[ CAS No. 10160-87-9 ] {[proInfo.proName]}

Name: 10160-87-9|3,3-Diethoxyprop-1-yne|97%
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Quality Control of [ 10160-87-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 10160-87-9 ]

CAS No. :	10160-87-9	MDL No. :	MFCD00009237
Formula :	C₇H₁₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RGUXEWWHSQGVRZ-UHFFFAOYSA-N
M.W :	128.17	Pubchem ID :	66285
Synonyms :

Calculated chemistry of [ 10160-87-9 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.71
Num. rotatable bonds :	4
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	36.1
TPSA :	18.46 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) :	-6.44 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.28
Log Po/w (XLOGP3) :	0.91
Log Po/w (WLOGP) :	1.1
Log Po/w (MLOGP) :	1.22
Log Po/w (SILICOS-IT) :	1.15
Consensus Log Po/w :	1.33

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.94
Solubility :	14.6 mg/ml ; 0.114 mol/l
Class :	Very soluble
Log S (Ali) :	-0.88
Solubility :	16.8 mg/ml ; 0.131 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.04
Solubility :	11.8 mg/ml ; 0.0918 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.28

Safety of [ 10160-87-9 ]

Signal Word:	Danger	Class:	3
Precautionary Statements:	P261-P305+P351+P338	UN#:	1993
Hazard Statements:	H225-H315-H319-H335	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 10160-87-9 ]

* 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 [ 10160-87-9 ]
Downstream synthetic route of [ 10160-87-9 ]

[ 10160-87-9 ] Synthesis Path-Upstream 1~14

1
[ 10160-87-9 ]
[ 2986-19-8 ]
[ 823-09-6 ]

Reference： [1] Patent: US2455172, 1948, ,
[2] Patent: US2455172, 1948, ,

2
[ 10160-86-8 ]
[ 10160-87-9 ]

Reference： [1] Tetrahedron, 1981, vol. 37, p. 1653 - 1658
[2] Journal of the American Chemical Society, 2006, vol. 128, # 10, p. 3291 - 3302
[3] Helvetica Chimica Acta, 2009, vol. 92, # 8, p. 1626 - 1643
[4] Chemistry - A European Journal, 2004, vol. 10, # 20, p. 5087 - 5110
[5] Recueil des Travaux Chimiques des Pays-Bas, 1966, vol. 85, p. 117 - 134
[6] European Journal of Organic Chemistry, 2007, # 26, p. 4383 - 4401

3
[ 5221-17-0 ]
[ 64-17-5 ]
[ 10160-87-9 ]

Yield	Reaction Conditions	Operation in experiment
60 kg	at 82℃; for 10 h; Large scale	(2) adding sodium hydroxide in absolute ethanol solution obtained in step (1) of the product 1,Anhydrous ethanol solution was prepared from 155 kg of sodium hydroxide dissolved in 470 kg of absolute ethanol,The reaction was refluxed at 82 ° C for 10 hours, isolated and purified to obtain propyne acetal diethyl acetal;The separation and purification first using 20 ° C, centrifuge rejection filter, dried with a filter soaked in 80 kg of ethanol for 10 minutes,Then dried, and then the filtrate was added to the distillation flask, the first atmospheric distillation, steaming to the end of the temperature 100 for receiving bottles,Start decompression, slowly open big vacuum, steamed to vacuum -0.09Mpa bottom temperature 100 stop heating. Then the distillation, pressure at atmospheric pressure, reflux ratio 4: 1, packed column 600mm, the bottom temperature of 120 , after distillation, stratification,The organic phase was mixed and stirred with 10 kg of sodium hydroxide for 1 hour, then filtered with suction,The filtrate was added to the distillation unit, with -0.097Mpa vacuum, 600mm distillation column,Distillation at a reflux ratio of 4: 1. Bottom temperature 50 , temperature 42 out of qualified products, qualified products 60 kg content> 98percent moisture <0.1percent.

Reference： [1] Patent: CN106749127, 2017, A, . Location in patent: Paragraph 0057; 0061-0064; 0081; 0089-0094; 0115; 0119-0122

4
[ 408320-07-0 ]
[ 10160-87-9 ]

Reference： [1] Journal of the American Chemical Society, 1952, vol. 74, p. 2657,2661

5
[ 64-17-5 ]
[ 178425-55-3 ]
[ 10160-87-9 ]

Reference： [1] Acta Chemica Scandinavica, 1996, vol. 50, # 5, p. 446 - 453

6
[ 64-17-5 ]
[ 40745-72-0 ]
[ 10160-87-9 ]

Reference： [1] Acta Chemica Scandinavica, 1996, vol. 50, # 5, p. 446 - 453

7
[ 107-19-7 ]
[ 122-51-0 ]
[ 10160-87-9 ]

Reference： [1] Tetrahedron Letters, 2007, vol. 48, # 28, p. 4891 - 4894

8
[ 624-67-9 ]
[ 64-17-5 ]
[ 10160-87-9 ]

Reference： [1] Patent: US2879305, 1956, ,

9
[ 593-61-3 ]
[ 14444-77-0 ]
[ 10160-87-9 ]

Reference： [1] Journal of Chemical Research, Miniprint, 1981, # 11, p. 4016 - 4035

10
[ 122-51-0 ]
[ 74-86-2 ]
[ 10160-87-9 ]

Reference： [1] Journal of the American Chemical Society, 1938, vol. 60, p. 1715
[2] Bulletin de la Societe Chimique de France, 1961, p. 2387 - 2392

11
[ 22834-33-9 ]
[ 10160-87-9 ]

Reference： [1] Journal of Organic Chemistry USSR (English Translation), 1970, vol. 6, p. 421 - 426[2] Zhurnal Organicheskoi Khimii, 1970, vol. 6, p. 422 - 428

