CAS: 955373-56-5; 3-(3-(Trifluoromethl)Phenyl-N-(R)-1-(Naphthalen-1-yl)Ethyl)Prop-2-En-1-Amine

英文名称3-(3-(Trifluoromethl)Phenyl-N-(R)-1-(Naphthalen-1-yl)Ethyl)Prop-2-En-1-Amine
中文名称西那卡塞杂质4
IUPAC名称(R,E)-N-(1-(naphthalen-1-yl)ethyl)-3-(3-(trifluoromethyl)phenyl)prop-2-en-1-amine
其它别名2,3,-Dehydro-Cinacalcet; 3-(3-(Trifluoromethl)Phenyl-N-(R)-1-(Naphthalen-1-yl)Ethyl)Prop-2-En-1-Amine Hydrochloride; 3-(3-(Trifluoromethl)Phenyl-N-(R)-1-(Naphthalen-1-yl)Ethyl)Prop-2-En-1-Amine; Cinacalcet Impurity C Hcl; (R,E)-N-(1-(Naphthalen-1-yl)Ethyl); (E)-N-(1-(5,6-Dihydrophthalen-1-yl)Ethyl)-3-(3-(Trifluoromethyl)Phenyl)Acrylamide; (2E)-N-[(1R)-1-(1-Naphthyl)Ethyl]-3-[3-(Trifluoromethyl)Phenyl]Prop-2-En-1-Amine; (E)-2,3,-Dehydro-Cinacalcet
CAS编号955373-56-5
MFCD编号:MFCD28386704
分子式:C22H20F3N分子量:355.4
产品CID: 2008740
产品分类分析化学 → 标准品 → 药典标准品和杂质标准品

相似结构搜索
InChIKey: WFYGIZJPNJFYOP-IQIBNGDESA-N
InChI=1S/C22H20F3N/c1-16(20-13-5-10-18-9-2-3-12-21(18)20)26-14-6-8-17-7-4-11-19(15-17)22(23,24)25/h2-13,15-16,26H,14H2,1H3/b8-6+/t16-/m1/s1
计算化学: 氢键受体数4.0氢键供体数1.0可旋转键数5.0

物理性质

沸点468.8±45.0 °C(预测)
密度1.179±0.06 g/cm3(预测)
pKa:7.89±0.20(预测)
PSA:12.03
LogP:6.6135
溶解性Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
外观形态淡黄色至黄色油状物
储存条件安瓿瓶, -20°C 冰箱, 在惰性气其中

MSDS等安全信息

警示词Warning
危险描述H302-H315-H319-H335-
防范说明P261-P280-P301+P312-P302+P352-P305+P351+P338-

上下游产品

3-bromo-1-trifluoromethylbenzene (R)-N-(1-(naphthalen-1-yl)ethyl)prop-2-en-1-amine (E)-3-(3-(trifluoromethyl)phenyl)allyl acetate (R)-1-(1-Naphthyl)ethylaminecinacalcet N-[(1R)-1-(naphthalen-1-yl)ethyl]-3-[3-(trifluoromethyl)phenyl]prop-2-en-1-amine hydr°Chloride cinacalcet hydr°Chloride

合成工艺路线路线简述

129425-31-6 + 3886-70-2 = 955373-56-5
反应条件:1.1 Reagents: Benzaldehyde; 1 - 2 H,25 - 30 °C1.2 Solvents: N-Methyl-2-Pyrrolidone; 30 °C -> 130 °C; 12 H,125 - 130 °C1.3 Reagents: Water1.4 Reagents: Ammonia Solvents: Water; Ph 8 - 91.5 Reagents: Hydrochloric Acid Solvents: Water; Ph 0.5 - 1.5,Rt
标题:Industrial Application Of The Forster Reaction: Novel One-Pot Synthesis Of Cinacalcet Hydrochloride,A Calcimimetic Agent
作者:Shinde,Gorakshanath B.; Niphade,Navnath C.; Deshmukh,Shrikant P.; Toche,Raghunath B.; Mathad,Vijayavitthal T.
参考文献:Organic Process Research & Development 日期:2011 卷标:15(2) 页码:455-461]

1224568-02-8 = 955373-56-5
反应条件:1.1 Reagents: Acetic Acid,Sulfuric Acid Solvents: Toluene; 25 °C; 1 H,110 °C; 110 °C -> 5 °C1.2 Reagents: Ammonia Solvents: Water; Ph 10
标题:Process For Preparing Cinacalcet
参考文献:World Intellectual Property Organization]

