3-Benzoyl-2-phenyl-5-<(trimethylsilyl)methyl>-4,5-dihydrofuran

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-Benzoyl-2-phenyl-5-<(trimethylsilyl)methyl>-4,5-dihydrofuran
• 英文别名: Phenyl-[5-phenyl-2-(trimethylsilylmethyl)-2,3-dihydrofuran-4-yl]methanone
• 化学式: C₂₁H₂₄O₂Si
• 分子量: 336.506
• InChiKey: HNNSILGTIVLTAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.41
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  二苯甲酰基甲烷 、 烯丙基三甲基硅烷 在 manganese triacetate 作用下， 以 溶剂黄146 为溶剂， 反应 0.25h， 以91%的产率得到3-Benzoyl-2-phenyl-5-<(trimethylsilyl)methyl>-4,5-dihydrofuran
  参考文献：
  名称：

  Silicon-Controlled Allylation of 1,3-Dioxo Compounds by Use of Allyltrimethylsilane and Ceric Ammonium Nitrate

  摘要：

  A new method was developed for allylation of 1,3-diketones, beta-keto esters, and malonates. Treatment of those 1,3-dioxo compounds with allyltrimethylsilane (1.3 equiv) in the presence of eerie ammonium nitrate (2.1 equiv) in methanol at room temperature often gave the mono-C-allylated products in good to excellent yields (74-98%). These reactions, involving beta-carboradical and beta-carbocationic intermediates, were controlled by a silyl group. Replacement of eerie ammonium nitrate and methanol with manganese(III) acetate (2.4 equiv) and acetic acid afforded silicon-containing dihydrofurans in high yields at 80 degrees C.

  DOI：

  10.1021/jo00109a016

文献信息

• Solvent-Dependent Chemoselectivities in Ce(IV)-Mediated Oxidative Coupling Reactions
  作者：Yang Zhang、Andrew J. Raines、Robert A. Flowers

  DOI：10.1021/ol034763d

  日期：2003.6.1

  The oxidative coupling of 1,3-diketones, beta-keto esters, and beta-keto silyl enol ethers with allyl trimethylsilane in the presence of CTAN was investigated. In the case of acyclic diketones and esters, different chemoselectivities were observed in CH(3)CN and CH(2)Cl(2) leading to good yields of allylation and dihydrofuran products, respectively. [reaction: see text]

  研究了在CTAN存在下1,3-二酮，β-酮酯和β-酮甲硅烷基烯醇醚与烯丙基三甲基硅烷的氧化偶联作用。在无环二酮和酯的情况下，在CH（3）CN和CH（2）Cl（2）中观察到不同的化学选择性，分别导致良好的烯丙基化和二氢呋喃产物的产率。[反应：看文字]