12
[ 32798-36-0 ]
[ 124-41-4 ]
[ 10160-87-9 ]

Reference： [1] Bulletin de la Societe Chimique de France, 1956, p. 425,428

13
[ 122-51-0 ]
[ 107-02-8 ]
[ 10160-87-9 ]

Reference： [1] Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1966, vol. 345, p. 52 - 60

14
[ 408320-07-0 ]
[ 865-47-4 ]
[ 75-65-0 ]
[ 10160-87-9 ]

Reference： [1] Journal of the American Chemical Society, 1952, vol. 74, p. 2657,2661

[ 10160-87-9 ] Synthesis Path-Downstream 1~38

1
[ 10160-87-9 ]
[ 124-42-5 ]
[ 5053-43-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride

Reference： [1]Current Patent Assignee: Shell Devel. Co. - US2455172, 1948, A

2
[ 5093-70-9 ]
[ 10160-87-9 ]
[ 143952-63-0 ]

Reference： [1]Synthesis,1992,p. 746 - 748

3
[ 40263-57-8 ]
[ 10160-87-9 ]
[ 108444-31-1 ]

Yield	Reaction Conditions	Operation in experiment
82%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 70℃; for 14h;Inert atmosphere;	A mixture of <strong>[40263-57-8]2-iodo-3-hydroxypyridine</strong> (1 g, 4.5 mmol, 1.0 eq), 3,3-diethoxyprop-1-yne (754.0 mg, 5.9 mmol,1.3 eq), TEA (4.1 g, 41 mmol, 9.0 eq), CuT (172 mg, 905 imol, 0.2 eq) and Pd(PPh3)2C12 (318mg, 453 imol, 0.1 eq) in 10 mL of THF was degassed and purged with N2 three times. The mixture was stirred at 70 C for 14 hours under N2 atmosphere. The reaction mixture was concentrated in vacuo. The residue was purified by column chromatography (Si02, eluting with petroleum ether: ethyl acetate = 100:1 to 2:1) to afford 820 mg of 2-(diethoxymethyl)furo[3,2- bjpyridine (3.7 mmol, 82% yield) as yellow oil.
	With copper(l) iodide; triethylamine;bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide; for 17h;	2-Iodo-3-pyridinol (24 mmol), triethylamine (1.0 eq), 3,3-diethoxy-1-propyne (1.0 eq), bis(triphenylphosphine)palladium (II) chloride (0.02 eq), and copper(I) iodide (0.04 eq) were combined in DMF (14 mL) and allowed to stir for 17 hours. The mixture was diluted with ethyl acetate (100 mL) and filtered through a Celite pad. The filtrate was washed with saturated sodium bicarbonate (2*50 mls), dried over anhydrous magnesium sulfate, filtered, and the filtrate concentrated under reduced pressure to provide the title compound which was used in the next step without further purification. 1H NMR (CDCl3, 400 MHz) δ 1.28 (t, J=7.1 Hz, 6H), 3.70 (q, J=7.1 Hz, 4H), 5.68 (s, 1H), 7.05 (s, 1H), 7.23 (dd, J=8.5, 4.8 Hz, 1H), 7.77 (d, J=8.5 Hz, 1H), 8.57 (br, 1H). MS (DCI/NH3) m/z 222 (M+H)+.
	With copper(l) iodide;bis-triphenylphosphine-palladium(II) chloride; for 17h;	[2-IODO-3-PYRIDINOL] (24 mmol), triethylamine (1.0 [EQ),] 3, [3-DIETHOXY-1-PROPYNE] (1.0 eq), bis (triphenylphosphine) palladium [(II)] chloride (0.02 [EQ),] and copper [(I)] iodide (0.04 eq) were combined in DMF (14 mL) and allowed to stir for 17 hours. The mixture was diluted with ethyl acetate (100 mL) and filtered through a Celite pad. The filtrate was washed with saturated sodium bicarbonate (2x50mls), dried over anhydrous magnesium sulfate, filtered, and the filtrate concentrated under reduced pressure to provide the title compound which was used in the next step without further [PURIFICATION.'H] NMR [(CDC13,] [400MHZ)] [5] 1.28 (t, J=7. [1HZ,] 6H), 3.70 (q, J=7. [1HZ,] 4H), 5.68 (s, 1H), 7.05 (s, [1H),] 7.23 (dd, J=8.5, 4.8Hz, [1H),] 7.77 (d, J=8. 5Hz, 1H), 8.57 (br, 1H). MS (DCI/NH3) [M/Z] 222 (M+H) [+.]

Reference： [1]Synthesis,1986,p. 749 - 751
[2]Patent: WO2018/119395,2018,A1 .Location in patent: Page/Page column 184
[3]Patent: US2006/172995,2006,A1 .Location in patent: Page/Page column 56
[4]Patent: WO2003/101994,2003,A1 .Location in patent: Page 92-93

4
[ 7341-96-0 ]
[ 10160-87-9 ]
[ 55484-95-2 ]

Reference： [1]Phytochemistry,1985,vol. 24,p. 553 - 560

5
[ 10160-87-9 ]
[ 4044-58-0 ]
[ 62358-84-3 ]

Reference： [1]Journal of Organic Chemistry,1977,vol. 42,p. 2626 - 2629

6
[ 10160-87-9 ]
[ 1956-30-5 ]
[ 181224-62-4 ]

Reference： [1]Helvetica Chimica Acta,1996,vol. 79,p. 1462 - 1474

7
[ 10160-87-9 ]
[ 7803-49-8 ]
[ 288-14-2 ]

Reference： [1]Chemische Berichte,1903,vol. 36,p. 3671

8
[ 18671-97-1 ]
[ 10160-87-9 ]
[ 352197-19-4 ]

