2,3-dihydro-5-methoxy-2-methylbenzofuran | 13391-29-2

• 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-methoxy-2-methylbenzofuran
• 英文别名: 5-methoxy-2-methyl-2,3-dihydrobenzofuran；5-methoxy-2-methylcoumaran；5-Methoxy-2-methyl-2,3-dihydro-benzofuran；5-methoxy-2-methyl-2,3-dihydro-1-benzofuran
• CAS: 13391-29-2
• 化学式: C₁₀H₁₂O₂
• 分子量: 164.204
• InChiKey: DHLIJVBAPFOASD-UHFFFAOYSA-N

物化性质

• 沸点：
  85 °C(Press: 12 Torr)
• 密度：
  1.069±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-dihydro-5-methoxy-2-methylbenzofuran 在 ammonium acetate 、 三氯氧磷 作用下， 反应 3.5h， 生成 5-methoxy-2-methyl-6-(2-nitro-1-propenyl)-2,3-dihydrobenzofuran
  参考文献：
  名称：

  Synthesis and evaluation of 2,3-dihydrobenzofuran analogs of the hallucinogen 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane: drug discrimination studies in rats

  摘要：

  Two analogues, 6-(2-aminopropyl)-5-methoxy-2,3-dihydrobenzofuran and 6-(2-aminopropyl)-5-methoxy-2-methyl-2,3-dihydrobenzofuran, of the hallucinogenic agent 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM) were synthesized and tested in the two-lever drug discrimination paradigm. In rats trained to discriminate saline from LSD tartrate (0.08 mg/kg), stimulus generalization occurred to both of the 2,3-dihydrobenzofuran analogues but at doses more than 10-fold higher than for DOM. A possible explanation for this dramatic attenuation of LSD-like activity could involve a highly directional electrophilic binding site on the receptor that cannot accept the orientation of the unshared electron pairs on the heterocyclic oxygen atom in the benzofurans.

  DOI：

  10.1021/jm00152a022
• 作为产物：
  描述：

  1-(3-methoxyphenyl)isopropanol 在 p-tolyl-λ³-iodanediyl bis(2,2,2-trifluoroacetate) 、 三乙胺 、 copper(II) hexafluoroacetylacetonate 作用下， 以 2,2,2-三氟乙醇 为溶剂， 反应 16.0h， 以96%的产率得到2,3-dihydro-5-methoxy-2-methylbenzofuran
  参考文献：
  名称：

  温和条件下直接形成芳基 C−O 键合成功能化二氢苯并呋喃

  摘要：

  描述了一种通过直接形成芳基 CO 键来合成二氢苯并呋喃的方法。该反应的机械途径与之前描述的类似转化不同，允许温和的反应条件，预计与功能化底物兼容。

  DOI：

  10.1002/anie.201605648

文献信息

• Imidazolium and pyridinium salts – solvents influencing the rate and direction of the Fries, Beckmann, and Claisen rearrangements
  作者：S. Katkevica、A. Zicmanis、P. Mekss

  DOI：10.1007/s10593-010-0487-0

  日期：2010.6

  The Fries, Beckmann, and Claisen rearrangements have been investigated in ionic liquid media. The effect of the structural elements of the latter on the direction of these rearrangements and the product yields has been studied.

  已经在离子液体介质中研究了Fries，Beckmann和Claisen重排。已经研究了后者的结构元件对这些重排方向和产物产率的影响。
• Investigation and mechanistic study into intramolecular hydroalkoxylation of unactivated alkenols catalyzed by cationic lanthanide complexes
  作者：Xuehua Zhu、Guoyao Li、Fan Xu、Yong Zhang、Mingqiang Xue、Qi Shen

