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Chemical Structure| 105-60-2
Chemical Structure| 105-60-2
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Product Details of [ 105-60-2 ]

CAS No. :105-60-2 MDL No. :MFCD00006936
Formula : C6H11NO Boiling Point : -
Linear Structure Formula :HNCH2CH2CH2CH2CH2CO InChI Key :JBKVHLHDHHXQEQ-UHFFFAOYSA-N
M.W : 113.16 Pubchem ID :7768
Synonyms :

Calculated chemistry of [ 105-60-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.83
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 35.76
TPSA : 29.1 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.06 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.47
Log Po/w (XLOGP3) : -0.1
Log Po/w (WLOGP) : 0.3
Log Po/w (MLOGP) : 0.47
Log Po/w (SILICOS-IT) : 1.55
Consensus Log Po/w : 0.74

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.48
Solubility : 37.6 mg/ml ; 0.332 mol/l
Class : Very soluble
Log S (Ali) : -0.06
Solubility : 98.9 mg/ml ; 0.874 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.43
Solubility : 4.21 mg/ml ; 0.0372 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.01

Safety of [ 105-60-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312+P330-P302+P352-P304+P340+P312-P305+P351+P338-P312-P332+P313-P337+P313-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H302+H332-H313-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 105-60-2 ]

* 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 [ 105-60-2 ]
  • Downstream synthetic route of [ 105-60-2 ]

