67107-87-3|12-Amino-1-dodecanol| Ambeed

CAS No. :	67107-87-3
Formula :	C₁₂H₂₇NO
M.W :	201.35
SMILES Code :	OCCCCCCCCCCCCN
MDL No. :	MFCD01851111
InChI Key :	IIWXYWWVCBRBCJ-UHFFFAOYSA-N
Pubchem ID :	5182020

Safety of [ 67107-87-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319
Precautionary Statements:	P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313

Computational Chemistry of [ 67107-87-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	14
Num. arom. heavy atoms	0
Fraction Csp3	1.0
Num. rotatable bonds	11
Num. H-bond acceptors	2.0
Num. H-bond donors	2.0
Molar Refractivity	63.67
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	46.25 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	3.07
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	3.81
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.84
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.	2.49
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	3.11
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.06

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.76
Solubility	0.348 mg/ml ; 0.00173 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.	-4.48
Solubility	0.00673 mg/ml ; 0.0000334 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately 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	-3.81
Solubility	0.0313 mg/ml ; 0.000155 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	Yes
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.	-4.82 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	1.0
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	0.0
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<3.0
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)	1.75

Application In Synthesis of [ 67107-87-3 ]

* 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 [ 67107-87-3 ]

[ 67107-87-3 ] Synthesis Path-Downstream 1~54

1
[ 85-44-9 ]
[ 67107-87-3 ]
[ 82583-84-4 ]

References: [1]British Journal of Pharmacology and Chemotherapy,1955,vol. 10,p. 116,117.

2
[ 52162-19-3 ]
[ 67107-87-3 ]

References: [1]British Journal of Pharmacology and Chemotherapy,1955,vol. 10,p. 116,117.

3
[ 67107-87-3 ]
[ 81313-55-5 ]

References: [1]Bulletin de la Societe Chimique de France,1967,p. 588 - 596.

4
[ 67107-87-3 ]
[ 24424-99-5 ]
[ 67341-03-1 ]

Yield	Reaction Conditions	Operation in experiment
98%	With sodium hydroxide; In water; tert-butyl alcohol; for 18h;Inert atmosphere;	To a mixture of NaOH (43 mg, 1.1 mmol), in water/tert-BuOH 1:1 (1.0 mL) was added di-tert-butyl dicarbonate (225 muL, 1.05 mmol) and <strong>[67107-87-3]12-amino-dodecan-1-ol</strong> (199 mg, 1.00 mmol). After the viscous mixture was stirred for 18 h, 0.3 M HCl solution (1.5 mL) was added and the aqueous layer was extracted with ethyl acetate (3 × 30 mL). The combined organic layers were washed with brine (5 mL) and dried over MgSO4. The solvent was removed under reduced pressure and 294 mg (98%) of the product was obtained as white solid. Mp 75 C. 1H NMR (300 MHz, CDCl3) delta 4.51 (s, 1H, NH), 3.66 (dd, J = 11.1, 6.5 Hz, 2H, NHCH2), 3.11 (dd, J = 13.2, 6.6 Hz, 2H, CH2OH), 1.73-1.16 (m, 21H, (CH2)10, OH), 1.46 (s, 9H, OtBu). 13C NMR (151 MHz, CDCl3) delta 155.94, 78.96, 63.03, 40.60, 32.77, 30.03, 29.53, 29.48, 29.48, 29.37, 29.23, 28.40, 26.77, 25.69. IR (film) nu = 3368 cm-1, 2919, 2851, 1685, 1653, 1558, 1523, 1481, 1469, 1457, 1443, 1389, 1364, 1337, 1288, 1266, 1243, 1225, 1173, 1142, 1059, 1027, 994, 978, 867, 781, 741, 720, 679, 661. HRMS (ESI) calcd for C17H35NNaO3 [M+Na]+ 324.2515, found 324.2509.
	In tetrahydrofuran; at 50℃; for 3h;Inert atmosphere;	General procedure: To a solution of an aminoalcohol (66.6 mmol) in THF (67 mL) was added di-tert-butyl dicarbonate (15.3 g, 66.6 mmol) at 50 C under an argon atmosphere. After 3 h stirring, the solvent was removed in vacuo. The crude product was purified by silica gel column chromatography (EtOAc / hexane, 50:50) to give a N-Boc aminoalcohol. Iodine (12.5 g, 49.3 mmol) was added to a solution of N-Boc aminoalcohol (17.6 mmol), PPh3 (6.92 g, 26.3 mmol) and imidazole (1.79 g, 26.3 mmol) in CH2Cl2 (98 mL) at 0 C. The mixture was stirred at room temperature for 1 h under an argon atmosphere. The reaction mixture was quenched with saturated aqueous Na2S2O3, diluted with CH2Cl2 and extracted with CH2Cl2. The organic layer was washed with H2O and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane, 10:90) to afford a N-BOC aminoalkyliodide. To a solution of NaH (60% in oil, 0.673 g, 16.8 mmol) in DMF (15.3 mL) was added dropwise a solution of N-hydroxyphthalimide (2.49 mmol) in DMF (10 mL) at 0 C under an argon atmosphere. After 15 min of stirring, a solution of the iodide (15.3 mmol) in DMF (10 mL) was added dropwise to the solution and stirred at 70 C for 12 h. After cooled to 0 C, the reaction was quenched with H2O and filtrated to afford colorless solid, which was recrystallized to give a N-alkoxyphthalimide 13a-d.

