCy2; palladium diacetate; In toluene; at 115℃; under 18751.9 Torr; for 20h;Autoclave;Product distribution / selectivity;	(ii) Reductive carbonylation of ethyl 4-bromobenzoate using different phosphonium salts 0.0025 mmol Pd(OAc)2, 0.0075 mmol ligand (phosphonium salts) and 0.385 mmol TMEDA were diluted in toluene to a total volume of 10 ml. 0.5 mmol of ethyl 4-bromobenzoate was introduced directly in the autoclaves, and then 1 ml of the catalyst solution was added to the autoclave. After purging with synthesis gas (CO/H2 1:1), the pressure was set to 25 bar CO/H2 and the autoclave was stirred while warming up to 115C. The reactions were hold at 115C for 20h. After cooling down and releasing the pressure the raw mixtures were filtered through a short path of Al2O3 and the conversion was determined via GC.
	With N,N,N,N,-tetramethylethylenediamine; hydrogen;(1,2,3,4,5-pentamethyl-2,4-cyclopentadien-1-yl)dicyclhexylphosphine; palladium diacetate; In toluene; at 115℃; under 18751.9 Torr; for 20h;Autoclave;Product distribution / selectivity;	(ii) Reductive carbonylation of ethyl 4-bromobenzoate using different phosphonium salts 0.0025 mmol Pd(OAc)2, 0.0075 mmol ligand (phosphonium salts) and 0.385 mmol TMEDA were diluted in toluene to a total volume of 10 ml. 0.5 mmol of ethyl 4-bromobenzoate was introduced directly in the autoclaves, and then 1 ml of the catalyst solution was added to the autoclave. After purging with synthesis gas (CO/H2 1:1), the pressure was set to 25 bar CO/H2 and the autoclave was stirred while warming up to 115C. The reactions were hold at 115C for 20h. After cooling down and releasing the pressure the raw mixtures were filtered through a short path of Al2O3 and the conversion was determined via GC.
	With N,N,N,N,-tetramethylethylenediamine; hydrogen;EtFluP(nButBu); palladium diacetate; In toluene; at 115℃; under 18751.9 Torr; for 20h;Autoclave;Product distribution / selectivity;	(ii) Reductive carbonylation of ethyl 4-bromobenzoate using different phosphonium salts 0.0025 mmol Pd(OAc)2, 0.0075 mmol ligand (phosphonium salts) and 0.385 mmol TMEDA were diluted in toluene to a total volume of 10 ml. 0.5 mmol of ethyl 4-bromobenzoate was introduced directly in the autoclaves, and then 1 ml of the catalyst solution was added to the autoclave. After purging with synthesis gas (CO/H2 1:1), the pressure was set to 25 bar CO/H2 and the autoclave was stirred while warming up to 115C. The reactions were hold at 115C for 20h. After cooling down and releasing the pressure the raw mixtures were filtered through a short path of Al2O3 and the conversion was determined via GC.
	With N,N,N,N,-tetramethylethylenediamine; hydrogen;palladium diacetate; (1-methyl-9-ethyl-fluorenyl-9-yl)dicyclohexylphosphine; In toluene; at 115℃; under 18751.9 Torr; for 20h;Autoclave;Product distribution / selectivity;	(ii) Reductive carbonylation of ethyl 4-bromobenzoate using different phosphonium salts 0.0025 mmol Pd(OAc)2, 0.0075 mmol ligand (phosphonium salts) and 0.385 mmol TMEDA were diluted in toluene to a total volume of 10 ml. 0.5 mmol of ethyl 4-bromobenzoate was introduced directly in the autoclaves, and then 1 ml of the catalyst solution was added to the autoclave. After purging with synthesis gas (CO/H2 1:1), the pressure was set to 25 bar CO/H2 and the autoclave was stirred while warming up to 115C. The reactions were hold at 115C for 20h. After cooling down and releasing the pressure the raw mixtures were filtered through a short path of Al2O3 and the conversion was determined via GC.

Reference： [1]Organic and Biomolecular Chemistry,2015,vol. 13,p. 938 - 945
[2]Patent: EP1894938,2008,A1 .Location in patent: Page/Page column 67
[3]Patent: EP1894938,2008,A1 .Location in patent: Page/Page column 67
[4]Patent: EP1894938,2008,A1 .Location in patent: Page/Page column 67
[5]Patent: EP1894938,2008,A1 .Location in patent: Page/Page column 67
[6]Patent: EP1894938,2008,A1 .Location in patent: Page/Page column 67
[7]Patent: EP1894938,2008,A1 .Location in patent: Page/Page column 67
[8]Patent: EP1894938,2008,A1 .Location in patent: Page/Page column 67
[9]Patent: EP1894938,2008,A1 .Location in patent: Page/Page column 67
[10]Patent: EP1894938,2008,A1 .Location in patent: Page/Page column 67

21
[ 94-08-6 ]
[ 6287-86-1 ]

Reference： [1]RSC Advances,2016,vol. 6,p. 14547 - 14551
[2]Chemistry - A European Journal,2015,vol. 21,p. 14937 - 14942
[3]Tetrahedron Letters,1998,vol. 39,p. 1981 - 1984
[4]Journal of Medicinal Chemistry,1985,vol. 28,p. 116 - 124
[5]European Journal of Organic Chemistry,2014,vol. 2014,p. 3402 - 3410

22
[ 6287-86-1 ]
[ 19675-63-9 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1885,vol. 231,p. 363

23
[ 6287-86-1 ]
[ 71441-28-6 ]

Reference： [1]Patent: DE2854354,1979,
Chem.Abstr.,1979,vol. 91

24
[ 5400-88-4 ]
[ 6287-86-1 ]
[ 307989-10-2 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of ethyl 4-formylbenzoate (6 g, 33.7 mmol) in DMF was added 4-tert-butylcyclohexylamine (5.8 g, 37.1 mmol), sodium cyanoborohydride (3.2 g, 50.6 mmol) and a catalytic amount of TFA. The solution was stirred at room temperature for 5 hours. The reaction was diluted with ethyl acetate and washed with aqueous sodium bicarbonate (3x), brine (3x), dried over MgSO4, and concentrated to a syrup. The desired secondary amine was purified by silica gel column chromatography using ethyl acetate.1H NMR (DMSO-d6): delta 0.78 (s, 9H), 0.91 (brd m, 5H), 1.30 (t,3H), 1.67 (brd m, 2H), 1.93 (brd m, 2H), 2.21 (1H), 3.77 (s, 2H), 4.30 (qt, 2H), 7.44 (d, 2H), 7.87 (d, 2H)

Reference： [1]Patent: EP1183229,2005,B1 .Location in patent: Page/Page column 104

