CAS: 84-26-4; 7,8-Dihydroindolo[2',3':3,4]Pyrido[2,1-B]Quinazolin-5(13H)-One

• 英文名称7,8-Dihydroindolo[2',3':3,4]Pyrido[2,1-B]Quinazolin-5(13H)-One
• 中文名称吴茱萸次碱
• IUPAC名称8,13-dihydroindolo[2',3':3,4]pyrido[2,1-b]quinazolin-5(7H)-one
• 其它别名C18H13N3O; Rutecarpine [mi]; Indolo[2',4]Pyrido[2,1-B]Quinazolin-5(7H)-One, 8,13-Dihydro-; Rutaecarpine, > (Hplc); Rutacarpine; Rutaecarpin; Rutecarpine
• CAS编号84-26-4
• MFCD编号:MFCD00210551
• EINECS号:635-907-6
• FDA UNII编号:8XZV289PRY
• 分子式:C18H13N3O
• 分子量:287.32
• 产品CID: 1831198
• 产品分类生物化工 → 中草药成分

• 相似结构搜索
• 产品信息参考;;;;
• InChIKey: ACVGWSKVRYFWRP-UHFFFAOYSA-N
• InChI=1S/C18H13N3O/c22-18-13-6-2-4-8-15(13)20-17-16-12(9-10-21(17)18)11-5-1-3-7-14(11)19-16/h1-8,19H,9-10H2…
• 计算化学: 氢键受体数2.0氢键供体数1.0可旋转键数0.0

物理性质

• 熔点259.5 - 260 °C
• 沸点550.1±60.0 °C at 760 mmHg
• 闪点286.5±32.9 °C
• 密度1.5±0.1 g/cm3
• pKa:15.79±0.20(预测)
• PSA:50.68
• LogP:2.03
• 折射率1.792
• 蒸汽压0.0±1.5 mmHg at 25°C
• 溶解性DMSO: 18 mg/mL Clear Yellow Solution, Soluble
• 外观形态白色固体
• 储存条件密封干燥,2-8°C
• 产品应用RUTAECARPINE,又名NSC 258317, 原与E. RUTAECCARPA隔离的丙烯丙烯酮碱碱碱,具有多种生物活动,RUTAECARPARINE通过激活TRPV1,防止OX-LDL引起的内皮间隔热关节功能失调.RUTECARPAINE抑制了大鼠血管光滑肌肉细胞中乙酰乙酰胺引起的扩散.RUTAECCARPINE通过调节IRS-1/P3K/AKT和AMPK/ACC2信号路径,改善脂肪喂养和经链阻切处理的老鼠中的高脂性贫血和高血糖.

MSDS等安全信息

• GHS象形图
• GHS符号GHS06;
  注释: Skull and crossbones
• 危险类别急性毒性 类别2(经口)
  急性毒性 类别4(经口)
• 警示词Danger(危险)
• 危险描述H300 |吞咽致命.
  H302 |吞咽有害.
• 防范说明P301+P312+P330
• UN编号UN 2811 6.1/PG 3
• 危险品标志T
• 安全声明45-36-26
• 危险类别码25-36/37/38
• WGK Germany3

欧盟法规

上下游产品

合成工艺路线路线简述

• 合成目标产物 Rutaecarpine 主要起始原料 Ethanamine, N-[(3,5-Dichlorophenyl)Methylene]-2,2-Diethoxy-
• 95274-40-1 = 84-26-4
  反应条件:1.1 Reagents: Potassium Hydroxide Solvents: Ethanol,Water; 10 Min,Heated; 15 Min,Reflux
  标题:Palladium-Catalyzed Three-Component Carbonylative Synthesis Of 2-(Trifluoromethyl)Quinazolin-4(3H)-Ones From Trifluoroacetimidoyl Chlorides And Amines
  作者:Chen,Zhengkai; Wang,Le-Cheng; Zhang,Jiajun; Wu,Xiao-Feng
  参考文献:Organic Chemistry Frontiers 日期:2020 卷标:7(17) 页码:2499-2504]
  
  80776-66-5 = 84-26-4
  反应条件:1.1 180 °C
  标题:A Facile Total Synthesis Of Rutaecarpine
  作者:Chavan,Subhash P.; Rasapalli,Sivappa
  参考文献:Tetrahedron Letters 日期:2004 卷标:45(5) 页码:997-999]
  
  368858-21-3 = 84-26-4
  反应条件:1.1 Solvents: Ethanol
  标题:A Simple Synthesis Of Rutaecarpine
  作者:Lee,Seung Ho; Kim,Seung Ill; Park,Jae Gyu; Lee,Eung Seok; Jahng,Yurngdong
  参考文献:Heterocycles 日期:2001 卷标:55(8) 页码:1555-1559]
  