References: [1]Chemistry and Physics of Lipids,1993,vol. 66,p. 111 - 122.
[2]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 583 - 591.
[3]Tetrahedron,2016,vol. 72,p. 6492 - 6498.

5
[ 73782-16-8 ]
[ 67107-87-3 ]

References: [1]Advanced Functional Materials,2011,vol. 21,p. 4510 - 4518.
[2]Chemistry and Physics of Lipids,1993,vol. 66,p. 111 - 122.

6
[ 67107-87-3 ]
[ 3019-71-4 ]
[ 78177-99-8 ]

References: [1]Collection of Czechoslovak Chemical Communications,1980,vol. 45,p. 2784 - 2803.

7
[ 67107-87-3 ]
[ 4652-65-7 ]
(S)-4-Benzyloxycarbonylamino-4-(12-hydroxy-dodecylcarbamoyl)-butyric acid methyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 1909 - 1926.

8
[ 67107-87-3 ]
[ 24424-95-1 ]
12-isocyanato-dodecan-1-ol [ No CAS ]

References: [1]Angewandte Chemie - International Edition,1999,vol. 38,p. 2917 - 2919.

9
[ 693-57-2 ]
[ 67107-87-3 ]

Yield	Reaction Conditions	Operation in experiment
79%		To a stirred suspension of l2-aminododecanoic acid (4.3 g, 20 mmol) in 20 mL MeOH at 0 C was added acetyl chloride (3.6 mL, 2.5 equiv) dropwise. The mixture was then refluxed for 3 h. The solvent was then distilled off under reduced pressure. The white solid obtained was used for the next step without further purification. 100 mL anhydrous THF was added, and then Lithium aluminum hydride (3.2 g, 84 mmol) was added portionwise at 0 C. The mixture was heated under reflux for 16 h. The mixture was cooled down to 0 C, and quenched by 10 mL ice water. 6 mL 15% NaOH(aq) solution was added, and the mixture was stirred at room temperature for 1 h. The gray L1AIH4 turned into off white precipitates and was filtered off, washed with CH2CI2 and MeOH. The filtrate was concentrated to give 12-amino- l-dodecanol (26b) as a white solid (3.18 g, 79%). This material was used for the next step reaction without further purification. 'H NMR (400 MHz, CDCh): d 3.64 (t, J= 6.6 Hz, 2H), 2.68 (t, J= 7.0 Hz, 2H), 1.56 (m, 2H), 1.44 (m, 2H), 1.40- 1.20 (m, 16H).

