2-benzyloxetan-3-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-benzyloxetan-3-one
• 化学式: C₁₀H₁₀O₂
• 分子量: 162.188
• InChiKey: YCQKQLGMXZKXCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-benzyloxetan-3-one 、 D-色氨酸乙酯盐酸盐 在 碘 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以67%的产率得到(2S,3S,3'S)-ethyl-2-benzyl-2',3',4',9'-tetrahydrospiro[oxetane-3,1'-pyrido[3,4-b]indole]-3'-carboxylate
  参考文献：
  名称：

  Asymmetric Synthesis of 2-Substituted Oxetan-3-ones via Metalated SAMP/RAMP Hydrazones

  摘要：

  2-Substituted oxetan-3-ones can be prepared in good yields and enantioselectivities (up to 84% cc) by the metalation of the SAMP/RAMP hydrazones of oxetan-3-one, followed by reaction with a range of electrophiles that include alkyl, ally!, and benzyl halides. Additionally, both chiral 2,2- and 2,4-disubstituted oxetan-3-ones can be made in high ee (86-90%) by repetition of this lithiation/allcylation sequence under appropriately controlled conditions. Hydrolysis of the resultant hydrazones with aqueous oxalic acid provides the 2-substituted oxetan-3-ones without detectable racemization.

  DOI：

  10.1021/jo4020485
• 作为产物：
  描述：

  N,N-dimethyl-N′-oxetan-3-ylidenehydrazine 、 溴甲苯 在 叔丁基锂 、 草酸 作用下， 以 四氢呋喃 、 正戊烷 、 乙醚 、 水 为溶剂， 反应 18.0h， 生成 2-benzyloxetan-3-one
  参考文献：
  名称：

  Asymmetric Synthesis of 2-Substituted Oxetan-3-ones via Metalated SAMP/RAMP Hydrazones

  摘要：

  2-Substituted oxetan-3-ones can be prepared in good yields and enantioselectivities (up to 84% cc) by the metalation of the SAMP/RAMP hydrazones of oxetan-3-one, followed by reaction with a range of electrophiles that include alkyl, ally!, and benzyl halides. Additionally, both chiral 2,2- and 2,4-disubstituted oxetan-3-ones can be made in high ee (86-90%) by repetition of this lithiation/allcylation sequence under appropriately controlled conditions. Hydrolysis of the resultant hydrazones with aqueous oxalic acid provides the 2-substituted oxetan-3-ones without detectable racemization.

  DOI：

  10.1021/jo4020485

文献信息

• Asymmetric Synthesis of 2-Substituted Oxetan-3-ones via Metalated SAMP/RAMP Hydrazones
  作者：Joanna V. Geden、Benjamin O. Beasley、Guy J. Clarkson、Michael Shipman

  DOI：10.1021/jo4020485

  日期：2013.12.6

  2-Substituted oxetan-3-ones can be prepared in good yields and enantioselectivities (up to 84% cc) by the metalation of the SAMP/RAMP hydrazones of oxetan-3-one, followed by reaction with a range of electrophiles that include alkyl, ally!, and benzyl halides. Additionally, both chiral 2,2- and 2,4-disubstituted oxetan-3-ones can be made in high ee (86-90%) by repetition of this lithiation/allcylation sequence under appropriately controlled conditions. Hydrolysis of the resultant hydrazones with aqueous oxalic acid provides the 2-substituted oxetan-3-ones without detectable racemization.