methyl (1R,6R,7R,7aR)-7a-[(trimethylsilyl)oxy]hexahydro-5-oxo-6,7-bis(benzyloxy)-1H-pyrrolizine-1-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯里西啶类
• 英文名称: methyl (1R,6R,7R,7aR)-7a-[(trimethylsilyl)oxy]hexahydro-5-oxo-6,7-bis(benzyloxy)-1H-pyrrolizine-1-carboxylate
• 英文别名: methyl (1R,6R,7R,8R)-5-oxo-6,7-bis(phenylmethoxy)-8-trimethylsilyloxy-2,3,6,7-tetrahydro-1H-pyrrolizine-1-carboxylate
• 化学式: C₂₆H₃₃NO₆Si
• 分子量: 483.637
• InChiKey: FXYGNYRCKUEVEA-NZCWTCFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.74
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-氨基丁酸甲酯盐酸盐 在 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 氘代氯仿 、 乙腈 为溶剂， 反应 47.0h， 生成 methyl (1R,6R,7R,7aR)-7a-[(trimethylsilyl)oxy]hexahydro-5-oxo-6,7-bis(benzyloxy)-1H-pyrrolizine-1-carboxylate
  参考文献：
  名称：

  Silylative Dieckmann-Like Cyclizations of Ester-Imides (and Diesters)

  摘要：

  Trialkylsilyl triflates effect cyclization of ester-imides such as 2 to produce adducts such as 4a. Trapping of the in situ generated, nucleophilic ketene acetal (cf. 5a) is a key aspect of the transformation. A range of substrates amenable to this operationally simple reaction is reported. In many instances the levels of diastereoselectivity are very high. Mechanistic points are inferred from spectroscopic observations.

  DOI：

  10.1021/ol061988q

文献信息

• Silylative Dieckmann-Like Cyclizations of Ester-Imides (and Diesters)
  作者：Thomas R. Hoye、Vadims Dvornikovs、Elena Sizova

  DOI：10.1021/ol061988q

  日期：2006.11.9

  Trialkylsilyl triflates effect cyclization of ester-imides such as 2 to produce adducts such as 4a. Trapping of the in situ generated, nucleophilic ketene acetal (cf. 5a) is a key aspect of the transformation. A range of substrates amenable to this operationally simple reaction is reported. In many instances the levels of diastereoselectivity are very high. Mechanistic points are inferred from spectroscopic observations.