(2R,4R)-2-benzyltetrahydro-2H-pyran-4-ol

• 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: (2R,4R)-2-benzyltetrahydro-2H-pyran-4-ol
• 英文别名: (2R,4R)-2-benzyloxan-4-ol
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: BMKHAXBXHPGZPN-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (S)-2-[2-(p-tolylsulfinyl)phenyl]acetaldehyde 在 4 A molecular sieve 、 镍 、 ytterbium(III) triflate 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 5.08h， 生成 (2R,4R)-2-benzyltetrahydro-2H-pyran-4-ol
  参考文献：
  名称：

  Efficient trans-Selectivity in the Cyclocondensation of (S)-2-[2-(p-Tolylsulfinyl)phenyl]acetaldehyde with Activated Dienes Catalyzed by Yb(OTf)₃

  摘要：

  Reactions of (S)-2-[2-(p-tolylsulfinyl)phenyl]acetaldehyde 1 with Danishefsky's and related dienes took place in the presence of Yb(OTf)(3) in a completely stereoselective manner, mediated by a remote sulfinyl group (1,5-asymmetric induction), to afford the corresponding 2,3-dihydro-4H-pyran-4-ones. These reactions followed a stepwise mechanism, as was corroborated by isolation of the corresponding intermediates, with a high level of trans-selectivity for 4-methyl-substituted dienes. Treatment of the adducts with Raney Ni provided concomitant cleavage of the C-S bond and reduction of the conjugated carbonyl grouping.

  DOI：

  10.1021/jo061128n

文献信息

• Efficient <i>trans</i>-Selectivity in the Cyclocondensation of (<i>S</i>)-2-[2-(<i>p</i>-Tolylsulfinyl)phenyl]acetaldehyde with Activated Dienes Catalyzed by Yb(OTf)₃
  作者：José L. García Ruano、M. Ángeles Fernández-Ibáñez、M. Carmen Maestro

  DOI：10.1021/jo061128n

  日期：2006.9.1

  Reactions of (S)-2-[2-(p-tolylsulfinyl)phenyl]acetaldehyde 1 with Danishefsky's and related dienes took place in the presence of Yb(OTf)(3) in a completely stereoselective manner, mediated by a remote sulfinyl group (1,5-asymmetric induction), to afford the corresponding 2,3-dihydro-4H-pyran-4-ones. These reactions followed a stepwise mechanism, as was corroborated by isolation of the corresponding intermediates, with a high level of trans-selectivity for 4-methyl-substituted dienes. Treatment of the adducts with Raney Ni provided concomitant cleavage of the C-S bond and reduction of the conjugated carbonyl grouping.