180976-09-4|tert-Butyl (cyanomethyl)(methyl)carbamate| 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 [ 180976-09-4 ] Purity: 97% 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 [ 180976-09-4 ]

CAS No. :	180976-09-4
Formula :	C₈H₁₄N₂O₂
M.W :	170.21
SMILES Code :	O=C(OC(C)(C)C)N(CC#N)C
MDL No. :	MFCD06658361
InChI Key :	AXNPHDXTYKKHSJ-UHFFFAOYSA-N
Pubchem ID :	10654719

Safety of [ 180976-09-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 180976-09-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	0
Fraction Csp3	0.75
Num. rotatable bonds	4
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	44.93
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	53.33 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.1
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	0.9
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.38
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.	0.53
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	0.06
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.99

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.2
Solubility	10.8 mg/ml ; 0.0633 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.	-1.61
Solubility	4.23 mg/ml ; 0.0248 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very 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	-0.99
Solubility	17.5 mg/ml ; 0.103 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.	-6.7 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)	2.24

Application In Synthesis of [ 180976-09-4 ]

* 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 [ 180976-09-4 ]

[ 180976-09-4 ] Synthesis Path-Downstream 1~31

1
[ 24424-99-5 ]
[ 25808-30-4 ]
[ 180976-09-4 ]

Yield	Reaction Conditions	Operation in experiment
69%	With triethylamine; In dichloromethane; at 20℃; for 168h;	To a suspension of methylaminoacetonitrile hydrochloride (11.45 g, 107.4 mmol) in DCM (100 ml_) was added triethylamine (31.5 mL, 226 mmol), followed by di-tert-butyl dicarbonate (22.3 g, 102.2 mmol) and the reaction mixture was stirred at room temperature over the weekend. The reaction mixture was filtered, concentrated in vacuo and purified over silica using a gradient of 10-20percent ethyl acetate/cyclohexane. The pure fractions were combined and concentrated to afford the title compound (11.94 g, 69percent) as a colourless liquid. LC-MS (Method 5): 2.82 min, [M+H]+ 171.1.

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 3070 - 3088.
[2]Patent: WO2008/23157,2008,A1 .Location in patent: Page/Page column 115.

2
[ 94849-39-5 ]
[ 180976-09-4 ]

References: [1]Tetrahedron Letters,1997,vol. 38,p. 5335 - 5338.
[2]Synthesis,1996,p. 1246 - 1258.

3
[ 180976-09-4 ]
[ 121492-06-6 ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 3070 - 3088.
[2]Synthesis,1996,p. 1246 - 1258.
[3]Tetrahedron Letters,1997,vol. 38,p. 5335 - 5338.

4
[ 180976-09-4 ]
[ 74-88-4 ]
(cyano-methyl-methyl)-methyl-carbamic acid <i>tert</i>-butyl ester [ No CAS ]

References: [1]Organic Letters,2004,vol. 6,p. 2745 - 2748.

5
[ 180976-09-4 ]
[ 1009799-44-3 ]

Yield	Reaction Conditions	Operation in experiment
96%	With hydroxylamine; In ethanol; water; for 1h;Heating / reflux;	A solution of <strong>[180976-09-4]cyanomethyl-methyl-carbamic acid tert-butyl ester</strong> (6.01 g, 35.3 mmol) and hydroxylamine (5.13 g, 77.6 mmol, 50percent solution in water) in ethanol (30 mL) was <n="118"/>heated at reflux for 1 h. The reaction mixture was cooled to room temperature and concentrated in vacuo. The residue was azeotroped twice with ethanol, then once with isopropyl alcohol to afford a white solid. This was triturated with ether and collected by filtration, then dried under vacuum at room temperature to afford the title compound (5.27 g) as a white solid. A further crop could be obtained from the mother liquors by the same work-up procedure. Total yield 6.93 g (96percent). 1H NMR (CDCI3): 1.48 (S, 9 H), 2.87 (s, 3 H), 3.84 (s, 2 H), 4.73 (brs., 1 H), 5.09 (bra., 2 H).

References: [1]Patent: WO2008/23157,2008,A1 .Location in patent: Page/Page column 115-116.

6
[ 13734-36-6 ]
[ 180976-09-4 ]

References: [1]Tetrahedron Letters,1997,vol. 38,p. 5335 - 5338.
[2]Synthesis,1996,p. 1246 - 1258.

7
C₁₁H₁₉NO₆ [ No CAS ]
[ 180976-09-4 ]

References: [1]Tetrahedron Letters,1997,vol. 38,p. 5335 - 5338.

8
[ 24424-99-5 ]
[ 180976-09-4 ]

References: [1]Synthesis,1996,p. 1246 - 1258.

9
[ 180976-09-4 ]
[ 183444-91-9 ]

References: [1]Synthesis,1996,p. 1246 - 1258.

10
[ 180976-09-4 ]
[ 183444-93-1 ]

References: [1]Synthesis,1996,p. 1246 - 1258.

11
[ 180976-09-4 ]
[ 180976-10-7 ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 3070 - 3088.

12
[ 21950-36-7 ]
[ 180976-09-4 ]
[ 1261273-68-0 ]

References: [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 8158 - 8166.

13
[ 75-05-8 ]
[ 180976-09-4 ]
C₁₀H₁₇N₅O₂ [ No CAS ]

References: [1]Bioconjugate Chemistry,2016,vol. 27,p. 1707 - 1712.

14
[ 24424-99-5 ]
[ 5616-32-0 ]
[ 180976-09-4 ]