References: [1]Patent: WO2019/140270,2019,A1 .Location in patent: Paragraph 0083.
[2]Angewandte Chemie - International Edition,2018,vol. 57,p. 555 - 559.
Angew. Chem.,2018,vol. 130,p. 564 - 568,5.
[3]Journal of Organic Chemistry,1999,vol. 64,p. 9337 - 9347.
[4]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1553 - 1556.
[5]European Journal of Medicinal Chemistry,2015,vol. 101,p. 367 - 383.

Yield	Reaction Conditions	Operation in experiment
		12-Amino-dodecanol-(1) (109) 11.0 g (52 mmol) 108 in 150 ml methanol containing 5.0 g Raney-Nickel catalyst was hydrogenated with hydrogen for 8 hours at 80 C./120 bar with addition of 50 ml liquid ammonia in a high-pressure hydrogenation instrument. 10.3 g (98%) 109 was obtained as a pale yellow oil after filtration, concentration and blow-off.

11
[ 67107-87-3 ]
[ 4411-25-0 ]
[ 860622-77-1 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane;	12-aminododecanaol (50 mg) was stirred in dichloromethane with 1- adamantylisocyanate (44mg) overnight. The reaction was evaporated and EPO <DP n="69"/>carbonyldiimidazole was added in 2 mL acetonitrile. This was refluxed 5 hrs. The solvent was removed in vacuo and the solid was partitioned between dichloromethane and water. The organic layer was washed repeatedly with water to yield the target compound (22mg). 1H NMR (300 MHz, CDCl3) delta = 8.17 (s, IH), 7.45 (s, IH), 7.05 (s, IH), 4.41 (t, J = 7.5 Hz, 2H)5 4.32 (br, IH), 4.21 (br, IH), 3.08 (q, J = 6.7 Hz, 2 H), 2.0 - 1.0 (m, 35H).

References: [1]Patent: WO2006/45119,2006,A2 .Location in patent: Page/Page column 67-68.

12
[ 67107-87-3 ]
[ 182883-93-8 ]
[ 878631-26-6 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1553 - 1556.

13
[ 53005-24-6 ]
[ 67107-87-3 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0℃; for 48h;Reflux; Inert atmosphere;	General procedure: Freshly distilled acetyl chloride (1.70 mL, 23.90 mmol) was added dropwise to a stirred suspension of 10-aminodecanoic acid 12 (1.80 g, 9.61 mmol) in anhydrous MeOH (20 mL) under N2 atmosphere at 0 C. Once the addition was complete, the mixture was heated under reflux for 3 h. After completion of the reaction, the solvent and excess acetyl chloride were distilled off under reduced pressure affording the corresponding methyl 10-aminodecanoate as a white solid (89%), which was used in the next reaction without further purification. Lithium aluminum hydride (1.65 g, 17.20 mmol) was added in small portions to a stirred suspension of the amino ester intermediate (1.73 g, 8.57 mmol) in anhydrous THF (100 mL) at 0 C. The reaction mixture was heated under reflux for 48 h, then cooled to room temperature and poured into crushed ice. The aqueous layer was vigorously extracted with CH2Cl2 (6 x 80 mL) and the combined organic phases were washed with brine and dried over anhydrous Na2SO4. The solvent was evaporated under reduced pressure and the crude product was recrystallized to obtain pure 16 (0.92 g, 62%).

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1553 - 1556.
[2]European Journal of Medicinal Chemistry,2015,vol. 101,p. 367 - 383.

14
[ 3344-77-2 ]
[ 67107-87-3 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen;palladium 10% on activated carbon; In methanol; under 1551.49 Torr;	vi) Cholesteryl 12-hydroxydodecylcarbamate from cholesteryl chloroformate and 12-aminododecan-1-ol. 12-Aminododecanl-1-ol is prepared from 12-bromododecan-1-ol and sodium azide in refluxing 95% ethanol, followed by catalytic hydrogenation (10% Pd/C catalyst, 30 psi hydrogen) in methanol.