25
1-(1,1-dioxo-5,5-dimethyl-8-octyloxy-2,3,4,5-tetrahydro-1-benzothiepin-7-yl)-ethanol [ No CAS ]
[ 6287-86-1 ]
[ 6399-81-1 ]
[ 153561-08-1 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; In tetrahydrofuran; EtOEt; hexane; dichloromethane; acetonitrile;	EXAMPLE 9 1.84 g of 1-(1,1-dioxo-5,5-dimethyl-8-octyloxy-2,3,4,5-tetrahydro-1-benzothiepin-7-yl)-ethanol were placed in 20 ml of acetonitrile and treated with 1.84 g of triphenylphosphine hydrobromide. The mixture was heated under reflux for 65 hours, cooled and evaporated i.v. The residue was taken up in CH2 Cl2, dried over Na2 SO4 and again evaporated. Trituration in 100 ml of EtOEt/hexane (1:1) finally yielded 2.82 g of phosphonium salt as white crystals which were reacted as follows: The crystals are dissolved in 25 ml of abs. THF under argon and deprotonized at 0 C. by the dropwise addition of 3.9 ml of 1.55M nBuLi (hexane). 814 mg of ethyl 4-formylbenzoate were added to the red ylid solution after 15 minutes and the mixture was left to react at 0 C. for 1 hour and at room temperature for 1 hour. Extraction with AcOEt, washing with water, drying, evaporation, flash chromatography on silica gel (hexane/AcOEt=85/15) and three-fold recrystallization from hexane/AcOEt finally gave 702 mg of methyl (E)-4-[2-(8-octyloxy-5,5-dimethyl-1,1-dioxo-2,3,4,5-tetrahydro-1-benzothiepin-7-yl)-propenyl]-benzoate as white crystals, m.p. 79-80 C. The 1-(1,1-dioxo-5,5-dimethyl-8-octyloxy-2,3,4,5-tetrahydro-1-benzothiepin-7-yl)-ethanol used as the starting material can be prepared as follows:

Reference： [1]Patent: US5391766,1995,A

26
[ 6287-86-1 ]
[ 92788-07-3 ]
[ 88579-28-6 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; In ethanol; hexane;	Ethyl (E)-p[2-(4,4-Dimethylchroman-6-yl)propenyl]benzoate or Ethyl (E)-4-[2-(3,4-Dihydro-4,4-dimethyl-2H-1-benzopyran-6-yl)-1-propenyl]benzoate (X=O) A solution of n-butyllithium in hexane (1.55M, 2.13 mL, 3.30 mmol) was added dropwise under N2 to a stirred suspension of the phosphonium salt 13 (X=O) (1.75 g, 3 mmol) in dry ether (30 mL). The resulting dark, reddish brown mixture was stirred at room temperature for 5 minutes. A solution of the aldehyde 6 (0.60 g, 3.37 mmol) in dry ether (15 mL) was then added. The mixture changed from reddish brown to creamy yellow, and a large amount of off-white solid precipitated. After stirring at room temperature for 36 hours, the mixture was filtered The resulting solid was washed with ether (75 mL), and the combined filtrates were concentrated to give a yellow oil. The oil was chromatographed through a column (8*200 mm) packed with neutral alumina (about 10 g). The product was eluted with 5% ether/hexane (250 mL). Concentration of the eluent gave a viscous oil which was dissolved in a minimum amount of boiling 95% ethanol. Cooling the solution to 0 C. and scratching gave 0.30 grams (26.0%) of the compound (X=O) as a white granular solid: mp 72.5-73.5 C.; IR (KBr) 1710-1725 cm-1 (C=O); 1 H NMR (DCCl3) delta 1.37 [s, 6H, (CH3)2 C], 1.39 [t, 3H, OCH2 CH3 ], 1.81-1.87 [m, 2H, H(3)], 2.27 [s, 3H, CH=C(CH3)], 4.17-4.24 [m, 2H, H(2)], 4.38 [q, 2H, OCH2 CH3 ], 6.77 [s, 1H, CH=C(CH3)], 6.81 [d, J=9 Hz, 1H, H(8)], 7.26 [dd, J=9 Hz, J=3 Hz, 1H, H(7)], 7.41 [d, 2H, Ar--H], 7.44 [d, J=3 Hz, 1H, H(5)], 8.06 [d, 2H, Ar--H]; Mass spectral data for C23 H26 O3: m/e (M+) theoretical 350.1882; Found: 350.1884. The presence of the Z isomer in an oil obtained from the chromatography was indicated by the following 1 H NMR signals: delta 2.76-2.81 [m, H(3)], 2.20 [s, 3H, Z CH=C(CH3)], 4.16-4.20 [m, H(2)], 6.44 [br s, 1H, Z CH=C(CH3)].

Reference： [1]Patent: US4826984,1989,A

27
concentrated H₂ SO₄ [ No CAS ]
[ 94-08-6 ]
[ 99-94-5 ]
[ 6287-86-1 ]

Yield	Reaction Conditions	Operation in experiment
3.1 g (47.1%)	With acetic anhydride; In ethanol; water; acetic acid;	Ethyl 4-Formylbenzoate (6) A solution of ethyl p-toluate (compound 10; 6.0 g, 0.037 mol; prepared from p-toluic acid and ethanol by conventional techniques), glacial acetic acid (57 mL), and acetic anhydride (57 mL) in a flask equipped with a thermometer and a mechanical stirrer was cooled to 0 to 5 C. in an ice-salt bath. Concentrated H2 SO4 (8.5 mL) was added slowly to the stirred solution. Chromium trioxide (10.0 g, 0.10 mol) was added in small portions over a period of 25 minutes. The temperature of the mixture was maintained below 5 C. at all times. After stirring at 0 to 5 C. for an additional 20 minutes, the mixture was poured into a breaker (2/3 full) with ice. Cold water was then added to bring the total volume to 600 mL. The resulting dark green-brown mixture was extracted with ether (3250 mL), and the organic layers were combined. The organic layer was washed with water (3 200 mL), 5% aqueous Na2 CO3 (2200 mL), and brine (200 mL). After drying (Na2 SO4) the solution, the solvent was removed leaving the diacetate 11 as a pale yellow liquid. A mixture of the crude diacetate 11, concentrated H2 SO4 (2 mL), water (20 mL), and 95% ethanol (20 mL) was heated at reflux under N2 for 45 minutes. The solution was allowed to cool to room temperature. After diluting the solution with water (40 mL), the resulting mixture extracted with ether (340 mL). The combined organic layers were washed with 5% aqueous NaHCO3 (2*50 mL) and water (50 mL). After drying (Na2 SO4) the solution, the solvent was removed leaving a yellow liquid. Vacuum distillation gave 3.1 g (47.1%) of compound 6 as a colorless liquid: bp 80-84 C./0.05 mm (literature reports 142 C./13 mm; see K. H. Slotta and R. Kethur, Ber. 71, 335 [1938]); IR (neat) 1705-1735 cm-1 (C=O): 1 H NMR (DCCl3) delta1.42 [t, 3H, OCH2 CH3 ], 4.41 [q, 2H, OCH2 CH3 ], 7.87-8.22 [pseudo q, 4H, Ar--H], 10.08 [br s, 1H, CHO]; 13 C NMR (DCCl3) ppm 14.2 [OCH2 CH3 ], 61.4 [OCH2 CH3 ]; Ar--C [129.2, 129.9, 135.2, 138.9], 165.2 [CO2 C2 H5 ], 191.2 (CHO).

