(3aS,4S,6aR)-4-(2-methoxy-2-oxoethyl)-2,2-dimethyl-4,6a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyrrol-5-ium-5-olate | 891193-76-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aS,4S,6aR)-4-(2-methoxy-2-oxoethyl)-2,2-dimethyl-4,6a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyrrol-5-ium-5-olate
• 英文别名: methyl 2-[(3aS,4S,6aR)-2,2-dimethyl-5-oxido-4,6a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyrrol-5-ium-4-yl]acetate
• CAS: 891193-76-3
• 化学式: C₁₀H₁₅NO₅
• 分子量: 229.233
• InChiKey: FTZHGIRWPHSGRC-OOZYFLPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  73.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3aS,4S,6aR)-4-(2-methoxy-2-oxoethyl)-2,2-dimethyl-4,6a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyrrol-5-ium-5-olate 、 阿德福韦酯杂质12 以 甲苯 为溶剂， 以81%的产率得到9-{(3aS,4S,7R,8aR,8bR)-4-(2-methoxy-2-oxoethyl)-2,2-dimethylhexahydro[1,3]dioxolo[3,4]pyrrolo[1,2-b]isoxazol-7-yl}adenine
  参考文献：
  名称：

  手性环硝基在双环异恶唑烷核苷类似物非对映选择性合成中的应用

  摘要：

  新的双环异恶唑烷核苷类似物是通过对映体纯的环硝酮与适当的乙烯基核碱基进行1,3-偶极环加成而合成的。反应是非对映选择性的，给出exo-Re环加合物作为主要产物或唯一产物。非对映选择性取决于碱的种类和硝酮的取代模式。

  DOI：

  10.1080/15257770701572055
• 作为产物：
  描述：

  methyl (Z)-3-[(4S,5S)-5-formyl-2,2-dimethyl-1,3-dioxolan-4-yl]-2-propenoate 在 盐酸羟胺 、 碳酸氢钠 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以66%的产率得到(3aS,4S,6aR)-4-(2-methoxy-2-oxoethyl)-2,2-dimethyl-4,6a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyrrol-5-ium-5-olate
  参考文献：
  名称：

  Synthesis of enantiomerically pure hydroxylated pyrroline N-oxides from d-ribose

  摘要：

  A convenient way to obtain enantiomerically pure hydroxylated pyrroline N-oxides is reported. The key step is the formation of omega-oxo criciates from (D)-ribose and a subsequent 1,3-azaprotio cyclotransfer reaction of the resulting oximino alkenoate derivatives. The stereochemistry of the nitrones obtained is discussed in relation to that of the starting compounds. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.02.006

文献信息

• Water as the medium of choice for the 1,3-dipolar cycloaddition reactions of hydrophobic nitrones
  作者：Evdoxia Coutouli-Argyropoulou、Prodromos Sarridis、Petros Gkizis

  DOI：10.1039/b916765j

  日期：——

  1,3-Dipolar cycloadditions of different hydrophobic nitrones 1, 2, 3, 4 with acrylates 5 and 6 were studied in both homogenous organic solutions and aqueous suspensions. Reactions in water suspensions showed great rate accelerations over homogenous solutions. Small changes were also observed to the stereoselectivities of the reactions. Hydrophobic interactions are invoked for the observed behaviour.

  不同疏水性硝基化合物1、2、3、4与丙烯酸酯5和6的1,3-双极环加成反应在均相有机溶液和水悬浮液中进行了研究。水悬浮液中的反应显示出相对于均相溶液的显著速率加速。反应的立体选择性也观察到了一些小变化。观察到的行为被认为与疏水相互作用有关。
• Synthesis of enantiomerically pure hydroxylated pyrroline N-oxides from d-ribose
  作者：Nikolaos G. Argyropoulos、Theodoros D. Panagiotidis、John K. Gallos

  DOI：10.1016/j.tetasy.2006.02.006

  日期：2006.3

  A convenient way to obtain enantiomerically pure hydroxylated pyrroline N-oxides is reported. The key step is the formation of omega-oxo criciates from (D)-ribose and a subsequent 1,3-azaprotio cyclotransfer reaction of the resulting oximino alkenoate derivatives. The stereochemistry of the nitrones obtained is discussed in relation to that of the starting compounds. (c) 2006 Elsevier Ltd. All rights reserved.
• Application of Chiral Cyclic Nitrones to the Diastereoselective Synthesis of Bicyclic Isoxazolidine Nucleoside Analogues
  作者：Evdoxia Coutouli-Argyropoulou、Christos Xatzis、Nikolaos Argyropoulos

  DOI：10.1080/15257770701572055

  日期：2008.1

  New bicyclic isoxazolidine nucleoside analogues are synthesized through 1,3-dipolar cycloaddition of enantiopure cyclic nitrones to appropriate vinyl nucleobases. The reactions are diastereoselective, giving as the main or the sole product the exo-Re cycloadducts. The diastereoselectivity depends on both the kind of the base and the substitution pattern of the nitrone.

  新的双环异恶唑烷核苷类似物是通过对映体纯的环硝酮与适当的乙烯基核碱基进行1,3-偶极环加成而合成的。反应是非对映选择性的，给出exo-Re环加合物作为主要产物或唯一产物。非对映选择性取决于碱的种类和硝酮的取代模式。