2-allyl-3,5-dimethoxyphenol | 32977-07-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-allyl-3,5-dimethoxyphenol
• 英文别名: Phenol, 3,5-dimethoxy-2-(2-propenyl)-；3,5-dimethoxy-2-prop-2-enylphenol
• CAS: 32977-07-4
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: QHEQVNMRWJJAGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-allyl-3,5-dimethoxyphenol 在 Grubbs catalyst first generation 、 potassium tert-butylate 、 四丁基溴化铵 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 4.0h， 生成 4,6-dimethoxybenzofuran
  参考文献：
  名称：

  Synthetic Models Related to Methoxalen – CYP2A6 Interactions. Dimethoxybenzofuran Derivatives as Potent and Selective Inhibitors of CYP2A6

  摘要：

  The human CYP2A6 enzyme metabolizes several xenobiotics including nicotine, the addictive component in tobacco. Reduced activity of CYP2A6, either for genetic reasons or by administering inhibitors of CYP2A6, reduces tobacco smoking. The reported compound methoxalen had a potent inhibitory effect on activity of CYP2A6 with an IC50 value of 1.27 mu M. We selected methoxalen as a lead compound and prepared various dimethoxybenzofuran derivatives that have inhibitory effects on activity of human cytochrome P450 (CYP) 2A6. Synthetic benzofuran derivatives (3,6-dimethoxybenzofuran: IC50=1.92 mu M and 3,7-dimethoxybenzofuran: IC50=2.00 mu M) also exhibited comparable activities against CYP2A6 and were selective inhibitors of CYP2A6. These compounds can be used as lead compounds in the development of drugs for smoking reduction therapy.

  DOI：

  10.3987/com-13-12744
• 作为产物：
  描述：

  1-(烯丙氧基)-3,5-二甲氧基苯 在 氯化二乙基铝 作用下， 以 正己烷 为溶剂， 反应 1.0h， 以68%的产率得到2-allyl-3,5-dimethoxyphenol
  参考文献：
  名称：

  选择性克莱森重排和碘化反应合成多氧化烯丙基苯酚衍生物

  摘要：

  从商业或合成的苯酚开始制备烯丙基芳基醚和烯丙基苯酚衍生物。进行威廉姆森反应或Et 2 AlCl催化的克莱森重排以获得多加氧分子。然后通过甲基化，碘环化或亲电子碘化碘化对枢轴烯丙基苯酚进行改性，从而以良好或优异的收率得到多氧化衍生物。此外，还研究了它们对革兰氏阳性和革兰氏阴性细菌的抗菌性能。

  DOI：

  10.1016/j.tetlet.2016.07.079

文献信息

• Selective Claisen rearrangement and iodination for the synthesis of polyoxygenated allyl phenol derivatives
  作者：Antonella Bochicchio、Rossella Cefola、Sabine Choppin、Françoise Colobert、Maria Antonietta Di Noia、Maria Funicello、Gilles Hanquet、Isabella Pisano、Simona Todisco、Lucia Chiummiento

  DOI：10.1016/j.tetlet.2016.07.079

  日期：2016.9

  Allyl aryl ethers and allyl phenol derivatives were prepared starting from commercial or synthetized phenols. Either Williamson reaction or Et2AlCl catalyzed Claisen rearrangement was performed to obtain the polyoxygenated molecules. The pivotal allyl phenols were then modified by methylation, iodocyclization or electrophilic aromatic iodination to afford the polyoxygenated derivatives in good to excellent

  从商业或合成的苯酚开始制备烯丙基芳基醚和烯丙基苯酚衍生物。进行威廉姆森反应或Et 2 AlCl催化的克莱森重排以获得多加氧分子。然后通过甲基化，碘环化或亲电子碘化碘化对枢轴烯丙基苯酚进行改性，从而以良好或优异的收率得到多氧化衍生物。此外，还研究了它们对革兰氏阳性和革兰氏阴性细菌的抗菌性能。
• Design and Enantioselective Construction of Axially Chiral Naphthyl-Indole Skeletons
  作者：Hong-Hao Zhang、Cong-Shuai Wang、Can Li、Guang-Jian Mei、Yuxue Li、Feng Shi

