4-hydroxy-2,6-dimethyl-4-[[(R)-(4-methylphenyl)sulfinyl]methyl]cyclohexa-2,5-dien-1-one | 202120-31-8

• 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: 4-hydroxy-2,6-dimethyl-4-[[(R)-(4-methylphenyl)sulfinyl]methyl]cyclohexa-2,5-dien-1-one
• CAS: 202120-31-8
• 化学式: C₁₆H₁₈O₃S
• 分子量: 290.383
• InChiKey: KESLTOKWRZSZII-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  反-1,3-戊二烯 、 4-hydroxy-2,6-dimethyl-4-[[(R)-(4-methylphenyl)sulfinyl]methyl]cyclohexa-2,5-dien-1-one 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 (4S,4aR,8S,8aS)-4-hydroxy-2,8,8a-trimethyl-4-[[(R)-(4-methylphenyl)sulfinyl]methyl]-5,8-dihydro-4aH-naphthalen-1-one 、 (4R,4aS,8R,8aR)-4-hydroxy-2,8,8a-trimethyl-4-[[(R)-(4-methylphenyl)sulfinyl]methyl]-5,8-dihydro-4aH-naphthalen-1-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
• 作为产物：
  描述：

  (R)-(+)-甲基对甲苯砜 在 正丁基锂 、 草酸 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 2.0h， 生成 4-hydroxy-2,6-dimethyl-4-[[(R)-(4-methylphenyl)sulfinyl]methyl]cyclohexa-2,5-dien-1-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

• Studies of Diastereoselectivity in Conjugate Addition of Organoaluminum Reagents to (<i>R</i>)-[(<i>p</i>-Tolylsulfinyl)methyl]quinols and Derivatives
  作者：M. Carmen Carreño、Manuel Pérez González、María Ribagorda、K. N. Houk

  DOI：10.1021/jo980084i

  日期：1998.5.1

  (R)-4-Hydroxy-4-[(p-tolylsulfinyl)methyl]-2,5-cyclohexadienones 1-3, and 6 reacted with organoaluminum derivatives from the pro-R conjugated position in a highly pi-facial diastereoselective manner directed by the C-4 OH. A similar facial diastereoselectivity arose from reactions with 3-alkyl-substituted analogues 4 and 5 and 5-alkyl-4-hydroxy-4-[(p-tolylsulfinyl)methyl]-2-cyclohexenones 10a,b. Semiempirical calculations (AM1 model) provide data on transition-state energies for additions in full agreement with the experimental results.