N-(4-氰基-3-三氟甲基苯基)甲基丙烯酰胺 | 90357-53-2
中文名称:
N-(4-氰基-3-三氟甲基苯基)甲基丙烯酰胺
英文名称:
N-4-Cyano-3-(trifluoromethyl)phenyl-2-methylacrylamide
CAS No.:
90357-53-2
分子式:
C1 2 H9 F3 N2 O
分子量:
254.207873106003
名称和标识符
MDL
MFCD03411609
InChIKey
HHWDZLSGDDXUSM-UHFFFAOYSA-N
Inchi
1S/C12H9F3N2O/c1-7(2)11(18)17-9-4-3-8(6-16)10(5-9)12(13,14)15/h3-5H,1H2,2H3,(H,17,18)
SMILES
N#CC1C(C(F)(F)F)=CC(NC(C(C)=C)=O)=CC=1
别名信息
- 中文别名 -
N-(4-氰基-3-三氟甲基苯基)甲基丙烯酰胺
N-(4-氰基-3-三氟甲基苯基)甲基丙烯酰胺(中间体1)
N-[4-氰基-3-(三氟甲基)苯基]甲基丙烯酰胺
N-{4-氰基-3-(三氟甲基)苯基}甲基丙酰胺
比卡鲁胺杂质
比卡鲁胺杂质1
i>-[4-氰基-3-(三氟甲基)苯基]甲基丙烯酰胺
- 英文别名 -
N-(4-Cyano-3-(trifluoromethyl)phenyl)methacrylamide
N-Methacryloyl-4-cyano-3-trifluoromethylaniline
N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-methyl-2-propenamide
N-[4-Cyano-3-(trifluoromethyl)phenyl]methacrylamide
N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-methacrylamide
<i>N<
N-[4-cyano-3-(trifluoromethyl)phenyl]-2-methylprop-2-enamide
2-Propenamide, N-[4-cyano-3-(trifluoromethyl)phenyl]-2-methyl-
N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-methylacrylamide
PubChem13688
Bicalutamide Impurity 1
N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-methyl-2-propenamide (ACI)
物化性质
实验特性
LogP
3.16468
PSA
52.89000
沸点
395.5°C at 760 mmHg
熔点
141.0 to 145.0 deg-C
密度
1.28
计算特性
精确分子量
254.06700
氢键供体数量
1
氢键受体数量
5
可旋转化学键数量
2
重原子数量
18
复杂度
394
同位素原子数量
0
确定原子立构中心数量
0
不确定原子立构中心数量
0
确定化学键立构中心数量
0
不确定化学键立构中心数量
0
共价键单元数量
1
疏水参数计算参考值(XlogP)
2.7
互变异构体数量
2
表面电荷
0
拓扑分子极性表面积
52.9
海关数据
海关编码
2926909090
海关数据
中国海关编码:
2926909090
概述:
2926909090 其他腈基化合物. 增值税率:17.0% 退税率:9.0% 监管条件:无 最惠国关税:6.5% 普通关税:30.0%
申报要素:
品名, 成分含量, 用途
Summary:
HS:2926909090 other nitrile-function compounds VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:30.0%
合成路线
合成路线:1 步
1.1
Solvents:
Dimethylacetamide
;
10 min, rt; 3 h, rt
参考文献:
A new series of bicalutamide, enzalutamide and enobosarm derivatives carrying pentafluorosulfanyl (SF5) and pentafluoroethyl (C2F5) substituents: Improved antiproliferative agents against prostate cancer
Pertusati, Fabrizio
;
Ferla, Salvatore
;
Bassetto, Marcella
;
Brancale, Andrea
;
Khandil, Sahar; et al ,
European Journal of Medicinal Chemistry ,
2019 ,
180 ,
1-14
合成路线:1 步
1.1
Solvents:
Dimethylacetamide
;
5 - 10 °C; 4 h, 10 °C → rt; rt → 20 °C
1.2
Reagents:
Water
;
< 20 °C
参考文献:
Improved synthesis of N-[4-cyano-3-(trifluoromethyl)phenyl]-2-methyl-2-oxranecarboxamide
Chai, Hong-wei;
Xi, Zhen-hao;
Jin, Jian;
Zhang, Feng;
Wang, Wei; et al ,
Jingxi Huagong Zhongjianti ,
2014 ,
44(5) ,
43-45
合成路线:1 步
1.1
Solvents:
Dimethylformamide
;
rt → 5 °C; < 5 °C; 6 h, 5 °C → rt
1.2
Reagents:
Water
;
rt
参考文献:
Synthesis bicalutamide antiandrogen
Liu, Yaru;
Feng, Xuesong;
Meng, Fanhao;
Liu, Junting ,
Zhongguo Yike Daxue Xuebao ,
2005 ,
34(6) ,
518-519
合成路线:1 步
1.1
Solvents:
Dimethylformamide
;
rt → -20 °C
1.2
Reagents:
Sodium hydride
;
< 70 °C; 70 °C → rt; 4 h, rt
1.3
Reagents:
Hydrochloric acid
Solvents:
Hexane
,
Water
;
overnight, rt
参考文献:
Visible-Light-Mediated Regioselective Chlorosulfonylation of Acrylamides
Zurro, Mercedes;
Torres-Oya, Sergio;
Otarola, Guillermo G.;
Vaquero, Juan Jose;
Merino, Estibaliz ,
Synthesis ,
2023 ,
55(11) ,
1783-1791
合成路线:1 步
1.1
Solvents:
Dimethylacetamide
;
10 min, rt; 3 h, rt
参考文献:
