[2-(benzyloxy)-6-iodophenyl]methanol | 1383707-35-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: [2-(benzyloxy)-6-iodophenyl]methanol
• 英文别名: 6-benzyloxy-2-iodobenzyl alcohol；(2-Iodo-6-phenylmethoxyphenyl)methanol
• CAS: 1383707-35-4
• 化学式: C₁₄H₁₃IO₂
• 分子量: 340.161
• InChiKey: KJHCBPVHWOZOQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [2-(benzyloxy)-6-iodophenyl]methanol 在 palladium 10% on activated carbon 、 氢气 、 三苯基膦 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 20.0 ℃ 、800.01 kPa 条件下， 反应 11.0h， 生成 3-deoxoisoochracinic acid
  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：

  甲氧基苯甲酰氯 在 disodium hydrogenphosphate 、 四甲基乙二胺 、 仲丁基锂 、 三溴化硼 、 二异丁基氢化铝 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 环己烷 、 甲苯 、 乙腈 为溶剂， 反应 29.1h， 生成 [2-(benzyloxy)-6-iodophenyl]methanol
  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

• Synthesis of Functionalized Alkylidene Indanes and Indanones through Tandem Phosphine–Palladium Catalysis
  作者：Yi Chiao Fan、Ohyun Kwon

  DOI：10.1021/acs.orglett.5b00554

  日期：2015.5.1

  Densely functionalized alkylidene indanes and indanones can be prepared efficiently in On pot, in high yields with good stereoselectivities (in some cases exclusively the Z-isomer), through a route involving phosphine-catalyzed Michael addition followed by palladium-catalyzed Heck cyclization. These transformations tolerate substrates bearing various substituents around the indane/indanone motif. Employing this technology, a concise formal synthesis of sulindac, nonsteroidal anti-inflammatory drug, has been established.