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[ CAS No. 1660-04-4 ] {[proInfo.proName]}

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Chemical Structure| 1660-04-4
Chemical Structure| 1660-04-4
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Product Details of [ 1660-04-4 ]

CAS No. :1660-04-4 MDL No. :MFCD00074739
Formula : C12H18O Boiling Point : -
Linear Structure Formula :- InChI Key :DACIGVIOAFXPHW-UHFFFAOYSA-N
M.W : 178.27 Pubchem ID :123126
Synonyms :

Calculated chemistry of [ 1660-04-4 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.92
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 53.4
TPSA : 17.07 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.59 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.31
Log Po/w (XLOGP3) : 2.53
Log Po/w (WLOGP) : 2.79
Log Po/w (MLOGP) : 2.88
Log Po/w (SILICOS-IT) : 2.94
Consensus Log Po/w : 2.69

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.47
Solubility : 0.6 mg/ml ; 0.00336 mol/l
Class : Soluble
Log S (Ali) : -2.54
Solubility : 0.52 mg/ml ; 0.00292 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.28
Solubility : 0.936 mg/ml ; 0.00525 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.87

Safety of [ 1660-04-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1660-04-4 ]

* 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.

  • Upstream synthesis route of [ 1660-04-4 ]
  • Downstream synthetic route of [ 1660-04-4 ]

[ 1660-04-4 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 1660-04-4 ]
  • [ 5122-82-7 ]
YieldReaction ConditionsOperation in experiment
85% With N-Bromosuccinimide In methanol; Petroleum ether at 59.84℃; for 2 h; 1-Adamantyl methyl ketone was refluxed with N-bromo succinimide and petroleum ether in methanol at 333 K for two hours. The resultant 1-adamantyl bromomethyl ketone (1) precipitate was filtered and recrystallized with ethanol. After that, 1-adamantyl bromomethyl ketone (1) (0.51 g, 0.002 mol) was reacted with the corresponding carboxylic acid (0.003 mol) with the presence of potassium carbonate in DMF (8 mL) and stirred at room temperature for about 3 h. The reaction progress was monitored by thin layer chromatography (TLC). After the reaction completed, the reaction mixture was poured into ice-cooled water and kept stirring for 10 min. The solid obtained was filtered out, washed successively with distilled water and recrystallized from acetone after it dried [20]. All targeted compounds were synthesized in good yield and high purity. Suitable single-crystal specimens were obtained from various types of solvents, as described below. The chemical structures were characterized by using FTIR and NMR spectroscopies. The crystal structures for all compounds except 2m and 2q were determined by single-crystal X-ray diffraction analysis.
78% at 20℃; for 4 h; Cooling with ice [359] To an ice- cooling solution of 1-(adamantan-1-yl)ethanone (1.78 g, 10.0 mmol) in THF (30 mL) was added Br2 (1.70 g, 10.7 mmol, dissolved in 5 mL THF). The resultedmixture was stirred at room temperature for 4h, and then the reaction was quenched by addition of saturated sodium thiosulfate solution (20 mL), extracted with dichloromethane (100 mL). The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated to afford compound 19.1(2.0 g, yield: 78percent) as a yellow solid.
70% at 160℃; for 4 h; Sealed tube; Inert atmosphere General procedure: The reactions were carried out in glass ampoules (20 mL) or in a pressure microreactor of stainless steel (17 mL). The results of parallel experiments were identical. Into the microreactor (ampoule) in an argon atmosphere was charged 0.3 mmol of Fe(acac)3, 10 mmol of initial adamantane, 10 mmol of CBr4, and 150 mmol of CH2Br2. The reactor was hermetically closed (the ampoule was sealed) and heated while stirring. On the completion of the reaction the reactor (ampoule) was cooled to room temperature, opened, the solvent was distilled off, the residue was crystallized from hexane or ethanol. Yields are given in respect to converted adamantane (adamantine derivatives) (GLC procedure, internal reference decene; correction factor for adamantane 1.09, for bromoadamantane 1.53). The structure of compounds obtained was proved by comparison with known samples and published data.
Reference: [1] Molecules, 2015, vol. 20, # 10, p. 18827 - 18846
[2] Patent: WO2016/131380, 2016, A1, . Location in patent: Paragraph 358; 359
[3] Russian Journal of Organic Chemistry, 2015, vol. 51, # 2, p. 184 - 187[4] Zh. Org. Khim., 2015, vol. 51, # 2, p. 196 - 199
[5] Chemische Berichte, 1960, vol. 93, p. 2054 - 2057
[6] Tetrahedron, 2008, vol. 64, # 22, p. 5191 - 5199
  • 2
  • [ 1660-04-4 ]
  • [ 40430-66-8 ]
Reference: [1] Chemistry - A European Journal, 2009, vol. 15, # 33, p. 8251 - 8258
[2] Synlett, 2009, # 4, p. 558 - 561
[3] Chemistry - A European Journal, 2005, vol. 11, # 1, p. 308 - 320
[4] Chemical Papers, 2013, vol. 67, # 1, p. 29 - 39
[5] Organic and Biomolecular Chemistry, 2016, vol. 14, # 24, p. 5591 - 5594
  • 3
  • [ 1660-04-4 ]
  • [ 39269-10-8 ]
YieldReaction ConditionsOperation in experiment
79.2%
Stage #1: for 0.25 h;
Stage #2: at 0 - 80℃; for 11.5 h;
Equipped with a mechanical stirrer, reflux condenser, constant pressure dropping funnel,Thermometer 250mL four-necked flask was added concentrated sulfuric acid 100mL, with stirring,15 g (84.1 mmol) of 1-adamantane methyl ketone (R = CH3)After the addition was maintained for 15 minutes, ice water bath control 0 , and then within 30 minutes with a constant pressure dropping funnel slowly dropping mixed acid solution (fuming nitric acid 16ml (0.34mol) + concentrated sulfuric acid 16ml)Insulation 1h, naturally heated to 80 reaction 10h, the reaction was completed,The reaction solution was slowly poured into 200mL ice water, stirring while pouring, white solid precipitation, filtration was precipitated,A small amount of washing cake,Dried in vacuo to give a white powdery solid 14.9g, content 98percent, yield 79.2percent.
Reference: [1] Patent: CN105367413, 2017, B, . Location in patent: Paragraph 0023; 0024; 0025; 0026; 0027; 0028; 0029; 0030
  • 4
  • [ 1660-04-4 ]
  • [ 665-66-7 ]
Reference: [1] Patent: CN105399636, 2016, A, . Location in patent: Paragraph 0057-0061
  • 5
  • [ 1707-40-0 ]
  • [ 912361-56-9 ]
  • [ 281-23-2 ]
  • [ 6600-42-6 ]
  • [ 1660-04-4 ]
Reference: [1] Tetrahedron Letters, 2008, vol. 49, # 28, p. 4362 - 4365
  • 6
  • [ 1041846-07-4 ]
  • [ 912361-56-9 ]
  • [ 281-23-2 ]
  • [ 1660-04-4 ]
Reference: [1] Tetrahedron Letters, 2008, vol. 49, # 28, p. 4362 - 4365
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