CAS: 79200-56-9; (1R,4S)-2-Azabicyclo[2.2.1]Hept-5-En-3-One

该化合物是一个双环有机化合物,其特点是独特的双环结构,包括环状系统中的氮原子.该化合物具有一个可促进其反应性和潜在应用于有机合成的氯酮功能组.氮原子的存在将它分类为含氮的外转循环,经常显示有趣的生物活动.该化合物一般没有颜色,可粉色到黄色液体或固体,视其纯度和具体条件而定.其立体化学性质很重要,因为其命名表明它是具有特定光学活动的配生器.该化合物可被用于合成各种药品和农用化学物,因为其结构特性可促进与生物目标的相互作用.此外,其再活性可能受到双联和开酮的存在的影响,使其成为有机化学的多功能中间体.

英文名称(1R,4S)-2-Azabicyclo[2.2.1]Hept-5-En-3-One
中文名称(-)-文斯内酯
IUPAC名称(1R,4S)-2-azabicyclo[2.2.1]hept-5-en-3-one
其它别名(1R,4S)-2-Azabicyclo[2.2.1]Hept-5-En-3-One; (1R)-(-)-2-Azabicyclo[2.2.1]Hept-5-En-3-One; (1S,4R)-3-Azabicyclo[2.2.1]Hept-5-En-2-One; (1R,4S)-2-Azabicyclo(2.2.1)Hept-5-En-3-One; (1~{s},4~{r})-3-Azabicyclo[2.2.1]Hept-5-En-2-One; (+/-)-2-Azabicyclo[2.2
CAS编号79200-56-9
MFCD编号:MFCD00211274
EINECS号:616-668-7
分子式:C6H7NO
分子量:109.13
产品CID: 1786560
产品分类化学试剂 → 手性化学试剂

相似结构搜索
产品信息参考;
InChIKey: DDUFYKNOXPZZIW-UHNVWZDZSA-N
InChI=1S/C6H7NO/c8-6-4-1-2-5(3-4)7-6/h1-2,4-5H,3H2,(H,7,8)/t4-,5+/m1/s1…
计算化学: 氢键受体数1.0氢键供体数1.0可旋转键数0.0

物理性质

熔点94-97 °C(文献)
沸点319.3±0.0 °C at 760 mmHg
闪点167.1±9.8 °C
密度1.2±0.1 g/cm3
pKa:15.48±0.20(预测)
PSA:29.1
LogP:-1.22
折射率1.546
蒸汽压0.0±0.6 mmHg at 25°C
溶解性Chloroform (Slightly, Heated), DMSO (Slightly), Methanol (Slightly)
敏感性遵照规定使用和储存则不会分解。
外观形态类白色至米色晶体或结晶粉末
储存条件密封, 常温干燥保存
产品应用该化合物用于制造前体:AMINO-PERAMIVIR,一种强大的抗尿酶抑制剂;五种成员类比的4-氨基-5-卤开胃酸作为潜在的伽巴氨基转移酶(GABA-AT)活性剂.

MSDS等安全信息

GHS象形图
GHS符号GHS07 & GHS05;
注释: Exclamation mark & Corrosion
危险类别急性毒性类别4(经口)
严重眼损伤类别1
皮肤致敏类别1
警示词Danger(危险)
危险描述H302 |吞咽有害.
H318 |造成严重眼损伤.
H317 |可能引起皮肤过敏反应.
防范说明P280-P305+P351+P338
UN编号NONH for all modes of transport
危险品标志Xn
安全声明24-26-37/39
危险类别码22-41-43
WGK Germany1

欧盟法规

REACH注册C&L通报REACH预注册

上下游产品

合成工艺路线路线简述

合成目标产物 ((1R,4S)-2-Azabicyclo[2.2.1]Hept-5-En-3-One 主要起始原料 (1R,4S)-4-Aminocyclopent-2-Enecarboxylic Acid
24224-99-5 = 79200-56-9
反应条件:1.1 Reagents: Titanium,Dichloro[2,2-Dimethyl-α,α,α′,α′-Tetra-2-Naphthalenyl-1,3-Dioxolane-4,5... Solvents: Toluene
标题:Syntheses Of Nucleosides And Related Compounds. Xl. Hetero Diels-Alder Reaction Of Benzenesulfonyl Cyanide With Cyclopentadiene Using Chiral Lewis Acids
作者:Katagiri,Nobuya; Makino,Masashi; Tamura,Takahiro; Kaneko,Chikara
参考文献:Chemical & Pharmaceutical Bulletin 日期:1996 卷标:44(4) 页码:850-2]

