6,7-methylenedioxy-3-methylisocoumarin | 78873-85-5

• 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: 6,7-methylenedioxy-3-methylisocoumarin
• 英文别名: 7-Methyl-2H,5H-[1,3]dioxolo[4,5-g][2]benzopyran-5-one；7-methyl-[1,3]dioxolo[4,5-g]isochromen-5-one
• CAS: 78873-85-5
• 化学式: C₁₁H₈O₄
• 分子量: 204.182
• InChiKey: JYHGXTZETHCXFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6,7-methylenedioxy-3-methylisocoumarin 在 镍 一水合肼 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 3-methyl-6,7-methylenedioxy-1(2H)-isoquinolone
  参考文献：
  名称：

  Datta, Debashish; Usgaonkar, R. N., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1981, vol. 20, # 5, p. 376 - 379

  摘要：

  DOI：
• 作为产物：
  描述：

  4,5-methylenedioxyhomophthalic acid 在 吡啶 、 sodium hydroxide 、 硫酸 作用下， 反应 4.0h， 生成 6,7-methylenedioxy-3-methylisocoumarin
  参考文献：
  名称：

  Thakur; Walavalkar; Mashelkar, Journal of the Indian Chemical Society, 1991, vol. 68, # 9, p. 526 - 528

  摘要：

  DOI：

文献信息

• Synthesis of Isocoumarin Derivatives via the Copper-Catalyzed Tandem Sequential Cyclization of 2- Halo-<i>N</i>-phenyl Benzamides and Acyclic 1,3-Diketones
  作者：Veerababurao Kavala、Cheng-Chuan Wang、Deepak Kumar Barange、Chun-Wei Kuo、Po-Min Lei、Ching-Fa Yao

  DOI：10.1021/jo300501j

  日期：2012.6.1

  A facile and rapid synthesis of isocoumarin derivatives using a copper-catalyzed tandem C–C/C–O coupling strategy from readily available substrates is described. The reactions of a wide range of 2-iodo-N-phenyl benzamides and acyclic diketones as starting materials were investigated.

  本文描述了一种利用铜催化的串联式C–C / C–O偶联策略从容易获得的底物中轻松快速合成异香豆素衍生物的方法。研究了各种2-碘-N-苯基苯甲酰胺和无环二酮作为起始原料的反应。
• Novel One-pot Synthesis of Polysubstituted Isocoumarins from Arynes and Trifluoroacetylated β-Diketones
  作者：Kentaro Okuma、Koki Hirano、Yukiko Tanabe、Ryoichi Itoyama、Atsumi Miura、Noriyoshi Nagahora、Kosei Shioji

  DOI：10.1246/cl.131112

  日期：2014.4.5

  Polysubstituted isocoumarins such as thunberginol A were synthesized by the reaction of substituted 2-(trimethylsilyl)phenyl triflate with trifluoromethylated β-diketones in the presence of CsF. The reaction proceeded via carbon–carbon bond insertion of aryne followed by intramolecular cyclization and CF3 anion extrusion. The –C(···O)CF3 unit has high potential for not only the nucleophilic moiety but also a useful leaving group of CF3.

  多取代的异香豆素如Thunberginol A是通过在CsF存在下，将取代的2-(三甲基硅基)苯三氟甲磺酸酯与三氟甲基化的β-二酮反应合成的。该反应是通过芳基炔的碳-碳键插入，再进行分子内环化和CF3阴离子的挤出进行的。-C(···O)CF3单元不仅具有成为亲核基团的高潜力，还具有作为CF3有用离去基团的优点。
• Reaction of arynes with trifluoroacetylated β-diketones: Novel formation of isocoumarins and phenanthrenes
  作者：Kentaro Okuma、Yukiko Tanabe、Takuto Fukami、Yuto Ishibashi

  DOI：10.1002/hc.21444

  日期：2018.12

  AbstractPolysubstituted isocoumarins were synthesized by the reaction of substituted 2‐(trimethylsilyl)aryl triflates with trifluoromethylated β‐diketones in the presence of CsF. The reaction proceeded through carbon‐carbon bond insertion of aryne and intramolecular cyclization to form intermediates of alcohol anions, which extruded trifluoromethyl anion to afford isocoumarins. By using CuBr as a catalyst, 2 eq. of aryne reacted with β‐diketones to afford phenanthrenes and 1,2‐diarylethanones. Although reaction of 2‐(trimethylsilyl)phenyl triflate with 1,1,1‐trifluoro‐4′‐methylbenzoylacetone in the presence of CsF gave 3‐(4′‐methylphenyl)isocoumarin in 67% yield, addition of 0.2 eq. of CuCN resulted in the formation of 9‐(4‐methylbenzoyl)‐10‐trifluoromethylphenanthrene in 35% yield.
• Datta, Debashish; Usgaonkar, R. N., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1981, vol. 20, # 5, p. 376 - 379
  作者：Datta, Debashish、Usgaonkar, R. N.

  DOI：——

  日期：——
• Thakur; Walavalkar; Mashelkar, Journal of the Indian Chemical Society, 1991, vol. 68, # 9, p. 526 - 528
  作者：Thakur、Walavalkar、Mashelkar

  DOI：——

  日期：——