[ 105-60-2 ] Synthesis Path-Upstream   1~23

  • 1
  • [ 105-60-2 ]
  • [ 420-37-1 ]
  • [ 2525-16-8 ]
Reference: [1] Organic Preparations and Procedures International, 1992, vol. 24, # 2, p. 147 - 158
[2] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 19, p. 2651 - 2653
[3] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 19, p. 4359 - 4362
[4] Patent: US6046211, 2000, A,
[5] Patent: US5854234, 1998, A,
[6] Journal of the American Chemical Society, 2009, vol. 131, p. 8714 - 8718
[7] Patent: WO2010/68520, 2010, A2, . Location in patent: Page/Page column 29
  • 2
  • [ 105-60-2 ]
  • [ 77-78-1 ]
  • [ 2525-16-8 ]
Reference: [1] Arkivoc, 2016, vol. 2016, # 5, p. 118 - 141
[2] Journal of Medicinal Chemistry, 2007, vol. 50, # 25, p. 6307 - 6315
[3] Journal of Medicinal Chemistry, 2010, vol. 53, # 21, p. 7647 - 7663
[4] Journal of the Indian Chemical Society, 1988, vol. 65, p. 800 - 802
[5] Journal of Medicinal Chemistry, 1987, vol. 30, # 8, p. 1433 - 1454
[6] European Journal of Medicinal Chemistry, 2002, vol. 37, # 5, p. 419 - 425
[7] Journal of Medicinal Chemistry, 2016, vol. 59, # 7, p. 3018 - 3033
  • 3
  • [ 67-56-1 ]
  • [ 100-64-1 ]
  • [ 105-60-2 ]
  • [ 2525-16-8 ]
Reference: [1] Patent: US6344557, 2002, B1, . Location in patent: Page column 7
[2] Patent: US6344557, 2002, B1, . Location in patent: Page column 7-8
  • 4
  • [ 105-60-2 ]
  • [ 77-78-1 ]
  • [ 2525-16-8 ]
  • [ 2556-73-2 ]
Reference: [1] Journal of the American Chemical Society, 1948, vol. 70, p. 2115,2116[2] Org.Synth.Coll.Vol., 1963, vol. IV, p. 588
  • 5
  • [ 105-60-2 ]
  • [ 2525-16-8 ]
Reference: [1] Patent: WO2004/60376, 2004, A1, . Location in patent: Page/Page column 95
  • 6
  • [ 105-60-2 ]
  • [ 77-78-1 ]
  • [ 71-43-2 ]
  • [ 2525-16-8 ]
Reference: [1] Journal of the American Chemical Society, 1948, vol. 70, p. 2115,2116[2] Org.Synth.Coll.Vol., 1963, vol. IV, p. 588
  • 7
  • [ 105-60-2 ]
  • [ 74-86-2 ]
  • [ 2235-00-9 ]
Reference: [1] Patent: US2317804, 1940, ,
[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1952, p. 690,692; engl. Ausg. S. 633, 634
[3] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1957, p. 1457,1461; engl. Ausg. S. 1478, 1481
[4] Sint. org. Soedin., 1952, vol. 2, p. 44; dtsch. Ausg. S. 47[5] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1952, p. 682,685; engl. Ausg. S. 626, 629
[6] Journal of Molecular Structure, 1989, vol. 192, p. 141 - 152
[7] Patent: US6384216, 2002, B1, . Location in patent: Page column 7
[8] Patent: US2009/131657, 2009, A1, . Location in patent: Page/Page column 7-8
[9] Patent: US2806847, 1955, ,
[10] Patent: US2806848, 1956, ,
  • 8
  • [ 151455-49-1 ]
  • [ 105-60-2 ]
  • [ 2235-00-9 ]
Reference: [1] Gazzetta Chimica Italiana, 1993, vol. 123, # 8, p. 457 - 462
[2] Gazzetta Chimica Italiana, 1993, vol. 123, # 8, p. 457 - 462
  • 9
  • [ 105-60-2 ]
  • [ 2235-00-9 ]
Reference: [1] Gazzetta Chimica Italiana, 1993, vol. 123, # 8, p. 457 - 462
  • 10
  • [ 105-60-2 ]
  • [ 54-95-5 ]
Reference: [1] Patent: DE855711, 1950, ,
[2] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 17, p. 2605
  • 11
  • [ 105-60-2 ]
  • [ 143-15-7 ]
  • [ 59227-89-3 ]
YieldReaction ConditionsOperation in experiment
99.6% With sodium hydroxide In water; toluene EXAMPLE 1
A 1l reactor is charged with 34 g (0.3 mole) of azacycloheptane-2-one, 112 g (0.45 mole) of dodecyl bromide, 300 g of toluene, 3.4 g (3.3 mole percent based on the azacycloheptane-2-one) of crystalline tetrabutylammonium hydrogensulfate (TBAHS) and 90 g (2.25 moles) of flaky sodium hydroxide.
This heterogeneous mixture was stirred at 50° C. for 10 hours.
After the mixture was cooled to 40° C., 135 g of water was added to the mixture, followed by stirring at 40° C. for 30 minutes.
The oil layer was separated and the oil layer thus obtained was subjected to distillation, giving 84.0 g of 1-dodecylazacycloheptane-2-one having a boiling point of 195° to 200° C./3 mmHg (yield of 99.6percent based on the azacycloheptane-2-one), and also 0.8 g of dodecyl ether (yield of 1.0percent based on the dodecyl bromide).
95% With sodium hydroxide In toluene EXAMPLE 3
A 1l reactor was charged with 57 g (0.5 mole) of azacycloheptane-2-one, 125 g (0.5 mole) of dodecyl bromide, 182 g of toluene, 3.2 g (2 mole percent) of crystalline tetrabutylammonium bromide (TBAB) and 60 g (1.5 moles) of flaky sodium hydroxide.
This heterogeneous mixture was stirred at 50° C. for 10 hours.