Reference： [1]Patent: US4826984,1989,A

28
[ 21211-65-4 ]
[ 6287-86-1 ]
5,15-bis(4'-ethoxycarbonylphenyl)porphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40.9%		1) Synthesis of Raw Materials;The compound (4) that was a starting material used in Scheme 3 was synthesized according to the description in a reference, K. Ogawa, J. Dy, and Y. Kobuke, Journal of Porphyrins and Phthalocyanine 9, 735-744 (2005). The details are described below. First, dipyrromethane (167.4 mg, 1.14 mmol), 4-ethoxycarbonylbenzaldehyde (204 mg, 1.14 mmol), and chloroform (200 mL) were placed in a 500-mL three neck flask. Then nitrogen gas bubbling was carried out therein for three minutes and thereby a nitrogen gas atmosphere was obtained. Thereafter, trifluoroacetic acid (88.2 muL, 1.14 mmol) was added thereto. This was stirred at room temperature under a light-shielded condition for 20 hours. Then triethylamine (0.5 mL, 3.56 mmol) and chloranil (884 mg, 3.4 mmol) were added thereto and this was refluxed at 70 C. for 1.5 hours. Then the solvent was distilled away and purification was carried out by silica gel column chromatography (solvent:chloroform). Thus the compound (4) was obtained as a purplish-red solid (141.1 mg, 40.9%). The instrumental analysis data of the compound (4) is indicated below.Compound (4):1H-NMR (270 MHz, CDCl3) delta10.332 (s, 2H, meso), 9.405 (d, 4H, J=4.7 Hz, beta), 9.033 (d, 4H, J=4.7 Hz, B), 8.490 (d, 4H, J=8.1 Hz, Ph), 8.351 (d, 4H, J=8.1 Hz, ph), 4.607 (q, 4H, J=3.5 Hz, -CH2-), 1.342 (t, 6H, J=3.5 Hz, -CH3), MALDI-TOF mass (matrix:dithranol), m/z 606.90, calcd for C38H30N4O4 606.23.

Reference： [1]Chemistry - A European Journal,2019,vol. 25,p. 7847 - 7851
[2]Patent: US2007/224529,2007,A1 .Location in patent: Page/Page column 23

29
[ 1906-57-6 ]
[ 1122-91-4 ]
[ 6287-86-1 ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 5738 - 5739

30
[ 1008-89-5 ]
[ 6287-86-1 ]
[ 1173294-95-5 ]

Reference： [1]Organic Letters,2009,vol. 11,p. 3120 - 3123

31
[ 67097-50-1 ]
[ 6287-86-1 ]

Reference： [1]Synlett,2010,p. 2778 - 2780

32
[ 6287-86-1 ]
[ 868-59-7 ]
[ 1263098-07-2 ]

Yield	Reaction Conditions	Operation in experiment
98%	With potassium hydrogencarbonate; In methanol; water; at 20℃;Inert atmosphere;	General procedure: Aldehydes 2a-d (1.1 equiv) were suspended in MeOH, then a solution of the commercially available l-cysteine ethyl ester hydrochloride 1b (1.1 equiv) dissolved in H2O together with KHCO3 (1.0 equiv) was added and the resulting mixture was stirred at room temperature overnight. After evaporation of MeOH the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine (100-200 mL depending on the reaction scale) and dried over Na2SO4. Evaporation of the solvent afforded compounds 3a-d, which were used without further purification.

Reference： [1]Tetrahedron,2011,vol. 67,p. 267 - 274
[2]Phosphorus, Sulfur and Silicon and the Related Elements,2011,vol. 186,p. 1312 - 1315

33
[ 64-17-5 ]
[ 6287-86-1 ]
[ 15852-63-8 ]
[ 636-09-9 ]

Yield	Reaction Conditions	Operation in experiment
18%; 82%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; benzyl chloride; at 90℃; for 0.5h;Microwave irradiation;	General procedure: A 10 mL reaction vessel was charged in air with Pd(PPh3)4 (6 mg, 1 mol %), aldehyde (0.5 mmol), K2CO3 (207 mg, 1.5 mmol), benzyl chloride (70 muL, 0.6 mmol) and EtOH (1 mL). The vessel was sealed and submitted to microwave irradiation for 30 min at 90 C, using an initial power of 30 W. (Microwave reactions were carried out with a CEM Discover 300 W monomode microwave instrument. The closed vessels used were special glass tubes with self-sealing septa that controlled pressure with appropriate sensors on the top (outside the vial). The temperature was monitored through a non-contact infrared sensor centrally located beneath the cavity floor.) The mixture was then allowed to cool to room temperature, filtered over a pad of Celite and rinsed with EtOH (5 mL). The filtrate was concentrated in vacuo and the product was purified by flash chromatography on silica gel (CH2Cl2/hexane).

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 5319 - 5322

34
(S)-N-(piperidin-3-yl)-1H-indazol-5-amine dihydrochloride [ No CAS ]
[ 6287-86-1 ]
[ 1202566-20-8 ]

Yield	Reaction Conditions	Operation in experiment
		Ethyl 4-(((5)-3-(lH-indazoI-5-yIamino)piperidin-l-yI)methyl)benzoateA solution of (5)-N-(piperidin-3-yl)-lH-indazol-5-amine dihydrochloride and an equimolar amount of ethyl 4-formylbenzoate in THF was treated with a twofold excess of sodium triacetoxyborohydride for 18 hours. The reaction was monitored by HPLC for complete conversion of the starting materials to the product and when complete, was quenched with aqueous NaOH. The solution was extracted with ethyl acetate, washed with dilute HC1 and brine then dried over MgS04. Evaporation afforded a residue which was chromatographed on silica gel to yield the title compound. 1H NMR (CDC13) delta 9.82(br s,lH), 7.99(d,2H), 7.86(s,lH), 7.40(d,2H), 7.22-7.32(m,lH), 6.8-6.85(m,2H), 4.37(q,2H), 3.52-3.629m,3H), 2.7- 2.8(m,lH), 2.26-2.42(m,3H), 1.45-1.8(m,5H), 1.39(t,3H)

Reference： [1]Patent: WO2012/15760,2012,A1 .Location in patent: Page/Page column 41

