[ CAS No. 151978-58-4 ] {[proInfo.proName]}

Name: 151978-58-4|tert-Butyl hex-5-yn-1-ylcarbamate|95%
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SKU: A141036
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Quality Control of [ 151978-58-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 151978-58-4 ]

Product Details of [ 151978-58-4 ]

CAS No. :	151978-58-4	MDL No. :	MFCD18839148
Formula :	C₁₁H₁₉NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QUIDQZORWGPNKV-UHFFFAOYSA-N
M.W :	197.27	Pubchem ID :	11830384
Synonyms :

Calculated chemistry of [ 151978-58-4 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.73
Num. rotatable bonds :	7
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	57.67
TPSA :	38.33 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) :	-5.93 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.8
Log Po/w (XLOGP3) :	2.22
Log Po/w (WLOGP) :	2.39
Log Po/w (MLOGP) :	2.29
Log Po/w (SILICOS-IT) :	2.0
Consensus Log Po/w :	2.34

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.0
Solubility :	1.97 mg/ml ; 0.01 mol/l
Class :	Very soluble
Log S (Ali) :	-2.66
Solubility :	0.432 mg/ml ; 0.00219 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.54
Solubility :	0.572 mg/ml ; 0.0029 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.48

Safety of [ 151978-58-4 ]

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

Application In Synthesis of [ 151978-58-4 ]

* 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 [ 151978-58-4 ]
Downstream synthetic route of [ 151978-58-4 ]

[ 151978-58-4 ] Synthesis Path-Upstream 1~5

1
[ 15252-45-6 ]
[ 24424-99-5 ]
[ 151978-58-4 ]

Yield	Reaction Conditions	Operation in experiment
1.831 g	With sodium hydrogencarbonate In tetrahydrofuran; water at 0 - 20℃; for 2 h; Inert atmosphere	N-(5-hexynyl)phthalimide (4.66 g, 20.5 mmol) was dissolved in THF (250 ml) and hydrazine hydrate (410 mmol, 19.8 ml) was added. The obtained solution was refluxed for 3 h, forming a white precipitate after 1h. After the reaction was finished it was cooled down to 8°C and filtered. The filtrate was evaporated to obtain the crude amine 8 as yellow liquid. The crude amine was dissolved in THF (14 ml) and water (14 ml) was added followed by NaHCO₃ (2.27 g, 27.0 mmol). The solution was cooled to 0°C and Boc₂O (2 M in THF, 8.09 ml; 16.2 mmol) was added via a syringe. The temperature was maintained for 15 min before removing the ice-bath. After 2h at rt the reaction was diluted with EtOAc. It was washed with water, sat. NaHCO3 aq and brine. Drying and evaporation gave a crude oil that was purified on silica with CyHex/EtOAc (92/8) resulting in 1.831g (45percent) 9 as pale yellow oil.

Reference： [1] Bioconjugate Chemistry, 2013, vol. 24, # 9, p. 1624 - 1633
[2] Journal of the American Chemical Society, 2010, vol. 132, # 40, p. 14070 - 14072
[3] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 21, p. 6523 - 6532,10
[4] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 21, p. 6523 - 6532

2
[ 1101108-51-3 ]
[ 151978-58-4 ]

Reference： [1] Organic Letters, 2015, vol. 17, # 7, p. 1754 - 1757

3
[ 51779-32-9 ]
[ 151978-58-4 ]

Reference： [1] Organic Letters, 2015, vol. 17, # 7, p. 1754 - 1757

4
[ 928-90-5 ]
[ 151978-58-4 ]

Reference： [1] Organic Letters, 2015, vol. 17, # 7, p. 1754 - 1757

5
[ 6097-08-1 ]
[ 151978-58-4 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 21, p. 6523 - 6532,10
[2] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 21, p. 6523 - 6532

[ 151978-58-4 ] Synthesis Path-Downstream 1~42

1
[ 151978-58-4 ]
[ 151978-69-7 ]
3-[7-(6-tert-Butoxycarbonylamino-hex-1-ynyl)-1-(4-chloro-benzyl)-2,5-dioxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl]-propionic acid ethyl ester [ No CAS ]

Reference： [1]Tetrahedron Letters,1994,vol. 35,p. 2113 - 2116

2
[ 151978-58-4 ]
[ 151978-57-3 ]
[ 151978-59-5 ]

Reference： [1]Journal of the American Chemical Society,1994,vol. 116,p. 5077 - 5083

Yield	Reaction Conditions	Operation in experiment
		a) 1-(3-nitrobenzyl)-4-(2-carboxyethyl)-7-(N-boc-6-amino-1-hexynyl)-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione ethyl ester was prepared using the method described in part (f) of example 1. Thus, from 0.26 grams of 1-(3-nitrobenzyl)-4-(2-carboxyethyl)-7-iodo-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione ethyl ester and 0.19 grams of N-boc-6-amino-1-hexyne was prepared 226.3 mgs (78percent) 1-(3-nitrobenzyl)-4-(2-carboxyethyl)-7-(N-boc-6-amino-1-hexynyl)-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione ethyl ester (TLC, SiO2, 1:1 ethyl acetate/hexane, Rf =0.34, upsilonnu positive). 1 H NMR (CDCl3, deltaTMS) 8.09 [1H, dt, 3 JHH =7 Hz, 4 JHH =2 Hz, NCH2 (C4-Ar-H)], 8.02 [1H, bs, NCH2 (C2-Ar-H)], 7.83 (1H, d, 4 JHH =2 Hz, o-CON), 7.50-7.35 [ 3H, m, NCH2 (C5, C6-Ar-H), Ar-H p-CON], 7.05 (1H, d, 3 JHH =8 Hz, Ar-H m-CON), 5.22 (1H, d, 2 JHH =16 Hz, NCHHAr), 5.02 (1H, d, 2 JHH =16 Hz, NCHHAr), 4.60 (1H, bs, BocNH), 4.20-4.08 (3H, m, NCHHCO, OCH2), 4.0-3.8 (3H, m, NCH2 CH2, NCHHCO), 3.16 (2H, q, 3 JHH =6 Hz, BocNHCH2), 2.72 (1H, dt, 2 JHH =16 Hz, 3 JHH =8 Hz, CHHCO2), 2.62 (1H, dt, 2 JHH =16 Hz, 3 JHH =8 Hz, CHHCO2), 2.39 (2H, t, 3 JHH =6 Hz, C.integral.CCH2), 1.60 (4H, bs, CH2 CH2 CH2 CH 2), 1.41 (9H, s, t-Bu), 1.24 (3H, t, 3 JHH =7 Hz, CH3).

