(1'S)-1-(1'-phenylethyl)-2-tert-butyldimethylsilyloxy-1H-pyrrole | 212912-54-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: (1'S)-1-(1'-phenylethyl)-2-tert-butyldimethylsilyloxy-1H-pyrrole
• CAS: 212912-54-4
• 化学式: C₁₈H₂₇NOSi
• 分子量: 301.504
• InChiKey: ZLJJOSLZCQUOON-HNNXBMFYSA-N

物化性质

• 沸点：
  345.0±17.0 °C(Predicted)
• 密度：
  0.93±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.48
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  14.16
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1'S)-1-(1'-phenylethyl)-2-tert-butyldimethylsilyloxy-1H-pyrrole 在 Amberlyst 15 、 3 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 2.25h， 生成 5-Cyclopentylidene-1-((S)-1-phenyl-ethyl)-1,5-dihydro-pyrrol-2-one
  参考文献：
  名称：

  Highly Efficient Asymmetric Access to 1-Azaspiro[4.4]nonane Skeleton

  摘要：

  在酸性处理后，通过手性非消旋硅氧吡咯的Vinylogous Mukaiyama醛醇型反应，实现了1-氮杂螺[4.4]壬烷的高效不对称合成，其立体异构体过量高达79%。

  DOI：

  10.1055/s-2002-34232
• 作为产物：
  描述：

  叔丁基二甲硅基三氟甲磺酸酯 、 1-[(S)-1-phenylethyl]-1H-pyrrolidin-2(5H)-one 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (1'S)-1-(1'-phenylethyl)-2-tert-butyldimethylsilyloxy-1H-pyrrole
  参考文献：
  名称：

  Ytterbium triflate-catalyzed reactions of imines with a chiral non-racemic silyloxypyrrole

  摘要：

  In the presence of a catalytic amount of ytterbium triflate the reactions of various aromatic imines with a chiral non-racemic silyloxypyrrole proceeded smoothly to afford the corresponding aldol-type adducts in go od yields and diastereoselectivities. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00625-0

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.