Reference： [1]Journal of the Chemical Society. Perkin Transactions 1 (2001),2001,p. 978 - 984

9
[ 55686-93-6 ]
[ 10160-87-9 ]
7-Methoxy-2-(3,3-diethoxypropyn-1-yl)quinoxaline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With copper(l) iodide; triethylamine; triphenylphosphine In acetonitrile at 20℃;

Reference： [1]Armengol; Joule [Journal of the Chemical Society. Perkin Transactions 1 (2001), 2001, # 9, p. 978 - 984]

10
[ 10160-87-9 ]
[ 143468-13-7 ]
6-(3,3-diethoxy-prop-1-ynyl)-1<i>H</i>-pyrrolo[2,3-<i>b</i>]pyridine [ No CAS ]

Reference： [1]Synlett,2001,p. 609 - 612

11
[ 778-28-9 ]
[ 10160-87-9 ]
[ 18232-30-9 ]

Reference： [1]Tetrahedron Letters,2002,vol. 43,p. 5641 - 5644

12
[ 64248-56-2 ]
[ 10160-87-9 ]
1-(2,6-difluorophenyl)-3,3-diethoxyprop-1-yne [ No CAS ]

Reference： [1]Tetrahedron,2005,vol. 61,p. 9839 - 9847

13
[ 10160-87-9 ]
[ 314084-61-2 ]
1-(2,6-diethyl-4-methylphenyl)-3,3-diethoxyprop-1-yne [ No CAS ]

Reference： [1]Tetrahedron,2005,vol. 61,p. 9839 - 9847

14
[ 10160-87-9 ]
[ 61676-62-8 ]
[ 159087-48-6 ]

Yield	Reaction Conditions	Operation in experiment
60%	Stage #1: Propiolaldehyde diethyl acetal With n-butyllithium In diethyl ether; hexane at -78℃; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In diethyl ether; hexane at -78℃; for 2h;

Reference： [1]Posseme, Francoise; Deligny, Michael; Carreaux, Francois; Carboni, Bertrand [Journal of Organic Chemistry, 2007, vol. 72, # 3, p. 984 - 989]

15
[ 10160-87-9 ]
[ 78191-00-1 ]
[ 55402-04-5 ]

Yield	Reaction Conditions	Operation in experiment
72%		Propargylaldehyde diethylacetal (40 g, 312 mmol) was dissolved in THF (200 mL) under argon and cooled to -70° C. Then a 1.6 M solution of n-butyllithium in hexane (234 mL, 374 mmol) was added and stirring continued for 30 min at -30° C. Then N-methoxy-N-methylacetamide (38.6 g, 374 mmol) in THF (10 mL) was added. After 30 min at -30° C., the reaction was quenched by addition of saturated NH4Cl solution (20 mL). The product was extracted with AcOEt (2.x.200 mL), saturated solution of NH4Cl (2.x.200 mL), dried and concentrated. Chromatography on silica gel with a heptane/ethyl acetate gradient 100:0 to 95:5 gave 38.5 g (72percent) of a colorless oil. GC/MS: m/z=232(M).
72%		Propargylaldehyde diethylacetal (40 g, 312 mmol) was dissolved in THF (200 mL) under argon and cooled to-70 °C. Then a 1.6 M solution of n-butyllithium in hexane (234 mL, 374 mmol) was added and stirring continued for 30 min at-30 °C. Then N-methoxy-N- methylacetamide (38. 6 g, 374 mmol) in THF (10 mL) was added. After 30 min at-30 °C, the reaction was quenched by addition of saturated NH4C1 solution (20 mL). The product was extracted with AcOEt (2 x 200 mL), saturated solution of NH4Cl (2 x 200 mL), dried and concentrated. Chromatography on silica gel with a heptane/ethyl acetate gradient 100: 0 to 95: 5 gave 38.5 g (72 percent) of a colorless oil. GC/MS: m/z = 232 (M).

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 377 - 380
[2]Patent: US2005/197337,2005,A1 .Location in patent: Page/Page column 11
[3]Patent: WO2005/94828,2005,A1 .Location in patent: Page/Page column 24
[4]Synlett,2008,p. 3036 - 3040

16
[ 10160-87-9 ]
[ 66-25-1 ]
[ 3777-69-3 ]

Yield	Reaction Conditions	Operation in experiment
75%	Stage #1: Propiolaldehyde diethyl acetal With n-butyllithium In diethyl ether; hexane at 20℃; for 1h; Stage #2: hexanal With titanium(IV) isopropylate; isopropylmagnesium chloride In diethyl ether; hexane at -40 - -35℃; for 2.5h; Stage #3: With hydrogenchloride Further stages.;

Reference： [1]Eom, Deok Ki; Choi, Seong Jib; An, Duk Keun [Heterocycles, 2007, vol. 71, # 5, p. 1141 - 1146]

17
[ 10160-87-9 ]
[ 211029-67-3 ]
[ 853685-76-4 ]

Yield	Reaction Conditions	Operation in experiment
		2-(Diethoxymethyl)-1H-pyrrolo[3,2-c]pyridine-1-carboxylic acid 1,1-dimethylethyl ester, 8b-1 (Scheme 3, step h) Heat a solution of (3-iodo-pyridin-4-yl)carbamic acid 1,1-dimethylethyl ester (13.3 g, 41.56 mmol, Darnbrough, Shelley; Mervic, Miljenko; Condon, Stephen M.; Burns, Christopher J. Synthetic Communications (2001) 31(21), 3273-3280), 3,3-diethoxy-1-propyne (5.96 ml, 41.56 mmole), triethylamine (23 ml, 166 mmol), dichlorobis(triphenyl-phospine)palladium(II) (1.46 g, 2.08 mmol) and copper iodide (237 mg, 1.25 mmol) in dry DMF under argon to 90 C. for 3 h. Allow the reaction mixture to cool to 70 C. and add DBU (12.5 ml, 83.12 mmol). Stir the reaction at 70 C. for 3 h and then stir at room temperature overnight. Pour the reaction mixture into EtOAc, wash with water (2*) and brine, dry over MgSO4, filter and concentrate to give the title compound as an oil. Purify the oil by flash chromatography (silica, elute with 10-20% EtOAc/n-heptane) to provide 9.8 g of the title compound as a clear oil, tlc (silica, 30% EtOAc/heptane, Rf=0.30).

