Alternatived Products of [ 13490-70-5 ]
Product Details of [ 13490-70-5 ]
CAS No. : 13490-70-5
MDL No. : MFCD20483331
Formula :
C12 H16 O2
Boiling Point : -
Linear Structure Formula : -
InChI Key : DAOGRNTZCLFPNH-UHFFFAOYSA-N
M.W : 192.25 Pubchem ID : 11665557
Synonyms :
Calculated chemistry of [ 13490-70-5 ]
Physicochemical Properties
Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.42
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 56.95
TPSA : 37.3 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) : -5.24 cm/s
Lipophilicity
Log Po/w (iLOGP) : 1.94
Log Po/w (XLOGP3) : 3.14
Log Po/w (WLOGP) : 2.9
Log Po/w (MLOGP) : 2.86
Log Po/w (SILICOS-IT) : 2.48
Consensus Log Po/w : 2.66
Druglikeness
Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.85
Water Solubility
Log S (ESOL) : -3.13
Solubility : 0.143 mg/ml ; 0.000742 mol/l
Class : Soluble
Log S (Ali) : -3.59
Solubility : 0.0491 mg/ml ; 0.000255 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.03
Solubility : 0.179 mg/ml ; 0.000929 mol/l
Class : Soluble
Medicinal Chemistry
PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.83
Application In Synthesis of [ 13490-70-5 ]
* 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 [ 13490-70-5 ]
1
[ 124-38-9 ]
[ 1688-17-1 ]
[ 13490-70-5 ]
Yield Reaction Conditions Operation in experiment
(i) Mg, THF, (ii) /BRN= 1900390/; Multistep reaction;
(i) Mg, (ii) /BRN= 1900390/; Multistep reaction;
With magnesium; methyl iodide 1.) THF, ether, reflux, 1 h, 2.) 0 deg C, 1 h; Yield given. Multistep reaction;
Stage #1: 1-chloro-2,2-dimethyl-1-phenylpropane With magnesium In tetrahydrofuran Inert atmosphere; Reflux;
Stage #2: carbon dioxide In tetrahydrofuran at 0℃; for 1h; Inert atmosphere;
Reference：
[1]Cervinka,O.; Hub,L.
[Collection of Czechoslovak Chemical Communications, 1970, vol. 35, p. 721 - 723]
[2]Aaron,C. et al.
[Journal of Organic Chemistry, 1967, vol. 32, p. 2797 - 2803]
[3]Maryanoff, Bruce E.; McComsey, David F.; Almond, Harold R.; Mutter, Martin S.; Bemis, Guy W.; et al.
[Journal of Organic Chemistry, 1986, vol. 51, # 8, p. 1341 - 1346]
[4]Wang, Kaikai; Li, Yajun; Li, Xiaoyan; Li, Daliang; Bao, Hongli
[Organic Letters, 2021, vol. 23, # 22, p. 8847 - 8851]
2
[ 13490-70-5 ]
[ 13490-71-6 ]
Reference：
[1]Imajo,S. et al.
[Journal of Organic Chemistry, 1979, vol. 44, # 20, p. 3587 - 3589]
Bright, Danielle Angrand; Mathisen, Donald E.; Zieger, Herman E.
[Journal of Organic Chemistry, 1982, vol. 47, # 18, p. 3521 - 3524]
3
[ 13490-70-5 ]
[ 13491-16-2 ]
Reference：
[1]Craig,J.C. et al.
[Tetrahedron, 1971, vol. 27, p. 1173 - 1184]
Imajo,S. et al.
[Journal of Organic Chemistry, 1979, vol. 44, # 20, p. 3587 - 3589]
Bright, Danielle Angrand; Mathisen, Donald E.; Zieger, Herman E.
[Journal of Organic Chemistry, 1982, vol. 47, # 18, p. 3521 - 3524]
4
[ 67-56-1 ]
[ 13490-70-5 ]
[ 71214-37-4 ]
Yield Reaction Conditions Operation in experiment
With boron trifluoride methanol complex for 8h; Heating;
5
[ 57768-77-1 ]
[ 13490-70-5 ]
Yield Reaction Conditions Operation in experiment
With H2 O In water; acetonitrile at 25℃; var. pH and μ;
6
[ 13490-70-5 ]
[ 51631-70-0 ]
Yield Reaction Conditions Operation in experiment
94%
With thionyl chloride
With thionyl chloride In tetrachloromethane at 25℃;
With thionyl chloride for 1.5h; Heating;
Reference：
[1]Schaumann, Ernst
[Chemische Berichte, 1982, vol. 115, p. 2755 - 2765]
[2]Allen, Annette D.; Baigrie, Lynn M.; Gong, Leyi; Tidwell, Thomas T.
[Canadian Journal of Chemistry, 1991, vol. 69, # 1, p. 138 - 145]
[3]Maryanoff, Bruce E.; McComsey, David F.; Almond, Harold R.; Mutter, Martin S.; Bemis, Guy W.; et al.
