2-benzyl-8-(1,1-dimethyl-2-hydroxyethyl)-3,7-dioxa-2-azabicyclo[3.3.0]octane

• 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: 2-benzyl-8-(1,1-dimethyl-2-hydroxyethyl)-3,7-dioxa-2-azabicyclo[3.3.0]octane
• 英文别名: 2-[(3aR,6R,6aS)-1-benzyl-3a,4,6,6a-tetrahydro-3H-furo[3,4-c][1,2]oxazol-6-yl]-2-methylpropan-1-ol
• 化学式: C₁₆H₂₃NO₃
• 分子量: 277.364
• InChiKey: DJKMQFQWNJTOKL-ILXRZTDVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  41.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-benzyl-8-(1,1-dimethyl-2-hydroxyethyl)-3,7-dioxa-2-azabicyclo[3.3.0]octane 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以75%的产率得到(2RS,3SR,4SR)-[3-(benzylideneamino)-2-(1-hydroxy-2-methyl-prop-2-yl)-tetrahydrofur-4-yl]-methanol N-oxide
  参考文献：
  名称：

  Effect of the substitution pattern on the oxidation of the isoxazolidine moiety in bi- and tricyclic compounds

  摘要：

  The N-benzylated bicyclic compounds 5 were converted to C-phenyl nitrones 6 by highly regioselective oxidative opening of the isoxazolidine ring with MCPBA. One or both of the isoxazolidine rings of compound 8 were opened in the same way affording a mixture of compounds 9 and 10. Compounds 13a and b were formed by oxidation of N-methylated bicyclic compounds 11a and 4 respectively, with MCPBA, while Ile was decomposed under these conditions. A mixture of 15 and 16 was isolated after oxidation of the tricyclic compound 14, whereas oxidation of the diasteromeric 17 provided the oxime 19 as the single product. The reason for the different course of the oxidation is discussed. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00765-0
• 作为产物：
  描述：

  N-苄基羟胺 、 (3R)-3-allyloxy-4,4-dimethyloxolan-2-ol 在 molecular sieve 作用下， 以 二氯甲烷 为溶剂， 以62%的产率得到2-benzyl-8-(1,1-dimethyl-2-hydroxyethyl)-3,7-dioxa-2-azabicyclo[3.3.0]octane
  参考文献：
  名称：

  Intramolecular 1,3-Dipolar Cycloaddition of Transient Enantiomerically Pure Oxaalkenyl Nitrones

  摘要：

  多种手性纯的α-羟基酯通过以下反应序列转化为手性纯的3,7-二氧杂-2-氮杂双环[3.3.0]辛烷7。首先是羟基的烯丙基化，随后酯官能团被还原。生成的醛与N-烷基羟胺反应得到氧杂烯基硝酮6，该硝酮自发进行1,3-偶极环加成反应生成产物7。通过多种还原方法解开产物7中的异恶唑啉环，得到高度取代的四氢呋喃衍生物11。

  DOI：

  10.1055/s-1995-4060

文献信息

• Intramolecular 1,3-Dipolar Cycloaddition of Transient Enantiomerically Pure Oxaalkenyl Nitrones
  作者：Hans Günter Aurich、Frank Biesemeier

  DOI：10.1055/s-1995-4060

  日期：1995.9

  A variety of enantiomerically pure α-hydroxy esters were converted into enantiomerically pure 3,7-dioxa-2-azabicyclo[3.3.0]octanes 7 by the following reaction sequence. Allylation of the hydroxy group was followed by reduction of the ester group. The resulting aldehyde was treated with an N-alkylhydroxylamine to give an oxaalkenyl nitrone 6 which underwent spontaneously an intramolecular 1,3-dipolar cycloaddition affording 7. Opening of the isoxazolidine ring of 7 by various reductive methods yielded the highly substituted tetrahydrofuran derivatives 11.

  多种手性纯的α-羟基酯通过以下反应序列转化为手性纯的3,7-二氧杂-2-氮杂双环[3.3.0]辛烷7。首先是羟基的烯丙基化，随后酯官能团被还原。生成的醛与N-烷基羟胺反应得到氧杂烯基硝酮6，该硝酮自发进行1,3-偶极环加成反应生成产物7。通过多种还原方法解开产物7中的异恶唑啉环，得到高度取代的四氢呋喃衍生物11。
• Effect of the substitution pattern on the oxidation of the isoxazolidine moiety in bi- and tricyclic compounds
  作者：Subramanian Baskaran、Hans Günter Aurich、Frank Biesemeier、Klaus Harms

  DOI：10.1016/s0040-4020(98)00765-0

  日期：1998.10

  The N-benzylated bicyclic compounds 5 were converted to C-phenyl nitrones 6 by highly regioselective oxidative opening of the isoxazolidine ring with MCPBA. One or both of the isoxazolidine rings of compound 8 were opened in the same way affording a mixture of compounds 9 and 10. Compounds 13a and b were formed by oxidation of N-methylated bicyclic compounds 11a and 4 respectively, with MCPBA, while Ile was decomposed under these conditions. A mixture of 15 and 16 was isolated after oxidation of the tricyclic compound 14, whereas oxidation of the diasteromeric 17 provided the oxime 19 as the single product. The reason for the different course of the oxidation is discussed. (C) 1998 Elsevier Science Ltd. All rights reserved.