  DOI：10.1016/j.tet.2017.01.051

  日期：2017.3

  Cationic lanthanide complexes of the type [Ln(CH3CN)9]3+[(AlCl4)3]3–·CH3CN (Ln = Pr, Nd, Sm, Gd, Er, Yb, Y) served as effective catalysts for the intramolecular hydroalkoxylation/cyclization of unactivated alkenols to yield the cyclic ethers with Markovnikov regioselectivity under mild conditions. Novel cationic complexes, [AlCl(CH3CN)5]2+[(AlCl4)2]2–·CH3CN and [Nd(CH3CN)9]3+[(FeCl4)3]3–·CH3CN, were

  类型为[Ln（CH 3 CN）9 ] 3+ [（AlCl 4）3 ] 3- ·CH 3 CN（Ln = Pr，Nd，Sm，Gd，Er，Yb，Y）的阳离子镧系元素络合物有效催化剂用于未活化的烯醇的分子内加氢烷氧基化/环化反应，以在温和条件下产生具有马尔可夫尼科夫区域选择性的环状醚。新型阳离子络合物[AlCl（CH 3 CN）5 ] 2+ [（AlCl 4）2 ] 2- ·CH 3 CN和[Nd（CH 3 CN）9 ] 3+ [（FeCl 4）3 ] 3- ·CH 3 CN，合成并评价了未活化的链烯醇的用于比较的分子内hydroalkoxylation /环化。[Nd（CH 3 CN）9 ] 3+ [（FeCl 4）3 ] 3– ·CH 3 CN <[AlCl（CH 3 CN）5 ] 2+ [（AlCl 4）2 ] 2– · CH 3 CN <[Nd（CH 3 CN）9 ] 3+ [（AlCl
• Synthesis and antioxidant activity of 5-hydroxycoumarans, 6-hydroxychromanes and sulfur-containing derivatives on their base
  作者：S. E. Yagunov、S. V. Khol’shin、N. V. Kandalintseva、A. E. Prosenko

  DOI：10.1007/s11172-013-0200-4

  日期：2013.6

  A synthesis of 5-hydroxycoumarans, 6-hydroxychromanes and their dodecylthiomethylsubstituted derivatives was accomplished based on methylphenols through the intermediate preparation of 2-allyl-4-alkoxyphenols. The sulfur-containing compounds synthesized were shown to be highly efficient as inhibitors of autooxidation of methyl oleate.

  通过中间体2-丙烯基-4-烷氧基苯酚的制备，基于甲基酚成功合成了5-羟基香豆素、6-羟基克罗莫烯及其十二烷硫基甲基取代衍生物。合成的含硫化合物表现出作为甲基油酸自氧化抑制剂的高效性。
• Gold(I)-Catalyzed Synthesis of Dihydrobenzofurans from Aryl Allyl Ethers
  作者：Chuan He、Nicholas Reich、Cai-Guang Yang、Zhangjie Shi

  DOI：10.1055/s-2006-932491

  日期：——

  Formation of dihydrobenzofurans from aryl allyl ethers was catalyzed by in situ generated PPh 3 AuOTf. This reaction appears to proceed by a Claisen rearrangement, followed by addition of the resulting phenol to the allyl group.

  由芳基烯丙基醚形成二氢苯并呋喃由原位生成的 PPh 3 AuOTf 催化。该反应似乎是通过克莱森重排进行的，然后将所得苯酚加成到烯丙基上。
• A recyclable copper(ii) catalyst for the annulation of phenols with 1,3-dienes
  作者：Luis A. Adrio、King Kuok (Mimi) Hii

  DOI：10.1039/b719465j

  日期：——

  Air- and moisture-stable Cu(OTf)2–bipy catalyses the addition of phenols to 1,3-dienes under aerobic conditions in a tandem hydroalkoxylation–rearrangement–hydroalkylation sequence, furnishing O-heterocycles in moderate to good yields, and can be recycled without any loss in catalytic activity.

  稳定于空气和湿气的Cu(OTf)2–bipy催化在有氧条件下将酚类加成到1,3-二烯，进行串联的羟基烷基化–重排–羟基烷基化反应，生成O-杂环，产率中等到良好，并且可以循环使用而不会损失催化活性。