(E)-10-bromo-5-(triethylsilyloxy)dec-2-enal | 1357931-15-7

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (E)-10-bromo-5-(triethylsilyloxy)dec-2-enal
• 英文别名: (E)-10-bromo-5-triethylsilyloxydec-2-enal
• CAS: 1357931-15-7
• 化学式: C₁₆H₃₁BrO₂Si
• 分子量: 363.41
• InChiKey: XSWPAHRIWIHZGE-PKNBQFBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.48
• 重原子数：
  20
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-10-bromo-5-(triethylsilyloxy)dec-2-enal 、 乙醛 在 bismuth (III) nitrate pentahydrate 作用下， 以 二氯甲烷 为溶剂， 以74%的产率得到2-[6-(5-bromopentyl)-2-methyl-1,3-dioxan-4-yl]acetaldehyde
  参考文献：
  名称：

  Diastereoselective Construction of syn-1,3-Dioxanes via a Bismuth-Mediated Two-Component Hemiacetal/Oxa-Conjugate Addition Reaction

  摘要：

  The bismuth-mediated two-component hemiacetal/oxa-conjugate addition of delta-trialkylsilyloxy and delta-hydroxy alpha,beta-unsaturated aldehydes and ketones with alkyl aldehydes provides the syn-1,3-dioxanes in a highly efficient and stereoselective manner. The key advantages of this protocol are its operational simplicity and its ability to directly access electron-withdrawing groups without recourse to oxidation state adjustments.

  DOI：

  10.1021/ja208668u

文献信息

• Diastereoselective Construction of <i>syn</i>-1,3-Dioxanes via a Bismuth-Mediated Two-Component Hemiacetal/Oxa-Conjugate Addition Reaction
  作者：P. Andrew Evans、Aleksandr Grisin、Michael J. Lawler

  DOI：10.1021/ja208668u

  日期：2012.2.15

  The bismuth-mediated two-component hemiacetal/oxa-conjugate addition of delta-trialkylsilyloxy and delta-hydroxy alpha,beta-unsaturated aldehydes and ketones with alkyl aldehydes provides the syn-1,3-dioxanes in a highly efficient and stereoselective manner. The key advantages of this protocol are its operational simplicity and its ability to directly access electron-withdrawing groups without recourse to oxidation state adjustments.