2-(cyclopentyloxy)-1,3-dimethylbenzene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(cyclopentyloxy)-1,3-dimethylbenzene
• 英文别名: 2-Cyclopentyloxy-1,3-dimethylbenzene
• 化学式: C₁₃H₁₈O
• 分子量: 190.285
• InChiKey: MNROORKLZRYYJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2,6-二甲基苯酚 、 环戊醇 在 偶氮二甲酸二异丙酯 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以68%的产率得到2-(cyclopentyloxy)-1,3-dimethylbenzene
  参考文献：
  名称：

  Base catalyzed Mitsunobu reactions as a tool for the synthesis of aryl sec-alkyl ethers

  摘要：

  A facile and versatile method for the synthesis of aryl sec-alkyl ethers from phenols with alcohols in the presence of base via a Mitsunobu reaction is described. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.02.072

文献信息

• The Selective Reaction of Aryl Halides with KOH:  Synthesis of Phenols, Aromatic Ethers, and Benzofurans
  作者：Kevin W. Anderson、Takashi Ikawa、Rachel E. Tundel、Stephen L. Buchwald

  DOI：10.1021/ja0639719

  日期：2006.8.1

  direct and selective synthesis of phenols from aryl/heteroaryl halides and KOH has been achieved through the use of highly active monophosphine-based catalysts derived from Pd(2)dba(3) and ligands L1 or L2 and the biphasic solvent system 1,4-dioxane/H(2)O. We have also demonstrated a one-pot method of phenol formation/alkylation for the preparation of alkyl aryl ethers from aryl halides. In many instances

  通过使用衍生自 Pd(2)dba(3) 和配体 L1 或 L2 的高活性单膦基催化剂以及双相溶剂系统 1,4，从芳基/杂芳基卤化物和 KOH 直接和选择性地合成苯酚-二恶烷/H(2)O。我们还展示了一种苯酚形成/烷基化的一锅法，用于从芳基卤化物制备烷基芳基醚。在许多情况下，该协议克服了脂肪醇与芳基卤化物的现有 Pd 催化偶联反应的局限性。最后，我们证明了取代苯并呋喃可以通过 Pd 催化的苯酚形成/环化方案从 2-氯芳基炔烃有效制备。
• Azodicarbonyl dimorpholide (ADDM): an effective, versatile, and water-soluble Mitsunobu reagent
  作者：Maryanna E. Lanning、Steven Fletcher

  DOI：10.1016/j.tetlet.2013.06.049

  日期：2013.8

  One of the caveats of the Mitsunobu reaction is the often difficult and laborious purification of the reaction mixture. Herein, we show that azodicarbonyl dimorpholide (ADDM) is an effective and versatile Mitsunobu reagent, which, along with its reduced form ADDM-H-2, may be removed from the reaction mixture by a simple aqueous extraction. Furthermore, we demonstrate that the isolated ADDM-H-2 may be re-oxidized with silver(I) oxide to regenerate ADDM. Finally, a chromatography-free Mitsunobu reaction is presented. (C) 2013 Elsevier Ltd. All rights reserved.