1224568-02-8 = 955373-56-5
反应条件:1.1 Reagents: Sulfuric Acid Solvents: Toluene,Water; 25 °C; 1 H,110 °C; 110 °C -> 5 °C1.2 Solvents: Toluene,Water; 25 °C1.3 Reagents: Ammonia Solvents: Water; Ph 10,Cooled
标题:Process For The Preparation Of Cinacalcet Hydrochloride Using Reduction,Sulfonation And Elimination As Key Steps
参考文献:World Intellectual Property Organization]

401-78-5 = 955373-56-5
反应条件:1.1 Reagents: Potassium Carbonate Catalysts: Palladium Solvents: N-Methyl-2-Pyrrolidone; 15 Min,Rt; 3 H,Rt -> 140 °C
标题:Process For The Preparation Of Cinacalcet Base
参考文献:World Intellectual Property Organization]

= 955373-56-5 [标题:Reaction Conditions
标题:Process For Preparing Cinacalcet Hydrochloride
参考文献:United States]

1201910-96-4 + 144-62-7 = 955373-56-5
反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Ethyl Acetate,Water; Rt
标题:Green Preparation Of Cinacalcet Hydrochloride
参考文献:China]

401-81-0 + 2756409-54-6 = 955373-56-5
反应条件:1.1 Reagents: Sodium Carbonate Catalysts: 1,1-Bis(Diphenylphosphino)Ferrocene,Palladium,Bis(Acetonitrile)Dichloro- Solvents: 1,4-Dioxane; 18 H,80 °C
标题:Creating High Regioselectivity By Electronic Metal-Support Interaction Of A Single-Atomic-Site Catalyst
作者:Li,Wen-Hao; Yang,Jiarui; Jing,Hongyu; Zhang,Jian; Wang,Yu; Et Al
参考文献:Journal Of The American Chemical Society 日期:2021 卷标:143(37) 页码:15453-15461]

129425-31-6 + 3886-70-2 = 955373-56-5
反应条件:1.1 Reagents: Benzaldehyde; 1 - 2 H,25 - 30 °C1.2 Solvents: N-Methyl-2-Pyrrolidone; 30 °C -> 130 °C; 12 H,125 - 130 °C1.3 Solvents: Water1.4 Reagents: Ammonia Solvents: Water; Ph 8 - 91.5 Reagents: Hydrochloric Acid Solvents: Toluene,Water; 10 - 15 Min,Ph 0.5 - 1.5,Rt
标题:Process For Preparation Of Cinacalcet
参考文献:United States]

921610-47-1 + 3886-70-2 = 955373-56-5
反应条件:1.1 Catalysts: Tetrakis(Triphenylphosphine)Palladium Solvents: Tetrahydrofuran; 16 H,Rt
标题:Methods Of Synthesizing Cinacalcet And Salts Thereof
参考文献:World Intellectual Property Organization]

3886-70-2 + 262268-58-6 = 955373-56-5
反应条件:1.1 Reagents: Titanium Isopropoxide,Sodium Borohydride Solvents: Tetrahydrofuran; Rt1.2 Reagents: Hydrochloric Acid Solvents: Water; 0.5 H,Rt
标题:Process For The Preparation Of Cinacalcet Hydrochloride
参考文献:World Intellectual Property Organization]

= 955373-56-5 [标题:Reaction Conditions
标题:Process For Preparing Cinacalcet
参考文献:United States

📜3-(3-三氟甲基苯基)丙醇置于硫酸,氢溴酸,苯甲醛体系中,用水作为反应溶剂,化学反应 12.0H,反应生成西那卡塞杂质4
参考文献:Industrial Application Of The Forster Reaction: Novel One-Pot Synthesis Of Cinacalcet Hydrochloride,A Calcimimetic Agent
标题:Industrial Application Of The Forster Reaction: Novel One-Pot Synthesis Of Cinacalcet Hydrochloride,A Calcimimetic Agent
摘要:Described Is A New,Practical,And One-Pot Process,Based On The Forster Reaction,For The Synthesis Of Cinacalcet Hydrochloride (1),A Calcimimetic Agent And Calcium-Sensing Receptor Antagonist. The Synthesis Comprises The Condensation Of (1R)-(+)-1-Naphthylethyl Amine (2) With Benzaldehyde (3) Followed By Reaction Of Obtained Schiff'S Base 4 With 1-(3-Halopropyl)-3-(Trifluoromethyl)-Benzene (5) To Provide Highly Unstable Iminium Salt 6. Subsequent Hydrolysis Of 6 With Water In The Same Pot Yielded Cinacalcet. The Treatment Of Cinacalcet With Hydrochloric Acid During The Workup Process Furnished 1 With An Overall Yield Of Around 60%. Our Synthetic Approach For 1,Discussed In This Report Demonstrates Industrial Application Of The Century-Old,Unexplored Name Reaction,"Forster'S Reaction" Or Forster-Decker Synthesis.
DOI:10.1021/op200016A