[ CAS No. 63478-76-2 ] {[proInfo.proName]}

Name: 63478-76-2|6-Heptyn-1-ol|97%
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Quality Control of [ 63478-76-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 63478-76-2 ]

Product Details of [ 63478-76-2 ]

CAS No. :	63478-76-2	MDL No. :	MFCD00049198
Formula :	C₇H₁₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BVRCLEXKQNWTDK-UHFFFAOYSA-N
M.W :	112.17	Pubchem ID :	11007849
Synonyms :

Calculated chemistry of [ 63478-76-2 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.71
Num. rotatable bonds :	4
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	35.09
TPSA :	20.23 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) :	-6.01 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.08
Log Po/w (XLOGP3) :	1.37
Log Po/w (WLOGP) :	1.25
Log Po/w (MLOGP) :	1.74
Log Po/w (SILICOS-IT) :	1.54
Consensus Log Po/w :	1.6

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.13
Solubility :	8.23 mg/ml ; 0.0734 mol/l
Class :	Very soluble
Log S (Ali) :	-1.4
Solubility :	4.49 mg/ml ; 0.04 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.35
Solubility :	4.99 mg/ml ; 0.0445 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.54

Safety of [ 63478-76-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P301+P312-P302+P352-P304+P340-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 63478-76-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 63478-76-2 ]

[ 63478-76-2 ] Synthesis Path-Downstream 1~29

1
[ 110-87-2 ]
[ 63478-76-2 ]
[ 37011-86-2 ]

Yield	Reaction Conditions	Operation in experiment
86.9%	With toluene-4-sulfonic acid; In dichloromethane;Cooling with ice;	A. 1.5 g of <strong>[63478-76-2]6-<strong>[63478-76-2]heptyn-1-ol</strong></strong> lb was dissolved in 20 mL of methylene chloride with 0.02 g of p-toluenesulfonic acid and stirred in an ice bath. A solution of 2 g of 3,4-dihydro-2H-pyran 10mL of dichloromethane solution. The reaction was monitored by TLC. After completion of the reaction, the reaction solution was dissolved in 10 mL of diethyl ether, washed with 1% sodium hydroxide solution and water, dried over MgSO4, concentrated, To obtain 2.8 g of a pale yellow liquid intermediate, 2- (6-heptynyloxy) -tetrahydropyran 2b, in a yield of 86.9%;

Reference： [1]Patent: WO2015/51030,2015,A2 .Location in patent: Sheet 20/22
[2]Tetrahedron,1990,vol. 46,p. 6319 - 6330
[3]Journal of Organic Chemistry,2002,vol. 67,p. 6291 - 6296
[4]Journal of Organic Chemistry,2001,vol. 66,p. 853 - 861
[5]Organic Letters,1999,vol. 1,p. 399 - 401
[6]Lipids,2020
[7]Angewandte Chemie - International Edition,2005,vol. 44,p. 2397 - 2400
[8]Journal of Organic Chemistry,2009,vol. 74,p. 3680 - 3688
[9]Tetrahedron,1986,vol. 42,p. 2017 - 2024
[10]Journal of Organic Chemistry,2011,vol. 76,p. 4467 - 4481
[11]Patent: CN105669455,2016,A .Location in patent: Paragraph 0028; 0029; 0030
[12]ChemMedChem,2018,vol. 13,p. 1421 - 1436

2
[ 63478-76-2 ]
[ 67100-10-1 ]

Yield	Reaction Conditions	Operation in experiment
51%	With Dess-Martin periodane; In dichloromethane; at 0 - 23℃; for 5h;	A solution of Dess-Martin-periodinane (5.09 g, 12.0 mmol, 2.0 equiv) in dry DCM (27 mL) was cooled to 0 C, <strong>[63478-76-2]6-<strong>[63478-76-2]heptyn-1-ol</strong></strong> (673 mg, 6.00 mmol, 1.0 equiv) in DCM (3 mL) was added and the mixture was stirred at 23 C for 5 h. DCM (5 mL) was added, the mixture was washed with sat. aq. Na2S2O3-sol. (30 mL), 1 M NaOH (30 mL), and sat. aq. NaCl (30 mL). The aq. phase was extracted with DCM (90 mL), the combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and the solvent was removed under reduced pressure. The residue was purified on silica gel (n-pentane/Et2O, 9:1) to yield the title compound as a colourless oil (337 mg, 3.06 mmol, 51%).
		Using the methodology in stage (vi) of Process C, hept-6-ynal was prepared from <strong>[63478-76-2]hept-6-yn-1-ol</strong> (C. Crisan Chem . Abs . 51 :5061b). The preparation of hept-2-en-6-ynal and 1,1,1-trichloropentan-4-one is described in EP 029 4 229.
	With pyridinium chlorochromate; In dichloromethane; at 20℃; for 3.5h;	To a one-neck 50 mL round-bottomed flask equipped with a septum pierced with a needle and a stir bar, was added pyridinium chlorochromate (2.31 g, 10.7 mmol) and DCM (20 mL) with stirring. Alcohol S10 (0.600 g, 5.35 mmol) was added all at once via syringe, and the reaction turned dark brown and thick. The reaction was stirred at rt for 3.5 h until complete by TLC, followed by addition of Et2O (25 mL) and silica gel (10 g). The suspension was stirred for 30 min, filtered through a pad of silica gel with Et2O washings, and then concentrated under reduced pressure to yield the aldehyde xx as a yellow oil (0.478 g, 81%). The crude product was carried on without further purification.