35
(R)-N-(piperidin-3-yl)-1H-indazol-5-amine dihydrochloride [ No CAS ]
[ 6287-86-1 ]
[ 1202566-13-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium acetate; sodium cyanoborohydride; In methanol; for 18h;	Ethyl 4-(((R)-3-(lH-indazol-5-ylamino)piperidin-l-yl)methyl)benzoateAn equimolar solution of (R)-N-(piperidin-3-yl)-lH-indazol-5-amine dihydrochloride and ethyl 4-formylbenzoate in MeOH containing a twofold molar excess of sodium acetate was treated with a 1.5 molar excess of sodium cyanoborohydride for 18 hours. The reaction was monitored by HPLC for complete conversion of the starting materials to the product and when complete, was quenched with aqueous sodium bicarbonate. The solution was extracted with ethyl acetate, washed with dilute HC1 and brine then dried over MgS04. Evaporation afforded a residue which was chromatographed on silica gel to yield the title compound. 1HNMR (CDCI3) delta 9.87(br s,lH), 7.99(d,2H), 7.86(s,lH), 7.41(d,2H), 7.26-7.33(m,lH), 6.76- 6.84(m,2H), 4.37(q,2H), 3.46-3.62(m,4H), 2.75(br d,lH), 2.26-2.43(m,3H), 1.5-1.8(m,4H),1.42(t,3H)

Reference： [1]Patent: WO2012/15760,2012,A1 .Location in patent: Page/Page column 40-41

36
[ 6287-86-1 ]
[ 149-73-5 ]
[ 1379653-70-9 ]

Yield	Reaction Conditions	Operation in experiment
86%	With hydrogenchloride; water; In methanol; at 20℃; for 6h;	General procedure: Starting material (0.01 mol of 2a-e or 5a-e) and trimethyl orthoformate (1.59 g, 0.015 mol) in 1.5 mL of methanol were stirred at room temperature. Two drops of concentrated hydrochloric acid were added to this solution. Procedures for compounds 2a-d were left under stirring for two days at room temperature, and reactions with compounds 5a-d were kept for only 6 h under agitation at room temperature. Nevertheless, compounds 2e and 5e were prepared similarly to their analogues, but under somewhat higher temperature (50 C) and longer reaction times (four days). After these periods, all products were isolated by neutralization with KOH dissolved in methanol followed by evaporation of volatiles under reduced pressure, and extraction with ethyl ether and water (8 mL, 3:1). Organic phases were dried over anhydrous Na2SO4 followed by volatile removing on rotary evaporator. The compounds 3a-d and 6a-d were purified by distillation at reduced pressure resulting in colorless liquids. Compounds 3e and 6e were purified by flash chromatography in silica gel (hexane/ethyl acetate, 95:05, Rf 0.5 and 0.4, respectively).Compound 3a (81% yield); IR (NaCl, cm-1): nu 2983, 2821, 1610, 1512, 1242, 1052, 830; 1H NMR (250 MHz, CDCl3, TMS) delta (ppm): 7.35 (d, 2H, J = 8.5 Hz), 6.88 (d, 2H, J = 8.8 Hz), 5.34 (s, 1H), 4.03 (q, 2H, J = 7.0 Hz), 3.30 (s, 6H), 1.41 (t, 3H, J = 7.0 Hz); EI-MS, m/z 196 [M]+, 165 [CH3OCH-C6H4-OC2H5]+, 150 [OCH-C6H4-OC2H5]+. Compound 3b (70% yield);IR (NaCl, cm-1): nu 2964, 2825, 1611, 1513, 1246, 1055, 831; 1H NMR (250 MHz, CDCl3, TMS) delta (ppm): 7.36 (d, 2H, J = 8.6 Hz), 6.88 (d, 2H, J = 8.7 Hz), 5.34 (s, 1H), 3.92 (t, 3H, J = 6.5 Hz), 3.30 (s, 6H), 1.80 (h, 2H, J = 7.3 Hz), 1.03 (t, 3H, J = 7.4 Hz); EI-MS, m/z 210.1[M]+, 179.1 [CH3OCH-C6H4-OC3H7]+, 164.1 [OCH-C6H4-OC3H7]+. Compound 3c (62% yield); IR (NaCl, cm-1): nu 2957, 2820, 1610, 1507, 1242, 1055, 818; 1H NMR (250 MHz, CDCl3, TMS) delta (ppm): 7.34 (d, 2H, J = 8.7 Hz), 6.88 (d, 2H, J = 8.8 Hz), 5.34 (s, 1H), 3.96 (t, 2H, J = 6.5 Hz), 3.31 (s, 6H), 1.76 (p, 2H, J = 6.6 Hz), 1.49 (h, 2H, J = 7.5 Hz), 0.97 (t, 3H, J = 7.3 Hz); EI-HRMS, m/z calculated for C12H17O2 [M-OCH3]+ = [CH3OCH-C6H4-OC4H9]+m/z 193.1229, found: m/z 193.1203, 178.0967 [OCH-C6H4-OC4H9]+ (calcd 178.0994). Compound 3d (73% yield); IR (NaCl, cm-1): nu 2928, 2828, 1617, 1512, 1242, 1057, 826; 1H NMR (250 MHz, CDCl3, TMS) delta (ppm): 7.35 (d, 2H, J = 8.6 Hz), 6.88 (d, 2H, J = 8.6 Hz), 5.34 (s, 1H), 3.94 (t, 2H, J = 6.5 Hz), 3.31 (s, 6H), 1.77 (p, 2H, J = 6.6 Hz), 1.28-1.47 (m, 10H), 0.88 (t, 3H, J = 6.3 Hz); EI-HRMS: calculated for C17H28O3m/z 280.2038, found: m/z280.2093 [M]+, 249.1814[CH3OCH-C6H4-OC8H17]+ (calcd 249.1855), 234.1648 [OCH-C6H4-OC8H17]+ (calcd 234.1620). Compound 3e (isolated as a white solid, mp 42 C, in 71% yield); IR (KBr, cm-1): nu 2916, 2846, 1620, 1517, 1246, 1049, 808; 1H NMR (250 MHz, CDCl3, TMS) delta (ppm): 7.34 (d, 2H, J = 8.6 Hz), 6.87 (d, 2H, J = 8.7 Hz), 5.41 (s, 1H), 3.97 (t, 2H, J = 6.6 Hz), 3.31 (s, 6H), 1.77 (p, 2H, J = 6.5 Hz), 1.26-1.47 (m, 26H), 0.88 (t, 3H, J = 6.2 Hz); EI-MS, m/z 361.3 [CH3OCH-C6H4-OC16H33]+, 346.3 [OCH-C6H4-OC16H33]+.Compound 6a (86% yield); IR (NaCl, cm-1): nu 2982, 2827, 1714, 1277, 1105, 1062, 761; 1H NMR (250 MHz, CDCl3, TMS) delta (ppm): 8.00 (d, 2H, J = 8.4 Hz), 7.50 (d, 2H, J = 8.0 Hz), 5.44 (s, 1H), 4.38 (q, 2H, J = 7.2 Hz), 3.33 (s, 6H), 1.40 (t, 3H, J = 7.1 Hz); EI-MS, m/z 223 [M-H]+, 193 [CH3OCH-C6H4-CO2C2H5]+, 179 [H(CH3O)2C-C6H4-CO]+. Compound 6b (85% yield); IR (NaCl, cm-1): nu 2974, 2828, 1719, 1279, 1106, 1056, 762; 1H NMR (250 MHz, CDCl3, TMS) delta (ppm): 8.05 (d, 2H, J = 8.3 Hz), 7.50 (d, 2H, J = 8.3 Hz), 5.44 (s, 1H), 4.28 (t, 2H, J = 6.7 Hz), 3.33 (s, 6H), 1.80 (h, 2H, J = 7.2 Hz), 1.03 (t, 3H, J = 7.4 Hz); EI-MS, m/z 207[CH3OCH-C6H4-CO2C3H7]+, 179 [H(CH3O)2C-C6H4-CO]+. Compound 6c (77% yield); IR (NaCl, cm-1): nu 2990, 2832, 1724, 1280, 1105, 1056, 761; 1H NMR (250 MHz, CDCl3, TMS) delta (ppm): 8.04 (d, 2H, J = 8.4 Hz), 7.52 (d, 2H, J = 8.1 Hz), 5.44 (s, 1H), 4.32 (t, 2H, J = 6.5 Hz), 3.33 (s, 6H), 1.76 (p, 2H, J = 7.0 Hz), 1.48 (h, 2H, J = 7.8 Hz), 0.98 (t, 3H, J = 7.3 Hz); EI-MS, m/z 251 [M-H]+, 221 [CH3OCH-C6H4-CO2C4H9]+, 179 [H(CH3O)2C-C6H4-CO]+. Compound 6d (75% yield); IR (NaCl, cm-1): nu 2956, 2860, 1722, 1267, 1106, 1060, 759;1H NMR (250 MHz, CDCl3, TMS) delta (ppm): 8.05 (d, 2H, J = 8.4 Hz), 7.53 (d, 2H, J = 8.3 Hz), 5.44 (s, 1H), 4.31 (t, 2H, J = 6.7 Hz), 3.33 (s, 6H), 1.77 (p, 2H, J = 7.2 Hz), 1.28-1.46 (m, 10H), 0.88 (t, 3H, J = 7.0 Hz); EI-MS, m/z 277.1[CH3OCH-C6H4-CO2C8H17]+, 179 [H(CH3O)2C-C6H4-CO]+. Compound 6e (isolated as a white solid, mp 48 C, in 73% yield); IR (KBr, cm-1): nu 2955, 2854, 1719, 1273, 1105, 1050, 759; 1H NMR (250 MHz, CDCl3, TMS) delta (ppm): 8.04 (d, 2H, J = 8.3 Hz), 7.53 (d, 2H, J = 8.1 Hz), 5.44 (s, 1H), 4.31 (t, 2H, J = 6.6 Hz), 3.33 (s, 6H), 1.76 (p, 2H, J = 7. Hz), 1.23 (m, 26H), 0.88 (t, 3H, J = 6.7 Hz); EI-HRMS, m/z calculated for C25H41O3 [M-O...

