CAS: 6879-01-2; (2S,31R,7Ar,8R,8As,11S,11As,11Br)-8-Ethyl-11-Methyl-2-((2S,4S)-4-Methyl-5-Oxotetrahydrofuran-2-yl)Dodecahydroazepino[3,2,1-Hi]Furo[3,2-E]Indol-10(2H)-One
- 英文名称(2S,31R,7Ar,8R,8As,11S,11As,11Br)-8-Ethyl-11-Methyl-2-((2S,4S)-4-Methyl-5-Oxotetrahydrofuran-2-yl)Dodecahydroazepino[3,2,1-Hi]Furo[3,2-E]Indol-10(2H)-One
- 中文名称对叶百部碱
- IUPAC名称(2S,31R,7aR,8R,8aS,11S,11aS,11bR)-8-ethyl-11-methyl-2-((2S,4S)-4-methyl-5-oxotetrahydrofuran-2-yl)dodecahydroazepino[3,2,1-hi]furo[3,2-e]indol-10(2H)-one
- 其它别名Furo[2,3-H]Pyrrolo[3,2,1-Jk][1]Benzazepin-10(2H)-One, 8-Ethyldodecahydro-11-Methyl-2-[(2S,4S)-Tetrahydro-4-Methyl-5-Oxo-2-Furanyl]-, (2S,7Ar,8R,8As,11S,11As,11Br,11Cr)- ; (2S,31R,7Ar,8R,8As,11S,11As,11Br)-8-Ethyl-11-Methyl-2-((2S,4S)-4-Methyl-5-Oxotetrahy
- CAS编号6879-01-2
- MFCD编号:MFCD11111456
- EINECS号:110-077-3
- 分子式:C22H33NO4分子量:375.51
- 产品CID: 2332718
- 产品分类生物化工 → 提取物
物理性质
- 熔点86～88°C
- 沸点554.2±50.0 °C at 760 mmHg
- 闪点289.0±30.1 °C
- 密度1.2±0.1 g/cm3
- pKa:8.90±0.70(预测)
- PSA:55.84
- LogP:2.28
- 折射率1.556
- 蒸汽压0.0±1.5 mmHg at 25°C
- 溶解性DMF:10.0(Max Conc. mg/mL);26.63(Max Conc. Mm) DMF:Pbs (Ph 7.2) (1:2):0.33(Max Conc. mg/mL);0.88(Max Conc. Mm) DMSO:1.0(Max Conc. mg/mL);2.66(Max Conc. Mm)
- 外观形态白色至类白色固体
- 储存条件2-8°C(避光保存)
- 产品应用百部碱的用途:本品植物源杀虫剂,对害虫具有触杀和胃毒作用,也可杀卵.1.1% 百部・楝・烟乳油登记用于防治菜豆斑潜蝇和十字花科蔬菜害虫小菜蛾,菜青虫与蚜虫.
- 性质描述百部碱的性状:本品百部碱是百部属植物提取物中生物碱的总称.登记为杀虫剂成分的是对叶百部碱(tuberostemonine),熔点88°C,在氯仿中[α] 20D为-47°.
MSDS等安全信息
欧盟法规
C&L通报上下游产品
CAS号106861-40-9 二去氢对叶百部碱合成工艺路线路线简述
- 合成目标产物 Tuberostemonine 主要起始原料 Furo[2,3-H]Pyrrolo[3,2,1-Jk][1]Benzazepin-10(2H)-One, 8-Ethenyldodecahydro-11-Methyl-2-[(2S,4S)-Tetrahydro-4-Methyl-5-Oxo-2-Furanyl]-, (2S,7Ar,8R,8As,11S,11As,11Br,11Cr)-
- (文献来源)合成步骤主要原料 Furo[2,3-H]Pyrrolo[3,2,1-Jk][1]Benzazepin-10(2H)-One, 8-Ethenyldodecahydro-11-Methyl-2-[(2S,4S)-Tetrahydro-4-Methyl-5-Oxo-2-Furanyl]-, (2S,7Ar,8R,8As,11S,11As,11Br,11Cr)-
📜(2S,3Ar,7Ar)-3A-Hydroxy-6-Oxo-2,3,3A,6,7,7A-Hexahydroindole-1,2-Dicarboxylic Acid 1-Benzyl Ester 2-Methyl Ester置于palladium On Activated Charcoal,甲酸 吡啶,咪唑,Rucl2(1,3-Dimesityl-Imidazolidin-2-yl)(Pcy3)(=chph),三乙基硅烷,4-二甲氨基吡啶,Tris(Dibenzylideneacetone)Dipalladium(0) Chloroform Complex,Sodium Tetrahydroborate,Wilkinson'S Catalyst,Cerium(Iii) Chloride,四丙基高钌酸铵,偶氮二异丁腈,三氟甲苯,4,4'-二叔丁基苯并,N-Tritylprop-2-En-1-Amine,四丁基氟化铵,氢气,Palladium Diacetate,二甲基氯化铝,Lithium,双(三甲基硅烷基)氨基钾,L-Selectride,Potassium Carbonate,对甲苯磺酸,N-甲基吗啉氧化物,三乙胺,N,N-二异丙基乙胺,三苄基膦体系中,用 四氢呋喃,甲醇,乙醇,正己烷,二氯甲烷,水,甲苯,乙腈,Xylene 作为反应溶剂,-90.0~140.0 °C,101.33 Kpa 条件下,反应 322.5H,反应生成 对叶百部碱
参考文献:Asymmetric Total Syntheses Of Tuberostemonine,Didehydrotuberostemonine,And 13-Epituberostemonine
标题:Asymmetric Total Syntheses Of Tuberostemonine,Didehydrotuberostemonine,And 13-Epituberostemonine
摘要:Detailed Experimental Approaches Toward The Pentacyclic Stemona Alkaloids Tuberostemonine And Didehydrotuberostemonine And The Close Analogue 13-Epituberostemonine Are Described. The Syntheses Originate With A Hydroindolinone Derivative That Can Be Obtained On A Large Scale In A Single Step From Carbobenzoxy-Protected L-Tyrosine. Highlights Of The Conversion Of This Hydroindolinone To The Target Structures Are The Three-Fold Use Of Ruthenium Catalysts,First In Azepine Ring-Closing Metathesis And Then In Alkene Isomerization And Cross-Metathesis Propenyl-Vinyl Exchange,As Well As The Stereoselective Attachment Of A Y-Butyrolactone Ring To A Tetracycle Core Structure By Use Of A Lithiated Asymmetric Bicyclo[3.2.1]octane (Abo) Ortho Ester. Structural Analysis By Density Functional Theory (Dft) Methods Revealed That The Ease Of Oxidation Of The Natural Product Is Likely Due To The Conformational Preferences Of The Pyrrolidine And The Fused Cyclohexane Rings.
