cis-2,2-dimethyl-4-phenyl-5-ethenyl-1,3-dioxolane

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cis-2,2-dimethyl-4-phenyl-5-ethenyl-1,3-dioxolane
• 英文别名: 1,3-Dioxolane, 4-ethenyl-2,2-dimethyl-5-phenyl-；4-ethenyl-2,2-dimethyl-5-phenyl-1,3-dioxolane
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: QZAZBEJAECWYBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  (1R,2R)-2-(2-methoxypropan-2-yloxy)-1-phenylbut-3-en-1-ol 、 对甲苯磺酸一水合物 生成 cis-2,2-dimethyl-4-phenyl-5-ethenyl-1,3-dioxolane
  参考文献：
  名称：

  HOFFMANN, R. W.;KEMPER, B.;METTERNICH, R.;LEHMEIER, TH., LIEBIGS ANN. CHEM., 1985, N 11, 2246-2260

  摘要：

  DOI：

文献信息

• A New Protocol for the Acetoxyallylation of Aldehydes Mediated by Indium in THF
  作者：Marco Lombardo、Rugiada Girotti、Stefano Morganti、Claudio Trombini

  DOI：10.1021/ol016315g

  日期：2001.9.1

  [GRAPHICS]A new precursor of a formal 1-hydroxy allyl anion is represented by 3-bromo-1-acetoxy-1-propene, which is synthesized by the ZnCl2-catalyzed addition of acetyl bromide to propenal. 3-Bromo-1-acetoxy-1-propene reacts with indium powder in THF to give the corresponding 3-acetoxylated ally indium complex, which regioselectively adds to aldehydes, affording monoprotected 1-en-3,4-diols. Diastereoselectivity mainly depends on the nature of the aldehyde; saturated aldehydes afford anti adducts, whereas the alpha,beta -unsaturated aldehydes preferentially lead to the syn isomers.
• HOFFMANN, R. W.;KEMPER, B.;METTERNICH, R.;LEHMEIER, TH., LIEBIGS ANN. CHEM., 1985, N 11, 2246-2260
  作者：HOFFMANN, R. W.、KEMPER, B.、METTERNICH, R.、LEHMEIER, TH.

  DOI：——

  日期：——