4-氟-2-苯基-1-苯并呋喃 | 863870-89-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 中文名称: 4-氟-2-苯基-1-苯并呋喃
• 英文名称: 4-fluoro-2-phenylbenzo[b]furan
• 英文别名: 4-Fluoro-2-phenylbenzofuran；4-fluoro-2-phenyl-1-benzofuran
• CAS: 863870-89-7
• 化学式: C₁₄H₉FO
• 分子量: 212.223
• InChiKey: GZACZFRSOLDOFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 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：
  2

反应信息

• 作为产物：
  描述：

  3-氟苯酚 在 bis(triphenylphosphine) palladium (Il) acetate 哌啶 、 sodium hydroxide 、 copper(l) iodide 、 正丁基锂 、 四甲基乙二胺 、 仲丁基锂 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 环己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 43.0h， 生成 4-氟-2-苯基-1-苯并呋喃
  参考文献：
  名称：

  由2,3-二卤代酚新型高效合成4-官能化苯并[ b ]呋喃

  摘要：

  串联Sonogashira偶联/ 5-内切-挖上-2,3- dihalophenols环化反应假设一个简单的项，以4- halobenzo [ b ]呋喃，其可以容易地转化为4 -官能化苯并[ b ]呋喃，难以合成通过其他程序。另一方面，起始的2,3-二卤代苯酚是由市售的3-卤代苯酚经其N，N-二乙基氨基甲酸酯通过在低位用s -BuLi / TMEDA或LDA处理在2-位选择性锂化而有效制备的。温度和与卤素亲电子试剂的反应。

  DOI：

  10.1021/jo0508402

文献信息

• Transition Metal-Free Synthesis of Halobenzo[b]furans from O-Aryl Carbamates via o-Lithiation Reactions
  作者：Claudia Feberero、Cintia Virumbrales、Carlos Sedano、Lorena Renedo、Samuel Suárez-Pantiga、Roberto Sanz

  DOI：10.3390/molecules27020525

  日期：——

  A straightforward and transition metal-free one-pot protocol to synthesize halobenzo[b]furans has been developed employing simple and easily available starting materials such as O-aryl carbamates and alkynylsulfones. The fine-tuning of the different steps involved was key to achieving a successful one-pot procedure. Initially, a directed ortho-lithiation process, which uses the carbamate as the directed

  使用简单易得的起始材料（如 O-芳基氨基甲酸酯和炔基砜）开发了一种直接且不含过渡金属的一锅法合成卤代苯并 [b] 呋喃。所涉及的不同步骤的微调是成功实现一锅法的关键。最初，使用氨基甲酸酯作为定向金属化基团的定向邻位锂化过程对于通过邻锂化氨基甲酸酯的直接炔基化提供 O-2-炔基芳基 N,N-二乙基氨基甲酸酯至关重要，芳基磺酰基炔烃作为亲电试剂。通过涉及在常规加热或微波照射下原位氨基甲酸酯碱水解的策略，成功地完成了生成的邻炔基氨基甲酸酯的环化，再加上随后的杂环化步骤，提供所需的苯并[b]呋喃。已经合成了多种新的卤代苯并[b]呋喃，并通过进一步转化证明了它们的实用性。
• Photoremovable Protecting Groups for Phosphorylation of Chiral Alcohols. Asymmetric Synthesis of Phosphotriesters of (-)-3',5'-Dimethoxybenzoin
  作者：Michael C. Pirrung、Steven W. Shuey

  DOI：10.1021/jo00093a021

  日期：1994.7

  Procedures have been developed for the preparation of dimethoxybenzoinyl (DMB) phosphate triesters that can be deprotected photochemically. These compounds can be useful in light-directed synthesis and caging. The photochemistry of a wide variety of fluorine-, oxygen-, and nitrogen-substituted benzoin acetates was examined to determine the substitution pattern in the nonacylated aromatic ring producing optimum chemical yields. Two groups, 2',3'-dimethoxybenzoin and 3',5'dimethoxybenzoin, were found to give the highest yields of the benzofuran product and were further developed for the photochemical deprotection of phosphate esters. These reactions could not be quenched, suggesting a singlet photosolvolysis mechanism. An asymmetric synthesis of 3',5'dimethoxybenzoin via the benzaldehyde cyanohydrin was developed that minimizes the number of diastereomers formed in the phosphorylation of chiral alcohols. A phosphoramidite reagent for the derivatization of alcohols was prepared and used to produce scalemic dimethoxybenzoinyl phosphate esters from pantolactone and glycerol, serine, and tyrosine derivatives. These compounds were deprotected photochemically to produce the phosphodiesters in high yield.