methyl (3R,4R)-4-(3,4-bis[(triethylsilyl)oxy]-2,5-dioxo-1-pyrrolidinyl)butanoate | 916229-03-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (3R,4R)-4-(3,4-bis[(triethylsilyl)oxy]-2,5-dioxo-1-pyrrolidinyl)butanoate
• 英文别名: methyl 4-[(3R,4R)-2,5-dioxo-3,4-bis(triethylsilyloxy)pyrrolidin-1-yl]butanoate
• CAS: 916229-03-3
• 化学式: C₂₁H₄₁NO₆Si₂
• 分子量: 459.731
• InChiKey: UMOJUXJXHLMJNE-RTBURBONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.09
• 重原子数：
  30
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (3R,4R)-4-(3,4-bis[(triethylsilyl)oxy]-2,5-dioxo-1-pyrrolidinyl)butanoate 、 三氟甲磺酸三甲基硅酯 在 三乙胺 作用下， 以 氘代氯仿 为溶剂， 反应 48.0h， 以58%的产率得到methyl (1R,6R,7R,7aR)-7a-[(trimethylsilyl)oxy]hexahydro-5-oxo-6,7-bis[(triethylsilyl)oxy]-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
• 作为产物：
  描述：

  4-氨基丁酸甲酯盐酸盐 在 咪唑 、 三乙胺 、 乙酰氯 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 76.0h， 生成 methyl (3R,4R)-4-(3,4-bis[(triethylsilyl)oxy]-2,5-dioxo-1-pyrrolidinyl)butanoate
  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.