  DOI：10.1002/anie.201608150

  日期：2017.1.2

  The first enantioselective construction of a new class of axially chiral naphthyl‐indole skeletons has been established by organocatalytic asymmetric coupling reactions of 2‐naphthols with 2‐indolylmethanols (up to 99 % yield, 97:3 e.r.). This approach not only affords a new type of axially chiral heterobiaryl backbone, but also provides a new catalytic enantioselective strategy for constructing axially

  通过2-萘酚与2-吲哚基甲醇的有机催化不对称偶联反应建立了新型的轴向手性萘基-吲哚骨架的首个对映选择性结构（产率高达99％，er为97：3 er）。这种方法不仅提供了一种新型的轴向手性杂联芳基骨架，而且还提供了一种利用2-吲哚基甲醇的C3亲电性构建轴向手性联芳基骨架的新催化对映选择性策略。
• An Atom-Economical and Stereoselective Domino Synthesis of Functionalised Dienes
  作者：Caroline Souris、Marco Luparia、Frédéric Frébault、Davide Audisio、Christophe Farès、Richard Goddard、Nuno Maulide

  DOI：10.1002/chem.201300776

  日期：2013.5.17

  Open sesame: A direct synthesis of functionalised and stereodefined dienes, relying on a domino allylic alkylation/electrocyclic ring‐opening sequence, is reported. This method allows concise access to doubly vinylogous esters. A further systematic study of ring‐opening rates of carbon‐substituted cyclobutenes allowed the design of substrates amenable to sequential pericyclic reactions (see scheme)

  芝麻开裂：据报道，依赖于烯丙基烯丙基烷基化/电环开环序列的功能化和立体定义的二烯的直接合成。该方法允许简洁地获得双乙烯基酯。碳取代的环丁烯的开环速率的进一步系统研究允许设计适用于连续环周反应的底物（参见方案）。
• Conjugate addition to 3-arylsulfinylchromones as a synthetic route to homochiral 2-substituted chromanones: scope and limitations
  作者：Kevin J Hodgetts、Konstantina I Maragkou、Timothy W Wallace、Robert C.R Wootton

  DOI：10.1016/s0040-4020(01)00615-9

  日期：2001.7

  A route to homochiral 2-substituted chromanones via the diastereoselective conjugate addition of organocopper reagents to 3-(p-tolylsulfinyl)chromones has been improved and used to prepare 2,6-dimethylchromanone (S)-4 and LL-D253α methyl ether (S)-6. The attempted preparation of a 2-phenylchromanone (flavanone) using this strategy was unsuccessful due to the lability of the intermediate 2-phenyl-3

  通过将有机铜试剂非对映选择性共轭加成到3-（对甲苯磺亚磺酰基）色酮上的方法制备纯手性2-取代的苯并二氢吡喃酮已得到改进，并用于制备2,6-二甲基苯并二氢吡喃酮（S）-4和LL-D253α甲基醚（S）-6。由于中间体2-苯基-3-（对甲苯磺酰亚胺基）苯并二氢吡喃酮在室温下不易被亚砜消除而得到相应的2-苯基苯并二氢苯并酮，因此使用该策略尝试制备2-苯基苯并二氢吡喃酮（黄酮）是不成功的。（黄酮）。
• A novel enantioselective cyclization of a chiral epoxide to a benzofuran system
  作者：Kalakota S. Reddy、Ok-Hyun Ko、David Ho、Paul E. Persons、John M. Cassady

  DOI：10.1016/s0040-4039(00)96289-0

  日期：1987.1

  A convenient method has been established for the stereoselective construction of a dihydrobenzofuran ring system found in several bioactive natural products. The final step of the synthesis involves the concerted and efficient intramolecular displacement of mesylate 12 to give 2′R,3′R-dihydrobenzofuran a bicyclic analog of 1. This route was based on a proposed biosynthetic pathway patterned on related

  已经建立了一种便利的方法，用于在几种生物活性天然产物中立体选择性地构建二氢苯并呋喃环系统。合成的最后步骤涉及甲磺酸酯12的一致有效分子内置换，从而为2'R，3'R-二氢苯并呋喃提供1的双环类似物。该途径基于在相关类胡萝卜素上构图的拟议的生物合成途径。