(2E)-3-(1-[2-(trimethylsilyl)ethoxymethyl]-1H-imidazol-4-yl)-2-propenyl tert-butyl carbonate | 954426-18-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (2E)-3-(1-[2-(trimethylsilyl)ethoxymethyl]-1H-imidazol-4-yl)-2-propenyl tert-butyl carbonate
• 英文别名: tert-butyl [(E)-3-[1-(2-trimethylsilylethoxymethyl)imidazol-4-yl]prop-2-enyl] carbonate
• CAS: 954426-18-7
• 化学式: C₁₇H₃₀N₂O₄Si
• 分子量: 354.522
• InChiKey: BBDCUHQMODKQAX-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.16
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  62.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2E)-3-(1-[2-(trimethylsilyl)ethoxymethyl]-1H-imidazol-4-yl)-2-propenyl tert-butyl carbonate 在 tris(dibenzylideneacetone)dipalladium (0) 三苯基膦 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 72.0h， 生成 (+/-)-(4aS,8aR,9S)-7-benzhydryl-1-[2-(trimethylsilyl)ethoxymethyl]-9-{1-[2-(trimethylsilyl)ethoxymethyl]-1H-imidazol-4-yl}-8-oxo-4,4a,7a,8-tetrahydro-1H-[1,2]oxazino[4,5-f]benzimidazole
  参考文献：
  名称：

  Studies toward the Total Synthesis of Axinellamine and Massadine

  摘要：

  Intramolecular Diels-Alder reactions of several N-O linked 4-vinylimidazole dimers provide the expected adduct in moderate to good yield as a single, all trans stereoisomer, along with smaller amounts of the inverse electron demand adduct. Oxidative rearrangement of the cycloadducts occurs on treatment with Davis' reagent, providing a single spiro imidazolone in good yield and with excellent levels of stereocontrol albeit epimeric at the spiro center found in axinellamine and massadine.

  DOI：

  10.1021/ol0711568
• 作为产物：
  描述：

  (2E)-3-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-4-yl)propenoic acid methyl ester 在 sodium hydroxide 、 四丁基硫酸氢铵 、 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (2E)-3-(1-[2-(trimethylsilyl)ethoxymethyl]-1H-imidazol-4-yl)-2-propenyl tert-butyl carbonate
  参考文献：
  名称：

  Studies toward the Total Synthesis of Axinellamine and Massadine

  摘要：

  Intramolecular Diels-Alder reactions of several N-O linked 4-vinylimidazole dimers provide the expected adduct in moderate to good yield as a single, all trans stereoisomer, along with smaller amounts of the inverse electron demand adduct. Oxidative rearrangement of the cycloadducts occurs on treatment with Davis' reagent, providing a single spiro imidazolone in good yield and with excellent levels of stereocontrol albeit epimeric at the spiro center found in axinellamine and massadine.

  DOI：

  10.1021/ol0711568

文献信息

• Studies toward the Total Synthesis of Axinellamine and Massadine
  作者：Rasapalli Sivappa、Nora M. Hernandez、Yong He、Carl J. Lovely

  DOI：10.1021/ol0711568

  日期：2007.9.1

  Intramolecular Diels-Alder reactions of several N-O linked 4-vinylimidazole dimers provide the expected adduct in moderate to good yield as a single, all trans stereoisomer, along with smaller amounts of the inverse electron demand adduct. Oxidative rearrangement of the cycloadducts occurs on treatment with Davis' reagent, providing a single spiro imidazolone in good yield and with excellent levels of stereocontrol albeit epimeric at the spiro center found in axinellamine and massadine.