(5S)-5-acetyl-1-(9'-phenylfluoren-9'-yl)pyrrolidin-2-one | 191406-19-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (5S)-5-acetyl-1-(9'-phenylfluoren-9'-yl)pyrrolidin-2-one
• 英文别名: (5S)-5-acetyl-1-(9-phenylfluoren-9-yl)pyrrolidin-2-one
• CAS: 191406-19-6
• 化学式: C₂₅H₂₁NO₂
• 分子量: 367.447
• InChiKey: CZRAQRIDMDZTFQ-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5S)-5-acetyl-1-(9'-phenylfluoren-9'-yl)pyrrolidin-2-one 在 L-Selectride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以100%的产率得到(S)-5-((S)-1-hydroxyethyl)-1-(9-phenyl-9H-fluoren-9-yl)pyrrolidin-2-one
  参考文献：
  名称：

  Enantiomerically Pure Highly Functionalized α-Amino Ketones from the Reaction of Chiral Cyclic N-(9-Phenylfluoren-9-yl) α-Amido Esters with Organolithium Reagents

  摘要：

  The reaction of methyl N-(9-phenylfluoren-9-yl)pyroglutamate with several organolithium reagents afforded the corresponding ketones in excellent yields and with complete retention of enantiomeric purity. The success of this transformation is due to the unusual stability of the tetrahedral intermediates 5, which stems from two factors: the electron-withdrawing effect of the amide nitrogen and the Lithium complexing ability of the fluorenyl ring of the 9-phenylfluoren-9-yl group, This ester-to-ketone transformation was also successfully applied to oxazolidinone 9 and imidazolidinone 20 and provided a ketone (21b) that was ultimately transformed inter the urea-lactam 26 which incorporates the bicyclic core of streptolidine lactam, a component of the streptrothricin antibiotics.

  DOI：

  10.1021/jo970277q
• 作为产物：
  描述：

  (S)-2-(9-Phenyl-9H-fluoren-9-ylamino)-pentanedioic acid 1-methyl ester 在 吡啶 、 对甲苯磺酰氯 作用下， 以 四氢呋喃 为溶剂， 反应 11.0h， 生成 (5S)-5-acetyl-1-(9'-phenylfluoren-9'-yl)pyrrolidin-2-one
  参考文献：
  名称：

  Enantiomerically Pure Highly Functionalized α-Amino Ketones from the Reaction of Chiral Cyclic N-(9-Phenylfluoren-9-yl) α-Amido Esters with Organolithium Reagents

  摘要：

  The reaction of methyl N-(9-phenylfluoren-9-yl)pyroglutamate with several organolithium reagents afforded the corresponding ketones in excellent yields and with complete retention of enantiomeric purity. The success of this transformation is due to the unusual stability of the tetrahedral intermediates 5, which stems from two factors: the electron-withdrawing effect of the amide nitrogen and the Lithium complexing ability of the fluorenyl ring of the 9-phenylfluoren-9-yl group, This ester-to-ketone transformation was also successfully applied to oxazolidinone 9 and imidazolidinone 20 and provided a ketone (21b) that was ultimately transformed inter the urea-lactam 26 which incorporates the bicyclic core of streptolidine lactam, a component of the streptrothricin antibiotics.

  DOI：

  10.1021/jo970277q

文献信息

• Enantiomerically Pure Highly Functionalized α-Amino Ketones from the Reaction of Chiral Cyclic <i>N</i>-(9-Phenylfluoren-9-yl) α-Amido Esters with Organolithium Reagents
  作者：Eduardo Fernández-Megía、José M. Iglesias-Pintos、F. Javier Sardina

  DOI：10.1021/jo970277q

  日期：1997.7.1

  The reaction of methyl N-(9-phenylfluoren-9-yl)pyroglutamate with several organolithium reagents afforded the corresponding ketones in excellent yields and with complete retention of enantiomeric purity. The success of this transformation is due to the unusual stability of the tetrahedral intermediates 5, which stems from two factors: the electron-withdrawing effect of the amide nitrogen and the Lithium complexing ability of the fluorenyl ring of the 9-phenylfluoren-9-yl group, This ester-to-ketone transformation was also successfully applied to oxazolidinone 9 and imidazolidinone 20 and provided a ketone (21b) that was ultimately transformed inter the urea-lactam 26 which incorporates the bicyclic core of streptolidine lactam, a component of the streptrothricin antibiotics.