2-(4-Isopropylbenzyloxy)-tetrahydropyran | 394738-99-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-(4-Isopropylbenzyloxy)-tetrahydropyran
• 英文别名: 2-[(4-Propan-2-ylphenyl)methoxy]oxane
• CAS: 394738-99-9
• 化学式: C₁₅H₂₂O₂
• 分子量: 234.338
• InChiKey: OWUBPLOTTPHICC-UHFFFAOYSA-N

物化性质

• 沸点：
  327.4±37.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 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-(4-Isopropylbenzyloxy)-tetrahydropyran 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以73%的产率得到4-异丙基甲苯
  参考文献：
  名称：

  Cleavage of the THP protecting group under Pd/C-catalyzed hydrogenation conditions

  摘要：

  Alcohol and phenol THP or ethoxyethyl ether protecting groups may be cleaved in high yield under Pd/C-catalyzed hydrogenation conditions in EtOH, owing to the inadvertent presence of small quantities of HCl in the reaction mixture. MOM ethers are not cleaved under these conditions. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01630-6
• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 、 4-异丙基苯甲醇 在 ammonium cerium(IV) nitrate 、 1-butylpyridinium tetrachloroferrate(III) 作用下， 反应 0.55h， 以89%的产率得到2-(4-Isopropylbenzyloxy)-tetrahydropyran
  参考文献：
  名称：

  Efficient and Convenient Procedure for Protection of Hydroxyl Groups to the THP, THF and TMS Ethers and Oxidation of these Ethers to their Aldehydes or Ketones in [BPy]FeCl₄ as a Low Cost Room Temperature Ionic Liquid

  摘要：

  醇类在1-丁基吡啶氯铁介质中被转化为相应的THP、THF或TMS醚，产率高至极好。这是一种稳定且低成本的室温离子液体。此外，在这种离子液体中，这些醚被氧化为它们的醛或酮，而没有发生任何过氧化反应。

  DOI：

  10.1515/znb-2006-0313

文献信息

• Lithium triflate (LiOTf) catalyzed efficient and chemoselective tetrahydropyranylation of alcohols and phenols under mild and neutral reaction conditions
  作者：Babak Karimi、Jafar Maleki

  DOI：10.1016/s0040-4039(02)00892-4

  日期：2002.7

  Different types of alcohols and phenols were effectively converted to the corresponding THP ethers in the presence of DHP and a catalytic amount of lithium trifluoromethanesulfonate (LiOTf) in refluxing 1,2-dichloroethane under essentially neutral reaction conditions. The method also shows good chemoselectivity for mono-tetrahydropyranylation of symmetrical diols.

  在DHP和催化量的三氟甲烷磺酸锂（LiOTf）的存在下，在基本中性的反应条件下，将不同类型的醇和酚有效地转化为相应的THP醚。该方法对对称二醇的单四氢吡喃基化反应也显示出良好的化学选择性。
• Synthesis of Amino Substituted Pyrazoles
  作者：Okram Mukherjee Singh、Mohammad Farooque Ahmed、Sarangthem Joychandra Singh、Sang-Gyeong Lee

  DOI：10.3184/030823407x209723

  日期：2007.4

  An efficient and convenient synthesis of substituted pyrazoles with aryl and heteroarylamino substituents attached to the C-3 and C-5 positions by the action of hydrazine hydrate on either ketene N,S-acetals or mixed N,N-aminals hydrate is reported.

  报告了通过水合肼对烯酮 N,S-乙醛或混合 N,N-氨基水合物的作用，高效、方便地合成在 C-3 和 C-5 位上带有芳基和杂芳基氨基取代基的取代吡唑的方法。
• Oxidative deprotection of tetrahydropyranyl and trimethylsilyl ethers in water using 1,4-dichloro-1,4-diazoniabicyclo[2,2,2]octane bis-chloride under neutral conditions
  作者：Mahmood Tajbakhsh、Setareh Habibzadeh

  DOI：10.3184/030823407x218101

  日期：2007.7

  A facile oxidative deprotection of trimethylsilyl and tetrahydropyranyl ethers in water using 1,4-dichloro-1,4-diazoniabicyclo[2,2,2]octane bis-chloride as a new efficient reagent under neutral conditions is described. This methodology is ecofriendly and environmentally benign since it uses water as a solvent. In all reactions DABCO was regenerated, rechlorinated and reused several times.

  本研究介绍了在中性条件下，使用 1,4-二氯-1,4-二氮杂双环[2,2,2]辛烷二氯化物作为一种新型高效试剂，在水中对三甲基硅基醚和四氢吡喃基醚进行简易氧化脱保护的方法。由于该方法使用水作为溶剂，因此对生态和环境无害。在所有反应中，DABCO 都可以再生、再氯化并多次重复使用。
• Introduction of a New Ionic Liquid Catalyst for the Trimethylsilyl and Tetrahydropyranyl Protection of Alcohols
  作者：Farhad Shirini、Masoumeh Abedini、Nosratollah Mahmoodi、Mohammad Biglari、Mohaddeseh Safarpoor Nikoo Langrudi

  DOI：10.1080/10426507.2015.1034311

  日期：2015.11.2

  1,1-Disulfo-[2,2-bipyridine]-1,1-hydrogen sulfate, BiPy(SO3H)(2)(HSO4)(2), is prepared and identified as a new ionic liquid. This reagent was used for the promotion of the chemoselective trimethylsilyl and tetrahydropyranyl protection of alcohols. All reactions were performed under mild reaction conditions in high to excellent yields. Ease of the preparation of the heterogeneous catalyst, simplicity and easy work-up procedure, high reaction rates, and recyclability and reusability of the catalyst are the main advantages of this method.
• Pyridinium Chlorochromate Supported on Montmorillonite–KSF as a Versatile Oxidant under Ball Milling Conditions
  作者：Rahman Hosseinzadeh、Erfan Narimani、Mohammad Mavvaji

  DOI：10.1080/00304948.2021.1944733

  日期：2021.9.3