49805-30-3 = 79200-56-9
反应条件:1.1 Solvents: Water
标题:Chemoenzymic Synthesis Of (-)-Carbovir Utilizing A Whole Cell Catalyzed Resolution Of 2-Azabicyclo[2.2.1]Hept-5-En-3-One
作者:Taylor,Steven J. C.; Sutherland,Alan G.; Lee,Carol; Wisdom,Richard; Thomas,Steve; Et Al
参考文献:Journal Of The Chemical Society 日期:1990 卷标:(16) 页码:1120-1]

49805-30-3 = 79200-56-9
反应条件:1.1 Solvents: Water; 24 H,Ph 7.5
标题:Synthesis Of Rigid Bicycloheterocyclic Scaffolds From Vince'S Lactam (Enzymatic Resolution Of Vince'S Lactam)
作者:Gurjar,Mukund K.; Bera,Smritilekha; Joshi,Rohini R.; Joshi,Ramesh A.
参考文献:Heterocycles 日期:2003 卷标:60(10) 页码:2293-2303]

= 79200-56-9 [标题:Reaction Conditions
标题:Stereo- And Regiocontrolled Synthesis Of Highly Functionalized Cyclopentanes With Multiple Chiral Centers
作者:Nonn,Melinda; Binder,Adrienn; Volk,Balazs; Kiss,Lorand
参考文献:Synthetic Communications 日期:2020 卷标:50(8) 页码:1199-1209]

19158-51-1 = 79200-56-9
反应条件:1.1 22 °C1.2 Catalysts: Acetic Acid Solvents: Water
标题:P-Toluenesulfonyl Cyanide
作者:Griffiths,Gareth J.
参考文献:E-Eros Encyclopedia Of Reagents For Organic Synthesis 日期:2001]

49805-30-3 = 79200-56-9
反应条件:1.1 Catalysts: Lactamase,(+)γ- (Comamonas Acidovorans) Solvents: Water; 1 H,Ph 7.5,25 °C
标题:Novel Screening Methods-The Key To Cloning Commercially Successful Biocatalysts
作者:Taylor,Stephen J. C.; Brown,Rob C.; Keene,Phil A.; Taylor,Ian N.
参考文献:Bioorganic & Medicinal Chemistry 日期:1999 卷标:7(10) 页码:2163-2168]

262280-21-7 = 79200-56-9
反应条件:1.1 Reagents: Bromine Solvents: Dichloromethane; 0 °C; 2 H,0 °C
标题:A New Class Of Conformationally Rigid Analogs Of 4-Amino-5-Halopentanoic Acids,Potent Inactivators Of γ-Aminobutyric Acid Aminotransferase
作者:Qiu,Jian; Silverman,Richard B.
参考文献:Journal Of Medicinal Chemistry 日期:2000 卷标:43(4) 页码:706-720]

157810-21-4 = 79200-56-9
反应条件:1.1 Reagents: Ammonium Hydroxide Solvents: Methanol; 12 H,Rt
标题:Lipase-Catalyzed Resolution Of 2-Azabicyclo[2.2.1]Hept-5-En-3-Ones
作者:Nakano,Hiroto; Iwasa,Kazuto; Okuyama,Yuko; Hongo,Hiroshi
参考文献:Tetrahedron: Asymmetry 日期:1996 卷标:7(8) 页码:2381-2386]

49805-30-3 = 79200-56-9
反应条件:1.1 Solvents: Water; 4 D,Ph 8.3,Rt1.2 4 H,Rt; 2 D,Rt
标题:Synthesis And Fungistatic Activity Of Bicyclic Lactones And Lactams Against Botrytis Cinerea,Penicillium Citrinum,And Aspergillus Glaucus
作者:Walczak,Paulina; Pannek,Jakub; Boratynski,Filip; Janik-Polanowicz,Agata; Olejniczak,Teresa
参考文献:Journal Of Agricultural And Food Chemistry 日期:2014 卷标:62(34) 页码:8571-8578

2-氮杂双环[2.2.1]庚-5-烯-3-酮置于盐酸,甲醇,水,(Benzotriazo-1-Yloxy)Tris(Dimethylamino)Phosphonium Hexafluorophosphate,三乙胺,Lithium Hydroxide体系中,用水,N,N-二甲基甲酰胺作为反应溶剂,化学反应 52.0H,反应生成 (-)-文斯内酯
参考文献:一种具有光学活性的2-氮杂双环[2.2.1]庚-5-烯-3-酮的化学制备方法
标题:一种具有光学活性的2-氮杂双环[2.2.1]庚-5-烯-3-酮的化学制备方法
摘要:本发明公开了一种具有光学活性的2‑氮杂双环[2.2.1]庚‑5‑烯‑3‑酮的化学制备方法,以市场上易得的消旋2‑氮杂双环[2.2.1]庚‑5‑烯‑3‑酮为原料经过化学拆分得到具有光学活性的(+/﹣)4‑氨基环戊‑2‑烯‑1‑羧酸甲酯,再通过水解成(+/﹣)4‑氨基环戊‑2‑烯‑1‑羧酸后经分子内缩合制得,该方法避免使用酶发酵法,具有重复性好,产率高的优点.