Reference： [1]Chemistry - A European Journal,2001,vol. 7,p. 4378 - 4385
[2]Advanced Synthesis and Catalysis,2019,vol. 361,p. 2262 - 2267
[3]Journal of Organic Chemistry,2015,vol. 80,p. 11849 - 11862
[4]Journal of Organic Chemistry,2010,vol. 75,p. 2942 - 2954
[5]Synlett,2001,p. 1221 - 1224
[6]Journal of the American Chemical Society,2013,vol. 135,p. 14496 - 14499
[7]Tetrahedron,1990,vol. 46,p. 6319 - 6330
[8]Organic Letters,2012,vol. 14,p. 6278 - 6281
[9]Synthesis,2018,vol. 50,p. 3875 - 3885
[10]Organic Letters,2006,vol. 8,p. 4145 - 4148
[11]Chemical Communications,2019,vol. 55,p. 3654 - 3657
[12]Journal of Organic Chemistry,1993,vol. 58,p. 3912 - 3918
[13]Journal of Organic Chemistry,1997,vol. 62,p. 8595 - 8596
[14]Tetrahedron,1999,vol. 55,p. 8155 - 8167
[15]Journal of the American Chemical Society,2005,vol. 127,p. 6686 - 6692
[16]Synlett,2006,p. 1197 - 1200
[17]Chemistry - A European Journal,2001,vol. 7,p. 2435 - 2448
[18]Patent: EP372816,1990,A1
[19]Organic Letters,2012,vol. 14,p. 4430 - 4433
[20]Patent: US2013/310558,2013,A1 .Location in patent: Paragraph 0231
[21]Angewandte Chemie - International Edition,2013,vol. 52,p. 14214 - 14218
Angew. Chem.,2013,vol. 125,p. 14464 - 14468,5
[22]Organic Letters,2014,vol. 16,p. 1414 - 1417

3
[ 14916-79-1 ]
[ 63478-76-2 ]

Yield	Reaction Conditions	Operation in experiment
97%	With potassium hydride; Trimethylenediamine; at 20℃;Inert atmosphere;	Under a nitrogen atmosphere, potassium hydride (30 wt%, 11.2 g, 27.9 mmol) was washed with hexane (100 mL2) using a mechanical stirrer in a three-necked flask, and 1,3-diaminopropane (130 mL, 1.56 mol) was added. The mixture was stirred at ambient temperature for 2 h. Then, 3-heptyn-1-ol (13) (5.00 g, 44.6 mmol) was added dropwise, and stirring was continued overnight. The reaction mixture was poured into crushed ice and was extracted with diethyl ether. The combined organic layer was dried over anhydrous sodium sulfate and was filtered. After removal of solvent in the filtrate under reduced pressure, the residue was purified by column chromatography (silica gel, chloroform-ethyl acetate (7:3)) to give 4.86 g (97 %) of 14 as colorless liquid
48%	With lithium; Trimethylenediamine; at 40 - 60℃;	Part A: Synthesis of hept-6-vn-l-oI Lithium metal (8.1 g, 1.17 mol) was cut in small pieces and was added to 1.3- diaminopropane (490 ml) under stirring and under nitrogen. The mixture was heated to 50 deg until the lithium had reacted completely (disappearance of dark blue colour of the mixture). Then 3-heptyn-l-ol (1Og, 89.2 mmol) was added. The mixture was stirred at 50 - 60 deg for 3 h then over night at 40 deg. The reddish orange reaction mixture was cooled and slowly poured into 1200 ml of ice water under constant stirring. It was extracted with chloroform (3 x 300 ml). The combined organic layers were washed with saturated brine (2 x 300 ml), dried over MgSO4, filtered and concentrated under reduced pressure to yield crude hept-6-yn-l-ol as an orange oil (10.4 g).The crude product was dissolved in a 1:1 mixture of water and THF (940 ml) containing dissolved silver nitrate (32.9 g, 0.194 mol). The mixture was stirred at room temperature overnight. THF was removed by rotary evaporator.. The mixture was poured into an equal volume of acetone and stirred for 5 min. The white precipitate was filtered and washed with a small volume of cooled acetone. The precipitate was dissolved with warm 1.6 M HNO3 (1 litre). The resulting solution was cooled and extracted with dichloromethane (3 x equal volume). The combined organic layers were washed with saturated brine (3 x 200 ml), dried over Na2SO4, filtered and concentrated giving pure hept-6-yn-l-ol as a pale yellow oil (4.8 g, 48% yield). 1H-NMR (CDCl3, 400 MHz): delta[ppm] = 1.4 - 1.62 (m, 6 H), 1.94 (t, I H1 J = 2.5 Hz), 2.17 - 2.24 (m, 2 H), 3.65 (t, 2 H, J = 6.4 Hz)

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 8595 - 8596
[2]Chemistry - A European Journal,2014,vol. 20,p. 3183 - 3191
[3]Chemistry - A European Journal,2001,vol. 7,p. 4378 - 4385
[4]Bulletin of the Chemical Society of Japan,2017,vol. 90,p. 298 - 305
[5]RSC Advances,2015,vol. 5,p. 102981 - 102992
[6]Canadian Journal of Chemistry,1986,vol. 64,p. 1407 - 1413
[7]Journal of the American Chemical Society,2002,vol. 124,p. 2102 - 2103
[8]Tetrahedron,2004,vol. 60,p. 9695 - 9708
[9]ChemMedChem,2018,vol. 13,p. 1421 - 1436
[10]Organic and Biomolecular Chemistry,2012,vol. 10,p. 3080 - 3091
[11]Synlett,2010,p. 618 - 622
[12]Journal of Organic Chemistry,1990,vol. 55,p. 741 - 750
[13]Journal of the American Chemical Society,2013,vol. 135,p. 14496 - 14499
[14]Organic Letters,2012,vol. 14,p. 4430 - 4433
[15]Journal of Medicinal Chemistry,1984,vol. 27,p. 57 - 63
[16]Journal of the American Chemical Society,2009,vol. 131,p. 5411 - 5413
[17]Journal of Organic Chemistry,2010,vol. 75,p. 2942 - 2954
[18]Journal of Organic Chemistry,2009,vol. 74,p. 3680 - 3688
[19]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 2275 - 2284
[20]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 4555 - 4557
[21]Patent: WO2009/111830,2009,A1 .Location in patent: Page/Page column 62
[22]Angewandte Chemie - International Edition,2020,vol. 59,p. 7555 - 7560
Angew. Chem.,2020,vol. 132,p. 7625 - 7630,6
[23]Tetrahedron Letters,1987,vol. 28,p. 3857 - 3860
[24]Journal of Organic Chemistry,1984,vol. 49,p. 5175 - 5178
[25]Organic Letters,2012,vol. 14,p. 6278 - 6281

4
[ 1002-36-4 ]
[ 63478-76-2 ]

Yield	Reaction Conditions	Operation in experiment
74%		To 10 ml of 1,3-diaminopropane was added lithium metal (186 mg, 27 mmol) in argon atmosphere. After stirring for 2 hrs at 70 C., solution was cooled to rt. To a mixture was added t-BuOK (1.69 g). After 15 min of stirring, 2-heptynol (0.507 ml, 4 mmol) was added to a mixture then stirred for 1 hr at rt. Reaction was quenched by adding 20 ml of water, extracted with ether (30 ml three times), washed with 10% HCl solution, and dried over MgSO4. Solvent was removed-74% yield.

