rac-(2S,3S)-tert-butyldimethyl(2-phenyl-3-vinyl-3,6-dihydro-2H-pyran-3-yloxy)silane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: rac-(2S,3S)-tert-butyldimethyl(2-phenyl-3-vinyl-3,6-dihydro-2H-pyran-3-yloxy)silane
• 英文别名: tert-butyl-[[(2S,3S)-3-ethenyl-2-phenyl-2,6-dihydropyran-3-yl]oxy]-dimethylsilane
• 化学式: C₁₉H₂₈O₂Si
• 分子量: 316.516
• InChiKey: GGIRXEKDTMIHGP-HKUYNNGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.26
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (1-allyloxy-1-methoxymethyl-but-3-enyl)-benzene 在 Grubbs catalyst first generation 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 25.0h， 生成 rac-(2S,3S)-tert-butyldimethyl(2-phenyl-3-vinyl-3,6-dihydro-2H-pyran-3-yloxy)silane
  参考文献：
  名称：

  Diastereoselective Ring-Closing Metathesis in the Synthesis of Dihydropyrans

  摘要：

  An investigation into the factors influencing the diastereochemical outcome of the ring-closing metathesis based synthesis of dihydropyrans is presented in this paper. Divinyl carbinols derived from alpha-hydroxy carboxylic acid esters are elaborated to trienes with two diastereotopic vinyl moieties. Depending on the steric demand of the oxo substituent of the divinyl carbinol moiety (either unprotected OH, TBDMS, or benzyl ether) different diastereomers are preferrably formed upon ring-closing metathesis. An extension to diastereoselective double ring-closing metathesis in the formation of spirocycles has also been investigated.

  DOI：

  10.1021/jo005534x

文献信息

• Diastereoselective Ring-Closing Metathesis in the Synthesis of Dihydropyrans
  作者：Bernd Schmidt、Holger Wildemann

  DOI：10.1021/jo005534x

  日期：2000.9.1

  An investigation into the factors influencing the diastereochemical outcome of the ring-closing metathesis based synthesis of dihydropyrans is presented in this paper. Divinyl carbinols derived from alpha-hydroxy carboxylic acid esters are elaborated to trienes with two diastereotopic vinyl moieties. Depending on the steric demand of the oxo substituent of the divinyl carbinol moiety (either unprotected OH, TBDMS, or benzyl ether) different diastereomers are preferrably formed upon ring-closing metathesis. An extension to diastereoselective double ring-closing metathesis in the formation of spirocycles has also been investigated.