3-萘-1-基呋喃 | 560993-90-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 3-萘-1-基呋喃
• 英文名称: 3-(naphthalen-1-yl)furan
• 英文别名: 3-[1]-naphthylfuran；Furan, 3-(1-naphthalenyl)-；3-naphthalen-1-ylfuran
• CAS: 560993-90-0
• 化学式: C₁₄H₁₀O
• 分子量: 194.233
• InChiKey: XFXXHKSPWRZNSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  、 3-萘-1-基呋喃 在 bismuth(III) chloride 作用下， 生成
  参考文献：
  名称：

  苯并[b]咔唑的一锅法伸缩合成及其液晶性质探索

  摘要：

  我们描述了各种苯并[ b ]咔唑的多样性导向的一锅式伸缩合成，以吲哚的环烷化作为关键步骤，通过分子内呋喃-烯烃Diels-Alder反应实现。该策略在多种基材上都是通用且有效的。我们应用这种方法合成并表征了第一个苯并[ b ]咔唑基液晶材料，其中独特的分子设计导致在室温下形成罕见的向列相。

  DOI：

  10.1039/d4cc00721b
• 作为产物：
  描述：

  1-碘萘 在 bis-triphenylphosphine-palladium(II) chloride 、 dirhodium tetraacetate copper(l) iodide 、 氢气 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 20.0~65.0 ℃ 、4.83 MPa 条件下， 反应 26.0h， 生成 3-萘-1-基呋喃
  参考文献：
  名称：

  羰基化合成3-取代呋喃

  摘要：

  描述了一种使用乙酸铑和三苯基膦在二氯甲烷中通过取代的炔丙基醇的加氢甲酰化合成3-取代的呋喃的简单新颖的方法。加氢甲酰化反应在温和的反应条件下以区域选择性的方式进行。这种新颖的方法学用途广泛，可用于合成各种3-芳基取代的呋喃。

  DOI：

  10.1002/adsc.200505238

文献信息

• Imidazolylsulfonates: Electrophilic Partners in Cross-Coupling Reactions
  作者：Jennifer Albaneze-Walker、Ravinder Raju、Jennifer A. Vance、Andrew J. Goodman、Michael R. Reeder、Jing Liao、Mathew T. Maust、Patrick A. Irish、Peter Espino、David R. Andrews

  DOI：10.1021/ol802381k

  日期：2009.4.2

  Aryl imidazolylsulfonates participate as electrophilic coupling partners in palladium-mediated cross-coupling reactions. The aryl imidazolylsulfonates display good stability while maintaining good reactivity in a variety of palladium-catalyzed coupling reactions. Imidazolylsulfonates are a practical and economic alternative to triflates.

  芳基咪唑基磺酸盐作为亲电偶联伙伴参与钯介导的交叉偶联反应。芳基咪唑基磺酸盐显示出良好的稳定性，同时在各种钯催化的偶联反应中保持良好的反应性。咪唑基磺酸盐是三氟甲磺酸酯的一种实用且经济的替代品。
• Nickel-Catalyzed C−O Activation of Phenol Derivatives with Potassium Heteroaryltrifluoroborates
  作者：Gary A. Molander、Floriane Beaumard

  DOI：10.1021/ol101592r

  日期：2010.9.17

  A general method based on nickel-catalyzed C-O activation of various phenol derivatives with potassium (hetero)aryltrifluoroborates has been developed. A large number of heterobiaryls can be easily obtained with yields up to 99% using methanesulfonate cross-coupling partners.
• Suzuki−Miyaura Cross-Coupling of Aryl Carbamates and Sulfamates: Experimental and Computational Studies
  作者：Kyle W. Quasdorf、Aurora Antoft-Finch、Peng Liu、Amanda L. Silberstein、Anna Komaromi、Tom Blackburn、Stephen D. Ramgren、K. N. Houk、Victor Snieckus、Neil K. Garg

  DOI：10.1021/ja200398c

  日期：2011.4.27

  The first Suzuki-Miyaura cross-coupling reactions of the synthetically versatile aryl O-carbamate and O-sulfamate groups are described. The transformations utilize the inexpensive, bench-stable catalyst NiCl2(PCy3)(2) to furnish biaryls in good to excellent yields. A broad scope for this methodology has been demonstrated. Substrates with electron-donating and electron-withdrawing groups are tolerated, in addition to those that possess ortho substituents. Furthermore, heteroaryl substrates may be employed as coupling partners. A computational study providing the full catalytic cycles for these cross-coupling reactions is described. The oxidative addition with carbamates or sulfamates occurs via a five-centered transition state, resulting in the exclusive cleavage of the aryl C-O bond. Water is found to stabilize the Ni-carbamate catalyst resting state, which thus provides rationalization of the relative decreased rate of coupling of carbamates. Several synthetic applications are presented to showcase the utility of the methodology in the synthesis of polysubstituted aromatic compounds of natural product and bioactive molecule interest.