Yield	Reaction Conditions	Operation in experiment
0.124 grams (84%)		e) 1-(methyl)-4-(2-carboxyethyl)-7-(N-boc-6-amino-1-hexynyl)-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione ethyl ester was prepared using the method described in part (f) of example 1. Thus, 0.126 grams of 1-methyl-4-(2-carboxyethyl)-7-iodo-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione ethyl ester and 0.119 grams of N-boc-6-amino-1-hexyne yielded 0.124 grams (84percent) 1-(methyl)-4-(2-carboxyethyl)-7-(N-boc-6-amino-1-hexynyl)-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione ethyl ester (TLC, SiO2, 1:1 ethyl acetate/hexane, Rf =0.36, upsilonnu positive). 1 H NMR (CDCl3, deltaTMS) 7.84 (1H, d, 4 JHH =2 Hz, Ar-H o-CON), 7.47 (1H, dd, 4 JHH =2 Hz, 3 JHH =9 Hz, Ar-H p-CON), 7.07 (1H, d, 3 JHH =9 Hz, Ar-H m-CON), 4.60 (1H, bs, NH), 4.12 (2H, q, 3 JHH =7 Hz, OCH2), 4.0 (1H, d, 2 JHH =15 Hz, NCHHCO), 3.90 (2H, t, 3 JHH =7 Hz, NCH2), 3.84 (1H, d, 2 JHH =15 Hz, NCHHCO), 3.26 (3H, s, NCH3), 3.15 (2H, q, 3 JHH =7 Hz, BocNHCH2), 2.73 (1H, dt, 2 JHH =16 Hz, 3 JHH =9 Hz, CHHCO2), 2.63 (1H, dt, 2 JHH =16 Hz, 3 JHH =9 Hz, CHHCO2),2.40 (2H, t, 3 JHH =6 Hz, C.integral.CCH2), 1.62 (4H, m, CH2 CH2 CH2 CH2), 1.24 (3H, t, 3 JHH =7 Hz, CH3).

5
[ 944357-88-4 ]
[ 151978-58-4 ]
[ 958842-91-6 ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 556 - 565

6
[ 1005837-05-7 ]
[ 151978-58-4 ]
[ 1005837-11-5 ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 556 - 565

7
[ 1005837-03-5 ]
[ 151978-58-4 ]
[ 1005837-09-1 ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 556 - 565

8
[ 1225055-49-1 ]
[ 151978-58-4 ]
[ 1225055-51-5 ]

Reference： [1]Organic Letters,2010,vol. 12,p. 2104 - 2107

9
[ 15252-45-6 ]
[ 24424-99-5 ]
[ 151978-58-4 ]

Yield	Reaction Conditions	Operation in experiment
1.831 g	With sodium hydrogencarbonate; In tetrahydrofuran; water; at 0 - 20℃; for 2h;Inert atmosphere;	N-(5-hexynyl)phthalimide (4.66 g, 20.5 mmol) was dissolved in THF (250 ml) and hydrazine hydrate (410 mmol, 19.8 ml) was added. The obtained solution was refluxed for 3 h, forming a white precipitate after 1h. After the reaction was finished it was cooled down to 8°C and filtered. The filtrate was evaporated to obtain the crude amine 8 as yellow liquid. The crude amine was dissolved in THF (14 ml) and water (14 ml) was added followed by NaHCO3 (2.27 g, 27.0 mmol). The solution was cooled to 0°C and Boc2O (2 M in THF, 8.09 ml; 16.2 mmol) was added via a syringe. The temperature was maintained for 15 min before removing the ice-bath. After 2h at rt the reaction was diluted with EtOAc. It was washed with water, sat. NaHCO3 aq and brine. Drying and evaporation gave a crude oil that was purified on silica with CyHex/EtOAc (92/8) resulting in 1.831g (45percent) 9 as pale yellow oil.

Reference： [1]Bioconjugate Chemistry,2013,vol. 24,p. 1624 - 1633
[2]Journal of the American Chemical Society,2010,vol. 132,p. 14070 - 14072
[3]Bioorganic and medicinal chemistry,2012,vol. 20,p. 6523 - 6532,10

10
[ 28075-50-5 ]
[ 151978-58-4 ]
[ 1246242-16-9 ]

Reference： [1]Journal of the American Chemical Society,2010,vol. 132,p. 14070 - 14072

11
[ 151978-58-4 ]
[ 75-05-8 ]
[ 1308379-20-5 ]

Reference： [1]Journal of the American Chemical Society,2011,vol. 133,p. 8482 - 8485

12
[ 151978-58-4 ]
[ 1014024-69-1 ]