N-[(1S,2S)-2-(2,2-Dimethyl-propionylamino)-3-hydroxy-1-hydroxymethyl-propyl]-2,2-dimethyl-propionamide | 263752-05-2

• 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: N-[(1S,2S)-2-(2,2-Dimethyl-propionylamino)-3-hydroxy-1-hydroxymethyl-propyl]-2,2-dimethyl-propionamide
• CAS: 263752-05-2
• 化学式: C₁₄H₂₈N₂O₄
• 分子量: 288.387
• InChiKey: KMGUPCUOIRAMCC-NXEZZACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.03
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  98.66
• 氢给体数：
  4.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-[(1S,2S)-2-(2,2-Dimethyl-propionylamino)-3-hydroxy-1-hydroxymethyl-propyl]-2,2-dimethyl-propionamide 在 甲基磺酰氯 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以87%的产率得到(4S,4'S)-2,2'-Di-tert-butyl-4,5,4',5'-tetrahydro-[4,4']bioxazolyl
  参考文献：
  名称：

  Asymmetric cyclopropanation catalyzed by C2-symmetric bi(oxazolines)

  摘要：

  C-2-symmetric bi(oxazolines) 3a-e were prepared in three steps based on a tartaric-derived vicinal diamine as common precursor. These chiral ligands were studied with respect to their directive influence on the enantioselective copper catalyzed cyclopropanation of 1,1 -diphenylethylene and styrene. The highest enantioselectivities (79% ee) were achieved with bi(oxazoline) 3e, bearing bulky adamantyl groups even using commercial CuOTf. The presence of desiccants such as molecular sieves or magnesium sulfate was found to be crucial for high yields and reproducibility. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02220-0
• 作为产物：
  描述：

  N-[(1S,2S)-3-Benzyloxy-1-benzyloxymethyl-2-(2,2-dimethyl-propionylamino)-propyl]-2,2-dimethyl-propionamide 在 三氯化硼-甲硫醚 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以83%的产率得到N-[(1S,2S)-2-(2,2-Dimethyl-propionylamino)-3-hydroxy-1-hydroxymethyl-propyl]-2,2-dimethyl-propionamide
  参考文献：
  名称：

  Asymmetric cyclopropanation catalyzed by C2-symmetric bi(oxazolines)

  摘要：

  C-2-symmetric bi(oxazolines) 3a-e were prepared in three steps based on a tartaric-derived vicinal diamine as common precursor. These chiral ligands were studied with respect to their directive influence on the enantioselective copper catalyzed cyclopropanation of 1,1 -diphenylethylene and styrene. The highest enantioselectivities (79% ee) were achieved with bi(oxazoline) 3e, bearing bulky adamantyl groups even using commercial CuOTf. The presence of desiccants such as molecular sieves or magnesium sulfate was found to be crucial for high yields and reproducibility. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02220-0