2-benzyloxy-N-[3-(tert-butyldimethylsilyloxy)prop-1-en-1-yl]-N-isobutylacetamide | 1415693-31-0

• 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: 2-benzyloxy-N-[3-(tert-butyldimethylsilyloxy)prop-1-en-1-yl]-N-isobutylacetamide
• CAS: 1415693-31-0
• 化学式: C₂₂H₃₇NO₃Si
• 分子量: 391.626
• InChiKey: PNZJRZUJYQTEAJ-SDNWHVSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.22
• 重原子数：
  27.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 草酰氯 、 sodium hydride 、 magnesium sulfate 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 cis-3-benzyloxy-4-[2-(tert-butyldimethylsilyloxy)ethyl]-1-isobutylazetidin-2-one 、 2-benzyloxy-N-[3-(tert-butyldimethylsilyloxy)prop-1-en-1-yl]-N-isobutylacetamide
  参考文献：
  名称：

  Stereoselective synthesis of bicyclic tetrahydrofuran-fused ?-lactams and their conversion into methyl cis-3-aminotetrahydrofuran-2-carboxylates

  摘要：

  cis-3-Benzyloxy-4-(2-mesyloxyethyl)azetidin-2-ones were shown to be useful starting products for the synthesis of cis-2-oxa-6-azabicyclo[3.2.0]heptan-7-ones in high overall yields and purity upon hydrogenolysis of the benzyl ether substituent followed by intramolecular nucleophilic substitution using sodium hydride in THF. These unconventionally C-fused bicyclic beta-lactams were easily converted into the corresponding methyl cis-3-aminotetrahydrofuran-2-carboxylates via acidic methanolysis. This methodology constitutes a convenient alternative for the known preparation of cis-4,4-dimethy1-2-oxa-6-azabicyclo[3.2.0]heptan-7-ones and methyl cis-3-amino-4,4-dimethyltetrahydrofuran-2-carboxylates, as their 4,4-nor-dimethyl variants are usually considered to be more promising compounds within the field of drug design. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.01.001