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 3854 - 3858
    Angew. Chem.,2014,vol. 126,p. 3934 - 3939,5
[2]Journal of Organic Chemistry,1984,vol. 49,p. 2494 - 2496
[3]Organic and Biomolecular Chemistry,2009,vol. 7,p. 3663 - 3665
[4]Journal of Organic Chemistry,1993,vol. 58,p. 3912 - 3918
[5]Journal of Organic Chemistry,2011,vol. 76,p. 4467 - 4481
[6]Organic Letters,2001,vol. 3,p. 819 - 820
[7]Journal of the American Chemical Society,1994,vol. 116,p. 8116 - 8125
[8]Journal of Organic Chemistry USSR (English Translation),1985,vol. 21,p. 909 - 912
    Zhurnal Organicheskoi Khimii,1985,vol. 21,p. 1001 - 1004
[9]Organic Letters,2006,vol. 8,p. 6087 - 6090
[10]Patent: US2005/272954,2005,A1 .Location in patent: Page/Page column 3
[11]Organic Letters,1999,vol. 1,p. 399 - 401
[12]Angewandte Chemie - International Edition,2005,vol. 44,p. 2397 - 2400
[13]Tetrahedron Letters,2003,vol. 44,p. 7833 - 7835
[14]Tetrahedron,1990,vol. 46,p. 6319 - 6330
[15]Angewandte Chemie - International Edition,2018,vol. 57,p. 6572 - 6576
    Angew. Chem.,2018,vol. 130,p. 6682 - 6686,5
[16]Journal of Organic Chemistry,1984,vol. 49,p. 2332 - 2338
[17]Chemical and pharmaceutical bulletin,2003,vol. 51,p. 463 - 466

5
[ 63478-76-2 ]
[ 18162-48-6 ]
[ 119837-81-9 ]

Yield	Reaction Conditions	Operation in experiment
100%	With 1H-imidazole; In dichloromethane; at 20℃; for 24h;	To a stirred solution of <strong>[63478-76-2]6-<strong>[63478-76-2]heptyn-1-ol</strong></strong> 812 (3.33 mL, 26.75 mmol) in CH2CI2 (80 mL) at r.t. was added imidazole (1.76 g, 27.01 mmol) and terf-butyldimethylsilyl chloride (4.07 g, 27.01 mmol). The reaction mixture was allowed to stir at r.t. for 24 h. The mixture was then diluted with Et2<D (100 mL) a nd washed with water (3 x 100 mL) and brine (100 mL) . The orga nic layer was dried over anhydrous Na2SC>4 and concentrated in vacuo. The crude product was purified by filtration through silica gel to give alkyne 813 (5.68 g, q uant.) as a colourless liquid . Alkyne 813 was used in subsequent synthetic steps without characterisation.
100%	With 1H-imidazole; In dichloromethane; at 20℃; for 24h;	To a stirred solution of 6-heptyn-l-ol 812 (3.33 mL, 26.75 mmol) in CH2CI2 (80 mL) at r.t. was added imidazole (1.76 g, 27.01 mmol) and terf-butyldimethylsilyl chloride (4.07 g, 27.01 mmol). The reaction mixture was allowed to stir at r.t. for 24 h. The mixture was then diluted with Et2<D (100 mL) a nd washed with water (3 x 100 mL) and brine (100 mL) . The orga nic layer was dried over anhydrous Na2S04 and concentrated in vacuo. The crude product was purified by filtration through silica gel to give alkyne 813 (5.68 g, quant.) as a colourless liquid . Alkyne 813 was used in subsequent synthetic steps without characterisation.
77%	With 1H-imidazole; In tetrahydrofuran; at 20℃; for 16h;	Part A: Synthesis of tert-butyl(hep iIane To a stirred solution of hept-6-yn-l-ol (5.3 g, 47.25 mmol) in dry THF (450 ml) was added imidazole (7.08 g, 103.95 mmol) followed by tert-butyldimethylsilylchloride (7.83 g, 51.97 mmol) under nitrogen. The mixture was stirred for 16 h at room temperature before water (200 ml) and hexane (250 ml) were added. The layers were separated and the <n="82"/>aqueous phase was extracted with hexane. The combined organic phases were dried over MgSO4, filtered and concentrated to give the protected alcohol. The crude product was purified by column chromatography (SiO2, 0 - 1.5% ethyl acetate in petroleum spirit) to give the pure tert-butyl(hept-6-ynyloxy)dimethylsilane as a colourless oil (8.23 g, 77%). The product was used immediately in the next reaction step.

Reference： [1]Patent: WO2017/145097,2017,A2 .Location in patent: Page/Page column 146
[2]Patent: WO2019/43604,2019,A1 .Location in patent: Page/Page column 148
[3]Russian Journal of Bioorganic Chemistry,1998,vol. 24,p. 692 - 699
[4]Organic Letters,2013,vol. 15,p. 3086 - 3089
[5]Journal of Organic Chemistry,1990,vol. 55,p. 741 - 750
[6]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 4555 - 4557
[7]Patent: WO2009/111830,2009,A1 .Location in patent: Page/Page column 80-81
[8]Organic Letters,2012,vol. 14,p. 3808 - 3811
[9]Organic Letters,2020,vol. 22,p. 755 - 759
[10]Angewandte Chemie - International Edition,2020,vol. 59,p. 11010 - 11019
Angew. Chem.,2020,vol. 132,p. 11103 - 11112,10

6
[ 63478-76-2 ]
[ 98-59-9 ]
[ 87462-63-3 ]

Yield	Reaction Conditions	Operation in experiment
91%	With 4-dimethylaminopyridine; triethylamine In dichloromethane at 20℃; Inert atmosphere;
87%	With pyridine
84%	With 4-dimethylaminopyridine; triethylamine Inert atmosphere;

