diexo-3-aza-4-oxatetracyclo<4.2.1.0>nonane

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: diexo-3-aza-4-oxatetracyclo<4.2.1.0>nonane
• 英文别名: exo-3-azatricyclo[4.2.1.0^2,5]nonan-4-one；exo-3-azatricyclo<4.2.1.0^2,5>nonan-4-one；(rac-di-exo)-3-aza-tricyclo[4.2.1.0(2,5)]nonan-4-one；(1R,2S,5R,6S)-3-azatricyclo[4.2.1.02,5]nonan-4-one
• 化学式: C₈H₁₁NO
• 分子量: 137.181
• InChiKey: NPAUQPZSOILENA-WNJXEPBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  diexo-3-aza-4-oxatetracyclo<4.2.1.0>nonane 在 N-甲基吗啉 、 盐酸 、 氯化亚砜 、 sodium cyanoborohydride 、 碳酸氢钠 、 溶剂黄146 作用下， 以 乙醇 、 水 、 乙酸乙酯 、 乙腈 为溶剂， 反应 20.5h， 生成 N-[3-[(4aR,5S,8R,8aS)-1-[(4-氟苯基)甲基]-1,2,4a,5,6,7,8,8a-八氢-4-羟基-2-氧代-5,8-甲桥喹啉-3-基]-1,1-二氧代-2H-1,2,4-苯并噻二嗪-7-基]甲磺酰胺
  参考文献：
  名称：

  WO2008/124450

  摘要：

  公开号：
• 作为产物：
  描述：

  N-(Chlorosulfonyl)-exo-3-aza-4-ketotricyclo<4.2.1.0^2,5>nonane 在 水 、 sodium hydroxide 、 sodium sulfite 作用下， 生成 diexo-3-aza-4-oxatetracyclo<4.2.1.0>nonane
  参考文献：
  名称：

  Large-Scale Syntheses of FMOC-Protected Non-Proteogenic Amino Acids:  Useful Building Blocks for Combinatorial Libraries

  摘要：

  Convenient and reliable large-scale procedures for the protection of various amino acids with N-(9-fluorenyimethoxycarbonyl)oxysuccinimide (FMOC-OSu) are described. Commercially available 4-aminomethylbenzoic acid and trans-4-(aminomethyl)cyclohexanecarboxylic acid were converted into their corresponding FMOC-derivatives in excellent yields without the need for an extractive workup. In addition, FMOC-cis-beta -amino acids were also prepared, employing a [2 + 2]-cycloaddition strategy between a cyclic olefin and N-chlorosulfonyl isocyanate (CSI). The resulting N-chlorosulfonyl fl-lactams were reduced to the parent beta -lactams with sodium sulfite and then converted to the cis-fi-amino acid hydrochlorides by exposure to aqueous hydrochloric acid. The resulting cis-fi-amino acids were converted to their FMOC-derivatives under conditions similar to those developed for the commercially available amino acids. Differences in the conditions employed between these beta -amino acids and the commercial derivatives were observed, primarily in the nature of the base required for the reaction. A possible rationale for the differences in behavior is described. These FMOC-amino acid derivatives are valuable intermediates for the solid-phase synthesis of combinatorial libraries.

  DOI：

  10.1021/op010204f

文献信息

• [EN] A METHOD OF INHIBITING HEPATITIS C VIRUS BY COMBINATION OF A 5,6-DIHYDRO-1H-PYRIDIN-2-ONE AND ONE OR MORE ADDITIONAL ANTIVIRAL COMPOUNDS<br/>[FR] PROCÉDÉ D'INHIBITION DU VIRUS DE L'HÉPATITE C PAR COMBINAISON D'UNE 5,6-DIHYDRO-1H-PYRIDIN-2-ONE ET D'UN OU PLUSIEURS COMPOSÉS ANTIVIRAUX SUPPLÉMENTAIRES
  申请人：ANADYS PHARMACEUTICALS INC

  公开号：WO2010042834A1

  公开（公告）日：2010-04-15

  The invention is directed to a method of treating infections by hepatitis C virus by administering N-3-[(1R,2S,7R,8S)-3-(4-fluoro-benzyl)-6-hydroxy-4-oxo-3-aza-tricyclo[6.2.1.02,7]undec-5-en-5-yl]-1,1 -dioxo-l,4-dihydro-lλ6- benzo[l,2,4]thiadiazin-7-yl} -methanesulfonamide and one or more additional antiviral compounds or pharmaceutical compositions containing such compounds.

