5-(tetrahydro-2H-pyran-2-yloxy)pentan-1-ol | 76102-74-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 5-(tetrahydro-2H-pyran-2-yloxy)pentan-1-ol
• 英文别名: 5-(tetrahydropyran-2-yloxy)pentan-1-ol；5-(2-tetrahydropyranyloxy)pentan-1-ol；2-(5-hydroxypentyloxy)tetrahydropyran；1-Pentanol, 5-[(tetrahydro-2H-pyran-2-yl)oxy]-；5-(oxan-2-yloxy)pentan-1-ol
• CAS: 76102-74-4
• 化学式: C₁₀H₂₀O₃
• 分子量: 188.267
• InChiKey: WZJNQWCLHXVUPJ-UHFFFAOYSA-N

物化性质

• 沸点：
  150-170 °C(Press: 15 Torr)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(tetrahydro-2H-pyran-2-yloxy)pentan-1-ol 在 β-环糊精 水 作用下， 以 甲醇 为溶剂， 反应 10.0h， 以75%的产率得到1,5-戊二醇
  参考文献：
  名称：

  β-环糊精在水中对四氢吡喃基醚的选择性脱保护

  摘要：

  这 水解 四氢吡喃基醚 酒类β-环糊精催化的过程水 在中性条件下。

  DOI：

  10.1039/b009187l
• 作为产物：
  描述：

  1,5-戊二醇 在 tris(triphenylphosphine)ruthenium(II) chloride 作用下， 以 1,4-二氧六环 为溶剂， 反应 5.0h， 以35%的产率得到5-(tetrahydro-2H-pyran-2-yloxy)pentan-1-ol
  参考文献：
  名称：

  Ruthenium-Complex-Catalyzed N-(Cyclo)alkylation of Aromatic Amines with Diols. Selective Synthesis of N-(ω-Hydroxyalkyl)anilines of Type PhNH(CH₂)_nOH and of Some Bioactive Arylpiperazines

  摘要：

  A new class of well-defined neutral mono-, and dicationic ruthenium(II) complexes containing a neutral terdentate donor system [C5H3N(CH2E)(2)-2,6] (E = PPh2 (PNP) or NMe2 (NN'N)) has been found effective as catalyst precursor in N-(cyclo)alkylation reactions of aromatic amines with diols Y(CH2CH2OH)(2) (Y = CH2, NR). With these catalysts, N-phenylpiperidine is synthesized from aniline and 1,5-pentanediol in 85% yield (at 180 degrees C for 24 h in 1,4-dioxane). With neutral RuCl2(NN'N)(PPh3) as a catalyst precursor, aniline can be selectively N-monoalkylated with diols of the type HO(CH2)(n)OH (n = 4-6, 10) to give N-(n-hydroxyalkyl)anilines in 40-75% yield. To our knowledge, this represents the first useful catalytic route to this type of compounds. The new catalysts can also be used in the synthesis of arylpiperazines. For example, N-phenyl-N'-methylpiperazine is obtained from aniline and MeN(CH2CH2OH)(2) in yields up to 34%. N-[m-(Trifluoromethyl)phenyl]-N'-methylpiperazine, TFMPMP, is successfully produced from m-(trifluoromethyl)aniline and MeN(CH2CH2OH)(2) in 44% yield using monocationic [RuOTf(NN'N)(PPh3)]OTf as the catalyst precursor. A mechanism for the N-(cyclo)alkylation reaction is proposed.

  DOI：

  10.1021/jo972260d

文献信息

• The tandem intramolecular Diels-Alder reaction
  作者：Daniel R. Goldberg、Jeffrey A. Hansen、Raymond J. Giguere

  DOI：10.1016/s0040-4039(00)61435-1

  日期：1993.12

  The tandem intramolecular Diels-Alder (TIMDA) reaction of ketone 3 is reported. The reaction proceeds under mild conditions (BF3·Et2O, O °C) and affords two tetracyclic products diastereoselectively. TIMDA substrate 3 is prepared in a convergent manner from 1,5-pentanediol.