Reference： [1]Patent: US2005/131012,2005,A1 .Location in patent: Page/Page column 11; 20

18
[ 40263-57-8 ]
bis(triphenylphosphine)palladium(II) dichloride [ No CAS ]
[ 10160-87-9 ]
[ 108444-31-1 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine;copper(I) iodide; In N,N-dimethyl-formamide;	EXAMPLE 35a 2-(diethoxymethyl)furo[3,2-b]pyridine 2-Iodo-3-pyridinol (24 mmol), triethylamine (1.0 eq), 3,3-diethoxy-1-propyne (1.0 eq), bis(triphenylphosphine)palladium (II) chloride (0.02 eq), and copper(I) iodide (0.04 eq) were combined in DMF (14 mL) and allowed to stir for 17 hours. The mixture was diluted with ethyl acetate (100 mL) and filtered through a Celite pad. The filtrate was washed with saturated sodium bicarbonate (2*50 mls), dried over anhydrous magnesium sulfate, filtered, and the filtrate concentrated under reduced pressure to provide the title compound which was used in the next step without further purification. 1H NMR (CDCl3, 400 MHz) δ1.28 (t, J=7.1 Hz, 6H), 3.70 (q, J=7.1 Hz, 4H), 5.68 (s, 1H), 7.05 (s, 1H), 7.23 (dd, J=8.5, 4.8 Hz, 1H), 7.77 (d, J=8.5 Hz, 1H), 8.57 (br, 1H). MS (DCI/NH3) m/z 222 (M+H)+.

Reference： [1]Patent: US2004/2488,2004,A1

19
[ 10160-87-9 ]
[ 113778-69-1 ]
[ 81535-81-1 ]

Reference： [1]Synlett,2008,p. 3036 - 3040

20
[ 10160-87-9 ]
[ 124150-87-4 ]
[ 1111316-27-8 ]

Yield	Reaction Conditions	Operation in experiment
91%	Stage #1: Propiolaldehyde diethyl acetal With n-butyllithium In tetrahydrofuran; hexane at -78℃; Stage #2: tert-butyldimethylsilyl (R)-glycidyl ether In tetrahydrofuran; hexane at -78℃; Stage #3: With boron trifluoride diethyl etherate In tetrahydrofuran; hexane at -78 - -30℃;

Reference： [1]Nagasawa, Tomohiro; Kuwahara, Shigefumi [Organic Letters, 2009, vol. 11, # 3, p. 761 - 764]

21
[ 10160-87-9 ]
[ 6214-35-3 ]
[ 1188414-01-8 ]

Yield	Reaction Conditions	Operation in experiment
75%	With copper(l) iodide; palladium 10% on activated carbon; triethylamine; triphenylphosphine; In 1,4-dioxane; at 25 - 80℃; for 3.5h;Inert atmosphere;	General procedure: (a) The reaction was performed in a bigger scale using 100 mg of 10% Pd/C (0.092 mmol), PPh3 (0.37 mmol), CuI (0.184 mmol), Et3N (10.68 mmol), compound 1a (3.56 mmol), and acetylenic compound 2a (5.32 mmol) in 1,4-dioxane (20.0 mL). After stirring at 80 C for 3 h under nitrogen the mixture was cooled to room temperature. The Pd/C was filtered off and washed with water (2 10 mL), acetone (2 10 mL), and EtOAc (2 10 mL). Then the catalyst was collected, dried at 100 C in an oven, and reused for the next run. The co-catalyst CuI along with PPh3 was added in every repeated run. (b) General method for the preparation of 3: A mixture of compound 1 (0.89 mmol), 10% Pd/C (0.023 mmol), PPh3 (0.092 mmol), CuI (0.046 mmol), and Et3N (2.67 mmol) in 1,4-dioxane (5.0 mL) was stirred at 25 C for 30 min under nitrogen. The acetylenic compound 2 (1.33 mmol) was added slowly with stirring. The mixture was then stirred at 80 C for 3 h, cooled to room temperature, diluted with EtOAc (30 mL), and filtered through celite. The filtrate was collected and concentrated. The residue was purified by column chromatography (2-15% EtOAc/hexane) to afford the desired product

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 2151 - 2155
[2]Advanced Synthesis and Catalysis,2009,vol. 351,p. 779 - 788

22
[ 10160-87-9 ]
[ 147356-78-3 ]
[ 863672-50-8 ]