  80776-66-5 = 84-26-4
  反应条件:1.1 1 H,Rt -> 180 °C
  标题:Efficient Syntheses Of 2,3-Disubstituted Natural Quinazolinones Via Iridium Catalysis
  作者:Fang,Jie; Zhou,Jianguang
  参考文献:Organic & Biomolecular Chemistry 日期:2012 卷标:10(12) 页码:2389-2391]
  
  1701462-19-2 = 84-26-4
  反应条件:1.1 Reagents: 1,8-Diazabicyclo[5.4.0]Undec-7-Ene Solvents: Dimethylacetamide; 20 - 36 H,150 °C
  标题:A Simple Approach For The Syntheses Of Rutaecarpine And Its Analogs
  作者:Liang,Li-Na; An,Rui; Huang,Tao; Xu,Mei; Hao,Xiao-Jiang; Et Al
  参考文献:Tetrahedron Letters 日期:2015 卷标:56(19) 页码:2466-2468]
  
  59863-00-2 = 84-26-4
  反应条件:1.1 Reagents: Potassium Hydroxide,Hydrogen Peroxide Solvents: Ethanol,Water; 45 Min,Reflux
  标题:Glyoxylic Acid In The Reaction Of Isatoic Anhydride With Amines: A Rapid Synthesis Of 3-(Un)Substituted Quinazolin-4(3H)-Ones Leading To Rutaecarpine And Evodiamine
  作者:Rao,K. Raghavendra; Raghunadh,Akula; Mekala,Ramamohan; Meruva,Suresh Babu; Pratap,T. V.; Et Al
  参考文献:Tetrahedron Letters 日期:2014 卷标:55(43) 页码:6004-6006]
  
  754123-75-6 = 84-26-4
  反应条件:1.1 Reagents: Acetic Acid; 24 H,Reflux
  标题:Expeditious And Practical Synthesis Of The Bioactive Alkaloids Rutaecarpine,Euxylophoricine A,Deoxyvasicinone,And Their Heterocyclic Homologs
  作者:Hamid,Abdulkareem; Elomri,Abdelhakim; Daich,Adam
  参考文献:Tetrahedron Letters 日期:2006 卷标:47(11) 页码:1777-1781]
  
  95274-40-1 = 84-26-4
  反应条件:1.1 Reagents: Potassium Hydroxide Solvents: Ethanol
  标题:A Simple Heterocyclic Fusion Reaction And Its Application For Expeditious Syntheses Of Rutaecarpine And Its Analogs
  作者:Huang,Guozheng; Roos,Dominika; Stadtmuller,Patricia; Decker,Michael
  参考文献:Tetrahedron Letters 日期:2014 卷标:55(26) 页码:3607-3609]
  
  459157-64-3 = 84-26-4
  反应条件:1.1 Reagents: Trifluoroacetic Anhydride,Hydrochloric Acid
  标题:A Short Synthesis Of Quinazolinocarboline Alkaloids Rutaecarpine,Hortiacine,Euxylophoricine A And Euxylophoricine D From Methyl N-(4-Chloro-5H-1,2,3-Dithiazol-5-Ylidene)Anthranilates
  作者:Mohanta,Pramod K.; Kim,Kyongtae
  参考文献:Tetrahedron Letters 日期:2002 卷标:43(22) 页码:3993-3996]
  
  88783-83-9 = 84-26-4
  反应条件:1.1 Reagents: Tin,Hydrochloric Acid Solvents: Methanol,Water; 0 °C; 12 H,Rt1.2 Reagents: Triethylamine,Sodium Hydroxide Solvents: Chloroform,Water; 3 H,Rt
  标题:A New And Facile Synthesis Of Rutaecarpine Alkaloids
  作者:Lee,Chih-Shone; Liu,Cheng-Kuo; Cheng,Yen-Yao; Teng,Che-Ming
  参考文献:Heterocycles 日期:2009 卷标:78(4) 页码:1047-1056]
  
  17952-82-8 + 134-20-3 = 84-26-4
  反应条件:1.1 Reagents: Hydrochloric Acid Solvents: Chloroform1.2 Reagents: Phosphorus Oxychloride; 2 H,40 °C1.3 Solvents: Tetrahydrofuran; Rt1.4 Reagents: Ammonium Hydroxide Solvents: Water
  标题:A Facile Synthesis Of Simple Alkaloids-Synthesis Of 2,3-Polymethylene-4(3H)-Quinazolinones And Related Alkaloids
  作者:Lee,Eung Seok; Park,Jae-Gyu; Jahng,Yurngdong
  参考文献:Tetrahedron Letters 日期:2003 卷标:44(9) 页码:1883-1886]
  
