(S)-5-oxo-1-(3-{2-[3-(toluene-4-sulfonyl)prop-1-ynyl]phenyl}prop-2-ynyl)pyrrolidine-2-carboxylic acid methyl ester | 1253044-01-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-5-oxo-1-(3-{2-[3-(toluene-4-sulfonyl)prop-1-ynyl]phenyl}prop-2-ynyl)pyrrolidine-2-carboxylic acid methyl ester
• 英文别名: methyl (2S)-1-[3-[2-[3-(4-methylphenyl)sulfonylprop-1-ynyl]phenyl]prop-2-ynyl]-5-oxopyrrolidine-2-carboxylate
• CAS: 1253044-01-7
• 化学式: C₂₅H₂₃NO₅S
• 分子量: 449.527
• InChiKey: HPHNGXIZSOSCNI-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  89.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-5-oxo-1-(3-{2-[3-(toluene-4-sulfonyl)prop-1-ynyl]phenyl}prop-2-ynyl)pyrrolidine-2-carboxylic acid methyl ester 在 aluminum oxide 作用下， 以 苯 为溶剂， 反应 3.0h， 以30%的产率得到3-oxo-11-(toluene-4-sulfonyl)-2,3,4,4a,10a,11-hexahydro-1H-3a-aza-cyclopent[b]anthracene-11a-carboxylic acid methyl ester
  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：

  (S)-5-oxo-1-{3-[2-(3-p-tolylsulfanylprop-1-ynyl)phenyl]prop-2-ynyl}pyrrolidine-2-carboxylic acid methyl ester 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 以80%的产率得到(S)-5-oxo-1-(3-{2-[3-(toluene-4-sulfonyl)prop-1-ynyl]phenyl}prop-2-ynyl)pyrrolidine-2-carboxylic acid methyl ester
  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

• 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.