(S)-1-(3-Amino-propyl)-5-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-pyrrolidin-2-one | 280752-64-9

• 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-(3-Amino-propyl)-5-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-pyrrolidin-2-one
• CAS: 280752-64-9
• 化学式: C₁₆H₃₄N₂O₂Si
• 分子量: 314.544
• InChiKey: GHMNAUGWBCXUOP-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.98
• 重原子数：
  21.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  55.56
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-1-(3-Amino-propyl)-5-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-pyrrolidin-2-one 在 劳森试剂 、 4-二甲氨基吡啶 、 potassium fluoride 、 Amberlite IRA 400 、 四丁基氟化铵 、 三氟乙酸 、 碘甲烷 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 53.5h， 生成 (S)-9-hydroxymethyl-1,5-diazabicyclo<4.3.0>non-5-ene
  参考文献：
  名称：

  Synthesis and X-ray crystal structure of (S)-9-hydroxymethyl-1,5-diazabicyclo[4.3.0]non-5-ene, an enantiopure DBN-analogue

  摘要：

  Synthetic routes are described to two enantiopure analogues of 1, 5-diazabicyclo[4.3.0]non-5-ene (DBN) containing a hydroxyl function. Such compounds may be interesting as chiral bifunctional basic catalysts in enantioselective synthesis. Starting from (S)-malic acid silyl protected (S)-8-hydroxy-DBN was prepared, but this compound appeared unstable. The title compound prepared from (S)-pyro glutamic acid is a stable crystalline solid. Its crystal structure shows a strong intermolecular hydrogen bond.

  DOI：

  10.1016/0957-4166(96)00035-3
• 作为产物：
  描述：

  (S)-1-(2-cyanoethyl)-5-(thexyldimethylsilyloxymethyl)pyrrolidin-2-one 在 甲醇 、 ammonium hydroxide 、 sodium tetrahydroborate 、 cobalt(II) chloride 作用下， 反应 3.5h， 生成 (S)-1-(3-Amino-propyl)-5-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-pyrrolidin-2-one
  参考文献：
  名称：

  Synthesis and X-ray crystal structure of (S)-9-hydroxymethyl-1,5-diazabicyclo[4.3.0]non-5-ene, an enantiopure DBN-analogue

  摘要：

  Synthetic routes are described to two enantiopure analogues of 1, 5-diazabicyclo[4.3.0]non-5-ene (DBN) containing a hydroxyl function. Such compounds may be interesting as chiral bifunctional basic catalysts in enantioselective synthesis. Starting from (S)-malic acid silyl protected (S)-8-hydroxy-DBN was prepared, but this compound appeared unstable. The title compound prepared from (S)-pyro glutamic acid is a stable crystalline solid. Its crystal structure shows a strong intermolecular hydrogen bond.

  DOI：

  10.1016/0957-4166(96)00035-3