2-(4-羟基-3-氧代-1H-2-苯并呋喃-1-基)乙酸 | 66820-34-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 中文名称: 2-(4-羟基-3-氧代-1H-2-苯并呋喃-1-基)乙酸
• 英文名称: isoochracinic acid
• 英文别名: 1-Isobenzofuranacetic acid, 1,3-dihydro-4-hydroxy-3-oxo-, (+-)-；2-(4-hydroxy-3-oxo-1H-2-benzofuran-1-yl)acetic acid
• CAS: 66820-34-6
• 化学式: C₁₀H₈O₅
• 分子量: 208.171
• InChiKey: JUVHLXCMFDJFQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(4-羟基-3-氧代-1H-2-苯并呋喃-1-基)乙酸 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 以64%的产率得到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
• 作为产物：
  描述：

  2-甲氧基-N-甲基苯甲酰胺 在 盐酸 、 正丁基锂 、 三氯化铝 、 四甲基乙二胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 38.5h， 生成 2-(4-羟基-3-氧代-1H-2-苯并呋喃-1-基)乙酸
  参考文献：
  名称：

  Yeola, Suresh N.; Mali, R. S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 804 - 806

  摘要：

  DOI：

文献信息

• Directed ortho metalation of n,n-diethyl benzamides. Methodology and regiospecific synthesis of useful contiguously tri- and tetra-substituted oxygenated aromatics, phthalides and phthalic anhydrides
  作者：S.O. de Silva、J.N. Reed、R.J. Billedeau、X. Wang、D.J. Norris、V. Snieckus

  DOI：10.1016/s0040-4020(01)81579-9

  日期：1992.6

  contiguously 1,2,3- and 1,2,3,4-substituted benzamides (Tables 2) are given. The efficient conversion of these benzamides (6, 10, 12, 13, 18, 19) into phthalides (9a–b, 16b–c, 17) and phthalic anhydrides (8, 16a), compounds previously available by demanding, classical methods, is detailed. A short synthesis of iso-ochracinic acid (27) is described.

  针对各种直接邻位取代的N，N-二乙基苯甲酰胺（表1）和连续的1,2,3-和1,2,3,4-取代苯甲酰胺（表2）的定向邻位金属化的完整实验细节给出。这些苯甲酰胺（有效转化6，10，12，13，18，19）成苯酞（9A-B，图16B-C，17）和邻苯二甲酸酐（8，16A），化合物先前可用通过要求，经典方法，详细。描述了异och酸的简短合成（27）。
• 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。
• Regiocontrolled synthesis of hydroxyphthalides. Synthesis of (.+-.)-isoochracinic acid and a zealeranone intermediate
  作者：Barry M. Trost、Gordon T. Rivers、Jeffrey M. Gold

  DOI：10.1021/jo01298a017

  日期：1980.5
• 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.
• Yeola, Suresh N.; Mali, R. S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 804 - 806
  作者：Yeola, Suresh N.、Mali, R. S.

  DOI：——

  日期：——