rac-1-phenyl-2-vinylbut-3-ene-1,2-diol

• 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: rac-1-phenyl-2-vinylbut-3-ene-1,2-diol
• 英文别名: 2-Ethenyl-1-phenylbut-3-ene-1,2-diol
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: NTKSAHHHZTUOMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  碳酸丙烯乙酯 、 rac-1-phenyl-2-vinylbut-3-ene-1,2-diol 在 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 以93%的产率得到rac-3-(1-allyloxphenylmethyl)penta-1,4-dien-3-ol
  参考文献：
  名称：

  钯催化α-羟基羰基化合物的O-烯丙基化

  摘要：

  α-羟基羰基化合物使用碳酸烯丙酯和Pd（0）催化剂进行平滑的O-烯丙基化。与其他O-烯丙基化方法相比，该方法具有显着优势，因为它提供了以前针对此合成转化观察到的几个问题的解决方案。

  DOI：

  10.1002/adsc.200505361
• 作为产物：
  描述：

  DL-扁桃酸甲酯 、 乙烯基氯化镁 以 四氢呋喃 、 乙醚 为溶剂， 反应 13.0h， 以31%的产率得到rac-1-phenyl-2-vinylbut-3-ene-1,2-diol
  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

• Palladium-CatalyzedO-Allylation of α-Hydroxy Carbonyl Compounds
  作者：Bernd Schmidt、Stefan Nave

  DOI：10.1002/adsc.200505361

  日期：2006.3

  α-Hydroxy carbonyl compounds undergo smooth O-allylation using allylic carbonates and Pd(0) catalysts. This method has significant advantages over other O-allylation methods as it provides a solution to several problems previously observed for this synthetic transformation.

  α-羟基羰基化合物使用碳酸烯丙酯和Pd（0）催化剂进行平滑的O-烯丙基化。与其他O-烯丙基化方法相比，该方法具有显着优势，因为它提供了以前针对此合成转化观察到的几个问题的解决方案。
• 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.