2-(4-tert-Butyl-benzyloxy)-tetrahydro-pyran | 874960-58-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(4-tert-Butyl-benzyloxy)-tetrahydro-pyran
• 英文别名: 2-[(4-tert-Butylphenyl)methoxy]oxane
• CAS: 874960-58-4
• 化学式: C₁₆H₂₄O₂
• 分子量: 248.365
• InChiKey: ZUYTUKIGHBKVDH-UHFFFAOYSA-N

物化性质

• 沸点：
  337.1±37.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 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-tert-Butyl-benzyloxy)-tetrahydro-pyran 在 三氯异氰尿酸 、 盐酸羟胺 作用下， 以 neat (no solvent) 为溶剂， 反应 1.25h， 以78%的产率得到4-tert-butylbenzaldehyde oxime
  参考文献：
  名称：

  Tandem and Selective Conversion of Tetrahydropyranyl and Silyl Ethers to Oximes Catalyzed with Trichloroisocyanuric Acid

  摘要：

  Direct and oxidative conversion of tetrahydropyranyl and silyl ethers to oximes is described using trichloroisocyanuric acid (TCCA) as a relatively stable and inexpensive oxidant surprisingly in a catalytic amount and hydroxylamine hydrochloride under solvent-free conditions. Oximes can be synthesized from these protected alcohols in the presence of some other functional groups with excellent chemoselectivity using the present tandem catalytic method.

  DOI：

  10.1080/10426507.2014.990015
• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 、 4-叔丁基苄醇 在 ammonium cerium(IV) nitrate 、 1-butylpyridinium tetrachloroferrate(III) 作用下， 反应 0.58h， 以93%的产率得到2-(4-tert-Butyl-benzyloxy)-tetrahydro-pyran
  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

• 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
  作者：Ahmad R. Khosropour、Mohammad M. Khodaei、Sattar Ghaderi

  DOI：10.1515/znb-2006-0313

  日期：2006.3.1

  Alcohols were converted to the corresponding THP, THF or TMS ethers in high to excellent yields in 1-n-butylpyridinium chloroferrate media as a stable and low cost room temperature ionic liquid. In addition, oxidation of these ethers to their aldehydes or ketones without any overoxidation reactions in this ionic liquid was also performed.

  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。
• Highly efficient protection of alcohols and phenols catalysed by tin porphyrin supported on MIL-101
  作者：Farnaz Zadehahmadi、Shahram Tangestaninejad、Majid Moghadam、Valiollah Mirkhani、Iraj Mohammadpoor-Baltork、Reihaneh Kardanpour

  DOI：10.1002/aoc.3270

  日期：2015.4

  The catalytic activity of 5,10,15,20‐tetrakis(4‐aminophenyl)porphyrinatotin(IV) trifluoromethanesulfonate, [SnIV(TNH2PP)(OTf)2], supported on chloromethylated MIL‐101, was investigated in the trimethylsilylation of alcohols and phenols with hexamethyldisilazane (HMDS) and also their tetrahydropyranylation with 3,4‐dihydro‐2H‐pyran. Excellent yields, mild reaction conditions, short reaction times and

  在三甲基甲硅烷基化反应中研究了在氯甲基化的MIL-101上负载的5,10,15,20-四（4-氨基苯基）卟啉毒素（IV）三氟甲磺酸盐[Sn IV（TNH 2 PP）（OTf）2 ]的催化活性。与六甲基二硅氮烷（HMDS）合成醇和酚，以及它们与3,4-二氢-2H-吡喃的四氢吡喃基化作用。该载体催化剂的显着优点是优异的收率，温和的反应条件，较短的反应时间和催化剂的可重复使用性，而其初始活性没有显着降低。版权所有©2015 John Wiley＆Sons，Ltd.
• P4VPy–CuO nanoparticles as a novel and reusable catalyst: application at the protection of alcohols, phenols and amines
  作者：Farhad Shirini、Abdollah Fallah-Shojaei、Masoumeh Abedini、Laleh Samavi

  DOI：10.1007/s13738-016-0887-x

  日期：2016.9

  P4VPy–CuO nanoparticles were synthesized using ultrasound irradiations. Relevant properties of the synthesized nanoparticles were investigated by X-ray diffraction, scanning electron microscopy, transmission electron microscopy and Fourier transform infrared spectroscopy. After identification, the prepared reagent was used for the promotion of different types of protection reactions of alcohols, phenols and amines. Easy workup, short reaction times, excellent yields, relatively low cost and reusability of the catalyst are the striking features of the reported methods.

  采用了超声波辐照法合成了P4VPy–CuO纳米粒子。通过X射线衍射、扫描电子显微镜、透射电子显微镜和傅里叶变换红外光谱对合成的纳米粒子的相关性质进行了研究。在鉴定之后，制备的试剂被用于促进不同类型的醇、酚和胺的保护反应。操作简便、反应时间短、产率高、成本相对较低以及催化剂的重复使用性是所报道方法的显著特点。
• Efficient Trimethylsilylation and Tetrahydropyranylation of Alcohols in the Presence of 1,3-Dibromo-5,5-dimethylhydantoin
  作者：Farhad Shirini、Mohammad Zolfigol、Maryam Paktinat

  DOI：10.1055/s-2006-950350

  日期：——

  Chemoselective trimethylsilylation and tetrahydropyranylation of benzylic and primary and secondary aliphatic alcohols proceed efficiently in the presence of 1,3-dibromo-5,5-dimethylhydantoin (DBH) under mild and completely heterogeneous reaction conditions in excellent yields.

  在1,3-二溴-5,5-二甲基海因（DBH）存在下，苯甲位以及一级和二级脂族醇的化学选择性三甲基硅烷化和四氢吡喃化反应在温和且完全非均相的反应条件下高效进行，产率极佳。
• Silylation and Tetrahydropyranylation of Alcohols Catalyzed by Al(HSO₄)₃
  作者：Farhad Shirini、Mohammad Ali Zolfigol、Masoumeh Abedini

  DOI：10.1246/bcsj.78.1982

  日期：2005.11

  Trimethylsilylation and tetrahydropyranylation of alcohols are efficiently catalyzed by Al(HSO4)3. All reactions were performed under mild and completely heterogeneous conditions in good-to-high yields.

  醇的特戊酰化和四氢吡喃化反应在Al(HSO4)3的高效催化下进行，所有反应均在温和且完全非均相的条件下进行，产率良好至高。