4-(3,5-dimethylphenoxy)butan-1-ol | 40324-48-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(3,5-dimethylphenoxy)butan-1-ol
• CAS: 40324-48-9
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: CULVTNHKLIFMDJ-UHFFFAOYSA-N

物化性质

• 沸点：
  328.0±30.0 °C(Predicted)
• 密度：
  1.006±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-(3,5-二甲基苯氧基)丁酸乙酯 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 4-(3,5-dimethylphenoxy)butan-1-ol
  参考文献：
  名称：

  2-Aryloxytetrahydrofurans. Their Reductive Cleavage by Ether Solutions of AlH₂Cl and their Cleavage and Rearrangement by Ether Solutions of AlCl₃

  摘要：

  过量的AlH2Cl对2-芳氧基四氢呋喃的氢解反应，无论芳环上的取代基为何，都只产生预期的外向C-O键断裂产物，收率极高。没有检测到预期的环断裂产物4-芳氧基-1-丁醇。该反应比已知在相似条件下只产生环断裂产物的2-烷氧基四氢呋喃的AlH2Cl氢解反应要快得多。将2-芳氧基四氢呋喃或吡喃与AlCl3在醚中处理，会酸催化断裂为相应的酚和二氢呋喃或二氢吡喃，后者立即形成聚合物产物。对于那些芳环上没有取代基或芳环上带有电子给体基团的2-芳氧基四氢呋喃或吡喃，还会得到另一种产物，这种产物是由一个质子化的二氢呋喃或吡喃对酚的邻位或对位进行亲电攻击形成的。当2-芳氧基四氢呋喃与不足量的AlH2Cl氢解时，这些重排产物也会作为副产物产生，但数量很少。

  DOI：

  10.1139/v72-579

文献信息

• Copper(ii)-catalyzed C–O coupling of aryl bromides with aliphatic diols: synthesis of ethers, phenols, and benzo-fused cyclic ethers
  作者：Yajun Liu、Se Kyung Park、Yan Xiao、Junghyun Chae

  DOI：10.1039/c4ob00649f

  日期：——

  copper-catalyzed C–O cross-coupling reaction between aryl bromides and aliphatic diols has been developed employing a cheaper, more efficient, and easily removable copper(II) catalyst. A broad range of aryl bromides were coupled with aliphatic diols of different lengths using 5 mol% CuCl2 and 3 equivalents of K2CO3 in the absence of any other ligands or solvents to afford the corresponding hydroxyalkyl aryl ethers

  使用更便宜，更有效且易于去除的铜（II）催化剂，开发了一种高效的铜催化的芳基溴化物与脂肪族二醇之间的C-O交叉偶联反应。使用5 mol％的CuCl 2和3当量的K 2 CO 3将宽范围的芳基溴化物与不同长度的脂肪族二醇偶联在不存在任何其他配体或溶剂的情况下，以良好或优异的收率得到相应的羟烷基芳基醚。在这个新开发的方案中，脂族二醇具有多方面的功能，如偶联反应物，配体和溶剂。所得的羟烷基芳基醚进一步容易地转化成相应的苯酚，为从芳基溴化物得到的苯酚提供了一种有价值的替代方法。此外，已证明它们是用于更高级分子如苯并呋喃和苯并稠合的环醚的有用中间体。
• Ligand-free Cu-catalyzed O-arylation of aliphatic diols
  作者：Yufen Zheng、Wenxing Zou、Laichun Luo、Jiabei Chen、Songwen Lin、Qi Sun

  DOI：10.1039/c5ra12529d

  日期：——

  Coupling reaction between aryl iodides with aliphatic diols was realized with a ligand-free copper catalyst. This method was successfully applied in the process of scale-up synthesis of medicinal candidate product EMB-3.

  芳基碘化物与脂肪二醇之间的偶联反应是利用无配体铜催化剂实现的。该方法成功应用于药物候选产品EMB-3的放大合成过程中。
• New Oxidative Aromatization of α,β-Unsaturated Cyclohexenones with Iodine–Cerium(IV) Ammonium Nitrate in Alcohol
  作者：C. Akira Horiuchi、Hirotada Fukunishi、Mika Kajita、Akihisa Yamaguchi、Hiroshi Kiyomiya、Shinji Kiji

  DOI：10.1246/cl.1991.1921

  日期：1991.11

  (methanol, ethanol, 1-propanol, 2-propanol, and 1-butanol) under refluxing, gave the corresponding alkyl phenyl ethers in good yields. In the case of diol (ethylene glycol, 1,3-propanediol, and 1,4-butanediol), phenoxyalkanol derivatives were obtained. The present method was also applicable to oxidative rearrangement of isophorone.

  2-环己烯-1-酮衍生物与碘-铈（IV）硝酸铵在醇（甲醇、乙醇、1-丙醇、2-丙醇和1-丁醇）中回流反应，得到相应的烷基苯基醚良好的收益。在二醇（乙二醇、1,3-丙二醇和1,4-丁二醇）的情况下，获得苯氧基链烷醇衍生物。本方法也适用于异佛尔酮的氧化重排。
• 2-Aryloxytetrahydrofurans. Their Reductive Cleavage by Ether Solutions of AlH₂Cl and their Cleavage and Rearrangement by Ether Solutions of AlCl₃
  作者：P. C. Loewen、R. K. Brown

  DOI：10.1139/v72-579

  日期：1972.11.15

  The hydrogenolysis of 2-aryloxytetrahydrofurans by excess AlH₂Cl gave, in excellent yield, only those products expected from exo C—O bond cleavage regardless of the nature of the substituent in the aryl ring. None of the 4-aryloxy-1-butanol, the product expected from ring cleavage, was detected. The reaction was very much faster than the corresponding AlH₂Cl hydrogenolysis of 2-alkoxytetrahydrofurans which is known to give only ring cleavage products under similar conditions.Treatment of 2-aryloxytetrahydrofurans or pyrans with AlCl₃ in ether, resulted in acid-catalyzed cleavage to the corresponding phenol and dihydrofuran or dihydropyran, the latter immediately forming polymeric products. For those 2-aryloxytetrahydrofurans or pyrans, unsubstituted, or substituted with electron donor groups in the aryl ring, another product was obtained which resulted from electrophilic attack of one protonated dihydrofuran or pyran on the ortho or para position of the phenol. These rearrangement products were also obtained in small amounts as byproducts when 2-aryloxytetrahydrofurans were hydrogenolyzed with insufficient AlH₂Cl.

  过量的AlH2Cl对2-芳氧基四氢呋喃的氢解反应，无论芳环上的取代基为何，都只产生预期的外向C-O键断裂产物，收率极高。没有检测到预期的环断裂产物4-芳氧基-1-丁醇。该反应比已知在相似条件下只产生环断裂产物的2-烷氧基四氢呋喃的AlH2Cl氢解反应要快得多。将2-芳氧基四氢呋喃或吡喃与AlCl3在醚中处理，会酸催化断裂为相应的酚和二氢呋喃或二氢吡喃，后者立即形成聚合物产物。对于那些芳环上没有取代基或芳环上带有电子给体基团的2-芳氧基四氢呋喃或吡喃，还会得到另一种产物，这种产物是由一个质子化的二氢呋喃或吡喃对酚的邻位或对位进行亲电攻击形成的。当2-芳氧基四氢呋喃与不足量的AlH2Cl氢解时，这些重排产物也会作为副产物产生，但数量很少。