2,3-dihydro-5,6-dimethoxybenzofuran

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: 2,3-dihydro-5,6-dimethoxybenzofuran
• 英文别名: 5,6-dimethoxy-2,3-dihydrobenzofuran
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: IIFYVOBSONVRKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.64
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2,3-dihydro-5,6-dimethoxybenzofuran 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以74%的产率得到2,3-dihydrobenzofuran-5,6-diol
  参考文献：
  名称：

  Simple and efficient synthesis of benzofuran derivatives from tyrosol

  摘要：

  A convenient strategy for the preparation of compounds bearing the benzofuran skeleton starting from tyrosol, a phenol largely present in olive oil production waste, with no biological importance, is reported. A bromination/methoxylation sequence, already described for the synthetic transformation of naturally occurring compounds, was exploited. Depending on the solvent used for the methoxylation reaction together with the presence of a 4-phenol moiety respect to the side chain, benzodihydrofurans or a benzofurans derivative can be obtained.

  DOI：

  10.1080/00397911.2015.1133828
• 作为产物：
  描述：

  4-羟基-3-甲氧基苯乙醇 在 吡啶 、 Oxone 、 sodium methylate 、 potassium carbonate 、 sodium bromide 、 copper(I) bromide 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 生成 2,3-dihydro-5,6-dimethoxybenzofuran
  参考文献：
  名称：

  Simple and efficient synthesis of benzofuran derivatives from tyrosol

  摘要：

  A convenient strategy for the preparation of compounds bearing the benzofuran skeleton starting from tyrosol, a phenol largely present in olive oil production waste, with no biological importance, is reported. A bromination/methoxylation sequence, already described for the synthetic transformation of naturally occurring compounds, was exploited. Depending on the solvent used for the methoxylation reaction together with the presence of a 4-phenol moiety respect to the side chain, benzodihydrofurans or a benzofurans derivative can be obtained.

  DOI：

  10.1080/00397911.2015.1133828

文献信息

• Synthesis of Functionalized Indolines and Dihydrobenzofurans by Iron and Copper Catalyzed Aryl C–N and C–O Bond Formation
  作者：Martyn C. Henry、Hans Martin Senn、Andrew Sutherland

  DOI：10.1021/acs.joc.8b02888

  日期：2019.1.4

  triflimide-catalyzed iodination, followed by a copper(I)-catalyzed intramolecular N- or O-arylation step leading to indolines, dihydrobenzofurans, and six-membered analogues. The general applicability and functional group tolerance of this method were exemplified by the total synthesis of the neolignan natural product, (+)-obtusafuran. DFT calculations using Fukui functions were also performed, providing a molecular

  描述了一种简单有效的一锅两步分子内芳基C–N和C–O键形成过程，该过程可利用铁和铜催化制备各种苯并稠合的杂环骨架。对活化的芳基环进行高度区域选择性，三氟甲磺酸铁（III）催化的碘化，然后进行铜（I）催化的分子内N-或O-芳基化步骤，生成二氢吲哚，二氢苯并呋喃和六元类似物。该方法的一般适用性和官能团耐受性由新木脂素天然产物（+）-奥布他呋喃的全合成例示。还进行了使用Fukui函数的DFT计算，从而为高度区域选择性的芳烃碘化过程提供了分子轨道原理。
• Nucleophilic attack of intramolecular hydroxyl groups on electron-rich aromatics using hypervalent iodine(III) oxidation
  作者：Kayoko Hata、Hiromi Hamamoto、Yukiko Shiozaki、Simon B. Cämmerer、Yasuyuki Kita

  DOI：10.1016/j.tet.2007.02.118

  日期：2007.5

  The hypervalent iodine(III) reagent, phenyliodine bis(trifluoroacetate) (PIFA)-mediated oxidative nucleophilic substitution of electron-rich aromatics involving aromatic cation radical intermediates was utilized in the direct aromatic carbon–oxygen bond formation reaction, and a novel and simple synthetic method for chroman derivatives was developed. As an extension of this methodology, a facile access

  高价碘试剂（IIIFA），苯碘酸双（三氟乙酸盐）（PIFA）介导的涉及芳香族阳离子自由基中间体的富电子芳族化合物的氧化亲核取代反应被用于直接的芳族碳-氧键形成反应中，以及一种新颖而简单的合成方法开发了苯并二氢吡喃衍生物的方法。作为该方法的扩展，还可以轻松获得螺二烯酮衍生物。
• A novel and direct synthesis of chroman derivatives using a hypervalent iodine(III) reagent
  作者：Hiromi Hamamoto、Kayoko Hata、Hisanori Nambu、Yukiko Shiozaki、Hirofumi Tohma、Yasuyuki Kita

  DOI：10.1016/j.tetlet.2004.01.104

  日期：2004.3

  The direct aromatic carbon–oxygen bond-formation reaction was described and the novel and simple synthetic method for chroman derivatives involving aromatic cation radical intermediates was developed using the hypervalent iodine(III) reagent, phenyliodine(III) bis(trifluoroacetate) (PIFA).

  描述了直接的芳族碳-氧键形成反应，并使用高价碘（III）试剂，苯基碘（III）双（三氟乙酸盐）（PIFA）开发了涉及芳族阳离子自由基中间体的苯并二氢吡喃衍生物的新颖而简单的合成方法。