Yield	Reaction Conditions	Operation in experiment
43%		3,3-Diethoxy-1-propyne (10 mL, 70 mmol) was dissolved under argon in THF (150 mL) and cooled to -70 C. Then a 1.6 M solution of n-butyllithium in hexane (48 mL, 77 mmol) was added slowly at -70 C., then allowed to warm to -30 C. and stirred at -30 C. for 30 min, then cooled again to -70 C. Cyclopropanecarboxylic acid methoxy-methyl-amide (10 g, 77 mmol) was added at once at -70 C. (the temperature rose to -50) then stirred without cooling until 0 C. was reached, then quenched with sat. NH4Cl solution (20 mL). Extraction: 2×AcOEt, 1× sat. NH4Cl, 1× sat. NaCl. The crude brown oil (15 g) was purified by chromatography on silica gel in heptane/ethyl acetate 10:1. One obtained 6 g (43%) of a yellowish oil. MS: m/z=151(M).
43%		3, 3-Diethoxy-l-propyne (10 mL, 70 mmol) was dissolved under argon in THF (150 mL) and cooled to-70 C. Then a 1.6 M solution of n-butyllithium in hexane (48 mL, 77 mmol) was added slowly at-70 C, then allowed to warm to-30 C and stirred at-30 C for 30 min, then cooled again to-70 C. Cyclopropanecarboxylic acid methoxy-methyl- amide (10 g, 77 mmol) was added at once at-70 C (the temperature rose to-50 ) then stirred without cooling until 0 C was reached, then quenched with sat. NH4C1 solution (20 mL). Extraction: 2 x AcOEt, 1 x sat. NH4C1, 1 x sat. NaCl. The crude brown oil (15 g) was purified by chromatography on silica gel in heptane/ethyl acetate 10: 1. One obtained 6 g (43 %) of a yellowish oil. MS: m/z = 151 (M).

Reference： [1]Patent: US2005/197337,2005,A1 .Location in patent: Page/Page column 12-13
[2]Patent: WO2005/94828,2005,A1 .Location in patent: Page/Page column 24

23
[ 10160-87-9 ]
[ 13686-33-4 ]
[ 1257633-67-2 ]

Yield	Reaction Conditions	Operation in experiment
	With copper(ll) sulfate pentahydrate; sodium hydrogencarbonate; sodium L-ascorbate; In water; tert-butyl alcohol;	Synthesis of 1-tert-butyl-4-(diethoxymethyl)-1H-1,2,3-triazole (FIG. 11) To a 20-mL screw-capped scintillation vial equipped with a stirring bar were added 3,3-diethoxy-1-propyne (1.50 g, 11.8 mmol, 1.0 eq) and tert-butyl azide (1.34 g, 13.5 mmol, 1.15 eq) in 10 mL 1:1 mixture of tert-butyl alcohol and water. Sodium bicarbonate (1.40 g, 16.7 mmol, 1.41 eq), copper(II) sulfate pentahydrate (0.143 g, 0.57 mmol, 5.0 mol %), and sodium ascorbate (0.47 g, 2.35 mmol, 20 mol %) were added to the mixture. The reaction was stirred vigorously overnight, and TLC analysis indicated the formation of a new product (Rf=0.7 in ethyl acetate, KMnO4 stain). EDTA (2 mL, 0.5 M, pH=8) was added, the reaction mixture was diluted with EtOAc (90 mL), washed with sat aq NaHCO3 (250 mL), water (210 mL), and brine (30 mL). The combined organic phases were dried over anhydrous MgSO4, filtered, and concd in vacuo to provide 2.54 g of a light yellow oil (yield: 95%). The crude product was used without further purification. 1H NMR (300 MHz, CDCl3) delta 7.64 (s, 1H), 5.71 (s, 1H), 3.78-3.60 (m, 4H), 1.67 (s, 9H), 1.25 (t, J=7.0 Hz, 6H); 13C NMR (75 MHz, CDCl3) 146.5, 118.9, 97.2, 61.9, 59.4, 30.1, 15.2; HRMS cacld for [M+Na]- C11H21N3NaO2 250.1531, found 250.1531.
	With copper(ll) sulfate pentahydrate; sodium hydrogencarbonate; sodium L-ascorbate; In water; tert-butyl alcohol;	To a 20-mL screw-capped scintillation vial equipped with a stirring bar were added 3,3-diethoxy-1-propyne (1.50 g, 11.8 mmol, 10 eq) and tert-butyl azide (1.34 g, 13.5 mmol, 1.15 eq) in 10 mL 1:1 mixture of tertbutyl alcohol and water Sodium bicarbonate (1.40 g, 16.7 mmol, 1.41 eq), copper(II) sulfate pentahydrate (0.143 g, 0.57 mmol, 5.0 mol %), and sodium ascorbate (0.47 g, 2.35 mmol, 20 mol %) were added to the mixture. The reaction was stirred overnight, and then EDTA (2 mL, 0.5 M, pH=8) was added. The resulting mixture was diluted with EtOAc (90 mL), washed with sat. aq NaHCO3 (100 mL), water (50 mL), and brine (50 mL). The combined organic phases were dried over anhydrous MgSO4. Solvent was removed and the residue was used in the next step without purification. 1H NMR complies with the reported value.

Reference： [1]Journal of the American Chemical Society,2010,vol. 132,p. 16893 - 16899
[2]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 3485 - 3488
[3]Patent: US2013/295019,2013,A1 .Location in patent: Paragraph 0062; 0063
[4]Chemical Communications,2015,vol. 51,p. 17072 - 17075
[5]Patent: US2017/297008,2017,A1 .Location in patent: Paragraph 0055

24
[ 10160-87-9 ]
[ 622-37-7 ]
[ 1257633-67-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 3485 - 3488

25
[ 90272-84-7 ]
[ 10160-87-9 ]
[ 1431880-03-3 ]

Reference： [1]Chemical Communications,2013,vol. 49,p. 4343 - 4345

26
[ 10160-87-9 ]
[ 79839-49-9 ]
[ 1539295-71-0 ]
[ 1539295-99-2 ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 1302 - 1304