DOI:10.1021/ja044280K
参考文献:Asymmetric Total Syntheses Of Tuberostemonine,Didehydrotuberostemonine,And 13-Epituberostemonine
标题:Asymmetric Total Syntheses Of Tuberostemonine,Didehydrotuberostemonine,And 13-Epituberostemonine
摘要:Detailed Experimental Approaches Toward The Pentacyclic Stemona Alkaloids Tuberostemonine And Didehydrotuberostemonine And The Close Analogue 13-Epituberostemonine Are Described. The Syntheses Originate With A Hydroindolinone Derivative That Can Be Obtained On A Large Scale In A Single Step From Carbobenzoxy-Protected L-Tyrosine. Highlights Of The Conversion Of This Hydroindolinone To The Target Structures Are The Three-Fold Use Of Ruthenium Catalysts,First In Azepine Ring-Closing Metathesis And Then In Alkene Isomerization And Cross-Metathesis Propenyl-Vinyl Exchange,As Well As The Stereoselective Attachment Of A Y-Butyrolactone Ring To A Tetracycle Core Structure By Use Of A Lithiated Asymmetric Bicyclo[3.2.1]octane (Abo) Ortho Ester. Structural Analysis By Density Functional Theory (Dft) Methods Revealed That The Ease Of Oxidation Of The Natural Product Is Likely Due To The Conformational Preferences Of The Pyrrolidine And The Fused Cyclohexane Rings.
DOI:10.1021/ja044280K
供应商参考报价(招募中)
品牌试剂参考报价(招募中)
📌 第三方产品分析报告
主要参考文献
1: Tang A, Liu Y, Ding Q, Huang G, Sha Z, Yang C, Cao F. Tuberostemonine may alleviates proliferation of lung fibroblasts caused by pulmonary fibrosis. Int J Immunopathol Pharmacol. 2024 Jan-Dec;38:3946320241274225. doi: 10.1177/03946320241274225.
2: Xiong H, Sun S, Zhang W, Zhao D, Liu X, Tian Y, Feng S. Spatial metabolomics method to reveal the differences in chemical composition of raw and honey-fried Stemona tuberosa Lour. by using UPLC-Orbitrap Fusion MS and desorption electrospray ionization mass spectrometry imaging. Phytochem Anal. 2024 Jul 28. doi: 10.1002/pca.3428. Epub ahead of print.
220:114013. doi: 10.1016/j.phytochem.2024.114013. Epub 2024 Feb 7.
合成参考文献
参考文献:10.1055/s-0033-1338641
摘要:Zhang H. Syntheses of Bioactive Natural Products and Natural-Product-Like Compounds Based on Their Key Structural Units. Synlett. 2014 Jun 03;25(14):1953–70. doi: 10.1055/s-0033-1338641.
参考文献:10.1016/j.tet.2013.12.003
摘要:Gao Y, Wang J, Zhang C, Xu X, Zhang M, Kong L. Seven new alkaloids from the roots of Stemona tuberosa. Tetrahedron. 2014 Jan;70(4):967–74. doi: 10.1016/j.tet.2013.12.003.
参考文献:10.1021/np2004374
摘要:Kongkiatpaiboon S, Schinnerl J, Felsinger S, Keeratinijakal V, Vajrodaya S, Gritsanapan W, Brecker L, Greger H. Structural relationships of stemona alkaloids: assessment of species-specific accumulation trends for exploiting their biological activities. J Nat Prod. 2011 Sep 23;74(9):1931–8. doi: 10.1021/np2004374.
参考文献:10.1021/np50083a003
摘要:Lin W, Ye Y, Xu R. Chemical Studies on New Stemona Alkaloids, IV. Studies on New Alkaloids from Stemona tuberosa. J. Nat. Prod. 1992 May;55(5):571–6. doi: 10.1021/np50083a003.
参考文献:10.1016/j.jpba.2017.04.018
摘要:Tong Y, Xu W, Wu Y, Ou L, Zhang M, Xu X, Zhang C. Metabolic profiles of neotuberostemonine and tuberostemonine in rats by high performance liquid chromatography/quadrupole time-of-flight mass spectrometry. Journal of Pharmaceutical and Biomedical Analysis. 2017 Jul;141():210–21. doi: 10.1016/j.jpba.2017.04.018.
📝 需求与反馈
尽可能描述清楚需求与问题信息
