2-isopropyl-3-methylchromone | 1184976-45-1

• 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-isopropyl-3-methylchromone
• 英文别名: 2-isopropyl-3-methyl-4H-chromen-4-one；2-isopropyl-3-methylchromen-4-one；3-Methyl-2-propan-2-ylchromen-4-one
• CAS: 1184976-45-1
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: BJWXJACIJOYSPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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)-2,4-dimethyl-1,3-pentanedione 在 proline p-dodecylphenylsulphonylhydrazide 、 水 作用下， 以 甲醇 为溶剂， 反应 46.0h， 以99%的产率得到2-isopropyl-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。
• Nickel-Catalyzed Cycloaddition of Salicylic Acid Ketals to Alkynes via Elimination of Ketones
  作者：Akihiro Ooguri、Kenichiro Nakai、Takuya Kurahashi、Seijiro Matsubara

  DOI：10.1021/ja904068p

  日期：2009.9.23

  been developed where salicylic acid ketals react with alkynes to afford substituted chromones. A mechanistic rationale is proposed, implying beta-elimination of ketone from ring strained seven-membered nickelacycle to generate a five-membered oxa-nickelacycle intermediate.

  已开发出分子间镍催化的加成反应，其中水杨酸缩酮与炔烃反应得到取代的色酮。提出了一个机械原理，这意味着从环应变的七元镍环中β-消除酮以生成五元氧杂镍环中间体。
• Nickel-catalyzed [4 + 2] Cycloaddition of Alkynes to Carbonylsalicylamides via Elimination of Isocyanates
  作者：Yasufumi Yoshino、Takuya Kurahashi、Seijiro Matsubara

  DOI：10.1246/cl.2010.896

  日期：2010.8.5

  An intermolecular nickel-catalyzed [4 + 2] cycloaddition has been developed where carbonylsalicylamides react with alkynes to afford substituted chromones. The reaction involves an elimination of i...

  已开发出分子间镍催化的 [4 + 2] 环加成反应，其中羰基水杨酰胺与炔烃反应生成取代的色酮。该反应涉及消除我...