1,8-bistetrahydropyranyloxyoctan | 69891-87-8

• 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: 1,8-bistetrahydropyranyloxyoctan
• 英文别名: 1,8-di(2-terahydropyranyloxy)-octane；1.8-Bis(2-Tetrahydropyranyloxy)-octan；2,2'-[Octane-1,8-diylbis(oxy)]bis(oxane)；2-[8-(oxan-2-yloxy)octoxy]oxane
• CAS: 69891-87-8
• 化学式: C₁₈H₃₄O₄
• 分子量: 314.466
• InChiKey: NUSHPVVEEAOAGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,8-bistetrahydropyranyloxyoctan 在 对甲苯磺酸 作用下， 以 甲醇 、 水 为溶剂， 反应 8.0h， 以89%的产率得到1,8-辛二醇
  参考文献：
  名称：

  Vinczer, Peter; Juvanecz, Zoltan; Novak, Lajos, Acta Chimica Hungarica, 1987, vol. 124, # 5, p. 737 - 748

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 、 1,8-辛二醇 在 copper(II) sulfate 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以93%的产率得到1,8-bistetrahydropyranyloxyoctan
  参考文献：
  名称：

  五水合硫酸铜（CuSO 4 ·5H 2 O）：一种温和有效的醇和酚四氢吡喃基化/去吡喃基化催化剂

  摘要：

  在室温下，在温和的反应条件下，使用20 mol％的CuSO 4 ·5H 2 O可将各种醇和酚平稳地转化为相应的THP醚。该方法的一些主要优点是非水后处理，非常好的收率，较便宜的催化剂以及与其他保护基的相容性。

  DOI：

  10.1016/j.tetlet.2004.08.141

文献信息

• Silica‐Gel‐Supported Aluminium Chloride: A Stable, Efficient, Selective, and Reusable Catalyst for Tetrahydropyranylation of Alcohols and Phenols
  作者：Kaveh Parvanak Borujeni

  DOI：10.1080/00397910600764725

  日期：2006.9

  Abstract A simple, effective, and highly chemoselective method to form 2‐tetrahydropyranyl ethers of alcohols and phenols in the presence of silica‐gel‐supported aluminium chloride as a heterogeneous Lewis acid catalyst is described. The catalyst can be easily recovered and reused without appreciable change in its efficiency.

  摘要描述了一种在硅胶负载的氯化铝作为多相路易斯酸催化剂存在下形成醇和酚的 2-四氢吡喃基醚的简单、有效和高度化学选择性的方法。催化剂可以很容易地回收和再利用，而不会明显改变其效率。
• Studies on the terpenoids and related alicyclic compounds XXXIX. A synthesis of .ALPHA.-methylene-.GAMMA.-lactones fused to medium and large rings by intramolecular cyclization of formylated allyl halides.
  作者：Kiyoshi NISHITANI、Masashi ISOZAKI、Koji YAMAKAWA

  DOI：10.1248/cpb.38.28

  日期：——

  Carbocyclic rings fused to an α-methylene-γ-lactone unit were synthesized from ω-formylated β-ethoxycarbonylallyl halides (4a-g) through intramolecular cyclization by the use of a low-valent chromium reagent, prepared from CrCl3 and LiAlH4, in N, N-dimethylformamide. α-Methylene-γ-lactones fused to medium (eight-membered) or large (twelve-and fourteen-membered) ring system (5a, c and d) were synthesized by this method in good to fairly good yields. However, the formylated allyl halide (4b), expected to afford a ten-membered carbocyclic ring system, gave dilactones fused to a twenty-membered ring unit even under a high dilution reaction condition.

  与α-亚甲基-γ-内酯单元融合的碳环是通过将ω-甲酰化的β-乙氧基碳酰丙烯卤化物（4a-g）在N,N-二甲基甲酰胺中与低价铬试剂（由CrCl3和LiAlH4制备）通过分子内环化反应合成的。通过这种方法，融合中环（八元环）或大环（十二元和十四元环）系统的α-亚甲基-γ-内酯（5a、c和d）以良好到相当好的产率合成。然而，预计能形成十元碳环系统的甲酰化丙烯卤化物（4b），即使在高稀释反应条件下也只给出了与二十元环单元融合的二内酯。
• Highly selective monotetrahydropyranylation of symmetrical diols catalysed by a strongly acidic ion-exchange resin
  作者：Takeshi Nishiguchi、Masahumi Kuroda、Masahiko Saitoh、Akiko Nishida、Shizuo Fujisaki

  DOI：10.1039/c39950002491

  日期：——

  Several primary and secondary symmetrical diols, ranging from propane-1,3-diol to decane-1,10-diol, are selectively monoprotected by monotetrahydropyranyl ether formation catalysed by a strongly acidic ion-exchange resin (Dowex 50w × 2, 50–100 mesh) in a 3,4-dihydro-2H-pyran-hydrocarbon mixture.

  几个选自丙二醇-1,3至癸二醇-1,10的主、次对称二醇，在强酸性离子交换树脂（Dowex 50w× 2，50-100目）催化下，以3,4-二氢-2H-吡喃-烃混合物为介质，发生单四氢吡喃醚选择性单保护反应。
• Chemoselective tetrahydropyranylation of alcohols and phenols using polystyrene supported aluminium chloride as a catalyst
  作者：Bahman Tamami、Kaveh Parvanak Borujeny

  DOI：10.1016/j.tetlet.2003.11.056

  日期：2004.1

  A simple, efficient and highly chemoselective method for tetrahydropyranylation of alcohols and phenols has been developed by their reaction with 3,4-dihydro-2H-pyran at room temperature in the presence of a catalytic amount of polystyrene supported AlCl3. The method is also highly selective for monoprotection of symmetrical diols.

  通过在室温下在催化量的聚苯乙烯负载的AlCl 3存在下，它们与3,4-二氢-2 H-吡喃反应，开发了一种简单，有效且高度化学选择性的醇和酚四氢吡喃基化方法。该方法对于对称二醇的单保护也是高度选择性的。
• Selective Monotetrahydropyranylation of Symmetrical Diols Catalyzed by Ion-Exchange Resins
  作者：Takeshi Nishiguchi、Shizuo Fujisaki、Masahumi Kuroda、Kohtaro Kajisaki、Masahiko Saitoh

  DOI：10.1021/jo980659b

  日期：1998.11.1

  Primary and secondary symmetrical diols with 2-10 carbon atoms gave selectively monotetrahydropyranyl ethers in the reaction catalyzed by wet sulfonic acid-type ion-exchange resins in 3,4-dihydro-2H-pyran (DI-IP)/toluene or DHP/hexane. The yields of the monoethers were higher than 80% while those of the corresponding diethers were lower than 5%. In these reactions the rate of the formation of the diethers did not increase much even after most of the diols had been consumed. In the reaction of 1,10-decanediol in DHP/hexane, the yields of the monoether were increased by the addition of DMF or DMSO. Each diol was found to have a particular DHP/hydrocarbon ratio that gave the highest selectivity for the monoether. Generally, the larger the number of carbon atoms of the diols, the smaller the ratio of DHP in the solvents to give high selectivity for the monoether. This method of the selective etherification is quite simple and practical.