Reference： [1]Carbohydrate Research,2012,vol. 353,p. 69 - 78

37
[ 6287-86-1 ]
[ 771477-48-6 ]
[ 1380762-24-2 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 3206 - 3209

38
[ 24285-16-3 ]
[ 6287-86-1 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 4086 - 4089

39
[ 75-52-5 ]
[ 6287-86-1 ]
(+)-1-(4-ethoxycarbonyphenyl)-2-nitroethanol [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2012,vol. 354,p. 2511 - 2520

40
[ 366-84-7 ]
[ 6287-86-1 ]

Reference： [1]Synthetic Communications,2013,vol. 43,p. 1155 - 1160

41
[ 6287-86-1 ]
[ 232597-42-1 ]
[ 1487464-89-0 ]

Yield	Reaction Conditions	Operation in experiment
81%	With sodium In ethanol at 20℃; for 2h;

Reference： [1]Valente, Sergio; Trisciuoglio, Daniela; Tardugno, Maria; Benedetti, Rosaria; Labella, Donatella; Secci, Daniela; Mercurio, Ciro; Boggio, Roberto; Tomassi, Stefano; DiMaro, Salvatore; Novellino, Ettore; Altucci, Lucia; DelBufalo, Donatella; Mai, Antonello; Cosconati, Sandro [ChemMedChem, 2013, vol. 8, # 5, p. 800 - 811]

42
[ 619-66-9 ]
[ 75-03-6 ]
[ 6287-86-1 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 2334 - 2356
[2]Chemistry - A European Journal,2019,vol. 25,p. 7847 - 7851

43
[ 6287-86-1 ]
[ 1071476-83-9 ]

Yield	Reaction Conditions	Operation in experiment
		Azidotrimethylsilane (1.47 mL, 11.2 mmol) was added to a stirred solution of ethyl 4-formylbenzoate (713 mg, 4 mmol) in dichloromethane (12.0 mL) at rt, followed by the additionof Sc(OTf)3 (98 mg, 0.2 mmol). The reaction mixture was stirred at rt for 30 min. Thentriethylsilane (1.29 mL, 8 mmol) was added dropwise at the same temperature, the reactionfurther stirred for 30 min. After this time the reaction mixture was stirred at reflux temperaturefor 15h. The reaction mixture was then diluted with CH2Cl2 and washed with brine. The organiclayer was collected and dried over magnesium sulfate to yield 820 mg of crude product that wasused in the next step without further purification. 1H NMR (250 MHz, DMSO-d6) delta 7.99 (d, J =8.3 Hz, 2H), 7.51 (d, J = 8.4 Hz, 2H), 4.58 (s, 2H), 4.32 (q, J = 7.1 Hz, 2H), 1.32 (t, J = 7.1 Hz,3H).

Reference： [1]Organic Letters,2014,vol. 16,p. 2104 - 2107
[2]Bioorganic and Medicinal Chemistry,2019,vol. 27

44
[ 1201-90-7 ]
[ 6287-86-1 ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 3402 - 3410

45
[ 6287-86-1 ]
[ 41979-39-9 ]
[ 64-19-7 ]
diethyl 4,4'-(1E,1'E)-(4-oxopiperidine-3,5-diylidene)bis(methan-1-yl-1-ylidene)dibenzoate acetic acid salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With hydrogenchloride; at 20℃; for 3h;Cooling with ice; Sealed tube;	General procedure: To the appropriate aromatic aldehyde (20 mmol), acetic acid (125 mL) was added and the reaction mixture cooled on ice. 4-Piperidone hydrochloride monohydrate (10 mmol) was then added and dry HCl(g) passed briskly through the solution for 3 h. The reaction mixture was then sealed and allowed to stir at room temperature overnight, or until the product crystallized from solution. The resultant precipitate was filtered and washed with ice-cold methanol.

