(2'S,5R)-(-)-3-(4-methoxyphenyl)-4-<2-(methoxymethyl)tetrahydro-1H-1-pyrrolyl>-1-oxa-2,4-diazaspiro<4.5>deca-2,6-diene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2'S,5R)-(-)-3-(4-methoxyphenyl)-4-<2-(methoxymethyl)tetrahydro-1H-1-pyrrolyl>-1-oxa-2,4-diazaspiro<4.5>deca-2,6-diene
• 英文别名: (5R)-4-[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]-3-(4-methoxyphenyl)-1-oxa-2,4-diazaspiro[4.5]deca-2,6-diene
• 化学式: C₂₀H₂₇N₃O₃
• 分子量: 357.453
• InChiKey: NYXLQUNQKQXLDM-PXNSSMCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  46.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  对甲氧基苯甲醛肟 、 (+)-(2S)-N-[(1Z)-cyclohex-2-en-1-yliden]-2-(methoxymethyl)pyrrolidin-1-amine 在 N-氯代丁二酰亚胺 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 (2'S,5R)-(-)-3-(4-methoxyphenyl)-4-<2-(methoxymethyl)tetrahydro-1H-1-pyrrolyl>-1-oxa-2,4-diazaspiro<4.5>deca-2,6-diene 、 (2'S,5S)-(-)-3-(4-methoxyphenyl)-4-<2-(methoxymethyl)tetrahydro-1H-1-pyrrolyl>-1-oxa-2,4-diazaspiro<4.5>deca-2,6-diene
  参考文献：
  名称：

  Diastereo- and Enantioselective Synthesis of ∆2-1,2,4-Oxadiazolines by 1,3-Dipolar Cycloaddition of Nitrile Oxides with Chiral Hydrazones

  摘要：

  Diastereo- and enantioselective 1,3-dipolar cycloadditions of nitrile oxides (3) with alpha,beta-unsaturated hydrazones (2) gave spiro oxadiazolines (4) in good yields and low to excellent diastereomeric excesses (de = 5 - greater than or equal to 98%). Open chain hydrazones (6) afforded 5,5-disubstituted Delta(2)-1,2,4-oxadiazolines (7). A subsequent N-N bond cleavage to remove the chiral auxiliary was achieved with formic acid and gave the oxadiazolines (8) (ee = 0 - 91%).

  DOI：

  10.3987/com-98-s(h)100

文献信息

• Diastereo- and Enantioselective Synthesis of ∆2-1,2,4-Oxadiazolines by 1,3-Dipolar Cycloaddition of Nitrile Oxides with Chiral Hydrazones
  作者：Dieter Enders、Ilka Meyer、Jan Runsink、Gerhard Raabe

  DOI：10.3987/com-98-s(h)100

  日期：——

  Diastereo- and enantioselective 1,3-dipolar cycloadditions of nitrile oxides (3) with alpha,beta-unsaturated hydrazones (2) gave spiro oxadiazolines (4) in good yields and low to excellent diastereomeric excesses (de = 5 - greater than or equal to 98%). Open chain hydrazones (6) afforded 5,5-disubstituted Delta(2)-1,2,4-oxadiazolines (7). A subsequent N-N bond cleavage to remove the chiral auxiliary was achieved with formic acid and gave the oxadiazolines (8) (ee = 0 - 91%).