cyclopentyl trityl ether | 1241-40-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: cyclopentyl trityl ether
• 英文别名: Tritylcyclopentylether；Ether, cyclopentyl trityl；[cyclopentyloxy(diphenyl)methyl]benzene
• CAS: 1241-40-3
• 化学式: C₂₄H₂₄O
• 分子量: 328.454
• InChiKey: VMDKMEOIGXXRHB-UHFFFAOYSA-N

物化性质

• 熔点：
  58-60 °C
• 沸点：
  438.4±14.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  cyclopentyl trityl ether 在 lithium chloride 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以93%的产率得到环戊醇
  参考文献：
  名称：

  LiCl介导的，简便且低成本的方法，从受保护的醇和二醇中去除三苯甲基

  摘要：

  伯，仲，苯基，烯丙基和苄基三苯甲基醚与氯化锂在甲醇中在回流下的反应导致三苯甲基的脱保护，从而在温和的反应条件下以良好或优异的收率得到相应的醇。

  DOI：

  10.1016/j.tetlet.2016.06.110
• 作为产物：
  描述：

  2-trityloxyoctane 在 4-二甲氨基吡啶 、 indium 、 氯化铵 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 32.0h， 生成 cyclopentyl trityl ether
  参考文献：
  名称：

  铟介导的三苯甲基从受保护的醇和二醇上的裂解

  摘要：

  伯，仲，烯丙基和苄基三苯甲基醚与铟粉在MeOH / NH 4 Cl中的反应导致三苯甲基-氧键的还原裂解，从而在非常温和的反应条件下以良好或优异的收率提供了相应的醇。去三苯甲基化过程可以成功地扩展到单和去三苯甲基化的二醇。这种方法学代表了在温和的反应条件下的一种新的有效的去三苯甲基化程序。

  DOI：

  10.1016/j.tet.2016.10.020

文献信息

• FeCl₃-Catalyzed Tritylation of Alcohols in Ionic Liquids
  作者：B. Sreedhar、P. Radhika、B. Neelima、D. V. D. B. Chowdary、M. V. Basaveswara Rao

  DOI：10.1080/00397910902838888

  日期：2009.10.12

  Abstract A simple and efficient protection of alcohols as trityl ethers is described using trityl chloride in the presence of 5 mol% FeCl3 as catalyst in ionic liquids at room temperature in shorter reaction times. This mild and efficient method gives access to the protection of a wide range of alcohols in good yields. The use of ionic liquid allows easy separation of the product and recycling of catalyst

  摘要 描述了在离子液体中在 5 mol% FeCl3 存在下使用三苯甲基氯作为催化剂，在室温下以较短的反应时间将醇类保护为三苯甲基醚的方法。这种温和而有效的方法可以以良好的收率保护各种醇。离子液体的使用使得产品的分离和催化剂的循环利用变得容易。
• Application of Ball Milling Technology to Carbohydrate Reactions: I. Regioselective Primary Hydroxyl Protection of Hexosides and Nucleoside by Planetary Ball Milling‡
  作者：Premanand Ramrao Patil、K. P. Ravindranathan Kartha

  DOI：10.1080/07328300802218713

  日期：2008.7

  Dry ball milling of hexosides with trityl chloride in the presence of DABCO or Na2CO3 has been found to result in their complete conversion to the respective 6-O-trityl ethers. Further wet grinding of the reaction mixture with Ac2O in the presence of DMAP led to the respective fully protected hexosides in good to excellent yields after isolation. It has been found to be an effective one-pot two-step synthesis under solvent-free condition. The speed of homogenization has been shown to highly influence the rate and outcome of the reaction, and commercially available planetary ball mill has been proved to be very convenient for carrying out the reaction under standardized and reproducible conditions.
• In(III) triflate-catalyzed detritylation and glycosylation by solvent-free ball milling
  作者：Vajinder Kumar、Narender Yadav、K.P. Ravindranathan Kartha

  DOI：10.1016/j.carres.2014.08.002

  日期：2014.10

  A highly efficient In(III) triflate-assisted method for the detritylation of O-trityl derivatives of carbohydrates, phenols, and alcohols using solvent-free mechanochemical method is described. In the case of carbohydrates, further reaction in the presence of an acceptor sugar leads to highly efficient glycosylation in the same pot resulting in the formation of the desired glycoside-product in very high yields. The method was applied successfully to the synthesis of a combinatorial library of galactose-based (1,6)-linked cyclo-hexa-, hepta-, and octasaccharides on gram scale. (C) 2014 Elsevier Ltd. All rights reserved.
• LiCl-mediated, easy, and low-cost removal of the trityl group from protected alcohols and diols
  作者：Cherif Behloul、Aicha Chouti、Ihssene Chabour、Hind Bengliz Bey、David Guijarro、Francisco Foubelo、Carmen Nájera、Miguel Yus

  DOI：10.1016/j.tetlet.2016.06.110

  日期：2016.8

  The reaction of primary, secondary, phenyl, allyl, and benzyl trityl ethers with lithium chloride in methanol at reflux led to deprotection of the trityl group affording the corresponding alcohol in good to excellent yields under mild reaction conditions.

  伯，仲，苯基，烯丙基和苄基三苯甲基醚与氯化锂在甲醇中在回流下的反应导致三苯甲基的脱保护，从而在温和的反应条件下以良好或优异的收率得到相应的醇。
• Indium-mediated cleavage of the trityl group from protected alcohols and diols
  作者：Cherif Behloul、Aicha Chouti、David Guijarro、Francisco Foubelo、Carmen Nájera、Miguel Yus

  DOI：10.1016/j.tet.2016.10.020

  日期：2016.12

  The reaction of primary, secondary, allylic and benzylic trityl ethers with indium powder in MeOH/NH4Cl led to reductive cleavage of the trityl-oxygen bond, affording the corresponding alcohols in good to excellent yield under very mild reaction conditions. The detritylation process could successfully be extended to mono and detritylated diols. This methodology represents a new and efficient detritylation

  伯，仲，烯丙基和苄基三苯甲基醚与铟粉在MeOH / NH 4 Cl中的反应导致三苯甲基-氧键的还原裂解，从而在非常温和的反应条件下以良好或优异的收率提供了相应的醇。去三苯甲基化过程可以成功地扩展到单和去三苯甲基化的二醇。这种方法学代表了在温和的反应条件下的一种新的有效的去三苯甲基化程序。