References: [1]Patent: US2008/85869,2008,A1 .Location in patent: Page/Page column 27.
[2]Carbohydrate Research,2008,vol. 343,p. 2325 - 2328.
[3]Chemical Biology and Drug Design,2016,vol. 88,p. 197 - 208.

15
[ 67107-87-3 ]
<i>N</i>-(12-hydroxy-dodecyl)-<i>N</i>'-methyl-guanidine; compound with trifluoro-acetic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1553 - 1556.

16
[ 67107-87-3 ]
(S)-4-(12-Acetoxy-dodecylcarbamoyl)-4-amino-butyric acid methyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 1909 - 1926.

17
[ 67107-87-3 ]
(S)-2-((R)-2-Amino-propionylamino)-pentanedioic acid 5-amide 1-[(12-hydroxy-dodecyl)-amide] [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 1909 - 1926.

18
[ 67107-87-3 ]
(S)-4-(12-Acetoxy-dodecylcarbamoyl)-4-((R)-2-amino-propionylamino)-butyric acid methyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 1909 - 1926.

19
[ 67107-87-3 ]
[ 205252-41-1 ]

References: [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 1909 - 1926.

20
[ 67107-87-3 ]
(S)-4-(12-Acetoxy-dodecylcarbamoyl)-4-benzyloxycarbonylamino-butyric acid methyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 1909 - 1926.

21
[ 67107-87-3 ]
2-O-acetyl-1-β-[12-((R)-alanyl-(S)-glutaminylamino)dodec-1-yl]-D-mannopyranose [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 1909 - 1926.

22
[ 67107-87-3 ]
(S)-4-(12-Acetoxy-dodecylcarbamoyl)-4-((R)-2-benzyloxycarbonylamino-propionylamino)-butyric acid methyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 1909 - 1926.

23
[ 67107-87-3 ]
(S)-4-Amino-4-[12-((2S,3S,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-dodecylcarbamoyl]-butyric acid methyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 1909 - 1926.

24
[ 67107-87-3 ]
(S)-4-((R)-2-Amino-propionylamino)-4-[12-((2S,3S,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-dodecylcarbamoyl]-butyric acid methyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 1909 - 1926.

25
[ 67107-87-3 ]
(S)-4-Amino-4-[12-((2R,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-dodecylcarbamoyl]-butyric acid methyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 1909 - 1926.

26
[ 67107-87-3 ]
(S)-4-Benzyloxycarbonylamino-4-[12-((2S,3S,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-dodecylcarbamoyl]-butyric acid methyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 1909 - 1926.

27
[ 67107-87-3 ]
(S)-4-((R)-2-Amino-propionylamino)-4-[12-((2R,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-dodecylcarbamoyl]-butyric acid methyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 1909 - 1926.

28
[ 67107-87-3 ]
(S)-4-((R)-2-Benzyloxycarbonylamino-propionylamino)-4-[12-((2S,3S,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-dodecylcarbamoyl]-butyric acid methyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 1909 - 1926.

29
[ 67107-87-3 ]
(S)-4-Benzyloxycarbonylamino-4-[12-((2R,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-dodecylcarbamoyl]-butyric acid methyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 1909 - 1926.

30
[ 67107-87-3 ]
(S)-4-((R)-2-Benzyloxycarbonylamino-propionylamino)-4-[12-((2R,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-dodecylcarbamoyl]-butyric acid methyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 1909 - 1926.

31
[ 1611-56-9 ]
[ 67107-87-3 ]

References: [1]Chemistry and Physics of Lipids,1993,vol. 66,p. 111 - 122.
[2]Advanced Functional Materials,2011,vol. 21,p. 4510 - 4518.

32
[ 67107-87-3 ]
[ 154371-99-0 ]

References: [1]Chemistry and Physics of Lipids,1993,vol. 66,p. 111 - 122.

33
[ 67107-87-3 ]
[ 154371-97-8 ]

References: [1]Chemistry and Physics of Lipids,1993,vol. 66,p. 111 - 122.

34
[ 67107-87-3 ]
1-O-(12-NBD-aminododecyl)-sn-glycerol [ No CAS ]

References: [1]Chemistry and Physics of Lipids,1993,vol. 66,p. 111 - 122.

