(S)-1-<(3-tert-butoxycarbonylamino)propyl>-5-(thexyldimethylsilyloxymethyl)-pyrrolidin-2-thione | 175659-97-9

• 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-tert-butoxycarbonylamino)propyl>-5-(thexyldimethylsilyloxymethyl)-pyrrolidin-2-thione
• CAS: 175659-97-9
• 化学式: C₂₁H₄₂N₂O₃SSi
• 分子量: 430.728
• InChiKey: WNAJTCVEKZRURH-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.35
• 重原子数：
  28.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  50.8
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-1-<(3-tert-butoxycarbonylamino)propyl>-5-(thexyldimethylsilyloxymethyl)-pyrrolidin-2-thione 在 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 为溶剂， 反应 51.0h， 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 劳森试剂 、 甲醇 、 4-二甲氨基吡啶 、 ammonium hydroxide 、 sodium tetrahydroborate 、 cobalt(II) chloride 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 12.0h， 生成 (S)-1-<(3-tert-butoxycarbonylamino)propyl>-5-(thexyldimethylsilyloxymethyl)-pyrrolidin-2-thione
  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