80%	With 4-dimethylaminopyridine; triethylamine In dichloromethane at 0 - 20℃; for 16h;
52%	With triethylamine In dichloromethane at 25℃; for 12h;	4.1 Step 1: hept-6-ynyl 4-methylbenzenesulfonate To a solution of hept-6-yn-1-ol (2 g, 17.8 mmol) in DCM (30 mL) was added TEA (5.41 g, 53.5 mmol) and 4-methylbenzenesulfonyl chloride (5.10 g, 26.8 mmol).The mixture was stirred at 25 °C for 12 hr. The reaction was filtered and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (SiO2, Petroleum ether/Ethyl acetate=20:1) to give the title compound (2.5 g, 52% yield) as a brown oil. LC/MS (ESI, m/z): [M+1]+= 267.1.
50.63%	Stage #1: 1-hydroxy-6-heptyne With triethylamine In dichloromethane at 0℃; for 0.5h; Stage #2: 4-methylbenzenesulfonyl chloride In dichloromethane for 4h;	29 Example 29: Synthesis of [3-(5-(7-((4-((5-chloro-4-((2- (isopropylsulfonyl)phenyl)amino)pyrimidin-2-yl)amino)-5-methoxy-2- methylphenethyl)amino)hept-1-yn-1-yl)-1-oxoisoindolin-2-yl)piperidine-2,6-dione (92) To a solution of hept-6-yn-1-ol (10 g, 89.21 mmol) in DCM (100 mL) was added triethylamine (13.5 g, 133.82 mmol) and the mixture was stirred at 0°C. After 30 minutes, p- TsCl (20 g, 107.06 mmol) was added and the solution was stirred for 4 hours. After TLC showed reaction completion, the solvent was removed under reduced pressure and the residue was purified by column chromatography eluted with (petroleum ether/ethyl acetate = 20/1 to 15/1) to afford hept-6-yn-1-yl 4-methylbenzenesulfonate as a colorless, transparent liquid (12 g, 50.63%).
25%	With potassium hydroxide In diethyl ether at 0℃; for 5h; Inert atmosphere;
	With triethylamine In dichloromethane at 0 - 20℃;
	With triethylamine In dichloromethane
	With triethylamine In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere;

Reference： [1]Su, Shang; Yang, Zimo; Gao, Hongying; Yang, Haiyan; Zhu, Songbiao; An, Zixuan; Wang, Juanjuan; Li, Qing; Chandarlapaty, Sarat; Deng, Haiteng; Wu, Wei; Rao, Yu [Journal of Medicinal Chemistry, 2019, vol. 62, # 16, p. 7575 - 7582]
[2]Knapp, F.F.; Srivastava, P.C.; Callahan, A.P.; Cunningham, E.B.; Kabalka, G.W.; Sastry, K.A.R. [Journal of Medicinal Chemistry, 1984, vol. 27, # 1, p. 57 - 63]
[3]Location in patent: scheme or table Fang, Fang; Vogel, Megan; Hines, Jennifer V.; Bergmeier, Stephen C. [Organic and Biomolecular Chemistry, 2012, vol. 10, # 15, p. 3080 - 3091]
[4]Eubanks, Lisa M.; Stowe, G. Neil; De Lamo Marin, Sandra; Mayorov, Alexander V.; Hixon, Mark S.; Janda, Kim D. [Angewandte Chemie - International Edition, 2011, vol. 50, # 45, p. 10699 - 10702]
[5]Current Patent Assignee: KYMERA THERAPEUTICS INC - WO2020/251971, 2020, A1 Location in patent: Paragraph 00674; 00675
[6]Current Patent Assignee: DANA-FARBER CANCER INSTITUTE - WO2021/173677, 2021, A1 Location in patent: Paragraph 00277-00278
[7]Bucher, Janina; Wurm, Thomas; Nalivela, Kumara Swamy; Rudolph, Matthias; Rominger, Frank; Hashmi, A. Stephen K. [Angewandte Chemie - International Edition, 2014, vol. 53, # 15, p. 3854 - 3858][Angew. Chem., 2014, vol. 126, # 15, p. 3934 - 3939,5]
[8]Srivastava, Prem C.; Knapp, Furn F.; Kabalka, George W. [Phosphorus and Sulfur and the Related Elements, 1988, vol. 38, p. 49 - 58]
[9]Shao, Liang; Yang, Fan; Su, Yangqing; Li, Weijia; Zhang, Jihong; Xu, Huan; Huang, Boxuan; Sun, Mengsi; Mu, Yu; Zhang, Yuan; Yu, Fei [ACS Medicinal Chemistry Letters, 2021, vol. 12, # 11, p. 1759 - 1765]
[10]Zhou, Yidan; Wu, Jinyang; Liu, Zejiang; Xu, Weitao; Liu, Menglong; Jia, Along; Liu, Yuchen; Xiao, Xin; Li, Xiaowei; Yuan, Lihua [Chemical Communications, 2021, vol. 57, # 99, p. 13506 - 13509]
[11]Bohman, Benjamin O.; Davis, Rhen C.; Forson, Kelton G.; McKnight, Caitlyn E.; Michaelis, David J.; Owens, Rachel N.; Smith, Stacey J.; Stillwell, Lillian R.; Wayment, Coriantumr Z. [Journal of the American Chemical Society, 2022, vol. 144, # 1, p. 63 - 68]

7
[ 63478-76-2 ]
[ 164470-73-9 ]

Yield	Reaction Conditions	Operation in experiment
77%		Part A: Synthesis of 7-iodohept-6-vn-l-oI To a solution of hept-6-yn-l-ol (5 g, 44.58 mmol) in MeOH (50 ml) was added an aqueous solution of KOH (6.25 g, 111.44 mmol) in 10 ml of water at 00C. After 10 minutes I2 (12.44 g, 49.03 mmol) was added in one portion and the mixture was then warmed to room temperature. After being stirred at room temperature overnight the mixture was diluted with water (100 ml) and the aqueous layer was extracted with ether (3 x 100 ml). The combined organic layers were concentrated to give a yellow oil residue. The residue was dissolved in CH2Cl2 (100 ml) which was washed with saturated brine (100 ml) and half saturated aqueous sodiumthiosulphate solution (100 ml), dried over Na2SO4, filtered and concentrated. The crude product was chromatographed (SiO2, gradient eluent 5 - 20% ethyl acetate in petroleum spirit) giving a pale yellow oil (9.8 g, 77%). 1H-NMR (CDCl3, 400 MHz): delta[ppm] = 1.41 - 1.74 (m, 6H), 2.38 (tr, 2H, J = 6.8 Hz), 3.64 (tr, 2H, J = 6.4 Hz)
71%		To a solution of 6-heptynol (331 mg, 2.95 mmol) in 10 ml of methanol was added KOH in 5 ml of H2O. After 10 min, iodine (824 mg, 3.24 mmol) was added at 0 C. and warmed to rt and stirred for 2 hr. The reaction was then quenched with water and extracted with ether (20 ml three times). The solvent was removed in vacuo, the residue dissolved in CH2Cl2, washed with brine and dried over MgSO4. Purification by silica gel chromatography (hexane:ethyl acetate=4:1) gave the product 498 mg (71% yield).