The same aftertreatment as in Example 1 was repeated, giving 133.5 g of 1-dodecylazacycloheptane-2-one (yield of 95.0percent) and 0.7 g of dodecyl ether (yield of 0.8percent)
92.8% With sodium hydroxide; tetrabutylammomium bromide; potassium carbonate In cyclohexane EXAMPLE 1
Preparation of 1-n-dodecylazacycloheptan-2-one at a bath temperature of 55° C.
117 g of caprolactam (1.033 mole), 10 g of tetrabutylammonium bromide (0.03 mole), 100 g of anhydrous potassium carbonate (0.7 mole, dried for 2 hrs at 120 C.), 100 g of pulverized sodium hydroxide (2.5 mole), and 1 L of cyclohexane were placed in a flask equipped with a funnel, reflux condenser and a mechanical stirrer.
To this mixture were added dropwise a solution of 250 ml of 1-bromododecane (1.033 mole) and 250 ml of cyclohexane with vigorous stirring over one-half hour at a bath temperature of 55° C.
The stirring was continued; in the meanwhile thin-layer chromatography was used to monitor the course of the reaction, and it was found that the reaction was completed after 7 hours.
The reaction mixture was then cooled to room temperature and filtered.
The filtrate was washed with water (3*500 ml) to remove remaining caprolactam.
The organic phase was dried over anhydrous magnesium sulfate.
The filtrate was evaporated using a rotary film evaporator to remove cyclohexane (which can be used again), and the residue was distilled at reduced pressure to yield 270 g of colorless, odorless, transparent liquid product (yield: 92.8percent), b,p.200-201 C/0.7 mmHg.
Reference: [1] Patent: US4812566, 1989, A,
[2] Patent: US4812566, 1989, A,
[3] Patent: US4973688, 1990, A,
[4] JAOCS, Journal of the American Oil Chemists' Society, 1996, vol. 73, # 7, p. 847 - 850
[5] Journal of Pharmaceutical Sciences, 1993, vol. 82, # 2, p. 214 - 219
[6] Journal of Pharmaceutical Sciences, 1989, vol. 78, # 9, p. 738 - 741
  • 12
  • [ 105-60-2 ]
  • [ 143-15-7 ]
  • [ 59227-89-3 ]
Reference: [1] Patent: US4310525, 1982, A,
  • 13
  • [ 105-60-2 ]
  • [ 1634-04-4 ]
  • [ 143-15-7 ]
  • [ 59227-89-3 ]
Reference: [1] Patent: US5986092, 1999, A,
  • 14
  • [ 105-60-2 ]
  • [ 143-15-7 ]
  • [ 59227-89-3 ]
Reference: [1] Patent: US4525199, 1985, A,
  • 15
  • [ 105-60-2 ]
  • [ 59227-89-3 ]
Reference: [1] Journal of Organic Chemistry, 1953, vol. 18, p. 1087,1088
  • 16
  • [ 105-60-2 ]
  • [ 24566-95-8 ]
Reference: [1] Synthetic Communications, 1993, vol. 23, # 22, p. 3191 - 3194
  • 17
  • [ 105-60-2 ]
  • [ 4048-33-3 ]
YieldReaction ConditionsOperation in experiment
92 %Spectr. With sodium 2-methyl-2-adamantoxide; dichlorobis(dicyclohexylphosphinomethylpyridine)-ruthenium (II); hydrogen; sodium hydride In toluene; mineral oil at 160℃; for 24 h; Inert atmosphere; Autoclave General procedure: Under a continuous Ar flow, 2-methyl-2-adamantanol (16.6 mg, 0.1 mmol), NaH (60percent oil dispersion, 4.0 mg, 0.1 mmol), anhydrous toluene (1.5 mL) and a magnetic stirring bar were placed in a dried Teflon tube (21 mL capacity). The Teflon tube was stoppered with a rubber septum, and the mixture was stirred at room temperature for 2 h under Ar. After removing the septum, under a continuous Ar flow, to the mixture was added RUPCY (7.50 mg, 0.01 mmol) and N-benzylbenzamide (105.6 mg, 0.5 mmol). The Teflon tube was quickly inserted into an autoclave and the inside of the autoclave was purged several times with hydrogen gas (>5 MPa). The autoclave was pressurized with an 8 MPa of hydrogen gas at 25°C, and heated at 160°C for 24 h under stirring (800 rpm). The autoclave was cooled to room temperature in an ice–water (0°C) bath,and the reaction mixture was quenched with NH4Cl (5.3 mg, 0.1 mmol). The organic phase was removed in vacuo (ca. 100 mmHg, 40 °C). The residue was diluted with CDCl3, and analyzed by 1H NMR. The yields of benzyl alcohol (92percent) and benzylamine (92percent) were calculated based on the integral ratio among the signals of these compounds with respect to an internal standard (1,1,2,2-tetrachloroethane). Afterward, the reaction mixture was purified by column chromatography on silica gel (silica gel (ca. 100 g) was pretreated with Et3N (small amount)–Et2O/hexane (vol percent: 2/3), eluent; Et2O/hexane = 2/3, then EtOAc/Et3N = 100/1) to give N-benzylbenzamide (7.7 mg, 0.036 mmol, 7percent), benzyl alcohol (47.4 mg, 0.438 mmol, 88percent) and benzylamine (44.1 mg, 0.4187 mmol, 82percent).
