[(2S)-2,3-dihydro-1-benzofuran-2-yl]-phenylmethanone | 1309687-09-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2S)-2,3-dihydro-1-benzofuran-2-yl]-phenylmethanone
• CAS: 1309687-09-9
• 化学式: C₁₅H₁₂O₂
• 分子量: 224.259
• InChiKey: QSXAIMLSGHQQHX-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.87
• 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：
  0.13
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  3-(2-羟基苯基)-1-苯基丙酮 在 C₄₄H₃₂N⁽¹⁺⁾*I^(1-) 、 双氧水 、 sodium dodecyl-sulfate 作用下， 以 水 、 甲苯 为溶剂， 反应 1.0h， 以99%的产率得到[(2S)-2,3-dihydro-1-benzofuran-2-yl]-phenylmethanone
  参考文献：
  名称：

  Enantioselective Cycloetherification in a Micellar Catalysis System

  摘要：

  The enantioselective cycloetherification of substituted keto phenols into their corresponding dihydrobenzofuran derivatives was carried out using hydrogen peroxide and chiral quaternary ammonium iodide in micellar media. This approach increased the conversion rate of cycloetherification and also widened the scope of this particular reaction for various substituted keto phenols with electron withdrawing as well as electron donating functionalities. The use of a surfactant in the cycloetherification reaction increased the yield of the corresponding enantioselective dihydrobenzofuran four times. The conversion rate of keto phenols into their corresponding dihydrobcnzofuran derivatives was proportional to the concentration of the surfactant used in the reaction.

  DOI：

  10.1016/s1872-2067(10)60169-6

文献信息

• Catalytic Asymmetric Synthesis of Chiral Dihydrobenzofurans through a Formal [4+1] Annulation Reaction of Sulfur Ylides and In Situ Generated<i>ortho</i>-Quinone Methides
  作者：Qing-Qing Yang、Wen-Jing Xiao

  DOI：10.1002/ejoc.201601186

  日期：2017.1.10

  The first example of a catalytic asymmetric formal [4+1] annulation reaction between sulfur ylides and in situ generated ortho-quinone methides (o-QMs) is reported in this work. A C2-symmetric chiral urea was identified to be the best H-bonding catalyst, affording a wide range of chiral 2,3-dihydrobenzofurans in high yields and moderate enantioselectivities [70–98 % yields, up to 89:11 e.r. (enantiomeric

  在这项工作中报道了硫叶立德与原位生成的邻醌甲基化物 (o-QMs) 之间的催化不对称形式 [4+1] 环化反应的第一个例子。一种 C2 对称手性尿素被认为是最好的 H 键合催化剂，可提供范围广泛的手性 2,3-二氢苯并呋喃，收率高，对映选择性适中 [70–98% 收率，高达 89:11 er )]。
• Enantioselective Cycloetherification in a Micellar Catalysis System
  作者：Bhupesh S. SAMANT、Sunil S. BHAGWAT

  DOI：10.1016/s1872-2067(10)60169-6

  日期：2011.1

  The enantioselective cycloetherification of substituted keto phenols into their corresponding dihydrobenzofuran derivatives was carried out using hydrogen peroxide and chiral quaternary ammonium iodide in micellar media. This approach increased the conversion rate of cycloetherification and also widened the scope of this particular reaction for various substituted keto phenols with electron withdrawing as well as electron donating functionalities. The use of a surfactant in the cycloetherification reaction increased the yield of the corresponding enantioselective dihydrobenzofuran four times. The conversion rate of keto phenols into their corresponding dihydrobcnzofuran derivatives was proportional to the concentration of the surfactant used in the reaction.