(Z)-methyl 2-[3-cyclopropylisobenzofuran-1(3H)-ylidene]acetate | 1383707-60-5

• 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: (Z)-methyl 2-[3-cyclopropylisobenzofuran-1(3H)-ylidene]acetate
• 英文别名: methyl (2Z)-2-(3-cyclopropyl-3H-2-benzofuran-1-ylidene)acetate
• CAS: 1383707-60-5
• 化学式: C₁₄H₁₄O₃
• 分子量: 230.263
• InChiKey: HQSQZRNLPPOASB-WQLSENKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  2-碘苯甲醛 在 三苯基膦 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 11.0h， 生成 (Z)-methyl 2-[3-cyclopropylisobenzofuran-1(3H)-ylidene]acetate 、 (E)-methyl 2-[3-cyclopropylisobenzofuran-1(3H)-ylidene]acetate
  参考文献：
  名称：

  Phosphine/Palladium-Catalyzed Syntheses of Alkylidene Phthalans, 3-Deoxyisoochracinic Acid, Isoochracinic Acid, and Isoochracinol

  摘要：

  In this study we used sequential catalysis-PPh3-catalyzed nucleophilic addition followed by Pd(0)-catalyzed Heck cyclization-to construct complex functionalized alkylidene phthalans rapidly, in high yields, and with good stereoselectivities (E/Z ratios of up to 1:22). The scope of this Michael-Heck reaction includes substrates bearing various substituents around the alkylidene phthalan backbone. Applying this efficient sequential catalysis, we accomplished concise total syntheses of 3-deoxyisoochacinic acid, isoochracinic acid, and isoochracinol.

  DOI：

  10.1021/ol301154f

文献信息

• Phosphine/Palladium-Catalyzed Syntheses of Alkylidene Phthalans, 3-Deoxyisoochracinic Acid, Isoochracinic Acid, and Isoochracinol
  作者：Yi Chiao Fan、Ohyun Kwon

  DOI：10.1021/ol301154f

  日期：2012.7.6

  In this study we used sequential catalysis-PPh3-catalyzed nucleophilic addition followed by Pd(0)-catalyzed Heck cyclization-to construct complex functionalized alkylidene phthalans rapidly, in high yields, and with good stereoselectivities (E/Z ratios of up to 1:22). The scope of this Michael-Heck reaction includes substrates bearing various substituents around the alkylidene phthalan backbone. Applying this efficient sequential catalysis, we accomplished concise total syntheses of 3-deoxyisoochacinic acid, isoochracinic acid, and isoochracinol.