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 411 - 421

46
[ 6287-86-1 ]
[ 40064-34-4 ]
[ 64-19-7 ]
diethyl 4,4'-(1E,1'E)-(4-oxopiperidine-3,5-diylidene)bis(methan-1-yl-1-ylidene)dibenzoate acetic acid salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With hydrogenchloride; for 0.5h;Sealed tube;	General procedure: To a 250 mL round bottom oven dried flask, was added, 4-piperidone hydrate hydrochloride (0.10 mol), appropriate aromaticaldehyde (0.20 mol), acetic acid (150 ml). The reaction mixture wassealed and HCl (g) was passed through the reaction flask for 30 minwhile the reaction was stirred. During this time, the clear mixtureyielded thick yellow or orange precipitates. After the 30 min period,the HCl gas was turned off and the reaction was left to stirfor 24 h. The precipitate was then filtered using suction filtration.The products as acid salts thus obtained were quite pure and wereused for subsequent reactions without further purification.

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 6404 - 6417

47
[ 6287-86-1 ]
[ 70448-68-9 ]
2-(diethoxyphosphoryl)-N-(4-ethoxycarbonylbenzylidene)propan-2-amine oxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With magnesium sulfate; In 1,2-dichloro-ethane; at 100℃; for 4h;	General procedure: A mixture of 3 (4 mmol, 1 eq) and the corresponding benzaldehyde (4 mmol, 1 eq) in THF or DCE (30mL) was stirred at 100C for 4h in the presence of MgSO4 (spatula tip). The mixture was allowed to cool at room temperature and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by either precipitation or crystallization from a defined solvent.

Reference： [1]European Journal of Medicinal Chemistry,2016,vol. 119,p. 197 - 217

48
[ 6287-86-1 ]
C₁₀H₁₂N₄O*C₂HF₃O₂ [ No CAS ]
(4S)-4-methyl-2-(4-ethoxycarbonylphenyl)-3,4-dihydro-5H-pyrido[1',2':1,2]imidazo-[4,5-d][1,3]diazepin-5-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48 mg	With iodine; potassium carbonate; In tert-butyl alcohol; at 70℃;	General procedure: A solution of compound 3a-g (0.33mmol) in a 50/50 v/v mixture of trifluoroacetic acid and dichloromethane (5mL) was stirred at room temperature for 1h. After completion of the reaction (HPLC analysis), the solution was concentrated to dryness and co-evaporated several times with acetonitrile to completely remove TFA. Then were added, tert-butanol (8mL), K2CO3 (182mg, 4 equiv.), iodine (251mg, 3 equiv.), and the appropriate aldehyde (1 equiv.). The mixture was stirred under heating at 70C for one night. Tert-butanol was then removed under reduced pressure and 30mL of dichloromethane were added. The organic phase was successively washed with a 10% m/v sodium thiosulfate aqueous solution (2×30mL) and then with a saturated NaHCO3 aqueous solution (2×30mL). The organic layer was dried over Na2SO4, filtered, and the solvent was evaporated in vacuo. The residue was purified by chromatography on alumina, eluted by DCM/EtOH 99/1 v/v.

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 125,p. 1225 - 1234

49
[ 6287-86-1 ]
2'-hydroxy-5'-benzyloxy-3'-(1-adamantyl)acetophenone [ No CAS ]
8-(1-adamantyl)-6-benzyloxy-2-(4-ethoxycarbonylphenyl)dihydrochromanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium methylate; In methanol; for 6h;Inert atmosphere; Reflux;	Under nitrogen protection,5-benzyloxy-3- (1-adamantyl) -acetophenone (1.88 g, 5 mmol), sodium methoxide (0.67 g, 12.5 mmol) in a dry flask (100 mL) Anhydrous methanol (50 mL),Stirring dissolved;To the reaction system was further added ethyl 4-aldehydebenzoate (0.98 g, 6 mmol),After refluxing for 6 h,TLC detection reaction has reached equilibrium,The reaction solution eventually becomes blood red,The reaction was terminated.The reaction solution was concentrated under reduced pressure,To the residue by adding an appropriate amount of distilled water dissolved,The pH was adjusted to 7 with 1 M HCl,And extracted with ethyl acetate (50 mL x 3)The organic phases were combined,And dried over anhydrous sodium sulfate overnight,Filtration,The organic phase was concentrated under reduced pressure and the residue was separated by silica gel column chromatography (eluent: petroleum ether:Ethyl acetate = 10: 1 to give 1.84 g of the product as a yellow solid in 70.6% yield.

Reference： [1]Patent: CN106220600,2016,A .Location in patent: Paragraph 0071; 0072

50
[ 6287-86-1 ]
[ 2051-95-8 ]
4-(2-oxo-5-phenyl-furan-3-ylidenemethyl)-benzoic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
31%	With sodium acetate; acetic anhydride; at 95℃; for 2h;Inert atmosphere;	General procedure: A stirred solution of 3-benzoyl propanoic acid 4 (1 g, 5.6 mmol), the different benzaldehyde 5a-e (6.6 mmol) and sodium acetate (0.47 g, 5.6 mmol) in 7 mL of acetic anhydride was heated at 95 C for 2 h under N2 atmosphere . The reaction mixture was then cooled to r.t., diluted with MeOH and left in an ice-bath for 2 h. The resulting precipitate was filtered and washed with a cold 50% solution of MeOH in water. S.1.1.1 4-(2-Oxo-5-phenyl-furan-3-ylidenemethyl)-benzoic acid ethyl ester (6a) Obtained in 31% yield as a yellow solid. 1H-NMR (DMSO-d6), delta: 1.34 (t, J= 7.0 Hz, 3H), 4.34 (q, J= 7.0 Hz, 2H), 7.40 (s, 1H), 7.56-7.60 (m, 3H), 7.63 (s, 1H), 7.88-7.92 (m, 2H), 7.97 (d, J= 7.8 Hz, 2H), 8.01 (d, J= 8.3 Hz, 2H). 13C-NMR (DMSO-d6), delta: 14.0, 60.9, 101.0, 125.4, 126.5, 127.5, 129.0, 129.5, 130.5, 130.6, 130.9, 133.1, 138.6, 157.0, 165.1, 168.3.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 936 - 940