Reference： [1]Journal of the American Chemical Society,2002,vol. 124,p. 2102 - 2103
[2]Tetrahedron,2004,vol. 60,p. 9695 - 9708
[3]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 4555 - 4557
[4]Patent: WO2009/111830,2009,A1 .Location in patent: Page/Page column 92
[5]Tetrahedron Letters,1995,vol. 36,p. 2619 - 2622
[6]Patent: US2005/272954,2005,A1 .Location in patent: Page/Page column 3
[7]RSC Advances,2015,vol. 5,p. 102981 - 102992
[8]Chemical and pharmaceutical bulletin,2003,vol. 51,p. 463 - 466

8
[ 30964-00-2 ]
[ 63478-76-2 ]

Yield	Reaction Conditions	Operation in experiment
		Preparation of hept-6-yn-l-olTo a round bottom flask equipped with a stirring bar under N2 was added LAH (3.61 g, 95 mmol) and anhydrous diethyl ether (300 ml). The mixture was cooled to 0 0C in an acetonitrile-dry ice bath, a solution of <strong>[30964-00-2]hept-6-ynoic acid</strong> (6.00 g, 47.6 mmol) in dry diethyl ether (60.1 ml) was added dropwise with vigorous stirring. The mixture was then allowed to warm to ambient temperature and stirred for an additional hour. Next, IM HCl solution (159 ml, 159 mmol) was added dropwise and the reaction mixture was stirred at ambient temperature over the weekend. The layers were then separated. The aqueous layer was back-extracted with diethyl ether (150 mL). The combined organic phase was wash with brine (15OmL), dried (MgSO4) and concentrated to yield 5.89 g of colorless liquid. The crude liquid was purified via Analogix FCC system using Biotage RS 330g column, with a gradient of 0-50% ether/pet, ether over 10 min. at 40 mL/min. then held at 50% for 50 min. Fractions containing product were combined and concentrated to yield hept-6-yn- l-ol (4.94 g, 44.0 mmol) as colorless liquid. The title compound was also prepared according to procedure described by B. W. Gung et al, Tetrahedron: Asymmetry, 2005, 16, 3107-3114. 1H NMR (400 MHz, DMSO-J6) delta ppm 3.66 (t, J = 6.32, 6.32 Hz, 2H), 2.26-2.17 (m, 2H), 1.98-1.92 (m, IH), 1.66-1.53 (m, 4H), 1.53-1.45 (m, 2H)

Reference： [1]Synlett,2001,p. 1221 - 1224
[2]Tetrahedron Asymmetry,2005,vol. 16,p. 3107 - 3114
[3]Organic Letters,2014,vol. 16,p. 1414 - 1417
[4]Chemistry of Natural Compounds,2011,vol. 46,p. 841 - 847
[5]Journal of Organic Chemistry,2004,vol. 69,p. 1126 - 1136
[6]Journal of the American Chemical Society,2005,vol. 127,p. 6686 - 6692
[7]Russian Journal of Bioorganic Chemistry,1998,vol. 24,p. 692 - 699
[8]Bulletin de la Societe Chimique de France,1984,vol. 2,p. 49 - 55
[9]Tetrahedron Letters,2008,vol. 49,p. 2899 - 2901
[10]Patent: WO2008/79382,2008,A1 .Location in patent: Page/Page column 126

9
[ 15848-22-3 ]
[ 63478-76-2 ]

Reference： [1]Journal of Organic Chemistry,1993,vol. 58,p. 7170 - 7179

10
[ 63478-76-2 ]
[ 4617-33-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 58 percent / LiNH₂, Fe(NO₃)3 / tetrahydrofuran; NH₃ / 20 h 2: H₂ / PtO₂ / diethyl ether

Reference： [1]Riche, Francoise; Mathieu, Jean-Paul; Vincens, Maurice; Bardy, Andre; Comet, Michel; Vidal, Michel [Bulletin de la Societe Chimique de France, 1984, vol. 2, # 1-2, p. 49 - 55]

11
[ 63478-76-2 ]
[ 6214-23-9 ]
[ 1029269-68-8 ]

Reference： [1]Tetrahedron Letters,2008,vol. 49,p. 2899 - 2901

12
[ 63478-76-2 ]
[ 159217-89-7 ]
[ 1218817-14-1 ]

Yield	Reaction Conditions	Operation in experiment
48%	With diisopropylamine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In tetrahydrofuran; at 20℃; for 3h;	To a stirred solution of tert-bvXy 4-iodophenylcarbamate (3.00 g, 9.40 mmol), l-fluoro-4-(hept-6-ynyloxy)benzene (X) (2.13 g, 10.34 mmol), and diisopropylamine (2.85 g, 28.20 mmol) in tetrahydrofuran (50 mL) was added copper(I) iodide (0.179 g, 0.940 mmol) and bis(triphenylphosphine)palladium(II) chloride (0.330 g, 0.470 mmol). The reaction mixture was allowed to stir at room temperature. After 3 hours, the reaction mixture was diluted with ethyl acetate and washed with IN hydrochloric acid , 6N ammonium hydroxide, and brine. The organic phase was dried (magnesium sulfate), filtered, and concentrated to provide 5.25 g of an orange-brown solid. Flash chromatography using an Isco Combiflash unit (12O g SiO2 column, 30-60% dichloromethane/hexanes) afforded 1.80 g (48%) of tert-butyl 4-(7-(4- fluorophenoxy)hept-1-ynyl)phenylcarbamate as an off-white solid: 1H NMR (CDCl3) delta 7.34- 7.27 (m, 4H), 7.00-6.92 (m, 2H), 6.86-6.79 (m, 2H), 6.46 (br s, 1H), 3.94 (t, J = 6.4 Hz, 2H), 2.55-2.27 (m, 2H), 1.86-1.77 (m, 2H), 1.71-1.58 (m, 4H), 1.51 (s, 9H) ppm.

