2-[1(3H)-isobenzofuranylidene]-acetic acid ethyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: 2-[1(3H)-isobenzofuranylidene]-acetic acid ethyl ester
• 英文别名: (Z)-ethyl 2-(isobenzofuran-1(3H)-ylidene)acetate；ethyl (2Z)-2-(3H-2-benzofuran-1-ylidene)acetate
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: ATRMQGBHWZPEFR-XFFZJAGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-甲基苯基乙酮 在 N-甲基咪唑 、 乙醇 、 sodium 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 2-[1(3H)-isobenzofuranylidene]-acetic acid ethyl ester
  参考文献：
  名称：

  Photochemical Preparation of Highly Functionalized 1-Indanones

  摘要：

  A series of o-alkylphenyl alkyl ketones I were synthesized by different methods. The presence of a leaving group X adjacent to the carbonyl group is the special peculiarity of these ketones. Upon irradiation the keto carbonyl group of these compounds undergoes an n-pi* excitation followed by a 1,5-hydrogen migration from the o-alkyl substituent to the carbonyl oxygen atom. The thus formed 1,4-diradicals are subject to a very rapid elimination of acid HX, giving 1,5-diradicals. We called this process spin center shift. After intersystem crossing these diradicals cyclize to 1-indanones 20 in good yields. Depending on the solvent and on substituents, o-alkoxyalkyl ketones 22 or benzo[c]furanes 21 are obtained as byproducts. The mechanism of the cyclization was elucidated by quantum chemical calculations and kinetic measurements.

  DOI：

  10.1021/jo040173x

文献信息

• Organic acid induced olefination reaction of lactones
  作者：Hikaru Yanai、Takeo Taguchi

  DOI：10.1039/c2cc33606e

  日期：——

  (Z)-Selective olefination of several lactones with ketene silyl acetals was achieved by the catalysis of carbon acids (C–H acids) having a bis(triflyl)methyl group as an acidic functionality; in particular, the triple carbon acid having three bis(triflyl)methyl groups in phloroglucinol shows an excellent catalytic performance.

  通过含有双(triflyl)甲基作为酸性官能团的碳酸（C–H酸）催化，实现了几种内酯与酮烯丙基乙酯的 (Z)-选择性烯化；尤其是具有三个双(triflyl)甲基的三重碳酸的苯酚磷酸在催化性能上表现出色。