35
[ 67107-87-3 ]
[ 154371-98-9 ]

References: [1]Chemistry and Physics of Lipids,1993,vol. 66,p. 111 - 122.

36
[ 67107-87-3 ]
[ 14502-44-4 ]

References: [1]Bulletin de la Societe Chimique de France,1967,p. 588 - 596.

37
[ 67107-87-3 ]
[ 141546-90-9 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; water;	The crystals dissolved in 20 ml of tetrahydrofuran were added dropwise under ice-cooling to a solution of 1.39 g of <strong>[67107-87-3]12-aminododecanol</strong> and 1.4 ml of triethylamine in 25 ml of tetrahydrofuran. The mixture was stirred overnight while elevating gradually to room temperature and the solvent was distilled away. The residue mixed with water was extracted with chloroform, washed with water and a saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled away to obtain N-(12-hydroxy-1-dodecanyl)-6-chloronicotinamide.

References: [1]Patent: US5250526,1993,A .

38
[ 67107-87-3 ]
[ 10199-89-0 ]
[ 874894-55-0 ]

References: [1]Chemical Biology and Drug Design,2016,vol. 88,p. 197 - 208.
[2]Carbohydrate Research,2008,vol. 343,p. 2325 - 2328.

39
[ 67107-87-3 ]
[ 320393-85-9 ]
[ 1158777-10-6 ]

References: [1]Journal of the American Chemical Society,2009,vol. 131,p. 6964 - 6966.

40
[ 93-58-3 ]
[ 67107-87-3 ]
[ 1262145-13-0 ]

References: [1]Organic Letters,2011,vol. 13,p. 426 - 429.

41
[ 67107-87-3 ]
[ 4931-66-2 ]
C₁₇H₃₄N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	In 1,4-dioxane; at 75℃; for 4h;	Example 14A reaction vessel was charged with 260 parts by weight of <strong>[67107-87-3]12-amino-1-dodecanol</strong>, 184 parts by weight of methyl L-pyroglutamate, and 120 parts by weight of 1,4-dioxane, and the mixture was stirred at 75 C. for 4 hours. The resulting reaction mixture was stripped at 110 C. under reduced pressure to remove the 1,4-dioxane, and 408 parts by weight of white solid was obtained at a yield of 92%. Results of the 13C-NMR shown in Table 14, below, and absorption at 1685 cm-1 (from amide bond) in the measurement of IR spectrum confirmed that the resulting product was an amino acid compound represented by the following formula: TABLE 14 13C-NMR (CDCl3) 64.6ppm (-CH2-OH) 22~31.9ppm (-(CH2)10-] 39.6ppm (-CH2-NH-) 178.4ppm (-NH-CO-) 25.2ppm (-CO-CH2-CH2-) 28.6ppm (-CO-CH2-CH2-) 58.9ppm [-CH(NH2)(COOCH3)] 174.8ppm (-COOCH3) 59.3ppm (-COOCH3)

References: [1]Patent: US2011/144369,2011,A1 .Location in patent: Page/Page column 15.

42
[ 67107-87-3 ]
[ 1359753-03-9 ]

References: [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 583 - 591.

43
[ 67107-87-3 ]
(3RS,4RS)-4-[N-(tert-butoxycarbonyl)-11-aminoundecyl]-3-(non-8-enyl)-oxetan-2-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 583 - 591.

44
[ 67107-87-3 ]
[ 1256470-36-6 ]
[ 1353757-32-0 ]

References: [1]Advanced Functional Materials,2011,vol. 21,p. 4510 - 4518.

45
[ 67107-87-3 ]
[ 1256470-36-6 ]
[ 1353757-33-1 ]

References: [1]Advanced Functional Materials,2011,vol. 21,p. 4510 - 4518.

46
[ 67107-87-3 ]
[ 7144-08-3 ]
[ 1372789-59-7 ]

References: [1]Nucleic Acids Research,2012,vol. 40,p. 2330 - 2344.

