3-deoxoisoochracinic acid

• 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: 3-deoxoisoochracinic acid
• 英文别名: 2-(4-Hydroxy-1,3-dihydro-2-benzofuran-1-yl)acetic acid
• 化学式: C₁₀H₁₀O₄
• 分子量: 194.187
• InChiKey: WDZMAKLDQJGEFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 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

• 作为反应物：
  描述：

  3-deoxoisoochracinic acid 在 chromium(VI) oxide 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 42.0h， 以44%的产率得到2-(4-羟基-3-氧代-1H-2-苯并呋喃-1-基)乙酸
  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-苄氧基苯甲醇 在 N-羟基邻苯二甲酰亚胺 、 N-乙酰-L-缬氨酸 、 palladium 10% on activated carbon 、 氢气 、 silver(I) acetate 、 palladium diacetate 、 sodium hydride 、 三苯基膦 、 偶氮二甲酸二乙酯 、 molybdenum hexacarbonyl 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 乙酸乙酯 、 乙腈 为溶剂， -50.0~90.0 ℃ 、101.33 kPa 条件下， 反应 28.5h， 生成 3-deoxoisoochracinic acid
  参考文献：
  名称：

  Direct ortho-C–H Functionalization of Aromatic Alcohols Masked by Acetone Oxime Ether via exo-Palladacycle

  摘要：

  Use of an iridium catalyst allowed the efficient dehydrogenative functionalization of C-H bonds of azulenes with the production of hydrogen as the sole byproduct. The reaction occurred with excellent chemo- and regioselectivities to provide 2-silylazulenes even without any directing groups. Effective conjugation through the 2-position of the azulene ring was demonstrated by the unique stimuli-responsiveness against an acidbase reaction.

  DOI：

  10.1021/acs.orglett.5b00594

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.
• Direct <i>ortho</i>-C–H Functionalization of Aromatic Alcohols Masked by Acetone Oxime Ether via <i>exo</i>-Palladacycle
  作者：Kun Guo、Xiaolan Chen、Mingyu Guan、Yingsheng Zhao

  DOI：10.1021/acs.orglett.5b00594

  日期：2015.4.3

  Use of an iridium catalyst allowed the efficient dehydrogenative functionalization of C-H bonds of azulenes with the production of hydrogen as the sole byproduct. The reaction occurred with excellent chemo- and regioselectivities to provide 2-silylazulenes even without any directing groups. Effective conjugation through the 2-position of the azulene ring was demonstrated by the unique stimuli-responsiveness against an acidbase reaction.

表征谱图