  据报道，酮3的串联分子内Diels-Alder（TIMDA）反应。反应在温和的条件下（BF 3 ·Et 2 O，O°C）进行，非对映选择性地得到两种四环产物。TIMDA底物3由1，5-戊二醇以收敛的方式制备。
• Polystyrene-supported GaCl3: A new, highly efficient and recyclable heterogeneous Lewis acid catalyst for tetrahydropyranylation of alcohols and phenols
  作者：Ali Rahmatpour

  DOI：10.1016/j.poly.2012.06.063

  日期：2012.8

  highly chemoselective method for tetrahydropyranylation of alcohols and phenols with 3,4-dihydro-2H-pyran (DHP) in the presence of polystyrene-supported gallium trichloride (PS/GaCl3) as a highly active and reusable heterogeneous Lewis acid catalyst at room temperature is presented. In this catalytic system, primary, secondary and tertiary alcohols, as well as phenols, were converted to the corresponding

  在聚苯乙烯负载的三氯化镓（PS / GaCl 3）存在下，用3,4-二氢-2 H-吡喃（DHP）对醇和酚进行四氢吡喃基化的一种新的，简单且高度化学选择性的方法）是在室温下具有高活性和可重复使用的非均相路易斯酸催化剂。在该催化体系中，伯，仲和叔醇以及苯酚以短的反应时间和高收率转化为相应的四氢吡喃基（THP）醚。异质催化剂在吡喃基化反应中具有高可重复使用性和稳定性，并且被回收了数次，其活性损失可忽略不计且催化剂浸出可忽略不计，并且也不需要再生。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。
• [EN] INHIBITORS OF HEPATITIS C VIRUS POLYMERASE<br/>[FR] INHIBITEURS DE POLYMÉRASE DU VIRUS DE L'HÉPATITE C
  申请人：COCRYSTAL PHARMA INC

  公开号：WO2016154241A1

  公开（公告）日：2016-09-29

  The present invention provides, among other things, compounds represented by the general Formula I: (I) and pharmaceutically acceptable salts thereof, wherein L and A (and further substituents) are as defined in classes and subclasses herein and compositions (e.g., pharmaceutical compositions) comprising such compounds, which compounds are useful as inhibitors of hepatitis C virus polymerase, and thus are useful, for example, as medicaments for the treatment of HCV infection.

  本发明提供了一种由一般式I表示的化合物，以及其药学上可接受的盐，其中L和A（以及进一步的取代基）如本文中的类和子类中所定义，并且包括这些化合物的组合物（例如，药物组合物），这些化合物可用作丙型肝炎病毒聚合酶的抑制剂，因此可用作治疗HCV感染的药物。
• Highly Powerful and Practical Acylation of Alcohols with Acid Anhydride Catalyzed by Bi(OTf)₃
  作者：Akihiro Orita、Chiaki Tanahashi、Atsushi Kakuda、Junzo Otera

  DOI：10.1021/jo0107453

  日期：2001.12.1

  Bi(OTf)(3)-catalyzed acylation of alcohols with acid anhydride was evaluated in comparison with other acylation methods. The Bi(OTf)(3)/acid anhydride protocol was so powerful that sterically demanding or tertiary alcohols could be acylated smoothly. Less reactive acylation reagents such as benzoic and pivalic anhydride are also activated by this catalysis. In these cases, a new technology was developed

  与其他酰化方法相比，评估了Bi（OTf）（3）催化的酸酐与酸酐的酰化反应。Bi（OTf）（3）/酸酐操作规程如此强大，以至于空间需求量高的或叔醇都可以被平滑地酰化。反应性较低的酰化试剂，例如苯甲酸酯和新戊酸酐，也可以通过这种催化活化。在这些情况下，为了克服将酰化产物与剩余的酰化试剂分离的困难，开发了一种新技术：未反应的酸酐的甲醇化成易于分离的甲酯实现了所需酰化产物的非常容易的分离。Bi（OTf）（3）/酸酐方案适用于具有各种功能的多种醇。酸不稳定的THP或TBS保护的醇，糠醇，香叶醇和碱不稳定的醇也可以被酰化。在室温下甚至进行官能化叔醇的酰化。
• Intramolecular Diels-Alder reactions of internally-substituted trienylsulfones. Synthesis of bicyclo[4.3.0] and -[4.4.0] systems possessing a bridgehead sulfonyl group
  作者：Martin C. Clasby、Donald Craig、Alexandra M.Z. Slawin、Andrew J.P. White、David J. Williams

  DOI：10.1016/0040-4020(94)01045-2

  日期：1995.1

  possessing internally-activated vinylic sulfone dienophilic groups undergo intramolecular Diels-Alder (IMDA) reaction with high or complete selectivity for the cis-fused products. Incorporation of silyloxy groups within the carbon tether linking the diene and dienophile results in increased IMDA reactivity. The stereochemical outcomes of these processes are rationalised in terms of the preference for an exooriented

  一系列具有内部活化的乙烯基砜二亲核基团的三烯经过分子内Diels-Alder（IMDA）反应，对顺式融合产物具有高或完全选择性。在连接二烯和亲二烯体的碳系链中并入甲硅烷氧基基团会增加IMDA反应性。这些方法的立体化学结果根据对外向性苯基磺酰基的偏爱以及使甲硅烷氧基和砜取代基之间的未键合相互作用最小化而合理化。