47
[ 67107-87-3 ]
[ 7144-08-3 ]
[ 1013357-40-8 ]

References: [1]Nucleic Acids Research,2012,vol. 40,p. 2330 - 2344.

48
[ 67107-87-3 ]
[ 35013-72-0 ]
[ 1393360-95-6 ]

References: [1]Journal of Pharmaceutical Sciences,2012,vol. 101,p. 3249 - 3263.

49
[ 50-00-0 ]
[ 67107-87-3 ]
[ 16772-32-0 ]
[ 1422421-91-7 ]

Yield	Reaction Conditions	Operation in experiment
	In neat (no solvent); at 20℃;	General procedure: 4.2.1 Method A (0026) To a dioxane [15] solution (5 mL) of tocotrienol (4 mmol), the amine (20 mmol) was added. Mixture was cooled in an ice bath and 37% formaldehyde (21 mmol) was added drop wise while stirring. It was then stirred at room temperature for 1 h and then refluxed overnight. Reaction mixture was concentrated under vacuum and the yellow residue obtained was dissolved in ethyl acetate (20 mL), washed several times with saturated NaCl solution, dried over anhydrous MgSO4, and concentrated in vacuum. The residue obtained was subjected to column chromatography using normal phase silica gel as stationary phase and gradient ethyl acetate/n-hexane system as mobile phase (Scheme 1a).4.2.2 Method B (0027) A mixture of tocotrienol [25] (5.0 mmol), paraformaldehyde (5.0 mmol) and amines (5.0 mmol) was stirred and left overnight at rt. The reaction was carried out under solvent-less conditions (few drops of dioxane or ethanol may be added). The residue was purified by flash chromatography directly from the reaction mixture without any work-up (Scheme 1b).

References: [1]European Journal of Medicinal Chemistry,2013,vol. 59,p. 329 - 341.

50
[ 50-00-0 ]
[ 67107-87-3 ]
[ 14101-60-1 ]
[ 1422421-92-8 ]

Yield	Reaction Conditions	Operation in experiment
	In neat (no solvent); at 20℃;	General procedure: 4.2.1 Method A (0026) To a dioxane [15] solution (5 mL) of tocotrienol (4 mmol), the amine (20 mmol) was added. Mixture was cooled in an ice bath and 37% formaldehyde (21 mmol) was added drop wise while stirring. It was then stirred at room temperature for 1 h and then refluxed overnight. Reaction mixture was concentrated under vacuum and the yellow residue obtained was dissolved in ethyl acetate (20 mL), washed several times with saturated NaCl solution, dried over anhydrous MgSO4, and concentrated in vacuum. The residue obtained was subjected to column chromatography using normal phase silica gel as stationary phase and gradient ethyl acetate/n-hexane system as mobile phase (Scheme 1a).4.2.2 Method B (0027) A mixture of tocotrienol [25] (5.0 mmol), paraformaldehyde (5.0 mmol) and amines (5.0 mmol) was stirred and left overnight at rt. The reaction was carried out under solvent-less conditions (few drops of dioxane or ethanol may be added). The residue was purified by flash chromatography directly from the reaction mixture without any work-up (Scheme 1b).

References: [1]European Journal of Medicinal Chemistry,2013,vol. 59,p. 329 - 341.

51
[ 67107-87-3 ]
[ 200133-16-0 ]
C₅₇H₁₀₄N₄O₁₁ [ No CAS ]

References: [1]Patent: WO2014/179620,2014,A1 .Location in patent: Page/Page column 620.
[2]Patent: WO2015/168635,2015,A2 .Location in patent: Page/Page column 271-272.
[3]Patent: WO2015/168618,2015,A2 .Location in patent: Page/Page column 254-256.

52
[ 67107-87-3 ]
tert-butyl 12-hydroxydodecyl((7-methoxychroman-2-yl)methyl)carbamate [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2015,vol. 101,p. 367 - 383.

53
[ 67107-87-3 ]
tert-butyl 12-bromododecyl((7-methoxychroman-2-yl)methyl)carbamate [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2015,vol. 101,p. 367 - 383.