Reference： [1]Patent: WO2010/33701,2010,A2 .Location in patent: Page/Page column 68

13
[ 63478-76-2 ]
[ 75833-63-5 ]
[ 1258418-88-0 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 8585 - 8590

14
[ 4720-86-9 ]
[ 63478-76-2 ]
C₃₀H₃₈N₂O₄ [ No CAS ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 11180 - 11183,4

15
[ 4720-86-9 ]
[ 63478-76-2 ]
[ 1403759-91-0 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 11180 - 11183,4

16
[ 75-77-4 ]
[ 63478-76-2 ]
7-(trimethylsilyl)hept-6-yn-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%		Following a reported procedure,9 <strong>[63478-76-2]hept-6-yn-1-ol</strong> (50) (5.00 g, 44.6 mmol, 1.00 equiv.) was dissolved intetrahydrofuran (150 mL) and the solution was cooled down at - 78 C. A cooled 2.5 M solution of nbutyllithiumin hexanes (nBuLi, 39.2 mL, 98.0 mmol, 2.20 equiv.) was added dropwise, followed by 4-(dimethylamino)pyridine (DMAP, 1.36 g, 11.1 mmol, 0.25 equiv.). After stirring for 1 hour at thistemperature, trimethylsilyl chloride (TMS-Cl, 20.4 mL, 156 mmol, 3.50 equiv.) was added dropwise. Themixture was then allowed to warm to room temperature. After 2 hours of stirring, the reaction wasquenched with a 1.0 N aqueous hydrochloric acid (50 mL) and vigorously stirred at room temperatureover 30 minutes. The mixture was then diluted with ethyl acetate (200 mL) and the layers wereseparated. The aqueous phase was extracted with additional portions of ethyl acetate (3 x 50 mL). Thecombined organic layers were collected, washed with a solution of saturated aqueous sodiumbicarbonate (100 mL), brine (50 mL), dried over magnesium sulfate, filtered and concentrated in vacuo.After purification by column chromatography (SiO2, Pentane:Ethyl acetate 4:1), 7-(trimethylsilyl)<strong>[63478-76-2]hept-6-yn-1-ol</strong> (51) (6.58 g, 35.7 mmol, 80% yield) was obtained as a colorless oil.

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 16563 - 16573
[2]Chem,2019,vol. 5,p. 2243 - 2263
[3]Organic Letters,2012,vol. 14,p. 6278 - 6281
[4]Chemistry - A European Journal,2013,vol. 19,p. 2467 - 2477

17
[ 14150-95-9 ]
[ 63478-76-2 ]
[ 1613220-99-7 ]

Yield	Reaction Conditions	Operation in experiment
69%	Stage #1: 2-aminopyridine N-oxide With trifluoroacetic acid In dichloromethane for 0.166667h; Stage #2: 1-hydroxy-6-heptyne With dichloro(pyridine-2-carboxylato)gold(III) In dichloromethane at 40℃; for 15h; regioselective reaction;

Reference： [1]Talbot, Eric P. A.; Richardson, Melodie; McKenna, Jeffrey M.; Toste, F. Dean [Advanced Synthesis and Catalysis, 2014, vol. 356, # 4, p. 687 - 691]

18
[ 63478-76-2 ]
[ 81216-14-0 ]

Yield	Reaction Conditions	Operation in experiment
91%	With carbon tetrabromide; triphenylphosphine In dichloromethane at 20℃; for 1h; Cooling with ice;	9 Synthesis of 7-Bromo-hept-1-yne 9 A solution of 6-heptyn-1-ol (5g, 44.6 mmol) was made in dry DCM (60 ml) and cooled on ice. To this triphenylphosphine (17.6 g, 67 mmol) was added, upon complete dissolution tetrabromomethane (22.2 g, 67 mmol) was added slowly. The reaction mixture was brought to room temperature and stirred for 1 hr. After completion, the solvent was removed under reduced pressure. Hexane was added to the crude forming a white suspension. The hexanefraction was filtered, collected and then the solvent was removed. An oily residue remained which was purified by flash column chromatography with hexane: Yield = 91%, Rf = 0.45 (hexane); %); □ max(neat)/cm-1 540 (C-Br); 1H NMR (300 MHz, DMSO-d6) d 3.53 (t, J = 6.7 Hz, 2H), 2.75 (t, J = 2.7 Hz, 1 H), 2.23 - 2.10 (m, 2H), 1.89 - 1.74 (m, 2H), 1.50 - 1.43 (m, 4H).
86%	With carbon tetrabromide; triphenylphosphine In dichloromethane at 0℃; for 1.5h; Inert atmosphere;
83%	With carbon tetrabromide; triphenylphosphine In dichloromethane at 20℃; for 1h; Inert atmosphere;

54%	With carbon tetrabromide; triphenylphosphine In dichloromethane at 0 - 20℃;
	With carbon tetrabromide; triphenylphosphine In dichloromethane at 0 - 20℃;

Reference： [1]Current Patent Assignee: BURMING UNIV; UNIVERSITY OF BIRMINGHAM - WO2021/53346, 2021, A1 Location in patent: Page/Page column 17; 18; 19
[2]Gerken, Philip A.; Wolstenhulme, Jamie R.; Tumber, Anthony; Hatch, Stephanie B.; Zhang, Yijia; Müller, Susanne; Chandler, Shane A.; Mair, Barbara; Li, Fengling; Nijman, Sebastian M. B.; Konietzny, Rebecca; Szommer, Tamas; Yapp, Clarence; Fedorov, Oleg; Benesch, Justin L. P.; Vedadi, Masoud; Kessler, Benedikt M.; Kawamura, Akane; Brennan, Paul E.; Smith, Martin D. [Angewandte Chemie - International Edition, 2017, vol. 56, # 49, p. 15555 - 15559][Angew. Chem., 2017, vol. 129, p. 15761 - 15765,5]
[3]Coombs, John R.; Zhang, Liang; Morken, James P. [Journal of the American Chemical Society, 2014, vol. 136, # 46, p. 16140 - 16143]
[4]Chen, Junfeng; Wang, Jiang; Bai, Yugang; Li, Ke; Garcia, Edzna S.; Ferguson, Andrew L.; Zimmerman, Steven C. [Journal of the American Chemical Society, 2018, vol. 140, # 42, p. 13695 - 13702]
[5]An, Rui; Li, Huimin; Liao, Lihao; Wu, Jin-Ji; Xu, Yang; Zhao, Xiaodan [Angewandte Chemie - International Edition, 2020, vol. 59, # 27, p. 11010 - 11019][Angew. Chem., 2020, vol. 132, # 27, p. 11103 - 11112,10]

19
[ 63478-76-2 ]
[ 89238-99-3 ]
[ 1226762-13-5 ]

Yield	Reaction Conditions	Operation in experiment
70%	With (1S)-10-camphorsulfonic acid In dichloromethane at 20℃;	1-((Hept-6-yn-1-yloxy)methyl)-4-methoxybenzene (24) General procedure: The title compound was prepared according to the procedure described for 11, starting from compound 23. Yield: 70%.

