| 1402854-64-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• CAS: 1402854-64-1
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: ZBCRIWLACYFDLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.26
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  、 2-萘甲醛 在 iron(III) chloride 、 叔丁基二甲基氯硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以72%的产率得到ethyl 4-hydroxy-3-methyl-6-(naphthalen-2-yl)-4-phenyltetrahydro-2H-pyran-2-carboxylate
  参考文献：
  名称：

  Completely OH-Selective FeCl₃-Catalyzed Prins Cyclization: Highly Stereoselective Synthesis of 4-OH-Tetrahydropyrans

  摘要：

  The completely OH-selective Prins cyclization has been realized from the enantioselective ene reaction product. A variety of 4-hydroxyl-tetrahydropyrans were exclusively generated via FeCl3-catalyzed Prins reaction. Excellent stereoselectivities (up to >99:1 dr and >99.5:0.5 er) were obtained for a remarkably broad range of substrates under mild reaction conditions. The control experiments, including NOE effects and O-18-labeling studies, as well as DFT calculations were conducted to provide fundamental insights into the mechanism of the reaction. A different [2 + 2] cycloaddition process was suggested to rationalize the observed OH-selectivity.

  DOI：

  10.1021/ja3062002
• 作为产物：
  描述：

  乙醛酸乙酯 、 反式-2-苯基-2-丁烯 在 2,6-双[(3aR,8aS)-(+)-8H-茚[1,2-d]恶唑啉-2-基]吡啶 、 indium(III) chloride 、 silver hexafluoroantimonate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 48.0h， 以88%的产率得到
  参考文献：
  名称：

  Highly Enantioselective and Anti-Diastereoselective Catalytic Intermolecular Glyoxylate–Ene Reactions: Effect of the Geometrical Isomers of Alkenes

  摘要：

  An efficient method for the synthesis of homoallylic alcohols with high enantioselectivities and anti-diastereoselectivities via an In(III)-catalyzed intermolecular glyoxylateene reaction has been developed. The geometrical isomers of alkenes were shown to have different reactivities. Only the isomers of the alkenes having a proton beta-cis to the substituent reacted in this catalytic system.

  DOI：

  10.1021/acs.orglett.5b01151