Rational design and synthesis of novel anti-prostate cancer agents bearing a 3,5-bis-trifluoromethylphenyl moiety
Ferla, Salvatore;
Bassetto, Marcella
;
Pertusati, Fabrizio;
Kandil, Sahar;
Westwell, Andrew D.; et al ,
Bioorganic & Medicinal Chemistry Letters ,
2016 ,
26(15) ,
3636-3640
合成路线:1 步
1.1
Reagents:
Triethylamine
;
0.5 - 2 h, 0 °C
参考文献:
Synthesis and SAR of novel hydantoin derivatives as selective androgen receptor modulators
Zhang, Xuqing;
Allan, George F.;
Sbriscia, Tifanie;
Linton, Olivia;
Lundeen, Scott G.; et al ,
Bioorganic & Medicinal Chemistry Letters ,
2006 ,
16(22) ,
5763-5766
合成路线:1 步
1.1
Solvents:
Dimethylformamide
;
rt; rt → -20 °C
1.2
Reagents:
Sodium hydride
;
< 70 °C; 70 °C → rt; 4 h, rt
1.3
Reagents:
Hydrochloric acid
Solvents:
Hexane
,
Water
;
overnight, rt
参考文献:
Nucleophilic Aromatic Substitution of Methacrylamide Anion and its Application to the Synthesis of the Anticancer Drug Bicalutamide
Chen, Bang-Chi;
Zhao, Rulin;
Gove, Stacey;
Wang, Bei;
Sundeen, Joseph E.; et al ,
Journal of Organic Chemistry ,
2003 ,
68(26) ,
10181-10182
合成路线:1 步
1.1
Solvents:
Dimethylacetamide
;
10 min, rt; 24 h, rt
参考文献:
Synthesis, biological evaluation and X-ray analysis of bicalutamide sulfoxide analogs for the potential treatment of prostate cancer
Kandil, Sahar B.;
Kariuki, Benson M.
;
McGuigan, Christopher;
Westwell, Andrew D. ,
Bioorganic & Medicinal Chemistry Letters ,
2021 ,
36 ,
合成路线:1 步
1.1
Solvents:
Dimethylacetamide
;
3 h, rt
参考文献:
Design and synthesis of novel bicalutamide and enzalutamide derivatives as antiproliferative agents for the treatment of prostate cancer
Bassetto, Marcella;
Ferla, Salvatore
;
Pertusati, Fabrizio;
Kandil, Sahar;
Westwell, Andrew D.; et al ,
European Journal of Medicinal Chemistry ,
2016 ,
118 ,
230-243
合成路线:1 步
1.1
Solvents:
Dimethylacetamide
;
10 min, rt; 24 h, rt
参考文献:
Discovery of deshydroxy bicalutamide derivatives as androgen receptor antagonists
Kandil, Sahar
;
Lee, Kok Yung;
Davies, Laurie;
Rizzo, Sebastiano A.;
Dart, D. Alwyn; et al ,
European Journal of Medicinal Chemistry ,
2019 ,
167 ,
49-60
合成路线:1 步
1.1
Reagents:
Thionyl chloride
Solvents:
Dimethylacetamide
;
30 min, 0 °C
1.2
overnight, rt
1.3
Reagents:
Sodium bicarbonate
Solvents:
Water
;
rt
参考文献:
Design, synthesis, and in vivo SAR of a novel series of pyrazolines as potent selective androgen receptor modulators
Zhang, Xuqing;
Li, Xiaojie;
Allan, George F.;
Sbriscia, Tifanie;
Linton, Olivia; et al ,
Journal of Medicinal Chemistry ,
2007 ,
50(16) ,
3857-3869
合成路线:1 步
1.1
Reagents:
Triethylamine
Solvents:
Dichloromethane
参考文献:
Synthesis and Biological Evaluation of [18F]Bicalutamide, 4-[76Br]Bromobicalutamide, and 4-[76Br]Bromo-thiobicalutamide as Non-Steroidal Androgens for Prostate Cancer Imaging
Parent, Ephraim E.;
Dence, Carmen S.;
Jenks, Carl;
Sharp, Terry L.;
Welch, Michael J.; et al ,
Journal of Medicinal Chemistry ,
2007 ,
50(5) ,
1028-1040
合成路线:1 步
1.1
Reagents:
Triethylamine
Solvents:
Dichloromethane
;
0 °C; 4 - 12 h, rt
参考文献:
Antitumor agents 290. Design, synthesis, and biological evaluation of new LNCaP and PC-3 cytotoxic curcumin analogs conjugated with anti-androgens
Shi, Qian;
Wada, Koji;
Ohkoshi, Emika;
Lin, Li;
Huang, Rong; et al ,
Bioorganic & Medicinal Chemistry ,
2012 ,
20(13) ,
4020-4031