Reference： [1]Kajita, Daisuke; Nakamura, Masaharu; Matsumoto, Yotaro; Ishikawa, Minoru; Hashimoto, Yuichi; Fujii, Shinya [Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 16, p. 3350 - 3354]

20
[ 63478-76-2 ]
3-azidopropyl 9,10-dioxo-9,10-dihydroanthracene-2-carboxylate [ No CAS ]
dimethyl 4-(hept-6-yn-1-yloxy)pyridine-2,6-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%		General procedure: 300 mg (1 eq, 1.42 mmol) of 7 was suspended in 11 mL of freshly distilled THF under argon. 745 mg (2 eq, 2.84 mmol) of triphenylphosphine was then added, followed by 198 muL (1.5 eq, 2.13 mmol) of 4-pentyn-1-ol. The flask was then placed in an ice bath and stirred for 10 min. 391 muL (1.4 eq, 1.99 mmol) of diisopropylazodicarboxylate (DIAD) was then added drop-wise. The reaction was stirred, allowing it to return to room temperature, for 72 h at which point the reaction appeared done by TLC (EtOAc,KMnO4 stain). The solvent was removed under reduced pressure, giving a viscous oil that was then subjected to high vacuum for 1 h before being dissolved in the minimum amount of ethyl acetate. After purification by flash chromatography (50% EtOAc in hexanes), 350 mg (89% yield) of the product was obtained as a white powder.

Reference： [1]Molecules,2015,vol. 20,p. 16446 - 16465

21
[ 173772-63-9 ]
[ 63478-76-2 ]
7-(3-amino-4-chloropyridin-2-yl)hept-6-yn-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 65℃; for 2h;Inert atmosphere;	Triethylamine (14.11 mL, 101.23 mmol) was added to a stirred solution of <strong>[173772-63-9]2,4-dichloropyridin-3-amine</strong> (1.65 g, 10.12 mmol), copper (I) iodide (39 mg, 0.20 mmol) and bis(triphenylphosphine)palladium(II) dichloride (0.284 g, 0.40 mmol) in THF (70 mL) under nitrogen and the solution was degassed with a stream of nitrogen. A solution of hept-6-yn-1-ol (1.135 g, 10.12 mmol) in THF (3 mL) was added in one portion. The reaction solution was stirred at 65 C for 2 hours. The solution was adsorbed onto silica and the crude product was purified by flash silica chromatography, elution gradient 0 to 4% MeOH in DCM. Pure fractions were evaporated to dryness to afford 7-(3-amino-4-chloropyridin-2-yl)hept-6-yn-1-ol 11d

Reference： [1]Synlett,2016,vol. 27,p. 2368 - 2371

22
[ 63478-76-2 ]
[ 30964-00-2 ]

Yield	Reaction Conditions	Operation in experiment
88%	With Jones reagent; In acetone; at 0℃;	Compound 14 (3.00 g, 26.7 mmol) in 50 mL of acetone, the Jones reagent 7 was added dropwise at 0 C until the color of the mixture became dark green to orange. Then, 2-propanol was added dropwise until the color of the mixture returned to dark green. The mixture was poured into 100 mL of water, and it was extracted with chloroform. The combined organic layer was dried over anhydrous sodium sulfate. After filtration, solvent in the filtrate was removed under reduced pressure to give 2.95 g (88 %) of 15 as colorless liquid

Reference： [1]Bulletin of the Chemical Society of Japan,2017,vol. 90,p. 298 - 305

23
[ 63478-76-2 ]
[ 633-99-8 ]
1-chloro-2-(hept-6-yn-1-yloxy)naphthalene [ No CAS ]

Reference： [1]Chemistry - A European Journal,2017,vol. 23,p. 14133 - 14137

24
[ 63478-76-2 ]
[ 112-54-9 ]
(R)-nonadeca-6,7-dien-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%	With (S)-(-)-2-(1-hydroxy-1-methylethyl)-pyrrolidine; copper(ll) bromide In 1,4-dioxane at 130℃; for 12h; Inert atmosphere; Schlenk technique; Sealed tube; enantioselective reaction;	Synthesis of (R)-Pentadeca-2,3-dien-1-ol [(R)-4aa] Using (S)-3b; Typical Procedure I General procedure: To a flame-dried Schlenk tube with a polytetrafluoroethylene plug were added CuBr2 (0.0453 g, 0.2 mmol), (S)-3b (0.1299 g, 1.0 mmol), prop-2-yn-1-ol (1a; 0.0846 g, 1.5 mmol, dissolved in 1.5 mL of 1,4- dioxane), and dodecanal (2a; 0.2762 g, 1.5 mmol, dissolved in 1.5 mL of 1,4-dioxane) sequentially under N2. The Schlenk tube was then sealed by screwing the polytetrafluoroethylene plug tightly with the outlet being closed. Then the reaction mixture was heated in an oil bath preheated at 130 °C with stirring. After 12 h, the reaction was complete as monitored by TLC and the mixture was cooled to r.t. Afterwards, the resulting mixture was diluted with Et2O (30 mL) and washed with aq HCl (3 M, 20 mL). The organic layer was separated and the aqueous layer was extracted with Et2O (3 × 15 mL). The combined organic layers were washed with brine (20 mL) and dried (anhyd Na2SO4). After filtration and evaporation, the residue was purified by chromatography on silica gel (PE/EtOAc 8:1, 720 mL) to afford (R)- 4aa;9a yield: 0.1372 g (61%);

