10-[(E)-2-methyl-3-phenylprop-2-enoyl]acridin-9-one | 249919-39-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 10-[(E)-2-methyl-3-phenylprop-2-enoyl]acridin-9-one
• CAS: 249919-39-9
• 化学式: C₂₃H₁₇NO₂
• 分子量: 339.393
• InChiKey: QIEALCLKEWBLGK-FOCLMDBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  10-[(E)-2-methyl-3-phenylprop-2-enoyl]acridin-9-one 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 以90%的产率得到3-苯基-2-甲基丙-2-烯酸
  参考文献：
  名称：

  Lewis Acid Promoted Hetero [2 + 2] Cycloaddition Reactions of Aldehydes with 10-Propynyl-9(10H)-acridone. A Highly Stereoselective Synthesis of Acrylic Acid Derivatives and 1,3-Dienes Using an Electron Deficient Variant of Ynamine

  摘要：

  [GRAPHICS]Reactivities of 10 propynyl-9(10H)-acridone toward various aldehydes in BF3. Et2O-promoted hetero [2 + 2] cycloaddition reactions are described here. This electron deficient variant of ynamine is more stable and easier to handle than most ynamines but possesses comparable reactivity. These reactions lead to a highly stereoselective synthesis of trisubstituted alkenes. A mechanistic model based on the stereochemical assignment is also described here, 10-Propynyl-9(10H)-acridone is also reactive toward ag-unsaturated aldehydes and ketones. It provides hetero [2 + 2] products in reactions with alpha,beta-unsaturated aldehydes but gives only the inverse demand [4 + 2] cycloadduct in a reaction with methyl vinyl ketone.

  DOI：

  10.1021/ol990211c
• 作为产物：
  描述：

  10-(prop-2-yn-1-yl)acridone 在 氢氧化钾 、 三氟化硼乙醚 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 生成 10-[(E)-2-methyl-3-phenylprop-2-enoyl]acridin-9-one
  参考文献：
  名称：

  Lewis Acid Promoted Hetero [2 + 2] Cycloaddition Reactions of Aldehydes with 10-Propynyl-9(10H)-acridone. A Highly Stereoselective Synthesis of Acrylic Acid Derivatives and 1,3-Dienes Using an Electron Deficient Variant of Ynamine

  摘要：

  [GRAPHICS]Reactivities of 10 propynyl-9(10H)-acridone toward various aldehydes in BF3. Et2O-promoted hetero [2 + 2] cycloaddition reactions are described here. This electron deficient variant of ynamine is more stable and easier to handle than most ynamines but possesses comparable reactivity. These reactions lead to a highly stereoselective synthesis of trisubstituted alkenes. A mechanistic model based on the stereochemical assignment is also described here, 10-Propynyl-9(10H)-acridone is also reactive toward ag-unsaturated aldehydes and ketones. It provides hetero [2 + 2] products in reactions with alpha,beta-unsaturated aldehydes but gives only the inverse demand [4 + 2] cycloadduct in a reaction with methyl vinyl ketone.

  DOI：

  10.1021/ol990211c

文献信息

• Lewis Acid Promoted Hetero [2 + 2] Cycloaddition Reactions of Aldehydes with 10-Propynyl-9(10<i>H</i>)-acridone. A Highly Stereoselective Synthesis of Acrylic Acid Derivatives and 1,3-Dienes Using an Electron Deficient Variant of Ynamine
  作者：Richard P. Hsung、Craig A. Zificsak、Lin-Li Wei、Christopher J. Douglas、Hui Xiong、Jason A. Mulder

  DOI：10.1021/ol990211c

  日期：1999.10.1

  [GRAPHICS]Reactivities of 10 propynyl-9(10H)-acridone toward various aldehydes in BF3. Et2O-promoted hetero [2 + 2] cycloaddition reactions are described here. This electron deficient variant of ynamine is more stable and easier to handle than most ynamines but possesses comparable reactivity. These reactions lead to a highly stereoselective synthesis of trisubstituted alkenes. A mechanistic model based on the stereochemical assignment is also described here, 10-Propynyl-9(10H)-acridone is also reactive toward ag-unsaturated aldehydes and ketones. It provides hetero [2 + 2] products in reactions with alpha,beta-unsaturated aldehydes but gives only the inverse demand [4 + 2] cycloadduct in a reaction with methyl vinyl ketone.