(-)-(4S,5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-1-tosyl-4-[4-(trimethylsilyl)but-3-ynyl]pyrrolidin-2-one | 229160-60-5

• 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: (-)-(4S,5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-1-tosyl-4-[4-(trimethylsilyl)but-3-ynyl]pyrrolidin-2-one
• CAS: 229160-60-5
• 化学式: C₃₅H₄₅NO₄SSi₂
• 分子量: 631.984
• InChiKey: ZCZLDCKQOFOUCP-RYCFQHDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.14
• 重原子数：
  43.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  63.68
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (-)-(4S,5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-1-tosyl-4-[4-(trimethylsilyl)but-3-ynyl]pyrrolidin-2-one 在 quinolinium camphor-10-sulfonate 、 二异丁基氢化铝 、 potassium carbonate 作用下， 以 甲醇 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 16.17h， 生成 (-)-(2S,3S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-but-3-ynyl-1-tosyl-2,3-dihydro-1H-pyrrole
  参考文献：
  名称：

  Approaches to a synthesis of α-kainic acid

  摘要：

  alpha-Kainic acid A, first isolated in 1953 from the marine alga Digenea simplex,(1) is the parent member of the kainoids displaying potent anthelmintic properties and neurotransmitting activity(2,3) in the central nervous system. Among these properties, the neuroexcitatory activity is attributed to their trans C-2/C-3 : cis C-3/C-4 structure and the functionality at the C-4 center beside the 2-carboxy and 3-carboxymethyl functionalities.

  DOI：

  10.1016/s0040-4020(99)00284-7
• 作为产物：
  描述：

  叔丁基二苯基氯硅烷 在 咪唑 、 双氧水 、 magnesium 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 正己烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.42h， 生成 (-)-(4S,5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-1-tosyl-4-[4-(trimethylsilyl)but-3-ynyl]pyrrolidin-2-one
  参考文献：
  名称：

  Approaches to a synthesis of α-kainic acid

  摘要：

  alpha-Kainic acid A, first isolated in 1953 from the marine alga Digenea simplex,(1) is the parent member of the kainoids displaying potent anthelmintic properties and neurotransmitting activity(2,3) in the central nervous system. Among these properties, the neuroexcitatory activity is attributed to their trans C-2/C-3 : cis C-3/C-4 structure and the functionality at the C-4 center beside the 2-carboxy and 3-carboxymethyl functionalities.

  DOI：

  10.1016/s0040-4020(99)00284-7

文献信息

• Approaches to a synthesis of α-kainic acid
  作者：Janine Cossy、Manuel Cases、Domingo Gomez Pardo

  DOI：10.1016/s0040-4020(99)00284-7

  日期：1999.5

  alpha-Kainic acid A, first isolated in 1953 from the marine alga Digenea simplex,(1) is the parent member of the kainoids displaying potent anthelmintic properties and neurotransmitting activity(2,3) in the central nervous system. Among these properties, the neuroexcitatory activity is attributed to their trans C-2/C-3 : cis C-3/C-4 structure and the functionality at the C-4 center beside the 2-carboxy and 3-carboxymethyl functionalities.