6,8-dimethoxy-3-phenyl-1H-isochromen-1-one | 109480-70-8

• 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: 6,8-dimethoxy-3-phenyl-1H-isochromen-1-one
• 英文别名: 6,8-Dimethoxy-3-phenyl-1H-2-benzopyran-1-one；6,8-dimethoxy-3-phenylisochromen-1-one
• CAS: 109480-70-8
• 化学式: C₁₇H₁₄O₄
• 分子量: 282.296
• InChiKey: KIZKMSNLGKOFTM-UHFFFAOYSA-N

物化性质

• 熔点：
  163-164 °C
• 沸点：
  472.2±45.0 °C(Predicted)
• 密度：
  1.242±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-甲基-N-甲基苯甲酰胺 在 叔丁醇 sodium hydride 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 6,8-dimethoxy-3-phenyl-1H-isochromen-1-one
  参考文献：
  名称：

  A Convenient Synthesis of 3-Substituted 8-Methoxy-and 6,8-Dimethoxyisocoumarins

  摘要：

  N-甲氧基-N-甲基酰胺与2-甲氧基-乙基或2,4-二甲氧基-6-甲基苯甲酸根阴离子反应，生成相应的酮，这些酮环化后生成3-取代的8-甲氧基和6,8-二甲氧基异香豆素，总收率较高。

  DOI：

  10.1055/s-1986-31832

文献信息

• Regioselective One-Pot Synthesis of Isocoumarins and Phthalides from 2-Iodobenzoic Acids and Alkynes by Temperature Control
  作者：Manian Rajesh Kumar、Francis Mariaraj Irudayanathan、Joong Ho Moon、Sunwoo Lee

  DOI：10.1002/adsc.201300561

  日期：2013.11.11

  AbstractCopper‐catalyzed coupling reaction of 2‐iodobenzoic acids and alkynes such as terminal acetylenes, alkynyl carboxylic acids, and trimethylsilylacetylene selectively afforded isocoumarins and phthalides in the presence of cesium carbonate (Cs2CO3) and dimethyl sulfoxide (DMSO). Among the regioselective products, only the 6‐endo‐dig product, isocoumarin, was formed at 100 °C, and the 5‐exo‐dig product, phthalide, was formed as a major product at 25 °C. A variety of alkynes produced the corresponding isocoumarins and phthalides in good yields. A mechanism is suggested in which the formation of 2‐alkynylbenzoic acid as an intermediate via Sonogashira‐type coupling was ruled out in the reaction pathway.magnified image
• LEWIS CH. N.; SPARGO P. L.; STAUNTON J., SYNTHESIS,(1986) N 11, 944-946
  作者：LEWIS CH. N.、 SPARGO P. L.、 STAUNTON J.

  DOI：——

  日期：——
• A Convenient Synthesis of 3-Substituted 8-Methoxy-and 6,8-Dimethoxyisocoumarins
  作者：Christopher N. Lewis、Peter L. Spargo、James Staunton

  DOI：10.1055/s-1986-31832

  日期：——

  The reaction of N-methoxy-N-methylamides with the anion of ethyl 2-methoxy- , or 2,4-dimethoxy-6-methylbenzoate gives the corresponding ketones, which are cyclised to give the 3-substituted 8-methoxy- and 6,8-dimethoxy-isocoumarins in good overall yield.

  N-甲氧基-N-甲基酰胺与2-甲氧基-乙基或2,4-二甲氧基-6-甲基苯甲酸根阴离子反应，生成相应的酮，这些酮环化后生成3-取代的8-甲氧基和6,8-二甲氧基异香豆素，总收率较高。