27
[ 10160-87-9 ]
[ 193354-13-1 ]
5-(3,3-diethoxyprop-1-ynyl)indolin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; In tetrahydrofuran; at 50.0℃; for 4.0h;	Reference Example 21 Production of 5-(1-phenyl-1H-pyrazol-5-yl)indolin-2-one To a solution of 5-iodo-2-oxoindoline (497 mg, 1.9 mmol) in THF (20 ml) were added triethylamine (0.80 ml, 5.7 mmol), 3,3-diethoxyprop-1-yne (738 mg, 5.7 mmol), CuI (73 mg, 0.38 mmol) and Pd(PPh3)4 (222 mg, 0.19 mmol). The reaction mixture was stirred for 4 h at 50 C. The mixture was poured into H2O and EtOAc. The mixture was separated into an aqueous layer and an organic layer. The aqueous layer was extracted with ethyl acetate 3 times. The combined organic layer was washed with sat. NaHCO3 solution, and brine, and then dried over Na2SO4. The solvent was evaporated and the residue purified by column chromatography (EtOAc then CHCl3/MeOH) to give 5-(3,3-diethoxyprop-1-ynyl)indolin-2-one as a brown solid (292 mg, 59%). 1H NMR (400 MHz, DMSO-d6) delta 7.73 (s, 1H), 7.19 (d, 1H, J=8.0 Hz), 7.16 (s, 1H), 6.63 (d, 1H, J=8.0 Hz), 5.31 (s, 1H), 3.64 (dq, 2H, J=9.4, 7.1 Hz), 3.48 (dq, 2H, J=9.4, 7.1 Hz), 3.34 (s, 2H), 1.10 (t, 6H, J=7.1 Hz).

Reference： [1]Patent: US2014/275076,2014,A1 .Location in patent: Paragraph 0358; 0359; 0360

28
[ 7153-08-4 ]
[ 10160-87-9 ]
2-(diethoxymethyl)-7-iodofuro[3,2-c]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With pyridine; copper(II) oxide; for 12h;Reflux; Inert atmosphere;	A solution prepared by dissolving <strong>[7153-08-4]3,5-diiodopyridin-4-ol</strong> (20.0 mmol) in anhydrous pyridine (50 ml) was added with propargyl aldehyde diethyl acetal (24.0 mmol) and copper(II) oxide (14.0 mmol), and stirred under reflux for 12 hours under a nitrogen atmosphere. The reaction solution thus obtained was cooled to room temperature, filtered, and the filtrate was concentrated under reduced pressure. The residue was diluted with ethyl acetate, washed with aqueous ammonia, water and brine, in sequence, which was then dried over anhydrous magnesium sulfate and filtered. After the filtrate was concentrated under reduced pressure, the residue thus obtained was purified by silica gel column chromatography (n-hexane/ethyl acetate=10/1, v/v) to obtain the title compound as a light brown solid (yield: 87%).
87%	With pyridine; copper(II) oxide; for 12h;Reflux; Inert atmosphere;	Reference Example 1 2-(Diethoxymethyl)-7-iodofuro[3,2-c]pyridine A solution prepared by dissolving <strong>[7153-08-4]3,5-diiodopyridin-4-ol</strong> (20.0 mmol) in anhydrous pyridine (50 ml) was added with propargyl aldehyde diethyl acetal (24.0 mmol) and copper(II) oxide (14.0 mmol), and stirred under reflux for 12 hours under a nitrogen atmosphere. The reaction solution thus obtained was cooled to room temperature, filtered, and the filtrate was concentrated under reduced pressure. The residue was diluted with ethyl acetate, washed with aqueous ammonia, water and brine, in sequence, which was then dried over anhydrous magnesium sulfate and filtered. After the filtrate was concentrated under reduced pressure, the residue thus obtained was purified by silica gel column chromatography (n-hexane/ethyl acetate=10/1, v/v) to obtain the title compound as a light brown solid (yield: 87%). 1H NMR (CDCl3, 300 MHz) delta 8.78 (s, 1H), 8.72 (s, 1H), 6.99 (s, 1H), 5.69 (s, 1H), 3.69 (m, 4H), 1.28 (t, 6H)

Reference： [1]Patent: EP2876109,2015,A1 .Location in patent: Paragraph 0094-0095
[2]Patent: US2015/191478,2015,A1 .Location in patent: Paragraph 0191-0192

29
[ 10160-87-9 ]
[ 4181-20-8 ]
C₃₉H₄₅NO₆ [ No CAS ]

