1,10-bistetrahydropyranyloxydecane | 56599-49-6

• 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: 1,10-bistetrahydropyranyloxydecane
• 英文别名: 2H-Pyran, 2,2'-[1,10-decanediylbis(oxy)]bis[tetrahydro-；2-[10-(oxan-2-yloxy)decoxy]oxane
• CAS: 56599-49-6
• 化学式: C₂₀H₃₈O₄
• 分子量: 342.519
• InChiKey: PUNRUQMSVWYKJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  24
• 可旋转键数：
  13
• 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

• 作为产物：
  描述：

  5-((四氢吡喃-2-基)氧基)-1-溴戊烷 在 Ni(0)*2EC*Py complex 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以70%的产率得到1,10-bistetrahydropyranyloxydecane
  参考文献：
  名称：

  镍在室温下未活化烷基溴的镍催化还原均偶联反应及其合成应用

  摘要：

  描述了一种室温镍催化的还原方法，用于未活化的伯，仲和叔烷基溴的均相偶联。催化体系可以容易地由空气稳定且廉价的材料产生，并显示出宽泛的官能团耐受性，因此可以轻松获得有用的二聚三萜和木脂素样分子。而且，叔溴化物6的二聚作用有效地建立了位阻式邻位季碳（C3a和C3a'），这是有趣的双吡咯并[2,3- b ]二氢吲哚生物碱的关键连接，从而使我们能够完成总外消旋体的合成。烟嘌呤（9）和叶硫蒽（10））。另外，该二聚方法可扩展为双过氢呋喃[2,3- b ]呋喃（5a）和二聚螺酮5b的高度立体选择性合成，这表明可能涉及自由基。

  DOI：

  10.1021/jo401936v

文献信息

• 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。
• Photochemical<i>E</i>(<i>trans</i>)–<i>Z</i>(<i>cis</i>) Isomerization in 9-Anthraceneacrylic Esters
  作者：Majjigapu Janaki Ram Reddy、Uppalanchi Srinivas、Kolupula Srinivas、Vummadi Venkat Reddy、Vaidya Jayathirtha Rao

  DOI：10.1246/bcsj.75.2487

  日期：2002.11

  Several (1–6) 9-anthraceneacrylic esters were synthesized in order to study photochemical E(trans)–Z(cis) isomerization. All of the compounds 1–6 underwent selective E-to-Z isomerization upon direct excitation (> 400 nm) in organic solvents, leading to the formation of a thermodynamically less stable Z isomer over 96%. Triplet sensitized isomerization selectively produces the Z-to-E isomer in over

  为了研究光化学 E(trans)-Z(cis) 异构化，合成了几种 (1-6) 9-蒽丙烯酸酯。在有机溶剂中直接激发（> 400 nm）后，所有化合物 1-6 都经历了选择性 E-to-Z 异构化，导致形成超过 96% 的热力学稳定性较差的 Z 异构体。三重敏化异构化选择性地产生超过 98% 的 Z-to-E 异构体。在三重敏化 Z-to-E 异构化过程中观察到更高的异构化量子产率告诉我们，“量子链”过程正在运行。所有化合物的荧光数据表明 E-to-Z 异构化过程涉及电荷转移或极性单线激发态。
• 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。
• Natural Kaolinitic Clay: A Mild and Efficient Catalyst for the Tetrahydropyranylation and Trimethylsilylation of Alcohols
  作者：T. T. Upadhya、T. Daniel、A. Sudalai、T. Ravindranathan、K. R. Sabu

  DOI：10.1080/00397919608004777

  日期：1996.12

  Abstract Natural kaolinitic clay possessing transition metals such as Fe, Ti in its lattice has been found to catalyze efficiently the protection of a variety of alcohols with 2,3-dihydro-4H-pyran (DHP) and hexamethyldisilazane (HMDS) at ambient conditions.

  摘要 天然高岭土在其晶格中含有 Fe、Ti 等过渡金属，可在环境条件下有效地催化 2,3-二氢-4H-吡喃 (DHP) 和六甲基二硅氮烷 (HMDS) 对多种醇的保护。
• 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.