海关参考信息

2901210000-乙烯
2901220000-丙烯
2912110000-甲醛
2912120000-乙醛
💡 提示：海关信息按照顺序优先匹配，如需确认的海关信息，请参考相关资料。
详情请参考：📖 海关编码查询和海关进出口税则

专利信息

专利号:US-9334273-B1
优先权日:2014-03-05
标题:Efficient and stereoselective synthesis of 2â€²-fluoro-6â€²-methylene-carbocyclic adenosine (FMCA)
发明人：CHU DAVID C K; SINGH UMA S
权利人:UNIV GEORGIA
摘要:The invention provides a new convergent approach for the synthesis of 2â€²-fluoro-6â€²-methylene-carbocyclic adenosine (FMCA) from a readily available starting material (Vince lactam) in fourteen steps. An efficient and practical methodology for stereospecific preparation of a versatile carbocyclic key intermediate, D -2â€²-fluoro-6â€²-methylene cyclopentanol by diazotization, elimination, stereoselective epoxidation, fluorination and oxidative reduction of the Vince lactam in twelve steps is also provided.

专利号:US-10975096-B2
优先权日:2014-06-20
标题 :Synthesis of polycyclic-carbamoylpyridone compounds
发明人：CHIU ANNA; ENQUIST JR JOHN; GRIGGS NOLAN; HALE CHRISTOPHER; IKEMOTO NORIHIRO; KEATON KATIE ANN; KRAFT MATT; LAZERWITH SCOTT E; LEEMAN MICHEL; PENG ZHIHUI; SCHRIER KATE; TRINIDAD JONATHAN; VAN HERPT JOCHEM; WALTMAN ANDREW W
权利人:GILEAD SCIENCES INC
摘要:Methods of making compounds of Formula I are disclosed:

专利号:US-7358073-B2
优先权日:1997-11-27
标题:Process for the preparation of aminoalcohol derivatives and their further conversion to (1R, 4S)-4(2-amino-6-chloro-5-formamido-4- pyrimidinyl)-amino-2-cyclopentenyl-1-methanol
发明人：BRIEDEN WALTER; SCHROER JOSEF; BERNEGGER-EGLI CHRISTINE; URBAN EVA MARIA; PETERSEN MICHAEL; RODUIT JEAN-PAUL; BERCHTOLD KATJA; BREITBACH HOLGER
权利人:LONZA AG
摘要:The invention relates to a novel process for the preparation of an aminoalcohol of the formula n nracemically or optically active, starting from 2-azabicyclo[2.2.1]hept-5-en-3-one, its further conversion to give the corresponding acyl derivative and its further conversion to (1S,4R)- or (1R,4S)-4-(2-amino-6-chloro-9-H-purine-9-yl)-2-cyclopentenyl-1-methanol of the formulaen n nIn the latter synthesis, the aminoalcohol is converted into the corresponding D- or L-tartrate, which is then reacted with N-(2-amino-4,6-dichloropyrimidin-5-yl) formamide of the formulan n nto give (1S,4R)- or (1R,4S)-4-[(2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino]-2-cyclopentenyl-1-methanol of the formulaen n nand then cyclized to give the end compounds.

专利号:US-2018079755-A1
优先权日:2007-08-02
标题:Process for the synthesis of e1 activating enzyme inhibitors

专利号:US-12331006-B2
优先权日:2018-05-25
标题 :Process for the synthesis of (s) 3-amino-4-(difluoromethylenyl)cyclopent-1-ene-1-carboxylic acid
发明人：SILVERMAN RICHARD B; MOSCHITTO MATTHEW
权利人:UNIV NORTHWESTERN
摘要:Provided herein are processes, compounds and compositions for making (S)-3-amino-4-(difluoromethylenyl)cyclopent-1-ene-1-carboxylic acid. Also provided herein a pharmaceutical compositions containing (S)-3-amino-4-(difluoromethylenyl)cyclopent-1-ene-1-carboxylic acid.

专利号:US-2009036678-A1
优先权日:2007-08-02
标题 :Process for the synthesis of E1 activating enzyme inhibitors