2-(tetradecyl)tetrahydrofuran

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: 2-(tetradecyl)tetrahydrofuran
• 英文别名: tetrahydro-2-tetradecylfuran；2-tetradecyltetrahydrofuran；2-tetradecyloxolane
• 化学式: C₁₈H₃₆O
• 分子量: 268.483
• InChiKey: KQKGTCUKCPVIJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  19
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-(tetradecyl)furan 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 13.0h， 以96%的产率得到2-(tetradecyl)tetrahydrofuran
  参考文献：
  名称：

  Avocadofurans and Their Tetrahydrofuran Analogues:  Comparison of Growth Inhibitory and Insecticidal Activity

  摘要：

  The importance of the double bonds in the furan ring of avocadofurans with relation to their insecticidal activity was examined. The insecticidal activity of two naturally occurring avocadofurans, 2-(pentadecyl)furan and 2-(heptadecyl)furan, was compared to the toxicity of five tetrahydrofurans with alkyl chains at position 2 and varying side chains from 14 to 18 carbons. We found that eliminating the sites of unsaturation in the furan ring of avocadofurans significantly reduced the detrimental effects on the mortality and growth of the generalist insect herbivore Spodoptera! exigua. In 7-day bioassays, S. exigua larvae were significantly more affected when fed a diet containing avocadofurans as compared to a larvae fed diet treated with the analogous tetrahydrofurans. Although larvae fed with the tetrahydrofurans showed reduced growth as compared to controls, larval mortality was not significantly increased. We conclude that the double bonds in the furan ring of avocadofurans play an important role in their insecticidal effects.

  DOI：

  10.1021/jf9910638

文献信息

• New method for C–H arylation/alkylation at α-position of cyclic aliphatic ethers by iron-oxide mediated reaction
  作者：Parvinder Pal Singh、Satish Gudup、Hariprasad Aruri、Umed Singh、Srinivas Ambala、Mahipal Yadav、Sanghapal D. Sawant、Ram A. Vishwakarma

  DOI：10.1039/c1ob06660a

  日期：——

  We report a new and efficient iron oxide catalyzed cross-coupling reaction between organometallic species such as alkyl/arylmagnesium halides or organolithium species and α-hydrogen bearing cyclic unbranched and branched aliphatic ethers via activation of C(sp3)–H. In the presence of 1 mol% of iron oxide, five and six membered unbranched cyclic ethers such as tetrahydrofuran and tetrahydropyran gave

  我们报告了一种新的和有效的氧化铁催化的烷基/芳基镁卤化物或有机锂物种等有机金属物种之间的交叉偶联反应。 α氢通过活化C（sp 3）–H携带环状的直链和支链脂族醚。在1摩尔％的氧化铁存在下，五元和六元直链环状醚如四氢呋喃 和 四氢吡喃交联产品的良率和良率都很高。而在支链醚的情况下2-甲基四氢呋喃，观察到芳基化发生在两侧，并给出了中等产率的区域异构体混合物。与芳基有机金属相比，在所使用的有机金属物质中，烷基有机金属试剂的收率较低。
• Iron oxide mediated direct C–H arylation/alkylation at α-position of cyclic aliphatic ethers
  作者：Parvinder Pal Singh、Satish Gudup、Srinivas Ambala、Umed Singh、Sumit Dadhwal、Baldev Singh、Sanghapal D. Sawant、Ram A. Vishwakarma

  DOI：10.1039/c1cc11094b

  日期：——

  reaction between organometallic species such as alkyl/arylmagnesium halides or organolithium species and alpha-hydrogen bearing cyclic aliphatic ethers via activation of C(sp(3))-H. This is the first example of iron oxide mediated direct C-C bond formation without expensive or toxic ligands.

  我们报告了一种新的和有效的氧化铁催化的烷基/芳基镁卤化物或有机锂物质等有机金属物种与通过活化C（sp（3））-H的带有α-氢的环状脂肪族醚之间的交叉偶联反应。这是没有昂贵或有毒配体的氧化铁介导的直接CC键形成的第一个例子。
• Regioselective and Stereospecific Azidation of 1,2- and 1,3-Diols by Azidotrimethylsilane via a Mitsunobu Reaction
  作者：Linli He、Meni Wanunu、Hoe-Sup Byun、Robert Bittman

  DOI：10.1021/jo9906375

  日期：1999.8.1

  A one-pot regio- and stereospecific azidation reaction of 1,2- and 1,3-diols with azidotrimethylsilane (Me3SiN3) via a Mitsunobu reaction has been achieved. With 1,2- and 1,3-diols, the reaction of triphenylphosphine, diisopropyl azodicarboxylate, and Me3SiN3 in dichloromethane gave regioselective azidation at C-2 and C-3, respectively, in good yield (74-90% combined yield of 1a + 1b or of 2a + 2b). However, application of the same reaction conditions to a 1,4-diol led to the exclusive formation of the cyclic ether. The regioselectivity of this one-pot reaction is influenced by the solvent, the degree of steric bulk at C-2 of the 1,2-diol or at C-3 of the 1,3-diol, and the presence of electron-donating and electron-withdrawing groups near the secondary carbinol carbon. This selectivity is discussed in terms of the mechanistic model proposed by Mathieu-Pelta and Evans (Mathieu-Pelta, I.; Evans, S. A., Jr. J. Org. Chem. 1898, 57, 3409-3413), which involves reaction of the dioxaphospholane intermediate with Me3SiN3 to form oxyphosphonium ions 4 and 5.
• Avocadofurans and Their Tetrahydrofuran Analogues:  Comparison of Growth Inhibitory and Insecticidal Activity
  作者：Cesar Rodriguez-Saona、David F. Maynard、Scott Phillips、John T. Trumble

  DOI：10.1021/jf9910638

  日期：2000.8.1

  The importance of the double bonds in the furan ring of avocadofurans with relation to their insecticidal activity was examined. The insecticidal activity of two naturally occurring avocadofurans, 2-(pentadecyl)furan and 2-(heptadecyl)furan, was compared to the toxicity of five tetrahydrofurans with alkyl chains at position 2 and varying side chains from 14 to 18 carbons. We found that eliminating the sites of unsaturation in the furan ring of avocadofurans significantly reduced the detrimental effects on the mortality and growth of the generalist insect herbivore Spodoptera! exigua. In 7-day bioassays, S. exigua larvae were significantly more affected when fed a diet containing avocadofurans as compared to a larvae fed diet treated with the analogous tetrahydrofurans. Although larvae fed with the tetrahydrofurans showed reduced growth as compared to controls, larval mortality was not significantly increased. We conclude that the double bonds in the furan ring of avocadofurans play an important role in their insecticidal effects.