[Journal of Organic Chemistry, 1986, vol. 51, # 8, p. 1341 - 1346]
7
[ 5153-67-3 ]
[ 677-22-5 ]
[ 13490-70-5 ]
Yield Reaction Conditions Operation in experiment
49%
With sulfuric acid THF, -20 deg C, 10 min; THF, water, 0 deg C, 30 min;
21 % Spectr.
Stage #1: nitrostyrene; tert-butylmagnesium chloride at -20℃; for 0.166667h;
Stage #2: With sulfuric acid for 0.5h; ice cooling;
Reference：
[1]Yao, Ching-Fa; Chen, Wen-Chang; Lin, Yu-Mei
[Tetrahedron Letters, 1996, vol. 37, # 35, p. 6339 - 6342]
[2]Yao, Ching-Fa; Kao, Kuo-Hsi; Liu, Ju-Tsung; Chu, Cheng-Ming; Wang, Yeh; Chen, Wen-Chang; Lin, Yu-Mei; Lin, Wen-Wei; Yan, Ming-Chung; Liu, Jing-Yuan; Chuang, Ming-Ching; Shiue, Jin-Lien
[Tetrahedron, 1998, vol. 54, # 5-6, p. 791 - 822]
Yield Reaction Conditions Operation in experiment
Spaltung in opt. akt. Antipoden m. (+)-α-Phenyl-ethylamin;
Spaltung in opt. akt. Antipoden m. (-)-α-Phenyl-ethylamin;
9
methylammonium carbonate
[ No CAS ]
[ 13490-70-5 ]
10
[ 31469-23-5 ]
[ 13490-70-5 ]
Yield Reaction Conditions Operation in experiment
75%
Stage #1: 2-(tert-butyl)-1,1-bis(trimethylsilyloxy)ethene; benzenetricarbonylchromium With potassium <i>tert</i>-butylate In tetrahydrofuran; N,N-dimethyl-formamide at -35℃; for 2h;
Stage #2: With iodine at -70 - 20℃;
Reference：
[1]Rudler, Henri; Comte, Virginie; Garrier, Eva; Bellassoued, Moncef; Chelain, Evelyne; Vaissermann, Jaqueline
[Journal of Organometallic Chemistry, 2001, vol. 621, # 1-2, p. 284 - 298]
11
[ 110-89-4 ]
[ 13490-70-5 ]
1-(3,3-dimethyl-2-phenylbutanoyl)piperidine
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Stage #1: (+/-)-α-tert-butylphenylacetic acid With polymer-supported N,N',N'-trimethylfluoroformamidinium*PF6 ; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.5h;
Stage #2: piperidine In dichloromethane at 20℃; for 12h;
Reference：
[1]Barrett, Anthony G.M.; Bibal, Brigitte; Hopkins, Brian T.; Köbberling, Johannes; Love, Andrew C.; Tedeschi, Livio
[Tetrahedron, 2005, vol. 61, # 51, p. 12033 - 12041]
12
[ 938-16-9 ]
[ 13490-70-5 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: 100 percent / NaBH4 / ethanol; methanol / 2 h
2: 72 percent / SOCl2 / 23 °C
3: 1.) Mg, methyl iodide / 1.) THF, ether, reflux, 1 h, 2.) 0 deg C, 1 h
13
[ 1007-26-7 ]
[ 13490-70-5 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: 72 percent / SOCl2 / 23 °C
2: 1.) Mg, methyl iodide / 1.) THF, ether, reflux, 1 h, 2.) 0 deg C, 1 h
14
[ 13490-70-5 ]
[ 27561-40-6 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: SOCl2 / 1.5 h / Heating
2: 82 percent / concd. NH4 OH / diethyl ether / 0 °C
3: LiAlH4 / diethyl ether / 20 h
15
[ 13490-70-5 ]
[ 100366-87-8 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: SOCl2 / 1.5 h / Heating
2: 82 percent / concd. NH4 OH / diethyl ether / 0 °C
16
[ 13490-70-5 ]
[ 100366-88-9 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: SOCl2 / 1.5 h / Heating
2: 82 percent / concd. NH4 OH / diethyl ether / 0 °C
3: LiAlH4 / diethyl ether / 20 h
4: 72 percent / acetyl chloride / ethyl acetate / Heating
17
[ 13490-70-5 ]
[ 100366-80-1 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 5 steps
1: SOCl2 / 1.5 h / Heating
2: 82 percent / concd. NH4 OH / diethyl ether / 0 °C
3: LiAlH4 / diethyl ether / 20 h
4: 72 percent / acetyl chloride / ethyl acetate / Heating
5: NaBH4 , methanesulfonic acid
18
[ 13490-70-5 ]
[ 100366-85-6 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 6 steps
1: SOCl2 / 1.5 h / Heating
2: 82 percent / concd. NH4 OH / diethyl ether / 0 °C
3: LiAlH4 / diethyl ether / 20 h
4: 72 percent / acetyl chloride / ethyl acetate / Heating
5: NaBH4 , methanesulfonic acid
