2-benzofuran-1-yl(phenyl)methanol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异苯并呋喃
• 英文名称: 2-benzofuran-1-yl(phenyl)methanol
• 化学式: C₁₅H₁₂O₂
• 分子量: 224.259
• InChiKey: DTQIZQVJMCTIHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.51
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  33.37
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-benzofuran-1-yl(phenyl)methanol 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Oxidative Rearrangements of Isobenzofurans: Studies toward the Synthesis of the Ajudazols

  摘要：

  We present a new facet of isobenzofuran chemistry which allows for its efficient manipulation to generate biologically relevant entities. This methodology has been successfully applied toward the synthesis of ajudazol A.

  DOI：

  10.1021/ol8009336
• 作为产物：
  描述：

  benzofuran-2-yl(phenyl)methanone 在 dimethylsulfide borane complex 、 (1R,2S,3R,5R)-2-(1',3',2'-dioxaborolan-2'-yloxy)apopinan-3-amine 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以81%的产率得到2-benzofuran-1-yl(phenyl)methanol
  参考文献：
  名称：

  Chiral terpene auxiliaries III: spiroborate esters from (1R,2S,3R,5R)-3-amino-apopinan-2-ol as highly effective catalysts for asymmetric reduction of ketones with borane

  摘要：

  New spiroborate esters, derived from terpene amino alcohols, (S)-prolinol, and 2-aminoethanol, were employed as catalysts in the borane reduction of acetophenone and other aryl alkyl and halogenated ketones. The corresponding alcohols were obtained in high yields and with enantioselectivities up to 98% ee. The influence of the amino alcohol and the diol moieties of spiroborate on the reaction selectivity was examined. The catalyst load, the nature of the solvent, the borane source, and the reaction conditions were also investigated. (c) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2015.10.018

文献信息

• Chiral terpene auxiliaries IV: new monoterpene PHOX ligands and their application in the catalytic asymmetric transfer hydrogenation of ketones
  作者：Anna Kmieciak、Marek P. Krzemiński

  DOI：10.1016/j.tetasy.2017.02.003

  日期：2017.3

  New PHOX ligands, derived in three steps from (1R,2S,3R,5R)-3-amino-apopinan-2-ol 1 and (1R,2R,3S,5R)-3-amino-pinan-2-ol 2 were applied as chiral ligands for the formation of ruthenium catalysts. The catalysts were used in asymmetric transfer hydrogenations of prochiral ketones producing the corresponding alcohols in moderate to high yields and enantioselectivity. (C) 2017 Elsevier Ltd. All rights reserved.
• Chiral terpene auxiliaries III: spiroborate esters from (1R,2S,3R,5R)-3-amino-apopinan-2-ol as highly effective catalysts for asymmetric reduction of ketones with borane
  作者：Marta Ćwiklińska、Marek P. Krzemiński、Agnieszka Tafelska-Kaczmarek

  DOI：10.1016/j.tetasy.2015.10.018

  日期：2015.12

  New spiroborate esters, derived from terpene amino alcohols, (S)-prolinol, and 2-aminoethanol, were employed as catalysts in the borane reduction of acetophenone and other aryl alkyl and halogenated ketones. The corresponding alcohols were obtained in high yields and with enantioselectivities up to 98% ee. The influence of the amino alcohol and the diol moieties of spiroborate on the reaction selectivity was examined. The catalyst load, the nature of the solvent, the borane source, and the reaction conditions were also investigated. (c) 2015 Elsevier Ltd. All rights reserved.
• Oxidative Rearrangements of Isobenzofurans: Studies toward the Synthesis of the Ajudazols
  作者：Stephen J. Hobson、Andrew Parkin、Rodolfo Marquez

  DOI：10.1021/ol8009336

  日期：2008.7.3

  We present a new facet of isobenzofuran chemistry which allows for its efficient manipulation to generate biologically relevant entities. This methodology has been successfully applied toward the synthesis of ajudazol A.