[4R,(S)R]-4-amino-3-methyl-4-[p-(tolylsulfinyl)methyl]cyclohexa-2,5-dienone | 418808-81-8

• 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: [4R,(S)R]-4-amino-3-methyl-4-[p-(tolylsulfinyl)methyl]cyclohexa-2,5-dienone
• 英文别名: [4R,(S)R]-3-methyl-4-[(p-tolylsulfinyl)methyl]-p-quinamine；(4R)-4-amino-3-methyl-4-[[(R)-(4-methylphenyl)sulfinyl]methyl]cyclohexa-2,5-dien-1-one
• CAS: 418808-81-8
• 化学式: C₁₅H₁₇NO₂S
• 分子量: 275.371
• InChiKey: ZHOLYBVITFCZMR-HNAYVOBHSA-N

物化性质

• 沸点：
  483.0±45.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  79.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  三甲硅氧基-2-呋喃 、 [4R,(S)R]-4-amino-3-methyl-4-[p-(tolylsulfinyl)methyl]cyclohexa-2,5-dienone 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.0h， 以56%的产率得到[1R,2R,5S,6R,8R,9R,(S)R]-9-methyl-8-[(p-tolylsulfinyl)methyl]-3-oxa-7-azatetracyclo[6.4.0.0^2,6.0^5,9]dodecane-4,11-dione
  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：

  (R)-(+)-甲基对甲苯砜 在 草酸 、 三氟乙酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.5h， 生成 [4R,(S)R]-4-amino-3-methyl-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

文献信息

• Titanium-Promoted Stereoselective Synthesis of Hydroindolones from p-Quinamines by Domino Conjugate Additions
  作者：M. Carmen Carreño、María Ribagorda、Gary H. Posner

  DOI：10.1002/1521-3773(20020802)41:15<2753::aid-anie2753>3.0.co;2-m

  日期：2002.8.2
• Stereoselective Synthesis of Heterocyclic Cage Compounds by Domino Conjugate Additions
  作者：M. Carmen Carreño,、Carmen García Luzón、María Ribagorda

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

  日期：2002.1.4

  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.