S-1-trimethylsilyl-5-trimethylsilyloxymethyl-2-pyrrolidinone | 141694-95-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: S-1-trimethylsilyl-5-trimethylsilyloxymethyl-2-pyrrolidinone
• 英文别名: (5S)-1-trimethylsilyl-5-(trimethylsilyloxymethyl)pyrrolidin-2-one
• CAS: 141694-95-3
• 化学式: C₁₁H₂₅NO₂Si₂
• 分子量: 259.496
• InChiKey: QZOGWQIJKYIFPM-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.66
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  光气 、 S-1-trimethylsilyl-5-trimethylsilyloxymethyl-2-pyrrolidinone 在 三乙胺 作用下， 生成 (+)-S-2-oxarolziracetam
  参考文献：
  名称：

  Synthesis of 2-Oxa and 2-Aza Analogs of Pyrrolizidine-3,5-diones (Lukes-Sorm Dilactam)

  摘要：

  The synthesis of 2-oxa and 2-aza analogs of pyrrolizidine-3,5-dione (Lukes-Sorm dilactam), which has amnesia reversal activity, is reported. Optically active (+)-2-oxa and (+)-2-aza analogs [(+)-2 and (+)-3] and racemic 2-aza analog and its 1-methoxycarbonyl derivatives [(+)-3 and (+)-13 and -14] were prepared from (-)-S-pyroglutamic acid and succinimide, respectively.

  DOI：

  10.3987/com-91-s56
• 作为产物：
  描述：

  六甲基二硅氮烷 、 L-焦谷氨醇 在 三甲基氯硅烷 作用下， 以97.5%的产率得到S-1-trimethylsilyl-5-trimethylsilyloxymethyl-2-pyrrolidinone
  参考文献：
  名称：

  Synthesis of 2-Oxa and 2-Aza Analogs of Pyrrolizidine-3,5-diones (Lukes-Sorm Dilactam)

  摘要：

  The synthesis of 2-oxa and 2-aza analogs of pyrrolizidine-3,5-dione (Lukes-Sorm dilactam), which has amnesia reversal activity, is reported. Optically active (+)-2-oxa and (+)-2-aza analogs [(+)-2 and (+)-3] and racemic 2-aza analog and its 1-methoxycarbonyl derivatives [(+)-3 and (+)-13 and -14] were prepared from (-)-S-pyroglutamic acid and succinimide, respectively.

  DOI：

  10.3987/com-91-s56

文献信息

• Synthesis of Chiral Pyrrolidine Derivatives from (S)-Pyroglutamic Acid. I: 7-Substituted (2R,5S)-2-Aryl-1-aza-3-oxabicyclo(3.3.0)octan-8-ones, 7-Substituted (2R,5S)-2-Aryl-1-aza-3-oxabicyclo(3.3.0)oct-6-en-8-ones and 3-Substituted (S)-5-(Hydroxymethyl)-2-pyrrolidinones.
  作者：Tatsuo NAGASAKA、Tomoko IMAI

  DOI：10.1248/cpb.43.1081

  日期：——

  The following chiral pyrrolidine derivatives, 7-substituted (2R, 5S)-2-aryl-1-aza-3-oxabicyclo[3.3.0]octan-8-ones(18-24), 7-substituted (2R, 5S)-2-aryl-1-aza-3-oxabicyclo[3.3.0]oct-6-en-8-ones (25-29) and 3-substituted (S)-5-(hydroxymethyl)-2-pyrrolidinones (30-34), were synthesized starting from (S)-pyroglutamic acid and their absolute configurations were determined based on their 1H-NMR spectra.

  下列手性吡咯烷衍生物，7-取代的(2R, 5S)-2-芳基-1-氮杂-3-氧杂双环[3.3.0]辛-8-酮(18-24)，7-取代的(2R, 5S)-2-芳基-1-氮杂-3-氧杂双环[3.3.0]辛-6-烯-8-酮(25-29)和 3-取代的(S)-5-(羟甲基)-2-吡咯烷酮(30-34)。