3-(2-hydroxyethyl)-1H-isochromen-1-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异香豆素及其衍生物
• 英文名称: 3-(2-hydroxyethyl)-1H-isochromen-1-one
• 英文别名: 3-(2-Hydroxyethyl)isochromen-1-one
• 化学式: C₁₁H₁₀O₃
• 分子量: 190.199
• InChiKey: FFXZXDXQOBDRHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  methyl 2-(4-hydroxybut-1-yn-1-yl)benzoate 在 三氟化硼乙醚 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.0h， 以98%的产率得到3-(2-hydroxyethyl)-1H-isochromen-1-one
  参考文献：
  名称：

  Lactonization of 2-Alkynylbenzoates for the Assembly of Isochromenones Mediated by BF₃·Et₂O

  摘要：

  A general and efficient lactonization method of readily available 2-alkynylbenzoates affording biologically important isochromenones has been realized via a solely BF3 center dot Et2O-mediated 6-endo-dig cyclization process under mild conditions. An alternative mechanistic pathway in which BF3 center dot Et2O activates the carbonyl of the ester moiety, rather than the alkyne triple bond, was postulated on the basis of control experiment results. Gram-scale reaction and further application for the assembly of more complex molecules demonstrated the practicability of the protocol.

  DOI：

  10.1021/acs.joc.9b01601

文献信息

• Palladium complexes with an annellated mesoionic carbene (MIC) ligand: catalytic sequential Sonogashira coupling/cyclization reaction for one-pot synthesis of benzofuran, indole, isocoumarin and isoquinolone derivatives
  作者：Akshi Tyagi、Noor U Din Reshi、Prosenjit Daw、Jitendra K. Bera

  DOI：10.1039/d0dt02918a

  日期：——

  Two Pd(II) complexes (1 and 2) featuring a fused π-conjugated imidazo[1,2-a][1,8]naphthyridine-based mesoionic carbene ligand have been synthesized and structurally characterized. Both complexes effectively catalyze the one-pot synthesis of benzofuran starting from phenylacetylene and 2-iodophenol under mild conditions. Complex 1 is found to be an excellent catalyst for the straightforward access to

  合成了两个Pd（II）配合物（1和2），这些配合物具有基于π-共轭咪唑并[1,2- a ] [1,8]萘啶基的介电卡宾配体的稠合结构。两种络合物在温和条件下均能有效地催化苯乙炔和2-碘苯酚的一锅法合成苯并呋喃。通过末端炔烃与苯酚，N-甲基苯胺，苯甲酸和N的2-碘衍生物的反应，发现配合物1是直接访问苯并呋喃，吲哚，异香豆素和异喹诺酮衍生物库的极佳催化剂。-甲基苯甲酰胺。使用多种不同取代的末端炔烃证明了催化方法的通用性，并以良好或优异的收率获得了相应的所需产物。在对照实验的基础上，提出了一种二循环机理，该机理涉及2-碘衍生物与炔烃的Sonogashira偶联以及随后的相应2-炔基化合物的环化。
• An Apparent Umpolung Reactivity of Indole through [Au]‐Catalysed Cyclisation and Lewis‐Acid‐Mediated Allylation
  作者：Mahesh H. Shinde、Chepuri V. Ramana

  DOI：10.1002/chem.202003441

  日期：2020.12.18

  predesigned substrate and choice of reagents. The developed method comprises gold‐catalysed alkynol cycloisomerisation/intramolecular addition of C2 of indole and subsequent BF3⋅OEt2‐mediated regioselective C3 allylation, resulting in the synthesis of the functionalized indoloisoquinolinone scaffold. The reaction involves 5‐endo‐alkynol cycloisomerisation and the dearomative addition of indole C2 to the intermediate

  用预先设计的底物和试剂的选择，将吲哚C2和C3以功能增强的顺序官能化。所提出的方法包括：金-催化的炔醇cycloisomerisation /分子内加成C2的吲哚和随后的BF的3 ⋅ OET 2介导的区域选择性C3烯丙基化，从而导致在官能indoloisoquinolinone支架的合成。该反应涉及5-内炔基环异构化和将吲哚C2脱芳香基加成到中间氧碳鎓阳离子上，这导致两个平衡的稠合和螺环戊二烯中间体，在BF 3 · OEt 2存在下用烯丙基硅烷处理，进行选择性吲哚C3烯丙基化。还发现其他亲核试剂，例如氢化物，叠氮化物和吲哚也与此过程相容。
• Synthesis of Isocoumarins via Pd/C-Mediated Reactions of <i>o</i>-Iodobenzoic Acid with Terminal Alkynes
  作者：Venkataraman Subramanian、Venkateswara Rao Batchu、Deepak Barange、Manojit Pal

  DOI：10.1021/jo050440e

  日期：2005.6.1

  The coupling reaction of o-iodobenzoic acid with terminal alkynes by using a catalyst system of 10% Pd/C-Et3N-CuI-PPh3 has been studied in a variety of solvents. 3-Substituted isocoumarins were formed in good yields and with good regioselectivity when the reaction was performed in EtOH.