151978-58-4|tert-Butyl hex-5-yn-1-ylcarbamate| Ambeed

Size	Price	VIP Price	US Stock	Global Stock	In Stock
{[ item.pr_size ]}		Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

{[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

Quality Control of [ 151978-58-4 ] Purity: 95% SDS Specification

COA

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

NMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

CNMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

HPLC

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

LC-MS

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

1-2 Day Shipping
High Quality
Technical Support

Product Details of [ 151978-58-4 ]

CAS No. :	151978-58-4
Formula :	C₁₁H₁₉NO₂
M.W :	197.27
SMILES Code :	O=C(OC(C)(C)C)NCCCCC#C
MDL No. :	MFCD18839148
InChI Key :	QUIDQZORWGPNKV-UHFFFAOYSA-N
Pubchem ID :	11830384

Safety of [ 151978-58-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Computational Chemistry of [ 151978-58-4 ] Show Less

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 ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	38.33 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.8
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.22
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.39
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	2.29
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	2.0
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.34

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.0
Solubility	1.97 mg/ml ; 0.01 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.66
Solubility	0.432 mg/ml ; 0.00219 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-2.54
Solubility	0.572 mg/ml ; 0.0029 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.93 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	2.48

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.

Downstream synthetic route of [ 151978-58-4 ]

[ 151978-58-4 ] Synthesis Path-Downstream 1~35

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 ]

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

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

References: [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 ]

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

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

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

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

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

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

References: [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.

References: [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 ]

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

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

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

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