(1'S,2S)-2-dimethoxymethyl-1-(1'-phenylethyl)pyrrolidine | 212912-51-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (1'S,2S)-2-dimethoxymethyl-1-(1'-phenylethyl)pyrrolidine
• 英文别名: (2S)-2-(dimethoxymethyl)-1-[(1S)-1-phenylethyl]pyrrolidine
• CAS: 212912-51-1
• 化学式: C₁₅H₂₃NO₂
• 分子量: 249.353
• InChiKey: XNRCBSKADOSDOQ-JSGCOSHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1'S,2S)-2-dimethoxymethyl-1-(1'-phenylethyl)pyrrolidine 在 palladium dihydroxide 、 氢气 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 (2S)-2-dimethoxymethylpyrrolidine
  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：

  (1'S)-5-dimethoxymethyl-1-(1'-phenylethyl)pyrrolidin-2-one 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 反应 0.67h， 以87%的产率得到(1'S,2S)-2-dimethoxymethyl-1-(1'-phenylethyl)pyrrolidine
  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

文献信息

• 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.