2-iodomethyl-5-methoxy-2,3-dihydrobenzofuran | 508168-22-7

• 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-iodomethyl-5-methoxy-2,3-dihydrobenzofuran
• 英文别名: 5-methoxy-2,3-dihydro-2-(iodomethyl)benzofuran；2-(iodomethyl)-5-methoxy-2,3-dihydro-1-benzofuran；2,3-dihydro-2-(iodomethyl)-5-methoxybenzofuran；2-(Iodomethyl)-5-methoxy-2,3-dihydrobenzofuran
• CAS: 508168-22-7
• 化学式: C₁₀H₁₁IO₂
• 分子量: 290.101
• InChiKey: PLRNRCGIPZLBQM-UHFFFAOYSA-N

物化性质

• 沸点：
  338.3±30.0 °C(Predicted)
• 密度：
  1.672±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  2
• 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-iodomethyl-5-methoxy-2,3-dihydrobenzofuran 在 aluminum oxide 作用下， 反应 0.25h， 以82%的产率得到5-甲氧基-2-甲基苯并呋喃
  参考文献：
  名称：

  Simple and Efficient Access to 3-Ethoxycarbonylpyrroles, Benzofurans, and Naphthofurans

  摘要：

  开发出了一种从烯胺、酚和萘酚合成吡咯和呋喃衍生物的高效方法。关键步骤包括碘环化和氧化铝诱导的脱氢碘化反应。

  DOI：

  10.1055/s-0029-1217053
• 作为产物：
  描述：

  4-烯丙氧基苯甲醚 在 碘 作用下， 以 乙醇 、 水 为溶剂， 反应 12.0h， 生成 2-iodomethyl-5-methoxy-2,3-dihydrobenzofuran
  参考文献：
  名称：

  Design, synthesis and cytotoxic activities of novel hybrid compounds between dihydrobenzofuran and imidazole

  摘要：

  我们制备了一系列新型二氢苯并呋喃与咪唑杂化化合物，并对一系列人类肿瘤细胞系进行了体外评估。结果表明，咪唑-1-位被电子供体二氢苯并呋喃取代，咪唑-3-位被萘酰基或富含电子的苯酰基取代，这对调节细胞毒性活性至关重要。

  DOI：

  10.1039/c1ob05116d

文献信息

• 5-Hydroxy-2,3-dihydrobenzofuran-derived polyfunctional antioxidants
  作者：S. E. Yagunov、S. V. Kholshin、N. V. Kandalintseva、A. E. Prosenko

  DOI：10.1007/s11172-017-1850-4

  日期：2017.6

  2-Dodecylthiomethyl-5-hydroxy-2,3-dihydrobenzofurans, new sulfur-containing analogs of tocopherols, were synthesized based on methylphenols through the intermediate preparation of 4-alkoxy-2-allylphenols and then 5-alkoxy-2-iodomethyl-2,3-dihydrobenzofurans.

  2-十二烷基硫甲基-5-羟基-2,3-二氢苯并呋喃是新型含硫的生育酚类似物，基于甲基酚的合成途径首先制备了4-烷氧基-2-烯丙基酚，然后再制备了5-烷氧基-2-碘甲基-2,3-二氢苯并呋喃。
• 5-Hydroxy-2,3-dihydrobenzofuran-derived polyfunctional antioxidants 2. Synthesis of 2-dodecylselenomethyl-5-hydroxy-2,3-dihydrobenzofurans and their antioxidant profile versus 2-dodecylthiomethyl-substituted analogs
  作者：S. E. Yagunov、S. V. Kholshin、N. V. Kandalintseva、A. E. Prosenko

  DOI：10.1007/s11172-018-2148-x

  日期：2018.5

  were synthesized from the corresponding 5-alkoxy-2-iodomethyl-substituted derivatives. The rate constants of the reaction with peroxide radicals and stoichiometric coefficients of inhibition were measured for the synthesized compounds and their 2-dodecylthiomethyl substituted analogs in the model reaction of initiated styrene oxidation. The dissociation energies of O–H bond were also calculated. 2-

