1-(4-benzyl-5-(piperidin-1-yl)oxazol-2-yl)-2-methylpropan-1-ol | 1192583-16-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(4-benzyl-5-(piperidin-1-yl)oxazol-2-yl)-2-methylpropan-1-ol
• 英文别名: (S)-1-(4-benzyl-5-(piperidin-1-yl)oxazol-2-yl)-2-methylpropan-1-ol；(1S)-1-(4-benzyl-5-piperidin-1-yl-1,3-oxazol-2-yl)-2-methylpropan-1-ol
• CAS: 1192583-16-6
• 化学式: C₁₉H₂₆N₂O₂
• 分子量: 314.428
• InChiKey: HJXRYWKFRAWFAU-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  49.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  异丁醛 、 2-isocyano-3-phenyl-1-(piperidin-1-yl)propan-1-one 在 (R)-3,3'-bis-(triphenylsilyl)octahydrobinolphosphoric acid 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以98%的产率得到1-(4-benzyl-5-(piperidin-1-yl)oxazol-2-yl)-2-methylpropan-1-ol
  参考文献：
  名称：

  Chiral Brønsted Acid Catalyzed Enantioselective Addition of α-Isocyanoacetamides to Aldehydes

  摘要：

  A clean and highly efficient enantioselective addition-of alpha-isocyanoacetamides to aliphatic aldehydes catalyzed by chiral phosphoric acid in the presence of MS 5 angstrom in toluene at -40 degrees C was developed. Excellent yields (85-98%) and good to excellent enantioselectivities (up to >99% ee) were achieved.

  DOI：

  10.1021/ol1007789

文献信息

• Catalytic Asymmetric Passerini-Type Reaction: Chiral Aluminum−Organophosphate-Catalyzed Enantioselective α-Addition of Isocyanides to Aldehydes
  作者：Tao Yue、Mei-Xiang Wang、De-Xian Wang、Géraldine Masson、Jieping Zhu

  DOI：10.1021/jo9017765

  日期：2009.11.6

  equiv of chiral binol-derived organophosphoric acid and 1 equiv of Et2AlCl. In the presence of a catalytic amount of [4j]2Al(III)Cl complex (0.05 equiv), reaction between α-isocyanoacetamides (2) and aldehydes (3) afforded the corresponding 5-aminooxazoles (1) in good yields and enantioselectivities. Complex [4j]2Al(III)Cl isolated as a white solid displayed similar reactivity as that prepared in situ.

  通过混合2当量的手性二元醇衍生的有机磷酸和1当量的Et 2 AlCl来制备手性路易斯酸催化剂。在催化量的[ 4j ] 2 Al（III）Cl配合物（0.05当量）存在下，α-异氰基乙酰胺（2）与醛（3）之间的反应以良好的收率和对映选择性提供了相应的5-氨基恶唑（1）。 。分离为白色固体的复合物[ 4j ] 2 Al（III）Cl显示出与原位制备的相似的反应活性。
• Chiral Brønsted Acid Catalyzed Enantioselective Addition of α-Isocyanoacetamides to Aldehydes
  作者：Xiaofei Zeng、Kehan Ye、Min Lu、Pei Juan Chua、Bin Tan、Guofu Zhong

  DOI：10.1021/ol1007789

  日期：2010.5.21

  A clean and highly efficient enantioselective addition-of alpha-isocyanoacetamides to aliphatic aldehydes catalyzed by chiral phosphoric acid in the presence of MS 5 angstrom in toluene at -40 degrees C was developed. Excellent yields (85-98%) and good to excellent enantioselectivities (up to >99% ee) were achieved.