2,2-dimethyl-5-(trans-3-phenylallyl)tetrahydrofuran

• 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: 2,2-dimethyl-5-(trans-3-phenylallyl)tetrahydrofuran
• 英文别名: 2,2-dimethyl-5-(3-phenylallyl)tetrahydrofuran；2,2-dimethyl-5-[(E)-3-phenylprop-2-enyl]oxolane
• 化学式: C₁₅H₂₀O
• 分子量: 216.323
• InChiKey: STWHZCQABQOCAH-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (5Z,7E)-2-methyl-8-phenyl-5,7-octadien-2-ol 在 cerium(III) chloride 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以51%的产率得到2,2-dimethyl-5-(trans-3-phenylallyl)tetrahydrofuran
  参考文献：
  名称：

  CeCl3·7H2O–NaI catalyzed intramolecular addition reactions of 7-hydroxy-1,3-dienes: a facile approach to hexahydrobenzofurans and tetrahydrofurans

  摘要：

  CeCl3 center dot 7H(2)O-NaI effectively catalyzed intramolecular cyclization of cyclic 7-hydroxy-1,3-dienes, yielding hexahydrobenzofurans in diastereoselective fashion. This cyclization has been applied to synthesize tetrahydrofurans from acyclic 7-hydroxy-1,3-dienes. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.05.026

文献信息

• Stereoselective Synthesis of Tetrahydrofurans via the Palladium-Catalyzed Reaction of Aryl Bromides with γ-Hydroxy Alkenes:  Evidence for an Unusual Intramolecular Olefin Insertion into a Pd(Ar)(OR) Intermediate
  作者：John P. Wolfe、Michael A. Rossi

  DOI：10.1021/ja0394838

  日期：2004.2.1

  A new, stereoselective method for the synthesis of substituted tetrahydrofurans from gamma-hydroxy alkenes that forms both a C-C and a C-O bond with diastereoselectivities of up to >20:1 is described. Initial mechanistic studies that suggest the reactions proceed via the intramolecular insertion of an olefin into a Pd(Ar)(OR) intermediate are discussed.

  描述了一种新的立体选择性方法，用于从 γ-羟基烯烃合成取代的四氢呋喃，该方法形成 CC 和 CO 键，非对映选择性高达 > 20:1。初步的机理研究表明反应是通过烯烃分子内插入 Pd(Ar)(OR) 中间体进行的。
• CeCl3·7H2O–NaI catalyzed intramolecular addition reactions of 7-hydroxy-1,3-dienes: a facile approach to hexahydrobenzofurans and tetrahydrofurans
  作者：Ming-Chang P. Yeh、Wei-Jou Yeh、Ling-Hsien Tu、Jia-Ru Wu

  DOI：10.1016/j.tet.2006.05.026

  日期：2006.7

  CeCl3 center dot 7H(2)O-NaI effectively catalyzed intramolecular cyclization of cyclic 7-hydroxy-1,3-dienes, yielding hexahydrobenzofurans in diastereoselective fashion. This cyclization has been applied to synthesize tetrahydrofurans from acyclic 7-hydroxy-1,3-dienes. (c) 2006 Elsevier Ltd. All rights reserved.