Reference： [1]Journal of Materials Chemistry C,2015,vol. 3,p. 7345 - 7355

30
[ 10160-87-9 ]
[ 3747-74-8 ]
2-((4-(diethoxymethyl)-1H-1,2,3-triazol-1-yl)methyl)quinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With copper(l) iodide; sodium azide; sodium carbonate; In methanol; water; at 50℃; for 20h;	General procedure: <strong>[3747-74-8]2-(Chloromethyl)quinoline hydrochloride</strong> (428 mg, 2 mmol), Na2CO3 (210 mg, 2 mmol), NaN3(143 mg, 2.4 mmol), alkyne (4 mmol) and CuI (23 mg, 0.12 mmol) were placed in a reaction tubecontaining a mixed solvent of CH3OH/H2O (1:1 v:v, 4 mL). Each reaction was stirred at 50 C for 20 hon a MultiMax reactor. The alkynes, 3,3-diethoxy-1-propyne, 3-ethynyltoluene and 4-ethynyltoluenewere used for the synthesis of 1-3, respectively. (Scheme 2) On completion, each mixture wasextracted with ethyl acetate three times. The combined organic extract was washed with brine,concentrated and purified by column chromatography on silica. 2-((4-(diethoxymethyl)-1H-1,2,3-triazol-1-yl)methyl)quinoline (1), C17H20N4O2, 312.37. Yield: 560 mg, 90%. ESI-MS (m/z, %): [1 + H]+(313, 100). Main IR bands (cm-1): 3111 (m), 3069 (m), 2976 (m), 2926 (m), 2904 (m), 2878 (m), 1618 (m),1598 (m), 1567 (m), 1506 (m), 1455 (m), 1426 (m), 1385 (m), 1345 (m), 1320 (m), 1309 (m), 1271 (m),1225 (m), 1178 (m), 1117 (m), 1097 (m), 1061 (s), 1050 (s), 1038 (m), 1021 (m), 1004 (m), 910 (m),873 (m), 847 (m), 823 (m), 803 (m), 778 (m), 745 (m), 734 (m), 618 (m), 491 (m), 479 (m) and 432 (m).The bands among 1004-1117 cm-1 should be attributed to the C-O stretching vibrations. 1H-NMR(CDCl3, 500.2 MHz) delta 8.15 and 8.13 (d, 1H, J = 9 Hz), 8.07 and 8.05 (d, 1H, J = 9 Hz), 7.82 and 7.80(d, 1H, J = 8 Hz), 7.76-7.73 (m, 2H), 7.58-7.55 (m, 1H), 7.28 and 7.27 (d, 1H, J = 9 Hz), 5.83 (s, 2H,quinoline-CH2), 5.71 (1H, CHO2), 3.73-3.56 (m, 4H, CH2CH3), 1.22, 1.21 and 1.19 (t, 6H, CH3).13C-NMR (CDCl3, 125.8 MHz) delta 154.6, 147.85, 147.77, 137.8, 130.3, 129.3, 127.8, 127.7, 127.3, 122.8 and119.7 (quinoline and triazole groups), 96.9, 61.8, 56.5 (quinoline-CH2-triazole) and 15.2.

Reference： [1]Molecules,2017,vol. 22

31
[ 10160-87-9 ]
[ 88-82-4 ]
3-diethoxymethyl-5,7-diiodoisocoumarin [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2017,vol. 2017,p. 6131 - 6136

32
[ 10160-87-9 ]
[ 13544-44-0 ]
2,4-dichloro-5-(3,3-diethoxyprop-1-yn-1-yl)pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.1 g		Under N2 atmosphere, to a solution of <strong>[13544-44-0]2,4-dichloro-5-iodopyrimidine</strong> (253, 1 g, 3.65 mmol) and DIEA (1.42 g, 10.99 mmol) in THF (20 mL) was added CuT (70 mg, 0.37 mmol)and Pd(PPh3)2C12 (100 mg, 0.14 mmol). After stirring at room temperature for 10 mm,solution of 3,3-diethoxyprop-1-yne (470 mg, 3.67 mmol) in THF (5 mL) was added. After stirring at room temperature for 12 h, the reaction mixture was quenched with water (20 mL) and extracted with EtOAc (20 mL x 2). The combined organic phases were concentratedvacuo. The resulting residue was purified by column chromatography to provide 2,4-dichloro-5-(3,3-diethoxyprop-1-yn-1-yl)pyrimidine (254, 1.1 g, 4.0 mmol).

Reference： [1]Patent: WO2018/5860,2018,A1 .Location in patent: Page/Page column 172; 194

33
[ 10160-87-9 ]
[ 2296-23-3 ]
3-(3,3-diethoxyprop-1-yn-1-yl)-4-hydroxybenzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 16h;Inert atmosphere;	Reference Example 33-1 3-(3,3-Diethoxyprop-1-yn-1-yl)-4-hydroxybenzonitrile In a nitrogen atmosphere, <strong>[2296-23-3]4-hydroxy-3-iodobenzonitrile</strong> (600 mg, 2.5 mmol), 3,3-diethoxypropyne (388 muL, 2.7 mmol), triethylamine (374 muL, 2.7 mmol), copper(I) iodide (19 mg, 0.10 mmol), and bis(triphenylphosphine)palladium (II) dichloride (34 mg, 0.048 mmol) were dissolved in DMF (2.5 mL), and the solution was stirred for 16 hours at room temperature. Water was added to the reaction liquid, the mixture was stirred for a while, and then the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and was dried over anhydrous sodium sulfate. Insoluble materials were filtered, and then the solvent was distilled off under reduced pressure. A residue thus obtained was purified by silica gel column chromatography (hexane:ethyl acetate) (concentration gradient: 29% to 50%), and thus the title compound (brown oily material, 356 mg, 59%) was obtained. 1H NMR(CDCl3, 400MHz):delta=1.28(t, 6H, J=7Hz), 3.6-3.8(m, 4H), 5.67(s, 1H), 6.87(s, 1H), 7.57(s, 2H), 7.9-8.0(m, 1H).

Reference： [1]Patent: EP3404021,2018,A1 .Location in patent: Paragraph 0194

34
[ 10160-87-9 ]
[ 60811-18-9 ]
C₁₃H₁₄ClFO₂ [ No CAS ]

Reference： [1]Chemical Science,2019,vol. 10,p. 3481 - 3485

35
[ 10160-87-9 ]
[ 7745-93-9 ]
C₁₄H₁₇NO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With di-tert-butyl(2,2-diphenyl-1-methyl-1-cyclopropyl)phosphine; potassium phosphate monohydrate; bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)] In water at 45℃; for 51h; Inert atmosphere;

Reference： [1]Jin, Bo; Gallou, Fabrice; Reilly, John; Lipshutz, Bruce H. [Chemical Science, 2019, vol. 10, # 12, p. 3481 - 3485]

36
[ 10160-87-9 ]
[ 35371-03-0 ]
C₁₄H₁₈O₂S [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 3594 - 3599

