13063-60-0|4-Octylmorpholine| Ambeed

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Quality Control of [ 13063-60-0 ] Purity: 95% SDS Specification

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Product Details of [ 13063-60-0 ]

CAS No. :	13063-60-0
Formula :	C₁₂H₂₅NO
M.W :	199.33
SMILES Code :	CCCCCCCCN1CCOCC1
MDL No. :	MFCD00047423
InChI Key :	NMLNNXGEQCSYGQ-UHFFFAOYSA-N
Pubchem ID :	83099

Safety of [ 13063-60-0 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 13063-60-0 ] Show Less

Physicochemical Properties

Num. heavy atoms	14
Num. arom. heavy atoms	0
Fraction Csp3	1.0
Num. rotatable bonds	7
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	65.58
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	12.47 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	3.42
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	3.31
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.3
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.	2.09
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	3.17
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.86

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.7
Solubility	0.398 mg/ml ; 0.002 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.25
Solubility	0.113 mg/ml ; 0.000565 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	-3.29
Solubility	0.102 mg/ml ; 0.000512 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.	-5.17 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	0.0 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)	1.95

Application In Synthesis of [ 13063-60-0 ]

* 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 [ 13063-60-0 ]

[ 13063-60-0 ] Synthesis Path-Downstream 1~20

1
[ 13063-60-0 ]
[ 111-85-3 ]

References: [1]Tetrahedron Letters,1987,vol. 28,p. 427 - 430.

2
[ 5338-65-8 ]
[ 13063-60-0 ]

References: [1]Chemical and Pharmaceutical Bulletin,1992,vol. 40,p. 3234 - 3244.

3
[ 111-86-4 ]
[ 111-46-6 ]
[ 13063-60-0 ]

References: [1]Journal of Organic Chemistry,1985,vol. 50,p. 1365 - 1370.

4
[ 629-06-1 ]
2.) ROCH₂N(CH₂)4O [ No CAS ]
[ 13063-60-0 ]

References: [1]Tetrahedron Letters,1987,vol. 28,p. 427 - 430.

5
[ 5765-65-1 ]
n-octyl-Mg-X [ No CAS ]
[ 13063-60-0 ]

References: [1]Synlett,2005,p. 1799 - 1801.

6
[ 96517-27-0 ]
[ 13063-60-0 ]

References: [1]Journal of the American Chemical Society,2007,vol. 129,p. 13792 - 13793.

7
[ 31866-75-8 ]
[ 13063-60-0 ]

References: [1]Tetrahedron Letters,1987,vol. 28,p. 427 - 430.

8
[ 13063-60-0 ]
[ 25727-94-0 ]

References: [1]Tetrahedron Letters,1987,vol. 28,p. 427 - 430.

9
[ 13063-60-0 ]
[ 2473-01-0 ]

References: [1]Tetrahedron Letters,1987,vol. 28,p. 427 - 430.

10
[ 13063-60-0 ]
[ 1002-69-3 ]

References: [1]Tetrahedron Letters,1987,vol. 28,p. 427 - 430.

11
[ 13063-60-0 ]
[ 82394-19-2 ]

References: [1]Tetrahedron Letters,1987,vol. 28,p. 427 - 430.

12
[ 543-59-9 ]
[ 13063-60-0 ]

References: [1]Tetrahedron Letters,1987,vol. 28,p. 427 - 430.

13
[ 544-10-5 ]
[ 13063-60-0 ]

References: [1]Tetrahedron Letters,1987,vol. 28,p. 427 - 430.

14
[ 82394-18-1 ]
[ 13063-60-0 ]

References: [1]Tetrahedron Letters,1987,vol. 28,p. 427 - 430.

15
[ 110-91-8 ]
[ 111-83-1 ]
[ 13063-60-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; In acetone;	EXAMPLE 1C Preparation of N-Octyl Morpholinium Acetonitrile (OMA) Combined were 51.5 g of octylbromide, 29.88 g morpholine, and 28.0 g anhydrous sodium carbonate with 150 ml of acetone in a large round bottom flask. This mixture was refluxed for 8 hours at the boiling point of acetone or approximately 60 C., then cooled to room temperature and the solid sodium carbonate filtered. Acetone was removed using a roto-evaporator. The resulting oil was dissolved in ether and washed twice with water and once with brine solution. The ether solution was dried over anhydrous sodium sulfate. After filtering, ether was removed in-vacuo, leaving a slightly-colored oil. Gas chromatography showed the oil to be N-octyl morpholine, obtained with a yield of 98% and having greater than 95% purity.