54
[ 67107-87-3 ]
1-(12-(tert-butoxycarbonyl(((R,S)-7-methoxychroman-2-yl)methyl)amino)dodecyl)-3-((S)-1-methylpyrrolidin-2-yl)pyridinium bromide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2015,vol. 101,p. 367 - 383.

Historical Records

Technical Information

• Appel Reaction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Chugaev Reaction • Corey-Kim Oxidation • Dess-Martin Oxidation • Heat of Combustion • Hydride Reductions • Jones Oxidation • Leuckart-Wallach Reaction • Mannich Reaction • Martin's Sulfurane Dehydrating Reagent • Mitsunobu Reaction • Moffatt Oxidation • Oxidation of Alcohols by DMSO • Petasis Reaction • Preparation of Alcohols • Preparation of Amines • Reactions of Alcohols • Reactions of Amines • Reactions with Organometallic Reagents • Ritter Reaction • Sharpless Olefin Synthesis • Specialized Acylation Reagents-Vilsmeier Reagent • Swern Oxidation • Ugi Reaction

Related Functional Groups of
[ 67107-87-3 ]

Aliphatic Chain Hydrocarbons

A481895 [4048-33-3]

6-Aminohexan-1-ol

Similarity: 1.00

A916261 [13325-10-5]

4-Aminobutan-1-ol

Similarity: 0.93

A210536 [68889-62-3]

(S)-3-Aminohexan-1-ol hydrochloride

Similarity: 0.78

A113629 [42042-68-2]

4-(Methylamino)butan-1-ol

Similarity: 0.76

A513786 [158741-04-9]

(R)-2-Aminohexan-1-ol hydrochloride

Similarity: 0.74

Alcohols

A481895 [4048-33-3]

6-Aminohexan-1-ol

Similarity: 1.00

A916261 [13325-10-5]

4-Aminobutan-1-ol

Similarity: 0.93

A210536 [68889-62-3]

(S)-3-Aminohexan-1-ol hydrochloride

Similarity: 0.78

A113629 [42042-68-2]

4-(Methylamino)butan-1-ol

Similarity: 0.76

A283033 [6850-65-3]

4-Aminocyclohexan-1-ol(only contains trans)

Similarity: 0.74

Amines

A481895 [4048-33-3]

6-Aminohexan-1-ol

Similarity: 1.00

A916261 [13325-10-5]

4-Aminobutan-1-ol

Similarity: 0.93

A210536 [68889-62-3]

(S)-3-Aminohexan-1-ol hydrochloride

Similarity: 0.78

A113629 [42042-68-2]

4-(Methylamino)butan-1-ol

Similarity: 0.76

A283033 [6850-65-3]

4-Aminocyclohexan-1-ol(only contains trans)

Similarity: 0.74

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
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

{[proInfo.proName]}

CAS No.: 67107-87-3

{[proInfo.proName]}

CAS No.: 67107-87-3

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[ 67107-87-3 ] Synthesis Path-Downstream 1~54

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[ 67107-87-3 ]

Aliphatic Chain Hydrocarbons

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{[proInfo.proName]}

CAS No.: 67107-87-3

{[proInfo.proName]}

CAS No.: 67107-87-3

Alternative Products

Product Details of [ 67107-87-3 ]

Safety of [ 67107-87-3 ]

Computational Chemistry of [ 67107-87-3 ] Show Less

Physicochemical Properties

Lipophilicity

Water Solubility

Pharmacokinetics

Druglikeness

Medicinal Chemistry

Application In Synthesis of [ 67107-87-3 ]

[ 67107-87-3 ] Synthesis Path-Downstream 1~54

Related Products

Historical Records

Technical Information

Categories

Related Functional Groups of [ 67107-87-3 ]

Aliphatic Chain Hydrocarbons

Alcohols

Amines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Molarity Calculator

Total Compounds Calculator

Dissolution Calculator

Related Functional Groups of
[ 67107-87-3 ]