2-benzyl-3-methylchromone | 1334228-55-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-benzyl-3-methylchromone
• 英文别名: 2-benzyl-3-methylchromen-4-one；2-Benzyl-3-methylchromen-4-one
• CAS: 1334228-55-5
• 化学式: C₁₇H₁₄O₂
• 分子量: 250.297
• InChiKey: UFIVXBCJPUIVFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-(2-hydroxyphenyl)-2-methyl-4-phenyl-1,3-butanedione 在 proline p-dodecylphenylsulphonylhydrazide 、 水 作用下， 以 甲醇 为溶剂， 反应 60.0h， 以98%的产率得到2-benzyl-3-methylchromone
  参考文献：
  名称：

  Synthesis of functionalized chromones via organocatalysis

  摘要：

  A facile and versatile organocatalytic approach to access 2-substituted and 2,3-disubstituted chromone derivatives under mild conditions was developed, which was effectively catalyzed by novel proline phenylsulphonylhydrazide or pyrrolidine. As a result, diversely functionalized chromones were obtained in up to 99% yield. In addition, further modification of the corresponding chromones afforded novel polycyclic chromones. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.10.045

文献信息

• Efficient Assembly of Chromone Skeleton from 2,3-Allenoic Acids and Benzynes
  作者：Guobi Chai、Youai Qiu、Chunling Fu、Shengming Ma

  DOI：10.1021/ol202076c

  日期：2011.10.7

  Chromone derivatives were synthesized from 2,3-allenoic acids and benzynes in moderate to excellent yields under mild conditions. Instead of the cyclic conjugate addition of the intermediate A formed by the nucleophilic addition of allenoic acid with benzyne, this intermediate undergoes 1,2-addition with the carbonyl group, which was followed by the ring opening, conjugate addition, and protonolysis

  在温和的条件下，由2,3-烯丙基酸和苯并炔以中等至极好的收率合成了色酮衍生物。取代通过烯丙基酸与苯炔的亲核加成反应形成的中间体A的环状共轭加成，该中间体与羰基进行1,2-加成，然后开环，共轭加成和质子分解得到色酮衍生品。由于2,3-烯基酸和苯炔的取代基负载能力，该协议允许多样性。
• Synthesis of functionalized chromones via organocatalysis
  作者：Sai-Shuai Wen、Jing Wang、Yi-Ming Luo、Hua Yang

  DOI：10.1016/j.tet.2014.10.045

  日期：2014.12

  A facile and versatile organocatalytic approach to access 2-substituted and 2,3-disubstituted chromone derivatives under mild conditions was developed, which was effectively catalyzed by novel proline phenylsulphonylhydrazide or pyrrolidine. As a result, diversely functionalized chromones were obtained in up to 99% yield. In addition, further modification of the corresponding chromones afforded novel polycyclic chromones. (C) 2014 Elsevier Ltd. All rights reserved.