[(S)R]-4-(tert-butoxycarbonyl)amino-4-[p-(tolylsulfinyl)methyl]cyclohexa-2,5-dienone | 418808-76-1

• 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: [(S)R]-4-(tert-butoxycarbonyl)amino-4-[p-(tolylsulfinyl)methyl]cyclohexa-2,5-dienone
• CAS: 418808-76-1
• 化学式: C₁₉H₂₃NO₄S
• 分子量: 361.462
• InChiKey: DNBAYPSKJKKXNB-RUZDIDTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.06
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  72.47
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  [(S)R]-4-(tert-butoxycarbonyl)amino-4-[p-(tolylsulfinyl)methyl]cyclohexa-2,5-dienone 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以97%的产率得到[(S)R]-4-amino-4-[(p-tolylsulfinyl)methyl]-2,5-cyclohexadienone
  参考文献：
  名称：

  Stereoselective Synthesis of Heterocyclic Cage Compounds by Domino Conjugate Additions

  摘要：

  Heterocyclic cage compounds have been stereoselectively synthesized from enantiopure [(S)R]-[(p-tolylsulfinyl)methyl]-p-quinols or their amine analogues and 2-(trimethylsilyloxy)furan in the presence of Bu4NF. The method is particularly valuable not only because of the stereochemical control but also because the reactions occur in an experimentally simple one-pot procedure through a domino sequence of three consecutive conjugate additions. The intermediate 1.4-adducts could be isolated when the reaction was carried out in the presence of BF3 (.) OEt2.

  DOI：

  10.1002/1521-3765(20020104)8:1<208::aid-chem208>3.0.co;2-0
• 作为产物：
  描述：

  tert-butyl (4,4-dimethoxycyclohexa-2,5-dien-1-ylidene)carbamate 在 草酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 7.5h， 生成 [(S)R]-4-(tert-butoxycarbonyl)amino-4-[p-(tolylsulfinyl)methyl]cyclohexa-2,5-dienone
  参考文献：
  名称：

  Stereoselective Synthesis of Heterocyclic Cage Compounds by Domino Conjugate Additions

  摘要：

  Heterocyclic cage compounds have been stereoselectively synthesized from enantiopure [(S)R]-[(p-tolylsulfinyl)methyl]-p-quinols or their amine analogues and 2-(trimethylsilyloxy)furan in the presence of Bu4NF. The method is particularly valuable not only because of the stereochemical control but also because the reactions occur in an experimentally simple one-pot procedure through a domino sequence of three consecutive conjugate additions. The intermediate 1.4-adducts could be isolated when the reaction was carried out in the presence of BF3 (.) OEt2.

  DOI：

  10.1002/1521-3765(20020104)8:1<208::aid-chem208>3.0.co;2-0