(1S,4R,4aS,8S,8aR)-8-Hydroxy-8-((R)-toluene-4-sulfinylmethyl)-4,4a,8,8a-tetrahydro-1H-1,4-methano-naphthalen-5-one | 170211-98-0

• 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: (1S,4R,4aS,8S,8aR)-8-Hydroxy-8-((R)-toluene-4-sulfinylmethyl)-4,4a,8,8a-tetrahydro-1H-1,4-methano-naphthalen-5-one
• 英文别名: (1R,2S,6S,7R,8S)-6-hydroxy-6-[[(R)-(4-methylphenyl)sulfinyl]methyl]tricyclo[6.2.1.02,7]undeca-4,9-dien-3-one
• CAS: 170211-98-0
• 化学式: C₁₉H₂₀O₃S
• 分子量: 328.432
• InChiKey: JLLXIZCBWLVXSY-SPRSMGIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  73.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,4R,4aS,8S,8aR)-8-Hydroxy-8-((R)-toluene-4-sulfinylmethyl)-4,4a,8,8a-tetrahydro-1H-1,4-methano-naphthalen-5-one 在 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以80%的产率得到(1R,4S,4aR,5S,8R,8aS)-5-((R)-Toluene-4-sulfinylmethyl)-1,4,4a,5,8,8a-hexahydro-1,4-methano-naphthalene-5,8-diol
  参考文献：
  名称：

  π-Facial Diastereoselection in Diels−Alder Reactions of (R)-4-[(p-Tolylsulfinyl)methyl]quinols

  摘要：

  Diels-Alder reactions of a range of (R)-4-hydroxy-4-[(p-tolylsulfinyl)methyl]-2,5-cyclohexadienones with cyclopentadiene and 1,3-pentadiene proceed in a total pi-facial diastereoselective manner from the C-4 OH side. Ab initio calculations at the RHF/6-31G* theory level provide data on transition-state energies for cycloadditions with cyclopentadiene in full agreement with the experimental results.

  DOI：

  10.1021/jo9712308
• 作为产物：
  描述：

  (R)-(+)-甲基对甲苯砜 在 正丁基锂 、 三氟化硼乙醚 、 草酸 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 3.0h， 生成 (1S,4R,4aS,8S,8aR)-8-Hydroxy-8-((R)-toluene-4-sulfinylmethyl)-4,4a,8,8a-tetrahydro-1H-1,4-methano-naphthalen-5-one
  参考文献：
  名称：

  π-Facial Diastereoselection in Diels−Alder Reactions of (R)-4-[(p-Tolylsulfinyl)methyl]quinols

  摘要：

  Diels-Alder reactions of a range of (R)-4-hydroxy-4-[(p-tolylsulfinyl)methyl]-2,5-cyclohexadienones with cyclopentadiene and 1,3-pentadiene proceed in a total pi-facial diastereoselective manner from the C-4 OH side. Ab initio calculations at the RHF/6-31G* theory level provide data on transition-state energies for cycloadditions with cyclopentadiene in full agreement with the experimental results.

  DOI：

  10.1021/jo9712308

文献信息

• π-Facial Diastereoselection in Diels−Alder Reactions of (<i>R</i>)-4-[(<i>p</i>-Tolylsulfinyl)methyl]quinols
  作者：M. Carmen Carreño、Manuel Pérez González、K. N. Houk

  DOI：10.1021/jo9712308

  日期：1997.12.1

  Diels-Alder reactions of a range of (R)-4-hydroxy-4-[(p-tolylsulfinyl)methyl]-2,5-cyclohexadienones with cyclopentadiene and 1,3-pentadiene proceed in a total pi-facial diastereoselective manner from the C-4 OH side. Ab initio calculations at the RHF/6-31G* theory level provide data on transition-state energies for cycloadditions with cyclopentadiene in full agreement with the experimental results.