90 %Spectr. With sodium 2-methyl-2-adamantoxide; C24H38Cl2N2P2Ru; hydrogen In toluene at 130 - 160℃; for 44 h; Autoclave; Sealed tube 1) Preactivation of Catalyst In an argon gas atmosphere, a stirrer, a ruthenium complex (Compound 2b; RUPIP2) (0.0067 mmol, 3.98 mg) and sodium-2-methyl-2-adamantoxide (0.067 mmol, 12.6 mg) were placed in a dried fluororesin tube (30 mL). Thereafter, the tube containing this compound was rapidly inserted into an autoclave, and toluene (2.0 mL) was added in an argon atmosphere. Subsequently, the autoclave was hermetically sealed while being grounded, and hydrogen gas was introduced into the autoclave from a hydrogen compressed gas cylinder connected via a stainless-steel pipe, thereby substituting the inside of the autoclave with hydrogen gas. More specifically, 1-MPa hydrogen gas pressure was applied inside the autoclave, and then the hydrogen gas pressure was removed through a leak valve. This operation (substitution and desubstitution) was repeated 10 times. Finally, the hydrogen gas inside the autoclave was set to 1 MPa, and a reaction was performed for 5 hours using a constant-temperature bath at 160° C. (2) Hydrogenation Reaction of Substrate (0285) After the reaction was completed, the autoclave was cooled to substantially room temperature by being immersed in an icy bath. Then, the leak valve of the autoclave was opened and the hydrogen gas inside the autoclave was released into the air. Subsequently, in an argon gas atmosphere, the reaction solution (1.5 mL) was obtained from the autoclave using a gas-tight syringe, and placed in another autoclave (a stirrer, and N-benzylbenzamide (0.5 mmol, 105.63 mg) were placed in a dried fluororesin tube (30 mL) in an argon gas atmosphere; thereafter, the tube containing this compound was rapidly inserted into an autoclave, and the inside of the autoclave was substituted with argon). Subsequently, the autoclave was hermetically sealed while being grounded, and hydrogen gas was introduced into the autoclave from a hydrogen compressed gas cylinder connected via a stainless-steel pipe, thereby substituting the inside of the autoclave with hydrogen gas. More specifically, 1-MPa hydrogen gas pressure was applied inside the autoclave, and then the hydrogen gas pressure was removed through a leak valve. This operation (substitution and desubstitution) was repeated 10 times. Finally, the hydrogen gas inside the autoclave was set to 1 MPa, and a reaction was performed for 24 hours using a constant-temperature bath at 110° C. For 1H NMR analysis, an internal standard substance (mesitylene) was added to the solution. Based on the hydrogen atom amount of the internal standard substance, the yield of the reaction product was calculated. The results of the analysis showed that the yields of benzyl alcohol and benzylamine were both 86percent (corresponding to Entry 8 in Table 2 described later). A hydrogenation reaction was performed in the same manner as in Reaction Example A5, except that the conditions specified in Table 2 were used. Tables 2 and 3 show the results.
Reference: [1] Chemical Communications, 2014, vol. 50, # 76, p. 11211 - 11213
[2] Canadian Journal of Chemistry, 1958, vol. 36, p. 147,149
[3] Angewandte Chemie - International Edition, 2011, vol. 50, # 44, p. 10377 - 10380
[4] Tetrahedron Letters, 2013, vol. 54, # 21, p. 2674 - 2678
[5] Patent: US9463451, 2016, B2, . Location in patent: Page/Page column 46-50
[6] ChemCatChem, 2017, vol. 9, # 22, p. 4275 - 4281
[7] Chemistry - An Asian Journal, 2018, vol. 13, # 17, p. 2559 - 2565
  • 18
  • [ 105-60-2 ]
  • [ 4224-70-8 ]
Reference: [1] Tetrahedron, Supplement, 1966, vol. 8, p. 313 - 319
[2] Journal of Organic Chemistry USSR (English Translation), 1966, vol. 2, # 11, p. 1990 - 1992[3] Zhurnal Organicheskoi Khimii, 1966, vol. 2, # 11, p. 2028 - 2031
[4] Patent: CN106632474, 2017, A,
  • 19
  • [ 105-60-2 ]
  • [ 64-17-5 ]
  • [ 25542-62-5 ]
Reference: [1] Chemische Berichte, 1954, vol. 87, p. 356,362
  • 20
  • [ 105-60-2 ]
  • [ 6404-29-1 ]
Reference: [1] Synlett, 2018, vol. 29, # 13, p. 1786 - 1790
  • 21
  • [ 105-60-2 ]
  • [ 501-53-1 ]
  • [ 1947-00-8 ]
Reference: [1] Patent: US2014/39219, 2014, A1, . Location in patent: Paragraph 0051; 0052
  • 22
  • [ 105-60-2 ]
  • [ 3633-17-8 ]
Reference: [1] Synthetic Communications, 1988, vol. 18, # 4, p. 1625 - 1636
  • 23
  • [ 105-60-2 ]
  • [ 50889-29-7 ]
Reference: [1] Patent: CN106632474, 2017, A,
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