(1'R)-1-(1'-phenylethyl)-1,5-dihydro-pyrrol-2-one | 173541-16-7

• 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: (1'R)-1-(1'-phenylethyl)-1,5-dihydro-pyrrol-2-one
• 英文别名: N-((R)-alpha-Methylbenzyl)-3-pyrrolin-2-one；1-[(1R)-1-phenylethyl]-2H-pyrrol-5-one
• CAS: 173541-16-7
• 化学式: C₁₂H₁₃NO
• 分子量: 187.241
• InChiKey: MIXFAEPWCWRDBG-SNVBAGLBSA-N

物化性质

• 沸点：
  361.5±22.0 °C(Predicted)
• 密度：
  1.133±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1'R)-1-(1'-phenylethyl)-1,5-dihydro-pyrrol-2-one 在 palladium on activated charcoal 三氟化硼乙醚 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 53.67h， 生成 (1'R,5R)-5-[1,3]-dithiolan-2-yl-1-(1'-phenylethyl)pyrrolidin-2-one
  参考文献：
  名称：

  A new asymmetric approach toward 5-substituted pyrrolidin-2-one derivatives

  摘要：

  The condensation between a chiral 2-silyloxypyrrole and either achiral or chiral formyl cation equivalents has been studied. The methodology has allowed to build-up 5-substituted pyrrolidin-2-one derivatives with a stereocontrol from good to excellent. The chiral auxiliary located on the silyloxypyrrole showed an intrinsic good level of diastereoface discrimination at C-5. However. the use of a 2-methoxy-3-tosyl-oxazolidine as chiral formylating agent allowed a total stereocontrol in the condensation. A rationale for the observed stereochemical outcome is presented. The stereoselective manipulation of these adducts provided new potentially interesting pyroglutamic aldehyde and prolinal derivatives. whereas treatment with TiCl4 triggered unexpectedly a Pomeranz-Fritsch type intramolecular condensation affording a benzocondensated indolizidinone. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00494-3
• 作为产物：
  描述：

  R(+)-alpha-甲基苄胺 在 双氧水 作用下， 以 吡啶 、 溶剂黄146 为溶剂， 反应 168.0h， 生成 (1'R)-1-(1'-phenylethyl)-1,5-dihydro-pyrrol-2-one
  参考文献：
  名称：

  A new asymmetric approach towards 2-pyrrolidinones and pyrrolidines: Simple versus double stereodifferentiation

  摘要：

  The condensation of a chiral 2-silyloxypyrrole derivative with achiral and chiral formyl cation equivalents has been studied for the first time. The methodology allows to build-up pyroglutammic aldehydes and prolinal systems with a stereocontrol from good to excellent. Whereas the chiral auxiliary residing on the pyrrole system shows an intrinsic good level of diastereoface discrimination at C-5, the combined use of a 2-methoxy-3-tosyl-oxazolidine as a chiral formylating agent allows a total stereocontrol of the condensation. A rationale for the observed stereochemical outcome is presented.

  DOI：

  10.1016/0040-4039(95)01788-j

文献信息

• A new asymmetric approach towards 2-pyrrolidinones and pyrrolidines: Simple versus double stereodifferentiation
  作者：Giovanni Poli、Simone Ciofi、Misa Maccagni、Nicola Sardone

  DOI：10.1016/0040-4039(95)01788-j

  日期：1995.11

  The condensation of a chiral 2-silyloxypyrrole derivative with achiral and chiral formyl cation equivalents has been studied for the first time. The methodology allows to build-up pyroglutammic aldehydes and prolinal systems with a stereocontrol from good to excellent. Whereas the chiral auxiliary residing on the pyrrole system shows an intrinsic good level of diastereoface discrimination at C-5, the combined use of a 2-methoxy-3-tosyl-oxazolidine as a chiral formylating agent allows a total stereocontrol of the condensation. A rationale for the observed stereochemical outcome is presented.
• A new asymmetric approach toward 5-substituted pyrrolidin-2-one derivatives
  作者：Giovanni Poli、Simone Ciofi Baffoni、Giuliano Giambastiani、Gianna Reginato

  DOI：10.1016/s0040-4020(98)00494-3

  日期：1998.8

  The condensation between a chiral 2-silyloxypyrrole and either achiral or chiral formyl cation equivalents has been studied. The methodology has allowed to build-up 5-substituted pyrrolidin-2-one derivatives with a stereocontrol from good to excellent. The chiral auxiliary located on the silyloxypyrrole showed an intrinsic good level of diastereoface discrimination at C-5. However. the use of a 2-methoxy-3-tosyl-oxazolidine as chiral formylating agent allowed a total stereocontrol in the condensation. A rationale for the observed stereochemical outcome is presented. The stereoselective manipulation of these adducts provided new potentially interesting pyroglutamic aldehyde and prolinal derivatives. whereas treatment with TiCl4 triggered unexpectedly a Pomeranz-Fritsch type intramolecular condensation affording a benzocondensated indolizidinone. (C) 1998 Elsevier Science Ltd. All rights reserved.