References: [1]Patent: US5739327,1998,A .

16
[ 110-91-8 ]
[ 111-87-5 ]
[ 13063-60-0 ]

Yield	Reaction Conditions	Operation in experiment
68%		General procedure: The reaction of 1-octyl p-cymenesulphonate (4a) and 2-octyl p-cymenesulphonate (4c) with sodium methoxide led to the formation of the desired methyl octyl ethers (Scheme 2), as evidenced by NMR spectroscopy and GC-MS (Supplementary Information). The yields of methyl 1-octyl ether (5a) and for optimal conditions methyl 2-octyl ether (5b) are presented in Table 4, and are comparable to those established in the literature on similar substrates. 27 When the activated alcohols were reacted with excess morpholine, the p-cymenesulphonate esters underwent the anticipated substitution reaction, with yields of 68% (N-1-octyl morpholine, 6a) and 82% (N-2-octylmorpholine, 6b) achieved (Scheme 3).

References: [1]Chemistry - A European Journal,2013,vol. 19,p. 3665 - 3675.
[2]Journal of the Brazilian Chemical Society,2015,vol. 26,p. 1914 - 1919.

17
[ 4394-85-8 ]
[ 111-83-1 ]
[ 13063-60-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium hydroxide; In water; at 100℃; for 12.0h;Green chemistry;	General procedure: KOH (2.4mmol), H2O (1.0mL), (pseudo)halides 1 (0.8mmol), and formamides 2 (1.6mmol) were successively added into a reaction tube. Then the reaction mixture was stirred under the conditions shown in Tables 1-5. After the reactions were completed, the mixture was extracted by ethyl acetate, dried over anhydrous Na2SO4, filtered, concentrated under reduced pressure, and purified by flash chromatography to give products 3.

References: [1]Tetrahedron,2014,vol. 70,p. 880 - 885.

18
[ 110-91-8 ]
[ 111-86-4 ]
[ 13063-60-0 ]
[ 1120-48-5 ]

Yield	Reaction Conditions	Operation in experiment
81%; 18%	With platinum-nickel nanoclusters on activated carbon; hydrogen; at 180℃; under 760.051 Torr;Flow reactor;	General procedure: The reactions were performed in a flow-through reactor at atmospheric pressure and temperature 160-230. The reduced humid catalyst was loaded in the reactor between the glass layers of the nozzle and dried in a hydrogen stream at 120 prior to the reaction. The laboratory-grade reaction was a 12Kh18N10T steel tube (inner diameter 9 mm) put in an electric oven (heating zone height 50 mm). Temperature in the reactor was measured using a thermocouple. Hydrogen feed was adjusted using a GV-7 hydrogen generator. The feeding rate of the starting amines was 0.9 and 3.6 L kgcat-1 h-1 and that of hydrogen was 0.5 L h-1 gcat-1 at atmospheric pressure.

References: [1]Russian Journal of General Chemistry,2017,vol. 87,p. 2757 - 2761.
Zh. Obshch. Khim.,2017,vol. 87,p. 1937 - 1941,5.

19
[ 155127-38-1 ]
[ 13063-60-0 ]

References: [1]Organic Letters,2021,vol. 23,p. 3803 - 3808.

20
[ 629-05-0 ]
[ 13063-60-0 ]

References: [1]Organic Letters,2021,vol. 23,p. 3803 - 3808.
[2]Organic Letters,2021,vol. 23,p. 3803 - 3808.

Historical Records

Related Parent Nucleus of
[ 13063-60-0 ]

Morpholines

A186064 [39793-32-3]

5-Morpholinopentan-1-amine

Similarity: 1.00

A504453 [95311-97-0]

4-Tetradecylmorpholine

Similarity: 1.00

A556775 [4344-62-1]

5-Morpholinopentan-1-ol

Similarity: 0.96

A112838 [1005-67-0]

4-Butylmorpholine

Similarity: 0.96

A857360 [6321-07-9]

4-Morpholinobutan-1-amine

Similarity: 0.96

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P322
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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.
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P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
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P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
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P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
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P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
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P401
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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

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CAS No.: 13063-60-0

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