(S)-4-phenyl-3-(3-{2-[3-(toluene-4-sulfonyl)prop-1-ynyl]phenyl}prop-2-ynyl)oxazolidin-2-one | 1253043-99-0

• 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: (S)-4-phenyl-3-(3-{2-[3-(toluene-4-sulfonyl)prop-1-ynyl]phenyl}prop-2-ynyl)oxazolidin-2-one
• 英文别名: (4S)-3-[3-[2-[3-(4-methylphenyl)sulfonylprop-1-ynyl]phenyl]prop-2-ynyl]-4-phenyl-1,3-oxazolidin-2-one
• CAS: 1253043-99-0
• 化学式: C₂₈H₂₃NO₄S
• 分子量: 469.561
• InChiKey: IDSIZQGABTWLRL-HHHXNRCGSA-N

物化性质

• 沸点：
  747.9±60.0 °C(predicted)
• 密度：
  1.34±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-4-phenyl-3-(3-{2-[3-(toluene-4-sulfonyl)prop-1-ynyl]phenyl}prop-2-ynyl)oxazolidin-2-one 在 potassium carbonate 作用下， 以 苯 为溶剂， 反应 1.5h， 以75%的产率得到(11S,11aS)-11a-phenyl-11-(toluene-4-sulfonyl)-1,4,4a,10a,11,11a-hexahydro-2-oxa-3a-aza-cyclopent[b]anthracen-3-one
  参考文献：
  名称：

  Memory of Chirality in Cascade Rearrangements of Enediynes

  摘要：

  The cascade rearrangement of chiral enediynes 1c-e, involving successively 1,3-proton shift, Saito-Myers cyclization, 1,5-hydrogen atom transfer, and intramolecular coupling of the resulting biradical, proceeded at 80 degrees C to form tri- and tetracyclic heterocycles possessing a quaternary stereogenic center with a very high level of memory of chirality.

  DOI：

  10.1021/ja106668d
• 作为产物：
  描述：

  (R)-4-phenyl-3-{3-[2-(3-p-tolylsulfanylprop-1-ynyl)phenyl]prop-2-ynyl}oxazolidin-2-one 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 以86%的产率得到(S)-4-phenyl-3-(3-{2-[3-(toluene-4-sulfonyl)prop-1-ynyl]phenyl}prop-2-ynyl)oxazolidin-2-one
  参考文献：
  名称：

  Memory of Chirality in Cascade Rearrangements of Enediynes

  摘要：

  The cascade rearrangement of chiral enediynes 1c-e, involving successively 1,3-proton shift, Saito-Myers cyclization, 1,5-hydrogen atom transfer, and intramolecular coupling of the resulting biradical, proceeded at 80 degrees C to form tri- and tetracyclic heterocycles possessing a quaternary stereogenic center with a very high level of memory of chirality.

  DOI：

  10.1021/ja106668d

文献信息

• Cooperative Use of VCD and XRD for the Determination of Tetrahydrobenzoisoquinolines Absolute Configuration: A Reliable Proof of Memory of Chirality and Retention of Configuration in Enediyne Rearrangements
  作者：Shovan Mondal、Jean-Valère Naubron、Damien Campolo、Michel Giorgi、Michéle P. Bertrand、Malek Nechab

  DOI：10.1002/chir.22221

  日期：2013.12

  absolute configurations (AC) of azaheterocylic compounds resulting from the cascade rearrangement of enediynes involving only light atoms were unambiguously assigned by the joint use of vibrational circular dichroism (VCD) and copper radiation single crystal X‐ray diffraction (XRD). These AC determinations proved that the rearrangements of enediynes proceeded with memory of chirality and retention of configuration

  由仅涉及轻原子的烯二炔的级联重排产生的氮杂杂环化合物的绝对构型（AC）通过振动圆二色性（VCD）和铜辐射单晶X射线衍射（XRD）的结合得到明确分配。这些AC测定证明，烯二炔的重排进行时具有手性的记忆和构型的保留。手性25：832–839，2013年。©2013 Wiley Periodicals，Inc.
• Memory of Chirality in Cascade Rearrangements of Enediynes
  作者：Malek Nechab、Damien Campolo、Julien Maury、Patricia Perfetti、Nicolas Vanthuyne、Didier Siri、Michèle P. Bertrand

  DOI：10.1021/ja106668d

  日期：2010.10.27

  The cascade rearrangement of chiral enediynes 1c-e, involving successively 1,3-proton shift, Saito-Myers cyclization, 1,5-hydrogen atom transfer, and intramolecular coupling of the resulting biradical, proceeded at 80 degrees C to form tri- and tetracyclic heterocycles possessing a quaternary stereogenic center with a very high level of memory of chirality.