37
[ 1010100-26-1 ]
[ 10160-87-9 ]
3-[5-(3,3-diethoxyprop-1-yn-1-yl)-1-oxo-3H-isoindol-2-yl]piperidine-2,6-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52.34%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 65℃; for 3h; Sealed tube;	1 Step 1: Preparation of 3-(5-(3,3-diethoxyprop-1-yn-1-yl)-1-oxoisoindolin-2- yl)piperidine-2,6-dione Into a 30-mL sealed tube, was placed 3-(5-bromo-1-oxo-3H-isoindol-2-yl)piperidine- 2,6-dione (2.00 g, 6.189 mmol, 1.00 equiv), Dimethyl Formamide (15.00 mL), CuI (0.12 g, 0.619 mmol, 0.10 equiv), Diisopropylethylamine (2.40 g, 18.567 mmol, 3.00 equiv), (3488) Pd(PPh3)2Cl2 (0.43 g, 0.619 mmol, 0.10 equiv), 3,3-diethoxy-propyne (1.19 g, 9.284 mmol, 1.50 equiv). The resulting solution was stirred for 3 h at 65 in an oil bath. The reaction was then quenched by the addition of water (20 mL). The resulting solution was extracted with ethyl acetate (2x20 mL). The resulting mixture was washed with brine (2 x10 mL). The mixture was dried over anhydrous sodium sulfate. The residue was applied onto a silica gel column with dichloromethane/methanol (10/1). The collected fractions were combined and concentrated under vacuum. This resulted in 1.2 g (52.34%) of 3-[5-(3,3-diethoxyprop-1-yn-1-yl)-1-oxo-3H- isoindol-2-yl]piperidine-2,6-dione as a yellow solid. LC/MS (ESI) m/z: 371.05 [M+1] +.
52%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 65℃; for 3h; Sealed tube;	Step 2: Synthesis of 3-[5-(3,3-diethoxyprop-1-yn-1-yl)-1-oxo-3H-isoindol-2- yl]piperidine-2,6-dione Into a 30-mL sealed tube, was placed 3-(5-bromo-1-oxo-3H-isoindol-2-yl)piperidine- 2,6-dione (2.00 g, 6.19 mmol, 1.00 equiv), DMF (15.00 mL), CuI (0.12 g, 0.619 mmol, 0.10 equiv), DIEA (2.40 g, 18.57 mmol, 3.00 equiv), Pd(PPh3)2Cl2 (0.43 g, 0.62 mmol, 0.10 equiv), 3,3-diethoxy-propyne (1.19 g, 9.28 mmol, 1.50 equiv). The resulting solution was stirred for 3 h at 65 in an oil bath. The reaction was then quenched by the addition of water (20 mL). The resulting solution was extracted with ethyl acetate (2x40 mL). The resulting mixture was washed with brine (1 x 20 ml). The mixture was dried over anhydrous sodium sulfate. The residue was applied onto a silica gel column eluting with dichloromethane/methanol (10/1). The collected fractions were combined and concentrated under vacuum. This resulted in 1.2 g (52 %) of 3-[5- (3,3-diethoxyprop-1-yn-1-yl)-1-oxo-3H-isoindol-2-yl]piperidine-2,6-dione as a yellow solid. MS (ES+): m/z 371.05 [MH+].
41.6%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide Inert atmosphere;	34 Example 34: Synthesis of 3-(5-(3-(4-(4-((5-chloro-4-((2- (isopropylsulfonyl)phenyl)amino)pyrimidin-2-yl)amino)-5-methoxy-2- methylphenyl)piperidin-1-yl)prop-1-yn-1-yl)-1-oxoisoindolin-2-yl)piperidine-2,6-dione (97) 3,3-diethoxyprop-1-yne (620.0 mg, 4.8 mmol), Pd(PPh3)2Cl2 (225.0 mg, 0.32 mmol), CuI (60.0 mg, 0.32 mmol) and Et3N (969.0 mg, 9.6 mmol) were added to a solution of 3-(5-bromo-1-oxoisoindolin-2-yl)piperidine-2,6-dione (1.0 g, 3.2 mmol) in DMF (10 mL). The resulting mixture stirred at 70°C under N2 for 16 hours. After TLC showed reaction completion, the reaction solution was diluted with H2O and extracted twice with EtOAc, washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM:MeOH = 20:1) to afford 3-(5-(3,3-diethoxyprop-1-yn-1-yl)-1- oxoisoindolin-2-yl)piperidine-2,6-dione as a white solid (500 mg, 41.6%). ESI-MS (EI+, m/z): 371.25.

Reference： [1]Current Patent Assignee: YALE UNIVERSITY; ARVINAS - WO2020/51564, 2020, A1 Location in patent: Paragraph 1908; 1909
[2]Current Patent Assignee: ARVINAS - WO2021/77010, 2021, A1 Location in patent: Paragraph 00641; 00642
[3]Current Patent Assignee: DANA-FARBER CANCER INSTITUTE - WO2021/173677, 2021, A1 Location in patent: Paragraph 00300-00301

38
[ 10160-87-9 ]
[ 20383-28-2 ]
(R)-4,4-diethoxy-N,N-diisopropyl-1-phenylbut-2-yn-1-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	Stage #1: N,N-diisopropyl benzamide With bis(triphenylphosphine)carbonyliridium(I) chloride; H₂SiEt₂ In toluene at 20℃; for 0.166667h; Schlenk technique; Glovebox; Stage #2: Propiolaldehyde diethyl acetal With copper(l) iodide; (R)-BTFM-Garphos; triethylamine In toluene at 20℃; for 1h; Schlenk technique; Glovebox; enantioselective reaction;

Reference： [1]Huang, Pei-Qiang; Li, Zhaokun; Ou, Wei; Wang, Xiaoming; Zhao, Feng [Angewandte Chemie - International Edition, 2021, vol. 60, # 51, p. 26604 - 26609][Angew. Chem., 2021, vol. 133, # 51, p. 26808 - 26813]

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