  本发明涉及一种治疗乙型肝炎病毒感染的方法，通过给予N-3-[(1R,2S,7R,8S)-3-(4-氟苯基)-6-羟基-4-氧代-3-氮杂三环[6.2.1.02,7]十一碳-5-烯-5-基]-1,1-二氧代-1,4-二氢-1λ6-苯并[1,2,4]噻二唑-7-基}-甲磺酰胺以及一个或多个附加的抗病毒化合物或含有此类化合物的药物组合物。
• [1,2,4]THIADIAZINE 1,1-DIOXIDE COMPOUNDS
  申请人：Ruebsam Frank

  公开号：US20090306057A1

  公开（公告）日：2009-12-10

  The invention is directed to [1,2,4]thiadiazine 1,1-dioxide compounds and pharmaceutical compositions containing such compounds that are useful in treating infections by hepatitis C virus.

  这项发明涉及[1,2,4]噻二嗪1,1-二氧化物化合物和含有这种化合物的药物组合物，可用于治疗丙型肝炎病毒感染。
• Enantiomeric discrimination of cyclic β-amino acids using (18-crown-6)-2,3,11,12-tetracarboxylic acid as a chiral NMR solvating agent
  作者：Cora D. Chisholm、Ferenc Fülöp、Eniko Forró、Thomas J. Wenzel

  DOI：10.1016/j.tetasy.2010.07.031

  日期：2010.9

  (18-Crown-6)-2,3,11,12-tetracarboxylic acid is an excellent chiral NMR solvating agent for cyclic β-amino acids with cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, bicyclo[2.2.1]heptane, and bicyclo[2.2.1]heptene rings. The crown ether was added to the neutral β-amino acids in methanol-d4. A neutralization reaction between the crown ether and β-amino acid forms the ammonium ion needed for

  （18-Crown-6）-2,3,11,12-四羧酸是一种出色的手性NMR溶剂，用于环β-氨基酸与环戊烷，环己烷，环庚烷，环戊烯，环己烯，双环[2.2.1]庚烷，和双环[2.2.1]庚烯环。将冠醚加入到甲醇-d 4中的中性β-氨基酸中。冠醚和β-氨基酸之间的中和反应形成有利缔合所需的铵离子。在所研究的每种底物上均观察到两个氢原子α与β-氨基酸的胺和羧酸部分的对映体区别。对于相似结构的底物，某些氢原子的对映异构顺序的变化趋势与绝对构型相关。
• 1-METHYL-BENZO[1,2,4]THIADIAZINE 1-OXIDE DERIVATIVES
  申请人：Zhou Yuefen

  公开号：US20080292588A1

  公开（公告）日：2008-11-27

  The invention is directed to 1-methyl-benzo[1,2,4]thiadiazine 1-oxide derivatives and pharmaceutical compositions containing such compounds that are useful in treating infections by hepatitis C virus.

  这项发明涉及1-甲基苯并[1,2,4]噻二嗪-1-氧化物衍生物和含有这种化合物的药物组合物，可用于治疗丙型肝炎病毒感染。
• Sterochemical Studies 107 Saturated heterocycles 111
  作者：Gábor Bernáth、Géza Stájer、Angela E. Szabó、Zsolt Szóke-Molnár、Pál Sohár、Gyula Argay、Alajos Kálmán

  DOI：10.1016/s0040-4020(01)81504-0

  日期：1987.1

  saturated methylene-bridged quinazoline-2,4-diones (7a-b) prepared from norbornane-diexo-β-amino acid (1) with isocyanates and PPA. When heated with PPA, compounds 9 can be isomerized to 7. For preparation of the unsaturated compounds 8, the amino acid 2 was converted into the acid amides (13) and cyclized with I,1'-carbonyl-diimidazole to tricyclic quinazoline-2,4-dione (8a-e), which decompose when

  由双异冰片降冰片烷和降冰片烯-氮杂环丁烷酮5和6与异氰酸芳基酯制备N-芳基氨基甲酰基取代的β-内酰胺（9和10）。与由降冰片烷-二exo-β-氨基酸（1）制得的饱和亚甲基桥连喹唑啉-2,4-二酮（7a-b）相比，该化合物的结构通过IR，NMR光谱和X射线分析得以阐明。与异氰酸酯和PPA。与PPA一起加热时，化合物9可以异构化为7。为制备不饱和化合物8，氨基酸2被转化为酰胺（13），并与I，1'-羰基-二咪唑环合成三环喹唑啉-2 ，4-二酮（8a-e），其在加热时分解，分解出环戊二烯以产生3-取代的尿嘧啶（14）。