  141276-50-8 = 84-26-4
  反应条件:1.1 Solvents: Methanol; Rt1.2 Reagents: Nickel Boride (Ni2B); Rt1.3 Reagents: Hydrochloric Acid Solvents: Water; Rt -> 52 °C; 2 Min,52 °C; 52 °C -> Rt1.4 Reagents: Sodium Bicarbonate Solvents: Water; Neutralized,Rt
  标题:Total Synthesis Of Rutaecarpine And Analogues By Tandem Azido Reductive Cyclization Assisted By Microwave Irradiation
  作者:Kamal,Ahmed; Reddy,M. Kashi; Reddy,T. Srinivasa; Santos,Leonardo Silva; Shankaraiah,Nagula
  参考文献:Synlett 日期:2011 卷标:(1) 页码:61-64]
  
  4894-26-2 = 84-26-4
  反应条件:1.1 Reagents: 1-Ethyl-3-(3′-Dimethylaminopropyl)Carbodiimide Hydrochloride Solvents: Dimethylformamide; 4 H,80 °C
  标题:Condensation Of Anthranilic Acids With Pyridines To Furnish Pyridoquinazolones Via Pyridine Dearomatization
  作者:Yang,Yajun; Zhu,Cuiju; Zhang,Min; Huang,Shijun; Lin,Jingjing; Et Al
  参考文献:Chemical Communications (Cambridge 日期:2016 卷标:52(87) 页码:12869-12872]
  
  4894-26-2 = 84-26-4
  反应条件:1.1 Reagents: Thionyl Chloride Solvents: Toluene; 2 H,Reflux1.2 2 H,Rt
  标题:Synthesis Of Rutaecarpine And Quinazolone Compounds
  作者:Wang,Cheng-Xue; Chu,Zhan-Fang
  参考文献:Yingyong Huaxue 日期:2008 卷标:25(12) 页码:1439-1443]
  
  17952-82-8 = 84-26-4
  反应条件:1.1 Reagents: Sulfuryl Chloride Solvents: Benzene; 4 H,Reflux1.2 Reagents: Ammonium Hydroxide Solvents: Water; Basified,Cooled
  标题:One-Pot Synthesis Of Simple Alkaloids: 2,3-Polymethylene-4(3H)-Quinazolinones,Luotonin A,Tryptanthrin,And Rutaecarpine
  作者:Jahng,Katherine Chae; Kim,Seung Ill; Kim,Dong Hyeon; Seo,Chang Seob; Son,Jong-Keun; Et Al
  参考文献:Chemical & Pharmaceutical Bulletin 日期:2008 卷标:56(4) 页码:607-609]
  
  95610-41-6 = 84-26-4
  反应条件:1.1 60 Min,180 °C1.2 Reagents: Ammonia Solvents: Water; Ph 5
  标题:Redox Condensations Of O-Nitrobenzaldehydes With Amines Under Mild Conditions: Total Synthesis Of The Vasicinone Family
  作者:Afanasyev,Oleg I.; Podyacheva,Evgeniya; Rudenko,Alexander; Tsygankov,Alexey A.; Makarova,Maria; Et Al
  参考文献:Journal Of Organic Chemistry 日期:2020 卷标:85(14) 页码:9347-9360]
  
  80776-66-5 = 84-26-4
  反应条件:1.1 Solvents: Acetic Acid; 5 H,Reflux
  标题:Facile Zeolite Induced Fischer-Indole Synthesis: A New Approach To Bioactive Natural Product Rutaecarpine
  作者:Mhaske,Santosh B.; Argade,Narshinha P.
  参考文献:Tetrahedron 日期:2004 卷标:60(15) 页码:3417-3420]
  
  16502-01-5 + 91-56-5 = 84-26-4
  反应条件:1.1 Reagents: Tert-Butyl Hydroperoxide Catalysts: Trifluoroacetic Acid Solvents: Toluene,Water; 12 H,120 °C
  标题:Tfa/tbhp-Promoted Oxidative Cyclisation For The Construction Of Tetracyclic Quinazolinones And Rutaecarpine
  作者:Jia,Feng-Cheng; Chen,Tian-Zhi; Hu,Xiao-Qiang
  参考文献:Organic Chemistry Frontiers 日期:2020 卷标:7(13) 页码:1635-1639

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