(Z)-N-((3aS,4S,6aS)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-1-phenylmethanimine oxide | 1391381-86-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-N-((3aS,4S,6aS)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-1-phenylmethanimine oxide
• CAS: 1391381-86-4
• 化学式: C₁₄H₁₇NO₄
• 分子量: 263.293
• InChiKey: QRKRYKTZTAUPCO-AVGNSLFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.49
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  53.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2,2,4,4-tetramethyl-3-thioxocyclobutanone 、 (Z)-N-((3aS,4S,6aS)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-1-phenylmethanimine oxide 以 四氢呋喃 为溶剂， 反应 0.17h， 以76%的产率得到(3a′S,4′S,6a′S,7S)-6-(2′,2′-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4′-yl)-1,1,3,3-tetramethyl-7-phenyl-5-oxa-8-thia-6-azaspiro[3.4]octan-2-one
  参考文献：
  名称：

  Stereoselective 1,3-dipolar cycloadditions of thioketones to carbohydrate-derived nitrones

  摘要：

  A series of cycloaliphatic thioketones was reacted with selected enantiopure nitrones bearing carbohydrate-derived moieties leading to 1,4,2-oxathiazolidine derivatives in a highly stereoselective manner. Analysis of spectroscopic data supplemented by X-ray diffraction analysis of the major products confirmed the anti-configuration in the series derived from D-glyceraldehyde and L-erythrose-functionalized nitrones bearing a sugar moiety at the C atom. In the case of the model benzaldehyde-derived nitrone decorated at the N atom with carbohydrate auxiliary, and also for a L-erythrose-derived cyclic nitrone, in the reaction with sterically crowded 2,2,4,4-tetramethyl-3-thioxocyclobutanone the exclusive formation of single diastereoisomeric products was observed indicating an excellent steric match of the substrates. Dissociation constants of selected (3+2)-cycloadducts were determined by H-1 NMR spectroscopy. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.08.007
• 作为产物：
  描述：

  在 manganese(IV) oxide 作用下， 生成 (Z)-N-((3aS,4S,6aS)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-1-phenylmethanimine oxide
  参考文献：
  名称：

  Carbohydrate-auxiliary assisted preparation of enantiopure 1,2-oxazine derivatives and aminopolyols

  摘要：

  本文介绍了一种制备对映纯的羟基化2H-1,2-噁嗪衍生物的方法，利用锂代烷氧基烯烃和L-赤藓糖衍生的N-糖基亚硝基作为前体，进行[3+3]环化反应。这一关键步骤只有中等的对映选择性，但可以进入所得3,6-双氢-2H-1,2-噁嗪的对映体系。然后，它们的烯醚双键经过氢硼化反应，然后进行氧化处理，最后去除辅助基。所述的三步法使合成了对映纯的羟基化1,2-噁嗪成为可能。典型的例子经过萨姆arium二碘化物处理，导致对映纯的无环氨基多醇。我们还报告了将这些化合物转化为对映纯的羟基化吡咯烷衍生物的尝试。

  DOI：

  10.3762/bjoc.8.74