6: polyphosphoric acid / 100 °C
19
[ 13490-70-5 ]
[ 100366-86-7 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 6 steps
1: SOCl2 / 1.5 h / Heating
2: 82 percent / concd. NH4 OH / diethyl ether / 0 °C
3: LiAlH4 / diethyl ether / 20 h
4: 72 percent / acetyl chloride / ethyl acetate / Heating
5: NaBH4 , methanesulfonic acid
6: polyphosphoric acid / 100 °C
20
[ 13490-70-5 ]
[ 133658-82-9 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: SOCl2 / CCl4 / 25 °C
2: 98 percent / Br2 / CCl4 / Heating
21
[ 13490-70-5 ]
[ 57768-77-1 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: SOCl2 / CCl4 / 25 °C
2: 98 percent / Br2 / CCl4 / Heating
3: 59 percent / activated Zn dust / tetrahydrofuran / 10 h / Heating
22
[ 13490-70-5 ]
[ 133659-00-4 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: SOCl2 / CCl4 / 25 °C
2: 98 percent / Br2 / CCl4 / Heating
3: 59 percent / activated Zn dust / tetrahydrofuran / 10 h / Heating
4: 1.) THF, -78 deg C, 5 h, 2.) THF, 0 to 25 deg C, 25 deg C (2 h)
23
[ 13490-70-5 ]
[ 133659-01-5 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: SOCl2 / CCl4 / 25 °C
2: 98 percent / Br2 / CCl4 / Heating
3: 59 percent / activated Zn dust / tetrahydrofuran / 10 h / Heating
4: 1.) THF, -78 deg C, 5 h, 2.) THF, 0 to 25 deg C, 25 deg C (2 h)
24
[ 13490-70-5 ]
[ 82372-89-2 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
2: 15.9 g
25
[ 13490-70-5 ]
[ 100702-91-8 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
2: 15.9 g
3: 31.2 percent / tetrahydrofuran / 3 h / Heating
4: 0.160 g / Na, NH3 / tetrahydrofuran; ethanol / 25 °C
26
[ 13490-70-5 ]
[ 82323-53-3 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
2: 15.9 g
3: 31.2 percent / tetrahydrofuran / 3 h / Heating
27
[ 13490-70-5 ]
[ 71214-37-4 ]
28
[ 3835-64-1 ]
[ 13490-70-5 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: SOCl2
2: (i) Mg, THF, (ii) /BRN= 1900390/
Multi-step reaction with 2 steps
1.1: thionyl chloride / 2 h / Reflux; Inert atmosphere
2.1: magnesium / tetrahydrofuran / Inert atmosphere; Reflux
2.2: 1 h / 0 °C / Inert atmosphere
Reference：
[1]Cervinka,O.; Hub,L.
[Collection of Czechoslovak Chemical Communications, 1970, vol. 35, p. 721 - 723]
[2]Wang, Kaikai; Li, Yajun; Li, Xiaoyan; Li, Daliang; Bao, Hongli
[Organic Letters, 2021, vol. 23, # 22, p. 8847 - 8851]
29
[ 630-19-3 ]
[ 13490-70-5 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1.1: tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
2.1: thionyl chloride / 2 h / Reflux; Inert atmosphere
3.1: magnesium / tetrahydrofuran / Inert atmosphere; Reflux
3.2: 1 h / 0 °C / Inert atmosphere
30
[ 100-58-3 ]
[ 13490-70-5 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1.1: tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
2.1: thionyl chloride / 2 h / Reflux; Inert atmosphere
3.1: magnesium / tetrahydrofuran / Inert atmosphere; Reflux
3.2: 1 h / 0 °C / Inert atmosphere
31
[ 13490-70-5 ]
C11 H15 N3
[ No CAS ]
C11 H15 N3
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1.1: dmap / dichloromethane; water / 0.17 h / 0 °C / Inert atmosphere
1.2: 1.5 h / 0 °C / Inert atmosphere
2.1: iron(II) triflate; C58 H62 N2 O3 ; trimethylsilylazide / tetrahydrofuran / 12 h / 20 °C / Schlenk technique; Inert atmosphere
32
[ 75-91-2 ]
[ 13490-70-5 ]
C16 H24 O3
[ No CAS ]
Yield Reaction Conditions Operation in experiment
88%
Stage #1: tert.-butylhydroperoxide; (+/-)-α-tert-butylphenylacetic acid With dmap In dichloromethane; water at 0℃; for 0.166667h; Inert atmosphere;
Stage #2: With dicyclohexyl-carbodiimide In dichloromethane; water at 0℃; for 1.5h; Inert atmosphere;
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