Reference： [1]Ma, Dengke; Duan, Xinyu; Fu, Chunling; Huang, Xin; Ma, Shengming [Synthesis, 2018, vol. 50, # 13, p. 2533 - 2545]

25
[ 1009820-21-6 ]
[ 63478-76-2 ]
[ 2254418-03-4 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: silmitasertib With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In acetone at 20℃; for 0.25h; Stage #2: With triethylamine In acetone at 20℃; for 0.25h; Stage #3: 1-hydroxy-6-heptyne In acetone for 24h; Reflux;	4.2. General procedure for preparation General procedure: General synthetic procedure of alkyne derivatives 6. A solution ofCX-4945 (350.0 mg, 1.0 mmol) and TBTU (385.0 mg, 1.2 mmol) in20 mL of acetone was stirred at room temperature. After 15 min, excessTEA was added and the reaction mixture was stirred for another 15 min.Alkynol 5 (1.2 mmol) was then added and the reaction mixture waskept stirring under reflux for 24 h. The solvent was then removed byevaporation under reduced pressure, and DCM was added. The organiclayer was washed with saturated NaHCO3 solution twice and wateronce, and dried over sodium sulfate. The filtrate was concentrated under reduced pressure to give crude compounds 6a-d as yellow oil.Yields: 6a: 82.3%, 6b: 91.2%, 6c: 83.7%, 6d: 87.2%. The crude productswere used directly for the subsequent reaction without further purification.

Reference： [1]Chen, Hong; Chen, Feihong; Liu, Nannan; Wang, Xinyi; Gou, Shaohua [Bioorganic Chemistry, 2018, vol. 81, p. 536 - 544]

26
[ 63478-76-2 ]
[ 76334-36-6 ]
C₁₁H₁₈O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; for 5h;

Reference： [1]Lee, Jaeyeon; Kim, Jiheon; Lee, Hee-Yoon [Organic Letters, 2020, vol. 22, # 11, p. 4073 - 4077]

27
[ 26166-92-7 ]
[ 63478-76-2 ]
2-(2,6-dioxopiperidin-3-yl)-5-(7-hydroxyhept-1-yn-1-yl)isoindoline-1,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; copper (I) iodide; N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 80℃; for 16h;	340.1 Step 1: Synthesis of 2- (2, 6-dioxopiperidin-3-yl) -5- (7-hydroxyhept-1-yn-1-yl) isoindoline-1, 3-dione A mixture of 5-bromo-2- (2, 6-dioxopiperidin-3-yl) isoindoline-1, 3-dione (100 mg, 298 umol) , Pd (dppf) Cl2 (22 mg, 29.8 umol) , hept-6-yn-1-ol (56 mg, 447 umol) , CuI (6 mg, 29.8 umol) and DIPEA (116 mg, 894 umol) in DMSO (6 mL) was stirred at 80 for 16 h. The reaction mixture was purified by reverse-phase chromatography to give the desired product (61 mg, 48%yield) as a light yellow solid. MS (ESI) m/z: 369.1 [M+H]+.
48%	With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; copper (I) iodide; N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 80℃; for 16h;	340.1 Step 1: Synthesis of 2- (2, 6-dioxopiperidin-3-yl) -5- (7-hydroxyhept-1-yn-1-yl) isoindoline-1, 3-dione A mixture of 5-bromo-2- (2, 6-dioxopiperidin-3-yl) isoindoline-1, 3-dione (100 mg, 298 umol) , Pd (dppf) Cl2 (22 mg, 29.8 umol) , hept-6-yn-1-ol (56 mg, 447 umol) , CuI (6 mg, 29.8 umol) and DIPEA (116 mg, 894 umol) in DMSO (6 mL) was stirred at 80 for 16 h. The reaction mixture was purified by reverse-phase chromatography to give the desired product (61 mg, 48%yield) as a light yellow solid. MS (ESI) m/z: 369.1 [M+H]+.

Reference： [1]Current Patent Assignee: CULLGEN SHANGHAI - WO2020/200291, 2020, A1 Location in patent: Page/Page column 173
[2]Current Patent Assignee: CULLGEN SHANGHAI - WO2022/68933, 2022, A1 Location in patent: Page/Page column 158

28
[ 10297-09-3 ]
[ 63478-76-2 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium aluminium tetrahydride In diethyl ether at 0℃; Inert atmosphere;

Reference： [1]Cohen, Yair; Marek, Ilan [Angewandte Chemie - International Edition, 2021, vol. 60, # 50, p. 26368 - 26372][Angew. Chem., 2021, vol. 133, # 20, p. 26572 - 26576]

29
[ 1010100-26-1 ]
[ 63478-76-2 ]
C₂₀H₂₂N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38.1%	With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; copper (I) iodide; triethylamine In N,N-dimethyl-formamide at 70℃; Inert atmosphere;	2 Step 2: [0320] Compound C163-3 (322 mg, 1mmol), compound C163-4 (280 mg,2.5mmol), cuprous iodide (38 mg, 0.2mmol), Pd(dppf)Cl2 (280 mg, 0.4mmol) and triethylamine (30.3 mg, 3mmol) were dissolved in 10 mL of anhydrous DMF. The mixture was reacted with stirring at 70°C under nitrogen protection overnight. The solvent was removed under reduced pressure. The crude product was purified by thin layer chromatography to afford off-white solid compound C163-5 (135 mg, yield: 38.1%). LCMS: [M + H]+ = 355.

Reference： [1]Current Patent Assignee: BEIJING TIDE PHARMACEUTICAL CO LTD; SINO BIOPHARMACEUTICAL LIMITED; BEIJING TEDE PHARMACEUTICAL - EP4019021, 2022, A1 Location in patent: Paragraph 0318; 0320

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P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

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

[ CAS No. 63478-76-2 ] {[proInfo.proName]}

Quality Control of [ 63478-76-2 ]

Related Doc. of [ 63478-76-2 ]

Product Details of [ 63478-76-2 ]

Calculated chemistry of [ 63478-76-2 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 63478-76-2 ]

Application In Synthesis of [ 63478-76-2 ]

[ 63478-76-2 ] Synthesis Path-Downstream 1~29

Related Functional Groups of [ 63478-76-2 ]

Alkynes

Aliphatic Chain Hydrocarbons

Alcohols

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

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[ 63478-76-2 ]