(Z)-3-(2'-hydroxy-2'-phenylethylidene)phthalide | 147454-73-7

• 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: (Z)-3-(2'-hydroxy-2'-phenylethylidene)phthalide
• 英文别名: (3Z)-3-(2-hydroxy-2-phenylethylidene)-2-benzofuran-1-one
• CAS: 147454-73-7
• 化学式: C₁₆H₁₂O₃
• 分子量: 252.269
• InChiKey: VGPFRBIYDMDWFN-GDNBJRDFSA-N

物化性质

• 沸点：
  459.0±45.0 °C(Predicted)
• 密度：
  1.384±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-3-(2'-hydroxy-2'-phenylethylidene)phthalide 在 jones reagent 作用下， 以 丙酮 为溶剂， 以20%的产率得到(Z)-3-(2'-oxo-2'-phenyl)ethylidene isobenzofuran-1(3H)-one
  参考文献：
  名称：

  Palladium-catalysed heteroannulation with terminal alkynes: synthesis of phthalides 1

  摘要：

  钯-铜催化的o-碘苯甲酸3与末端炔烃4-18的杂环化反应主要合成得到(Z)-3-烷亚基苯并呋喃19-33。在某些情况下，也会观察到异香豆素34-37的形成。

  DOI：

  10.1039/a705450e
• 作为产物：
  描述：

  、 一氧化碳 以 四氢呋喃 为溶剂， 反应 0.08h， 以42%的产率得到(Z)-3-(2'-hydroxy-2'-phenylethylidene)phthalide
  参考文献：
  名称：

  Synthesis and Aldol Reactivity of O- and C-Enolate Complexes of Nickel

  摘要：

  The often facile C-/O-tautomerization of transition metal enolates is severely hindered in the cyclic Ni complexes 1 and 2, allowing the study of their individual reactivities. At room temperature only the O-bound tautomer, 2, reacts with aldehydes, giving rise to the corresponding addition products.

  DOI：

  10.1021/ja028711f

文献信息

• Synthesis of phthalides through palladium-catalysed heteroannulation of acetylenic compounds
  作者：Nitya G. Kundu、Manojit Pal

  DOI：10.1039/c39930000086

  日期：——

  The reaction of o-iodobenzoic acid with various acetylenic compounds in the presence of a palladium catalyst leads to phthalides [1-(3H)isobenzofuran-3-ones] as major products and isocoumarins as minor products.

  邻碘苯甲酸与各种乙炔化合物在钯催化剂的存在下反应，主要生成酞烯 [1-(3H)异苯并呋喃-3-酮]，少量生成异香豆素。
• Cyclic Enolates of Ni and Pd: Equilibrium between C- and O-Bound Tautomers and Reactivity Studies
  作者：Juan Cámpora、Celia M. Maya、Pilar Palma、Ernesto Carmona、Enrique Gutiérrez、Caridad Ruiz、Claudia Graiff、Antonio Tiripicchio

  DOI：10.1002/chem.200500622

  日期：2005.11.18

  formed as the corresponding O-tautomers. Slow equilibration between O- and C-enolate tautomers is observed for the nickel complex with an unsubstituted enolate function (M-O-C=CH(2)). Theoretical DFT calculations suggest that the barrier for the tautomer exchange has its origin in the rigidity of the metallacycle. Whilst the C-enolate tautomer is unreactive towards aldehydes, the corresponding O-enolate

  Ni和Pd的螯合二膦的2-酰基芳基配合物与KtBuO反应生成金属环烯醇化物配合物。在Pd的情况下，最好通过碳原子进行配位，但形成的O-烯醇镍镍化合物是相应的O-互变异构体。对于具有未取代的烯酸酯功能（MOC = CH（2））的镍配合物，观察到O和C烯酸酯互变异构体之间的平衡缓慢。DFT理论计算表明，互变异构体交换的障碍源于金属环的刚性。C-烯醇式互变异构体对醛不具有反应性，而相应的O-烯醇式添加到MeCHO和PhCHO中，产生了保留烯醇式官能团的产物。这些产物的羰基化干净地导致以高度选择性的方式形成烯醇内酯。
• Palladium-catalysed heteroannulation with terminal alkynes: synthesis of phthalides 1
  作者：Nitya G. Kundu、Manojit Pal、Bidisha Nandi

  DOI：10.1039/a705450e

  日期：——

  The palladium–copper-catalysed heteroannulation of o-iodobenzoic acid 3 with terminal alkynes 4–18 leads to the synthesis of (Z)-3-alkylidenephthalides 19–33 as the major products. In certain cases, the formation of isocoumarins 34–37 is also observed.

  钯-铜催化的o-碘苯甲酸3与末端炔烃4-18的杂环化反应主要合成得到(Z)-3-烷亚基苯并呋喃19-33。在某些情况下，也会观察到异香豆素34-37的形成。
• Synthesis and Aldol Reactivity of <i>O</i>- and <i>C</i>-Enolate Complexes of Nickel
  作者：Juan Cámpora、Celia M. Maya、Pilar Palma、Ernesto Carmona、Enrique Gutiérrez-Puebla、Caridad Ruiz

  DOI：10.1021/ja028711f

  日期：2003.2.1

  The often facile C-/O-tautomerization of transition metal enolates is severely hindered in the cyclic Ni complexes 1 and 2, allowing the study of their individual reactivities. At room temperature only the O-bound tautomer, 2, reacts with aldehydes, giving rise to the corresponding addition products.