[(S)R]-4-amino-4-[(p-tolylsulfinyl)methyl]-2,5-cyclohexadienone | 418808-80-7

• 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-amino-4-[(p-tolylsulfinyl)methyl]-2,5-cyclohexadienone
• 英文别名: [(S)R]-4-amino-4-[p-(tolylsulfinyl)methyl]cyclohexa-2,5-dienone；[(S)R]-4-[(p-tolylsulfinyl)methyl]-p-quinamine；4-amino-4-[[(R)-(4-methylphenyl)sulfinyl]methyl]cyclohexa-2,5-dien-1-one
• CAS: 418808-80-7
• 化学式: C₁₄H₁₅NO₂S
• 分子量: 261.345
• InChiKey: LUITXWBSKZCLER-GOSISDBHSA-N

物化性质

• 沸点：
  479.3±45.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  60.16
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  [(S)R]-4-amino-4-[(p-tolylsulfinyl)methyl]-2,5-cyclohexadienone 在 lithium chloride 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以70%的产率得到6-amino-4a,6,7a-tris-(p-tolylsulfinyl)methyl-4a,5,5a,6,6a,7,7a,11,11a,11b,12a,12b-dodecahydro-1H-indolo-[2,3-b]carbazole-2,10,12-trione
  参考文献：
  名称：

  Stereoselective Trimerization of [(S)R]-[(p-Tolylsulfinyl)methyl]-p-quinols and p-Quinamines

  摘要：

  graphicThe asymmetric synthesis of pentacyclic derivatives was achieved in a single step starting from enantiopure [(S)R]-[(p-tolylsulfinyl)methyl]-p-quinols or the nitrogen analogue, through a domino sequence involving four conjugate additions in excellent yields. Eight new stereogenic centers were created in one step and in a highly diastereoselective manner.

  DOI：

  10.1021/ol034589t
• 作为产物：
  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

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