2,3-dihydro-3-(1-hydroxyethyl)benzofuran

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: 2,3-dihydro-3-(1-hydroxyethyl)benzofuran
• 英文别名: 1-(2,3-dihydrobenzofuran-3-yl)ethanol；1-(2,3-Dihydro-1-benzofuran-3-yl)ethanol
• 化学式: C₁₀H₁₂O₂
• 分子量: 164.204
• InChiKey: LWTVPVWUMHXGKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(3-butenyloxy)benzenediazonium tetrafluoroborate 在 水 作用下， 以 丙酮 为溶剂， 生成 2,3-dihydro-3-(1-hydroxyethyl)benzofuran
  参考文献：
  名称：

  Tetrathiafulvalene as a catalyst for radical–polar crossover reactions

  摘要：

  四硫富瓦烯在介导电子转移反应、自由基环化和亲核取代的反应循环中表现得像一种催化剂。

  DOI：

  10.1039/c39930000295

文献信息

• The role of neighbouring group participation in TTF-mediated ‘radical-polar crossover’ reactions: trapping of aliphatic radicals by TTF+·
  作者：Nadeem Bashir、John A. Murphy

  DOI：10.1039/b000786m

  日期：——

  Trapping of secondary alkyl radicals with tetrathiafulvalenium tetrafluoroborate (TTF+·BF4−) leads to S-alkyltetrathiafulvalenium tetrafluoroborate salts; the solvolysis of such salts is critically dependent on the presence of appropriately sited neighbouring groups.

  用四硫富瓦烯四氟硼酸盐（TTF+·BF4-）捕获二级烷基自由基会产生S-烷基四硫富瓦烯四氟硼酸盐盐；此类盐的溶解反应显著依赖于适当位置的邻近基团的存在。
• Radical-polar crossover reactions with polymer-supported tetrathiafulvalene
  作者：Balaram Patro、Martin Merrett、John A. Murphy、David C. Sherrington、Michael G.J.T. Morrison

  DOI：10.1016/s0040-4039(99)01679-2

  日期：1999.10

  Polymer-supported tetrathiafulvalene reagents have been prepared and their reactivity in redical-polar crossover reactions compared to tetrathiafulvalene itself. The reagents give easy separation of products. A regeneration step permits re-use of the polymer-supported reagent.

  已经制备了聚合物负载的四硫富瓦烯试剂，并且与四硫富瓦烯本身相比，它们在双极性交叉反应中具有反应性。试剂使产物易于分离。再生步骤允许重复使用聚合物负载的试剂。
• Preparation and chemistry of the active copper species derived from CuI.cntdot.PBu3, CuI.cntdot.PPh3, and CuCN.cntdot.nLiX complexes
  作者：Reuben D. Rieke、Douglas E. Stack、Bryan T. Dawson、Tse Chong Wu

  DOI：10.1021/jo00061a023

  日期：1993.4

  The preparation of highly reactive copper by the reduction of CuI.PBu3, CuI.PPh3, and CuCN-nLiX copper(I) complexes with the preformed lithium naphthalenide is described. It was found, for all three Cu(I) complexes, that the reduction temperature proved crucial to reactivity of the zerovalent copper species as measured by the ability of the active copper to undergo oxidative addition to carbon-halogen bonds. The lower the reduction temperature the more reactive the zerovalent copper species becomes. The low-temperature reduction allows for the formation of highly reactive copper from CuCN.nLiX complexes. This active copper species undergoes oxidative addition to alkyl and aryl bromides in high yield to form the corresponding organocopper reagent directly without the need for other organometallic precursors. Moreover, the alkyl and aryl bromides can contain a wide range of functional groups as they are not affected in the oxidative addition step. The functionalized organocopper reagents derived from CuCN-nLiX based active copper are the reagent of choice in the cross-coupling of acid chlorides to produce ketones as well as the 1,4-addition reaction with enones. The lack of phosphines associated with organocopper reagents stemming from CuCN-based active copper makes product isolation more facile. While the functionalized organocopper reagents derived from CuCN.nLiX complexes provide higher isolated yields in the formentioned reactions, they are not nucleophilic enough to undergo inter- or intramolecular epoxide openings. The use of both CuI.PBu3 and CuI.PPh3 Cu(I) complexes in the intramolecular epoxide openings of aryl bromoepoxides is presented. The regiochemistry, endo vs. exo, was shown to be affected by the Cu(I) complex used to generate the active copper species, the solvent, and the pattern of substitution around the epoxide moiety. The active copper species as well as the the resulting organocopper reagents derived from both CuI.PBu3 and CuCN-nLiX were investigated using both P-31 and C-13 NMR. The data from P-31 NMR investigation held some evidence for a highly reduced copper(0)-phosphine complex while the C-13 studies of the CuCN-nLiX complexes indicated that these species have limited solubility in THF.
• Fletcher, Rodney J.; Lampard, Christopher; Murphy, John A., Journal of the Chemical Society. Perkin transactions I, 1995, # 6, p. 623 - 634
  作者：Fletcher, Rodney J.、Lampard, Christopher、Murphy, John A.、Lewis, Norman

  DOI：——

  日期：——
• Radical-polar crossover reactions with a water-soluble tetrathiafulvalene derivative
  作者：Balaram Patro、Martin C Merrett、Scott D Makin、John A Murphy、Kevin E.B Parkes

  DOI：10.1016/s0040-4039(99)02075-4

  日期：2000.1

  The water-soluble TTF reagent 7 undergoes the radical-polar crossover reaction in 1:1 acetone:water with a range of arenediazonium tetrafluoroborates and in water with diazonium chlorides. Purification of the reaction products is greatly facilitated by using 7 compared with TTF. (C) 2000 Elsevier Science Ltd. All rights reserved.