ethyl (1S,2S,3R,5S)-2-(ethoxycarbonylamino)pinane-3-carboxylate | 327611-66-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl (1S,2S,3R,5S)-2-(ethoxycarbonylamino)pinane-3-carboxylate
• CAS: 327611-66-5
• 化学式: C₁₆H₂₇NO₄
• 分子量: 297.395
• InChiKey: RYXXKCPVUUMENQ-KZTGVZKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.74
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl (1S,2S,3R,5S)-2-(ethoxycarbonylamino)pinane-3-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以79%的产率得到(1S,2S,3R,5S)-(2-methylamino-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl)methanol
  参考文献：
  名称：

  Synthesis and transformations of enantiomeric 1,2-disubstituted monoterpene derivatives

  摘要：

  Regio- and stereospecific addition of chlorosulfonyl isocyanate to (+)- and (-)-alpha -pinene I resulted in enantiomerically pure beta -lactams 2, which were converted to enantiomeric beta -amino esters 3 and 1,3-amino alcohols 4 and 6 with ee >99%. The resulting 1,3-difunctional compounds 3, 4 and 6 were transformed to fused saturated 1,3-heterocycles such as tetrahydro-1,3-oxazines 7 and 9, 2,4-pyrimidinedione 11 and 2-thioxopyrimidin-4-one 13 enantiomers. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00435-3
• 作为产物：
  描述：

  (1S,2S,5R,7S)-2,8,8-trimethyl-3-azatricyclo[5.1.1.0^2,5]nonan-4-one 在 盐酸 、 碳酸氢钠 作用下， 反应 12.0h， 生成 ethyl (1S,2S,3R,5S)-2-(ethoxycarbonylamino)pinane-3-carboxylate
  参考文献：
  名称：

  Synthesis and transformations of enantiomeric 1,2-disubstituted monoterpene derivatives

  摘要：

  Regio- and stereospecific addition of chlorosulfonyl isocyanate to (+)- and (-)-alpha -pinene I resulted in enantiomerically pure beta -lactams 2, which were converted to enantiomeric beta -amino esters 3 and 1,3-amino alcohols 4 and 6 with ee >99%. The resulting 1,3-difunctional compounds 3, 4 and 6 were transformed to fused saturated 1,3-heterocycles such as tetrahydro-1,3-oxazines 7 and 9, 2,4-pyrimidinedione 11 and 2-thioxopyrimidin-4-one 13 enantiomers. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00435-3