3-benzoyl-2,3-dihydro-2-methyl-4H-1-benzopyran-4-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 高异黄酮
• 英文名称: 3-benzoyl-2,3-dihydro-2-methyl-4H-1-benzopyran-4-one
• 英文别名: trans-3-benzoyl-2-methylchroman-4-one；(2S,3R)-3-benzoyl-2-methyl-2,3-dihydrochromen-4-one
• 化学式: C₁₇H₁₄O₃
• 分子量: 266.296
• InChiKey: ZTPYASARXBWIQV-XHDPSFHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-benzoyl-2,3-dihydro-2-methyl-4H-1-benzopyran-4-one 在 甲烷磺酸 作用下， 以70%的产率得到2-phenyl-3-vinyl-4H-chromen-4-one
  参考文献：
  名称：

  Synthesis of 3-alkenyl-2-arylchromones and 2,3-dialkenylchromones via acid-catalysed retro-Michael ring opening of 3-acylchroman-4-ones

  摘要：

  3-Acylchromones and 3-acylflavones, readily available by acylation of 2'-hydroxydibenzoylmethane with acid anhydrides in the presence of base, undergo efficient conjugate reduction with NaBH4 in pyridine to give the corresponding chroman-4-ones/flavanones in high yields. The reduction is both regio- and chemoselective. Treatment of the chroman-4-ones with MeSO3H generates the 3-alkenyl-2-arylchromones by a dehydrative rearrangement initiated by retro-Michael cleavage of the pyranone ring. This reduction-rearrangement sequence can be extended to 2-alkyl-3-alkenoylchromones to generate 3-alkenyl-2-styrylchromones, the first examples of 2,3-dialkenylchromones. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.058
• 作为产物：
  描述：

  2-乙酰苯基苯甲酸酯 在 N-甲基吗啉 、 吡啶 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成 3-benzoyl-2,3-dihydro-2-methyl-4H-1-benzopyran-4-one
  参考文献：
  名称：

  黄烷酮衍生物的杀锥虫活性

  摘要：

  恰加斯病，也称为美洲锥虫病，被世界卫生组织列为被忽视的疾病。在临床治疗方面，目前市场上仅有苯硝唑和硝呋莫司两种药物上市，两者均推荐用于急性期，但慢性期治愈率较低。此外，强烈的副作用可能会导致停止这种治疗。面对这种情况，我们报告了 3-苯甲酰基-黄烷酮的合成和杀锥虫活性。在 3 步合成过程中以令人满意的产率制备了新型 3-苯甲酰基-黄烷酮衍生物。根据推荐的指南，使用了基于全细胞的筛选方法，允许同时使用导致人类感染的两种寄生虫形式。

  DOI：

  10.3390/molecules25020397

文献信息

• Conjugate addition to chromones: Synthesis of substituted 4-chromanones
  作者：Timothy W. Wallace

  DOI：10.1016/s0040-4039(01)81422-2

  日期：1984.1

  Chromones activated by carbonyl substituents at C-3 are transformed into the corresponding 2-methyl 4-chromanones by treating with lithium dimethylcuprate

  通过用二甲基二甲基碳酸锂处理，将在C-3处被羰基取代基活化的色酮转化为相应的2-甲基4-色酮
• Conjugate addition of cuprate reagents to chromones: A route to 2-substituted chroman-4-ones
  作者：Suthiweth T. Saengchantara、Timothy W. Wallace

  DOI：10.1016/s0040-4020(01)88394-0

  日期：1990.1

  Chromones (4-oxo-4H-1-benzopyrans) activated by electron-withdrawing groups attached to C-3 undergo efficient 1,4-additon of cuprate reagents, producing 2,3-disubstituted chroman-4-ones. The addition products from methyl chromone-3-carboxylates can be converted into 2-substituted chroman-4-ones by treatment with sodium chloride in wet dimethylsulphoxide.

  由与C-3相连的吸电子基团活化的苯并二氢呋喃酮（4-氧代-4H -1-苯并吡喃）经过有效的1,4-additon铜酸盐试剂，生成2,3-二取代的chroman-4-ones。通过在湿的二甲亚砜中用氯化钠处理，可以将苯甲酸三甲基苯甲酸酯的加成产物转化为2-取代的苯并四氢吡喃。
• Synthesis of 3-alkenyl-2-arylchromones and 2,3-dialkenylchromones via acid-catalysed retro-Michael ring opening of 3-acylchroman-4-ones
  作者：David S. Clarke、Christopher D. Gabbutt、John D. Hepworth、B. Mark Heron

  DOI：10.1016/j.tetlet.2005.06.058

  日期：2005.8

  3-Acylchromones and 3-acylflavones, readily available by acylation of 2'-hydroxydibenzoylmethane with acid anhydrides in the presence of base, undergo efficient conjugate reduction with NaBH4 in pyridine to give the corresponding chroman-4-ones/flavanones in high yields. The reduction is both regio- and chemoselective. Treatment of the chroman-4-ones with MeSO3H generates the 3-alkenyl-2-arylchromones by a dehydrative rearrangement initiated by retro-Michael cleavage of the pyranone ring. This reduction-rearrangement sequence can be extended to 2-alkyl-3-alkenoylchromones to generate 3-alkenyl-2-styrylchromones, the first examples of 2,3-dialkenylchromones. (c) 2005 Elsevier Ltd. All rights reserved.
• Trypanocidal Activity of Flavanone Derivatives
  作者：Gabriela Maciel Diogo、Josimara Souza Andrade、Policarpo Ademar Sales Junior、Silvane Maria Fonseca Murta、Viviane Martins Rebello Dos Santos、Jason Guy Taylor

  DOI：10.3390/molecules25020397

  日期：——

  rates in the chronic phase. Furthermore, strong side effects may result in discontinuation of this treatment. Faced with this situation, we report the synthesis and trypanocidal activity of 3-benzoyl-flavanones. Novel 3-benzoyl-flavanone derivatives were prepared in satisfactory yields in the 3-step synthetic procedure. According to recommended guidelines, the whole cell-based screening methodology

  恰加斯病，也称为美洲锥虫病，被世界卫生组织列为被忽视的疾病。在临床治疗方面，目前市场上仅有苯硝唑和硝呋莫司两种药物上市，两者均推荐用于急性期，但慢性期治愈率较低。此外，强烈的副作用可能会导致停止这种治疗。面对这种情况，我们报告了 3-苯甲酰基-黄烷酮的合成和杀锥虫活性。在 3 步合成过程中以令人满意的产率制备了新型 3-苯甲酰基-黄烷酮衍生物。根据推荐的指南，使用了基于全细胞的筛选方法，允许同时使用导致人类感染的两种寄生虫形式。