  许多 2-dodecylselenomethyl-5-hydroxy-2,3-dihydrobenzofurans 是由相应的 5-alkoxy-2-iodomethyl 取代的衍生物合成的。在引发苯乙烯氧化的模型反应中，对合成的化合物及其 2-十二烷基硫甲基取代的类似物测量了与过氧化物自由基反应的速率常数和化学计量的抑制系数。还计算了 O-H 键的解离能。2-Dodecylselenomethyl-5-hydroxy-2,3-dihydrobenzofurans 在油酸甲酯的热自动氧化中的抗氧化活性比它们的含硫类似物和生育酚分别高出 9-14 和 19-20 倍。
• Iodine‐Catalyzed Claisen‐Rearrangements of Allyl Aryl Ethers and Subsequent Iodocyclizations
  作者：Thiemo Arndt、Abhinav Raina、Martin Breugst

  DOI：10.1002/asia.202201279

  日期：2023.3

  Claisen Rearrangements with a Twist. Molecular iodine catalyzes the Claisen rearrangement of allyl aryl ethers and substantially reduces the required reaction temperature for these processes. The resulting allyl phenols rapidly undergo iodocyclizations to afford dihydrobenzofurans, which are important building blocks for medicinal applications. DFT calculations and mechanistic studies provide further

  扭曲的克莱森重排。分子碘催化烯丙基芳基醚的克莱森重排，并显着降低这些过程所需的反应温度。由此产生的烯丙基酚迅速进行碘环化反应，得到二氢苯并呋喃，这是医药应用的重要组成部分。DFT 计算和机理研究为这种转变提供了进一步的见解。
• Novel potent (dihydro)benzofuranyl piperazines as human histamine receptor ligands – Functional characterization and modeling studies on H3 and H4 receptors
  作者：Michelle F. Corrêa、André L. Balico-Silva、Dóra J. Kiss、Gustavo A.B. Fernandes、Jhonatan C. Maraschin、Lucas T. Parreiras-e-Silva、Marina T. Varela、Sarah C. Simões、Michel Bouvier、György M. Keserű、Claudio M. Costa-Neto、João Paulo S. Fernandes

  DOI：10.1016/j.bmc.2020.115924

  日期：2021.1
• Novel potent vasodilating agents: Evaluation of the activity and potency of LINS01005 and derivatives in rat aorta
  作者：Milton Ginoza、Gustavo A.B. Fernandes、Michelle F. Corrêa、João Paulo S. Fernandes

  DOI：10.1016/j.ejps.2019.105171

  日期：2020.2

  Cardiovascular diseases (CVDs) present high prevalence rates in the current world. It is estimated that approximately one-third of the global deaths are related to CVD5, and thus there is still a need for novel drugs to treat these disorders. We serendipitously discovered that LINS01005 (5a) is a potent vasodilating agent in rat aorta, and therefore a set of analogues were evaluated for the vasodilating potency in Wistar and SHR rat thoracic aorta precontracted with norepinephrine, with endothelium intact (E+) or denuded (E-) aortic rings. Compounds 5a and 5b were the most potent, showing submicromolar potency for endothelium intact vessels (EC50 853 and 941 nM, respectively) and micromolar values for E- vessels (EC50 2.4 and 7.1 pM, respectively). These compounds were indeed significantly more potent vasodilating agents in SHR-derived aortic rings (p < 0.001), showing nanomolar potency for 5a [EC50 2.4 nM (E+) 9.0 nM (E-)] and 5b [EC50 20 nM (E+) 2.1 mu M (E-)]. SAR analysis though PCA and HCA were performed, suggesting that N-phenylpiperazine is essential to the activity, while increasing volume in the substituted aromatic moiety is detrimental to the potency. This is the first report of the vasodilating properties of such compounds, and studies regarding the mechanism of action are in progress in our group.