O-benzyl-N-tetrahydro-2H-pyran-4-ylhydroxylamine | 1135444-75-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: O-benzyl-N-tetrahydro-2H-pyran-4-ylhydroxylamine
• 英文别名: N-phenylmethoxyoxan-4-amine
• CAS: 1135444-75-5
• 化学式: C₁₂H₁₇NO₂
• 分子量: 207.272
• InChiKey: MYKZLTBCVNCJHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  四氢吡喃酮 、 O-苄基羟胺 在 盐酸 、 2-picoline borane 作用下， 以 甲醇 、 溶剂黄146 、 水 为溶剂， 反应 2.5h， 以93%的产率得到O-benzyl-N-tetrahydro-2H-pyran-4-ylhydroxylamine
  参考文献：
  名称：

  One-Pot Synthesis of Alkoxyamine Derivatives by Reductive Alkoxyamination with a 2-Picoline-Borane Complex

  摘要：

  Reduction of oxime ethers with a 2-picoline-borane complex was examined to give alkoxyamine derivatives. The reduction was found to proceed in the presence of aqueous HCl in MeOH-AcOH. The method was extended to one-pot synthesis of alkoxyamine derivatives from aldehydes and ketones. The reaction of carbonyl compounds with alkoxyamines in MeOH-AcOH (10:1), followed by sequential treatment with 2-picoline-borane and 3M HCl afforded alkoxyamine derivatives in good yields. This procedure can be applied to the synthesis of various alkoxyamine derivatives from aliphatic/aromatic aldehydes and ketones.

  DOI：

  10.3987/com-08-11532

文献信息

• One-Pot Synthesis of Alkoxyamine Derivatives by Reductive Alkoxyamination with a 2-Picoline-Borane Complex
  作者：Tsutomu Yokomatsu、Yasushi Kawase、Takehiro Yamagishi、Teruo Kutsuma、Kimio Ueda、Takeo Iwakuma、Tadashi Nakata

  DOI：10.3987/com-08-11532

  日期：——

  Reduction of oxime ethers with a 2-picoline-borane complex was examined to give alkoxyamine derivatives. The reduction was found to proceed in the presence of aqueous HCl in MeOH-AcOH. The method was extended to one-pot synthesis of alkoxyamine derivatives from aldehydes and ketones. The reaction of carbonyl compounds with alkoxyamines in MeOH-AcOH (10:1), followed by sequential treatment with 2-picoline-borane and 3M HCl afforded alkoxyamine derivatives in good yields. This procedure can be applied to the synthesis of various alkoxyamine derivatives from aliphatic/aromatic aldehydes and ketones.