51
[ 6287-86-1 ]
[1-(5,6,7,8-tetrahydro-5,8-dimethyl-2-naphthyl)ethyl]trimethylphosphonium bromide [ No CAS ]
4-[(E)-2-(5,6,7,8-tetrahydro-5,8-dimethyl-2-naphthyl)propenyl]benzoic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		In a 1 L three-necked reaction flask, 300 ml of toluene, 106 g of [1- (5,6,7,8-tetrahydro-5,8-dimethyl-2-naphthyl) -ethyl] Trimethylene phosphonium bromide, 53 g of <strong>[6287-86-1]p-ethoxycarbonylbenzaldehyde</strong> and 4.2 g of tetrabutylammonium chloride. After stirring and stirring, 56 g of potassium hydroxide and 150 ml of a solution of potassium hydroxide were added and the temperature was raised to reflux. After 2 hours of reflux reaction, the reaction was monitored by HPLC until the intermediate [1- (5,6,7,8-tetrahydro-5,8-dimethyl-2-naphthyl) -ethyl] -trityl Phosphine / intermediate 4 - [(E) -2- (5,6,7,8-tetrahydro-5,8-dimethyl-2-naphthyl) propenyl] benzoate (peak area ratio) <5%, stop the reaction. The reaction solution was distilled off under reduced pressure to dry the solution, and 200 ml of ethanol, 40 g of potassium hydroxide and 400 ml of water were added to the aqueous potassium hydroxide solution, and the oil bath was heated to reflux under stirring. The reaction was refluxed for 1 hour and the reaction was monitored by HPLC until the starting material 4 - [(E) -2- (5,6,7,8-tetrahydro-5,8-dimethyl-2-naphthyl) Ethyl benzoate.

Reference： [1]Patent: CN102336660,2016,B .Location in patent: Paragraph 0062-0064

52
[ 6287-86-1 ]
[ 69251-24-7 ]
[ 71441-09-3 ]

Yield	Reaction Conditions	Operation in experiment
		In a 10 ml single-necked flask, 3 ml of dichloromethane, 558 mg of [l- (5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl) -ethyl] -triphenylphosphonium bromide, 246 mg of p-methoxycarbonylbenzaldehyde, 16 mg of tetrabutylammonium bromide, and after stirring, 200 mg of sodium hydroxide400mg water dubbed sodium hydroxide solution, heated to reflux. After 1 hour of reflux reaction, the reaction was monitored by HPLC,Until the intermediate [1- (5,6,7,8_tetrahydro-5,5,8,8-tetramethyl-2-naphthyl) -ethyl] -triphenylphosphonium bromide / intermediate4 - [(E) -2- (5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl) propenyl] benzoate (peak area ratio) EZ >9: 1, stops the reaction. The reaction solvent was evaporated under reduced pressure to stop, 2ml ofethanol was added sodium hydroxide solution, 250mg of sodium hydroxide and 4ml of waterto form, under stirring, was heated to reflux in an oil bath. After the reaction wasrefluxed for 2 hours, the HPLC monitoring of the reaction until the starting materialthe intermediate 4 - [(E) -2- (5,6,7,8- tetrahydro-5,5,8,8-tetramethyl-2-naphthyl yl)propenyl] benzoate The reaction completion.

Reference： [1]Patent: CN102336660,2016,B .Location in patent: Paragraph 0058; 0059

53
(4-(ethoxycarbonyl)phenyl)zinc(II) iodide lithium chloride [ No CAS ]
[ 27064-03-5 ]
[ 6287-86-1 ]

Reference： [1]Organic Letters,2017,vol. 19,p. 1646 - 1649

54
[ 167837-57-2 ]
[ 6287-86-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: pyridine; dmap / N,N-dimethyl-formamide / 5 h / 60 °C / Sealed tube 2: cobalt(II) bromide; [2,2]bipyridinyl; manganese; chloro-trimethyl-silane; pyridine / N,N-dimethyl-formamide / 20 h / 60 °C / Sealed tube

Reference： [1]Bourne-Branchu, Yann; Gosmini, Corinne; Danoun, Grégory [Chemistry - A European Journal, 2017, vol. 23, # 42, p. 10043 - 10047]

55
[ 64-17-5 ]
C₁₄H₁₇NO₄ [ No CAS ]
[ 6287-86-1 ]

Reference： [1]Chemistry - A European Journal,2017,vol. 23,p. 10043 - 10047

56
[ 6287-86-1 ]
ethyl (4-formaldehydeoxime)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydroxylamine hydrochloride; sodium hydroxide; In ethanol; water; at 0 - 20℃;	General procedure: 10 mmol of aldehyde was dissolved in 10 mL of H2O/EtOH(v/v) 1/1) mixture by stirring in a 100-mL round-bottomedflask. The solution was cooled to 0 C, and 10 mmol of hydroxylamine hydrochloride was added to this solution.Then 25 mmol of NaOH as a 50% solution in water was added dropwise. The reaction mixture is allowed to warm slowly to room temperature and stirred for 1 h. The solution was extracted with chloroform, and the aqueous phase was acidified to pH 6 by adding concentrated HCl while keeping the temperature below 30 C and extracted with chloroformto give the oxime products in 90-97% yield. For chlorination of oxime, 1.8 mmol of N-chlorosuccinimide (NCS) was added in one portion to a solution of 10 mmol of oxime in DMF (10 mL). A slight increase in the reaction temperature shows the beginning of the reaction. A small amount of HClgas can be bubbled through the solution when the reaction does not start. In the case of the electron-deficient oximes for starting the reaction, the mixture is heated to 45 C. Theremaining 8.2 mmol of NCS was added in small portions while keeping the temperature below 35 C (below 60 C for electron-deficient oximes). The mixture was then stirredat room temperature for 1 h and quenched with water and extracted with chloroform (3 × 10 mL) to give the imidoyl chloride products in 72-93% yield.

Reference： [1]Journal of the Iranian Chemical Society,2018,vol. 15,p. 813 - 821

57
[ 6287-86-1 ]
[ 27329-60-8 ]
[ 43122-55-0 ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 5695 - 5698
Angew. Chem.,2018,vol. 130,p. 5797 - 5800,4

58
[ 6287-86-1 ]
[ 27329-60-8 ]
ethyl 4-(1-(((1,1,1,3,3,3-hexafluoropropan-2-yl)oxy)sulfonyl)-3,3-diphenylaziridin-2-yl)benzoate [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 5695 - 5698
Angew. Chem.,2018,vol. 130,p. 5797 - 5800,4

59
[ 6287-86-1 ]
[ 17606-32-5 ]
C₁₆H₁₄O₅S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64.5%	With toluene-4-sulfonic acid; In toluene; for 12h;Reflux;	Compound 1b:158 mg of 3-acetylthiosuccinic acid was dissolved in 50 mL of toluene, and 196 mg of ethyl 4-formylbenzoate and 30 mg of p-toluenesulfonic acid were added, and the mixture was heated under reflux for 12 hours.After treatment: After 12 hours of reaction,Water is no longer produced in the azeotrope, and it is cooled in a refrigerator at 4 C to filter impurities, and the solvent is evaporated off by rotary evaporation.Purification by multiple extractions of ethyl acetate:methanol = 1:4 as a recrystallization solvent gave a yellow solid product.The yield was 64.5%.

