(2R,3R,(S)S)-3,5-dimethyl-2-[2-(p-tolylsulfinyl)benzyl]-2,3-dihydro-4H-pyran-4-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: (2R,3R,(S)S)-3,5-dimethyl-2-[2-(p-tolylsulfinyl)benzyl]-2,3-dihydro-4H-pyran-4-one
• 英文别名: (2R,3R)-3,5-dimethyl-2-[[2-[(S)-(4-methylphenyl)sulfinyl]phenyl]methyl]-2,3-dihydropyran-4-one
• 化学式: C₂₁H₂₂O₃S
• 分子量: 354.47
• InChiKey: GLHNINLTTXPWDQ-JIZVJVNCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  62.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3R,(S)S)-3,5-dimethyl-2-[2-(p-tolylsulfinyl)benzyl]-2,3-dihydro-4H-pyran-4-one 在 镍 作用下， 以 乙醇 为溶剂， 反应 14.0h， 以77%的产率得到(2R,3R)-2-benzyl-3,5-dimethyl-2,3-dihydro-4H-pyran-4-one
  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
• 作为产物：
  描述：

  (1E,3Z)-1-甲氧基-2-甲基-3-(三甲基硅氧基)-1,3-戊二烯 、 (S)-2-[2-(p-tolylsulfinyl)phenyl]acetaldehyde 在 4 A molecular sieve 、 ytterbium(III) triflate 、 三氟乙酸 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以51%的产率得到(2R,3R,(S)S)-3,5-dimethyl-2-[2-(p-tolylsulfinyl)benzyl]-2,3-dihydro-4H-pyran-4-one
  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.