3,4-bis(benzyloxymethyl)furan | 96194-82-0

• 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: 3,4-bis(benzyloxymethyl)furan
• 英文别名: 3,4-Bis(phenylmethoxymethyl)furan
• CAS: 96194-82-0
• 化学式: C₂₀H₂₀O₃
• 分子量: 308.377
• InChiKey: DWMKEJLZRUQYMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  31.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4-bis(benzyloxymethyl)furan 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 碳酸氢钠 作用下， 以 氯仿 、 丙酮 为溶剂， 生成 3,4-Bis-benzyloxymethyl-5H-furan-2-one
  参考文献：
  名称：

  取代呋喃的酸介导的高度区域选择性氧化：一种简单直接的取代丁烯内酯的进入

  摘要：

  描述了从 3-取代或 3,4-二取代呋喃快速合成取代丁烯内酯的范围和限制。整个过程包括呋喃核受控氧化为 2,5-二烷氧基-二氢呋喃中间体和区域选择性酸催化水解为丁烯内酯衍生物。3-取代的呋喃仅产生2-取代的丁烯内酯。计算研究为提议的机制提供了证据。

  DOI：

  10.1055/s-2005-869865
• 作为产物：
  描述：

  3,4-呋喃二羧酸二甲酯 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.25h， 生成 3,4-bis(benzyloxymethyl)furan
  参考文献：
  名称：

  Thermally Responsive Dendrons and Dendrimers Based on Reversible Furan-Maleimide Diels−Alder Adducts

  摘要：

  [GRAPHICS]Benzyl aryl ether dendrons and dendrimers containing thermally reversible furan-malelmide Diels-Alder adducts were prepared up to the third generation. The covalent cleavage and reassembly of the dendrons and dendrimers were evaluated by H-1 NMR.

  DOI：

  10.1021/ol0101281

文献信息

• Asymmetric Diels–Alder reaction between furans and propiolates
  作者：Akihiro Ogura、Taisuke Ito、Koujiro Moriya、Hiroki Horigome、Ken-ichi Takao

  DOI：10.1016/j.tetlet.2021.153075

  日期：2021.5

  We report the first asymmetric Diels–Alder reaction between furan and propiolates. Propiolate, a dienophile, was equipped with an Evans’ auxiliary and a sulfonyl group to control and facilitate diastereoselective cycloaddition. Treatment with furan as a diene and aluminium Lewis acid afforded a 7-oxabicyclo[2.2.1]heptadiene skeleton diastereoselectively. The origin of diastereoselectivity can be explained

  我们报道了呋喃和丙酸酯之间的第一个不对称Diels-Alder反应。丙二酸酯，一种亲二烯体，配备有埃文斯助剂和磺酰基，以控制和促进非对映选择性环加成。用呋喃作为二烯和铝路易斯酸处理可选择性地得到7-氧杂双环[2.2.1]庚二烯骨架。非对映选择性的起源可以通过铝中心与呋喃的羰基和氧的螯合来解释。当吡咯用作二烯时，获得了弗里德尔-克拉夫茨型产品。
• An Exploratory Study of Type II [3 + 4] Cycloadditions between Vinylcarbenoids and Dienes
  作者：Huw M. L. Davies、Rebecca L. Calvo、Robert J. Townsend、Pingda Ren、R. Melvyn Churchill

  DOI：10.1021/jo991959b

  日期：2000.7.1

  dirhodium tetracarboxylate catalyzed decomposition of vinyldiazoacetates. The [3 + 4] cycloaddition is generally considered to occur by a tandem cyclopropanation/Cope rearrangement, although evidence is presented that with these substrates the [3 + 4] cycloaddition may occur in a concerted manner.

  乙烯基类化合物和呋喃之间的分子内II型[3 + 4]环加成反应是构建5-oxo-10-oxatricyclo [6.2.1.0（4,9）] undeca-3，8（11）-二烯的一种实用方法，包含两个反布雷特双键。这些三环系统功能齐全，可以最终加工成天然产物CP-263,114。铑稳定的乙烯基类胡萝卜素是通过四羧酸二铑催化乙烯基重氮乙酸酯的分解而生成的。通常认为[3 + 4]环加成是通过串联环丙烷化/ Cope重排发生的，尽管有证据表明，使用这些底物，[3 + 4]环加成可能以协同方式发生。
• Synthesis and solid state structure of an unsymmetrical triurea
  作者：Xavier Garcías、Leticia M. Toledo、Julius Rebek

  DOI：10.1016/0040-4039(95)01829-7

  日期：1995.11

  The synthesis and single crystal X-ray diffraction analysis of 1 is reported. Hydrogen bonding and solvation play an important role in the solid state structure of 1.

  报道了1的合成和单晶X射线衍射分析。氢键和溶剂化发挥的固态结构的重要作用，1。
• Structural effects on intramolecular furan cycloadditions
  作者：Larry L. Klein

  DOI：10.1021/jo00210a046

  日期：1985.5
• Synthesis and Self-Assembly of Pseudo-Spherical Homo- and Heterodimeric Capsules
  作者：Carlos Valdes、Urs P. Spitz、Leticia M. Toledo、Stefan W. Kubik、Julius Rebek

  DOI：10.1021/ja00156a010

  日期：1995.12

  Experimental details are given for the synthesis and characterization of several new molecules capable of self-assembly. The new molecules feature glycoluril subunits held apart by various rigid spacers, ethylene (2), naphthalene (3), and ethenoanthracene (4), and assemble through hydrogen bonds into pseudo-spherical dimeric capsules. The nature of their assembly is demonstrated by the X-ray crystal structure of capsules 1.1. The capsules are shown to enclose smaller guest molecules in a reversible manner. Direct evidence of the guest molecules inside the capsules from NMR is presented. In addition to self-assembling dimerically, these new molecules are shown to disproportionate into hybrid species or heterodimers. The resulting new capsules feature internal cavities of varying sizes and shapes. Formation of hybrid dimers 1.2, 1.4, and 3.4 is observed in solutions containing mixtures of two homodimers. The dispropoaionation equilibria could be manipulated by the addition of appropriately sized solvents as guests. Even the energetically unlikely hybrids 1.4 and 3.4 are found to be the dominant species when suitable guests such as CDBr3 are present. Evidence of the existence of the heterodimers is presented from NOE measurements. Factors controlling the heterodimerization are discussed.