Reference： [1]Patent: CN108314672,2018,A .Location in patent: Paragraph 0019; 0021

60
ethyl 4-((1R*,2R*)-1,2-dihydroxy-2-phenylethyl)benzoate [ No CAS ]
[ 6287-86-1 ]
[ 100-52-7 ]

Reference： [1]Advanced Synthesis and Catalysis,2018,vol. 360,p. 3286 - 3296

61
[ 6287-86-1 ]
C₂₁H₂₅N₃O₃ [ No CAS ]
ethyl 4-[[4-[[6,7-dimethoxy-2-(5-methyl-2-furyl)-4-quinolyl]amino]-1-piperidyl]methyl]benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	With sodium cyanoborohydride; acetic acid; In methanol; at 60℃; for 12h;Inert atmosphere;	A mixture of commercially available ethyl 4-formylbenzoate (R-09a, 126 mg, 707 muetaetaomicronIota), intermediate 1-16d (200 mg, 544 muetaiotaomicronIota), AcOH (6 mg, 109 mol) and NaBH3CN (51 mg, 816 mol) in MeOH (5.00 mL) was degassed and purged with N2for 3 times. Then, the mixture was stirred at 60 C for 12 hours under N2atmosphere. The reaction mixture was filtrated and the filtrate was concentrated under vacuum to give a residue. The residue was purified by prep-HPLC (Method 2) to give intermediate 1-17e (120 mg, 42%) as a yellow solid. ESI-MS (M+1 ): 530.3 calc. for C31 H35N3O5: 529.3.

Reference： [1]Patent: WO2018/229139,2018,A1 .Location in patent: Page/Page column 62

62
[ 5798-75-4 ]
[ 201230-82-2 ]
[ 93-89-0 ]
[ 6287-86-1 ]

Reference： [1]ChemSusChem,2019,vol. 12,p. 326 - 337

63
[ 6287-86-1 ]
[ 98-86-2 ]
[ 87116-41-4 ]

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 2469 - 2473
Angew. Chem.,2019,vol. 131,p. 2491 - 2495,5

64
[ 6287-86-1 ]
[ 292638-85-8 ]
C₁₄H₁₆O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 1,4-diaza-bicyclo[2.2.2]octane; In methanol; at 20℃;	General procedure: To a mixture of an aldehyde (12.0 mmol) and DABCO (1.0 mmol, 0.11 mL) in MeOH (0.6 mL) was added acrylate (10.0 mmol). The solution was stirred at room temperature until the reaction was almost complete. The mixture was diluted with ethyl acetate. The organic layer was washed with water, brine, dried over Na2SO4, filtered and concentrated. The crude residue was purified by flash column chromatography over silica gel to afford the desired product.

Reference： [1]Tetrahedron Letters,2019,vol. 60,p. 953 - 956

65
[ 5192-23-4 ]
[ 6287-86-1 ]
[ 762-21-0 ]
diethyl 3-(4-(ethoxycarbonyl)phenyl)-1H-azepino[4,3,2-cd]indole-4,5-dicarboxylate [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2019,vol. 17,p. 5982 - 5989

66
C₁₈H₁₈O₃ [ No CAS ]
[ 6287-86-1 ]

Yield	Reaction Conditions	Operation in experiment
78%	With iron(II,III) oxide; 1,1,1,3,3-pentamethyl-1,3-disiloxane; In isopropyl alcohol; at 80℃; for 24h;	In the air, a 25 mL reaction flask was sequentially charged with triiron teoxide (0.05 mmol) and alkene 1z (0.5 mmol).Pentamethyldisiloxane (2.0mmol),Isopropyl alcohol (2.0 mL). After mixing at room temperature,The reaction mixture was reacted at 80 C for 24 h.At the end of the reaction, direct chromatographic separation gave a yield of 78%.

Reference： [1]Patent: CN109796293,2019,A .Location in patent: Paragraph 0111-0113; 0151

67
[ 6287-86-1 ]
[ 64747-71-3 ]

Yield	Reaction Conditions	Operation in experiment
	With diethylamino-sulfur trifluoride In dichloromethane at 20℃; for 12h;

Reference： [1]Zhang, Xue; Ling, Liang; Luo, Meiming; Zeng, Xiaoming [Angewandte Chemie - International Edition, 2019, vol. 58, # 47, p. 16785 - 16789][Angew. Chem., 2019, vol. 131, p. 16941 - 16945,5]

68
[ 713-57-5 ]
[ 6287-86-1 ]

Yield	Reaction Conditions	Operation in experiment
80%	With 1,2-bis(2,4,8,10-tetra-tert-butyl-5,7-dioxa-6-phosphadibenzo[a,c]cyclohepten-6-yloxy)ethane; methylphenylsilane; propionic acid anhydride; copper dichloride; In toluene; at 45℃; for 10h;Schlenk technique; Inert atmosphere;	Add 4- (ethoxycarbonyl) benzoic acid (146 mg, 1.0 mmol) to a dry 10 mL Schlenk reaction tube, and then add L1 (58 mg, 0.05 mmol) and CuCl2 (8.5 mg, 0.050 mmol) in sequence. Under nitrogen protection, Toluene (2.0 mL), propionic anhydride (100 muL, 1.2 mmol) and H2SiMePh (152 muL, 1.1 mmol) were added and reacted at 45 C. for 10 h. After the reaction, the reaction was extracted, the solvent was removed under reduced pressure, and the target product E was obtained by column chromatography (petroleum ether / ethyl acetate = 15/1, volume ratio). Experimental data of the compound: isolated yield 80%

Reference： [1]Patent: CN110803984,2020,A .Location in patent: Paragraph 0044-0047

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Precautionary Statements-General
Code	Phrase
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Prevention
Code	Phrase
P201	Obtain special instructions before use.
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P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
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P230	Keep wetted
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P233	Keep container tightly closed.
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Response
Code	Phrase
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P304	IF INHALED:
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P315	Get immediate medical advice/attention.
P320
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P321
P322
P330	Rinse mouth.
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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.
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P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
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P370	In case of fire:
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P372	Explosion risk in case of fire.
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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.
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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.
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P401
P402	Store in a dry place.
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P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
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P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
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P501	Dispose of contents/container to ...
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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
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H228	Flammable solid
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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. 6287-86-1 ] {[proInfo.proName]}

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[ 6287-86-1 ] Synthesis Path-Upstream 1~3

[ 6287-86-1 ] Synthesis Path-Downstream 1~68

Related Functional Groups of [ 6287-86-1 ]

Aryls

Aldehydes

Esters

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[ 6287-86-1 ]