(Z)-2-(isobenzofuran-1(3H)-ylidene)-1-phenylethanone | 935521-30-5

• 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)-2-(isobenzofuran-1(3H)-ylidene)-1-phenylethanone
• 英文别名: (Z)-2-[isobenzofuran-1(3H)-ylidene]-1-phenylethanone；(2Z)-2-(1(3H)-Isobenzofuranylidene)-1-phenylethanone；(2Z)-2-(3H-2-benzofuran-1-ylidene)-1-phenylethanone
• CAS: 935521-30-5
• 化学式: C₁₆H₁₂O₂
• 分子量: 236.27
• InChiKey: WWPOXRDUIFCTJB-YBEGLDIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  苯甲醛 在 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 10.0h， 生成 (E)-2-(isobenzofuran-1(3H)-ylidene)-1-phenylethanone 、 (Z)-2-(isobenzofuran-1(3H)-ylidene)-1-phenylethanone
  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

• Cyclocarbonylative Sonogashira Reactions of 1-Ethynylbenzyl Alcohols: Synthesis of 1-Carbonylmethylene-1,3-Dihydroisobenzofurans
  作者：Laura Antonella Aronica、Luca Giannotti、Giulia Tuci、Francesco Zinna

  DOI：10.1002/ejoc.201500539

  日期：2015.8

  In this work, we present a carbonylative Sonogashira reaction of o-ethynyl benzyl alcohols and aryl iodides, followed by a cyclization process to selectively give carbonylmethylene isobenzofurans in high yields and in an atom-economic fashion. The reaction can be carried out in the absence of CuI, with a small amount of PdCl2(PPh3)2 (0.2–0.5 mol-%), using aryl iodides bearing both electron-withdrawing

  在这项工作中，我们提出了邻乙炔基苄醇和芳基碘的羰基化 Sonogashira 反应，然后通过环化过程以高产率和原子经济的方式选择性地得到羰基亚甲基异苯并呋喃。该反应可以在不存在 CuI 的情况下，使用带有吸电子和给电子基团的芳基碘，使用少量 PdCl2(PPh3)2（0.2-0.5 mol%）进行。在两种可能的立体异构产物中，Z-异苯并呋喃衍生物是主要产物。但是，当反应扩展到仲醇时，观察到立体选择性的有趣转变。
• 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.