7-hydroxy-3-(2-hydroxyethyl)-1(3H)-isobenzofuranone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 7-hydroxy-3-(2-hydroxyethyl)-1(3H)-isobenzofuranone
• 英文别名: isoochracinol；7-hydroxy-3-(2-hydroxyethyl)-3H-2-benzofuran-1-one
• 化学式: C₁₀H₁₀O₄
• 分子量: 194.187
• InChiKey: FDAOUJHEWGCELW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  methyl 2-hydroxy-6-iodobenzoate 在 chromium(VI) oxide 、 硼烷四氢呋喃络合物 、 palladium 10% on activated carbon 、 氢气 、 二异丁基氢化铝 、 potassium carbonate 、 溶剂黄146 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 乙酸乙酯 、 甲苯 、 乙腈 为溶剂， -78.0~20.0 ℃ 、800.01 kPa 条件下， 反应 55.0h， 生成 7-hydroxy-3-(2-hydroxyethyl)-1(3H)-isobenzofuranone
  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

• Catalytic Dehydrative Lactonization of Allylic Alcohols
  作者：Ji Liu、Romain J. Miotto、Julien Segard、Ashley M. Erb、Aaron Aponick

  DOI：10.1021/acs.orglett.8b01063

  日期：2018.5.18

  the synthesis of phthalides and γ-butyrolactones is reported. The method utilizes readily prepared allylic alcohols in formal Au(I)- and Pd(II)-catalyzed SN2′ reactions. Using these catalysts, exclusive formation of the desired five-membered lactones is observed, completely avoiding the competing direct lactonization pathway that forms the undesired seven-membered ring with protic acids and alternative

  报道了合成邻苯二甲酸盐和γ-丁内酯的简便策略。该方法在正式的Au（I）和Pd（II）催化的S N 2'反应中利用易于制备的烯丙醇。使用这些催化剂，观察到所需五元内酯的排他形成，完全避免了竞争的直接内酯化途径，后者与质子酸和其他金属盐形成了不希望的七元环。这种温和且操作简单的方法尤其可以耐受环乙亚甲基，应在邻苯二甲酸酯和萜烯合成中找到用途。
• 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.

表征谱图