(3S*,3aR*,9aS*,9bS*)-Octahydro-3-(2-benzyloxy)ethyl-1H-furo<3',4':4,5>isoxazolo<2,3-a>pyridin-1-one | 139883-70-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3S*,3aR*,9aS*,9bS*)-Octahydro-3-(2-benzyloxy)ethyl-1H-furo<3',4':4,5>isoxazolo<2,3-a>pyridin-1-one
• 英文别名: (3S*,3aR*,9aS*,9bS*)-Octahydro-3-(2-benzyloxy)ethyl-1H-furo[3',4':4,5]isoxazolo[2,3-a]pyridin-1-one；(1R,2R,5R,6S)-5-(2-phenylmethoxyethyl)-4,7-dioxa-8-azatricyclo[6.4.0.02,6]dodecan-3-one
• CAS: 139883-70-8；139973-90-3；139973-91-4
• 化学式: C₁₈H₂₃NO₄
• 分子量: 317.385
• InChiKey: ARMJDZDNBARSFD-QBPKDAKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  Methyl (2RS,3RS,3aSR)-2-<(1'RS)-3-(benzyloxy)-1-hydroxypropyl>hexahydro-2H-isoxazolo<2,3-a>pyridine-3-carboxylate 在 sodium hydride 作用下， 以 四氢呋喃 、 paraffin 为溶剂， 反应 8.0h， 以5.5%的产率得到(3S*,3aR*,9aS*,9bS*)-Octahydro-3-(2-benzyloxy)ethyl-1H-furo<3',4':4,5>isoxazolo<2,3-a>pyridin-1-one
  参考文献：
  名称：

  Diastereofacial Selectivity in the Cycloaddition of Nitrones to (E)-γ-Oxygenated α,β-Unsaturated Esters

  摘要：

  The 1,3-dipolar cycloadditions of nitrones 1 and 2 to a series of 1,2-disubstituted electron-deficient olefins bearing an allylic stereocenter, 4-8, are reported. The synlanti stereochemistry of the major endo adducts may be rationalized through the Houk transition-state model, but the possibility of intramolecular hydrogen bonding must be taken into account. In the case of the minor exo adducts the syn stereochemistry always predominates.

  DOI：

  10.1021/jo960960x

文献信息

• 1,3-dipolar cycloadditions of 3,4,5,6-tetrahydropyridine 1-oxide to α,β-unsaturated lactones: stereochemical assignment and conformational analysis of the products
  作者：Pau Cid、Pedro de March、Marta Figueredo、Josep Font、Sergio Milán、Ángeles Soria、Albert Virgili

  DOI：10.1016/s0040-4020(01)90237-6

  日期：1993.4

  obtained heterocyclic compounds, an accurate conformational analysis has been performed. Important differences in their conformational behavior in solution have been found as a function of the lactone ring size and the presence or absence of a carbonyl group. This study points out the existence of an attractive interaction between the nitrogen lone electron pair and a carbonyl group at a fitting distance

  我们已经调查硝酮的1,3-偶极环加成1至七，六，五元α，β不饱和内酯类（2，3，和4-6）和2,5-二氢呋喃，18。在所有这些反应中，exo加合物可以作为主要或独家产品获得。为了阐明所获得的杂环化合物的立体化学，已经进行了准确的构象分析。已经发现它们在溶液中的构象行为的重要差异是内酯环大小和羰基存在与否的函数。本研究指出的氮孤电子对和羰基之间的吸引相互作用的存在在嵌合距离，其诱导对于偏好顺式型的融合Ë在furanonic外型加成物（10，12，13，15，和16）。在所有的其它情况下，该距离过长（7，8，9，11，14）或无羰基存在的分子（在20），该反式invertomers占优势。
• Stereochemical studies on the 1,3-dipolar cycloaddition of 3,4,5,6-tetrahydropyridine 1-oxide to 2(5H)-furanones
  作者：Pau Cid、Pedro de March、Marta Figueredo、Josep Font、Sergio Milán

  DOI：10.1016/s0040-4039(00)92338-4

  日期：1992.1

  The 1,3-dipolar cycloaddition of 3,4,5,6-tetrahydropyridine 1-oxide, 1, to 2(5H)-furanones 2, 3, and 4 is investigated. Crucial nmr data are indicated to determine the conformational equilibria and stereochemistry of the adducts. The major products arise from exo transition states.
• Diastereofacial Selectivity in the Cycloaddition of Nitrones to (<i>E</i>)-γ-Oxygenated α,β-Unsaturated Esters
  作者：Félix Busqué、Pedro de March、Marta Figueredo、Josep Font、Montserrat Monsalvatje、Albert Virgili、Ángel Álvarez-Larena、Juan F. Piniella

  DOI：10.1021/jo960960x

  日期：1996.1.1

  The 1,3-dipolar cycloadditions of nitrones 1 and 2 to a series of 1,2-disubstituted electron-deficient olefins bearing an allylic stereocenter, 4-8, are reported. The synlanti stereochemistry of the major endo adducts may be rationalized through the Houk transition-state model, but the possibility of intramolecular hydrogen bonding must be taken into account. In the case of the minor exo adducts the syn stereochemistry always predominates.