2-benzyltetrahydropyran | 55962-00-0

• 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: 2-benzyltetrahydropyran
• 英文别名: 2H-Pyran, tetrahydro-2-(phenylmethyl)-；2-benzyloxane
• CAS: 55962-00-0
• 化学式: C₁₂H₁₆O
• 分子量: 176.258
• InChiKey: AAGBIKHTRKXUGV-UHFFFAOYSA-N

物化性质

• 沸点：
  164-165 °C(Press: 1 Torr)
• 密度：
  1.052 g/cm3(Temp: 25 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  四氢吡喃-2-甲醇 在 copper(I) bromide 吡啶 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 1.33h， 生成 2-benzyltetrahydropyran
  参考文献：
  名称：

  苯丙胺与格氏试剂的铜（I）催化偶联反应的新方法

  摘要：

  在CuBr存在下，各种含有β-氧官能团的三氟甲磺酸与Grignard试剂有效反应，得到相应的偶联产物。

  DOI：

  10.1016/s0040-4039(00)72737-7

文献信息

• Electroorganic chemistry 139. Electroreductive decyanation of nitriles and its application to synthesis of α-alkylamines
  作者：Tatsuya Shono、Jun Terauchi、Kenji Kitayama、Yo-ichiro Takeshima、Yoshihiro Masumura

  DOI：10.1016/s0040-4020(01)80493-2

  日期：——

  Electroreduction of nitriles gave the corresponding decyanated products when Zn was used as the material of cathode in aprotic solvent (DMF or MeCN) containing Et4NOTs as a supporting electrolyte. Alkylation of amines at the α-position was effectively achieved by cyanation of amines at the α-position, and α-alkylation of the resultant α-amino nitriles followed by the electroreductive decyanation.

  当在含有Et 4 NOTs作为支持电解质的非质子传递溶剂（DMF或MeCN）中将Zn用作阴极材料时，腈的电还原得到相应的脱氰产物。通过使胺在α位氰化，然后将所得的α-氨基腈进行α-烷基化，然后进行电还原脱氰作用，可以有效地实现α-位胺的烷基化。
• Direct photochemical cross-coupling between aliphatic acids and BF₃K salts
  作者：Zhuming Sun、Bingqing Tang、Kevin K.-C. Liu、Hugh Y. Zhu

  DOI：10.1039/c9cc09164e

  日期：——

  We describe a novel photoredox hetero-coupling reaction of two C (sp3) radicals from aliphatic acids or BF3K salts. The kinetic differences in radical persistence provide cross-selectivity, using an organic photoredox catalyst and an oxidant with visible light. This method exhibits broad scope, including several examples constructing sterically hindered C(sp3)-C(sp3) bonds.

  我们描述了两个C（sp3）自由基从脂肪酸或BF3K盐的新型光氧化还原杂化偶联反应。使用有机光氧化还原催化剂和可见光氧化剂，自由基持久性的动力学差异提供了交叉选择性。该方法具有广阔的应用范围，包括构建位阻C（sp3）-C（sp3）键的几个示例。
• Direct anomeric substitution of pyranyl esters using organocopper reagents
  作者：V. Bolitt、C. Mioskowski、J.R. Falck

  DOI：10.1016/s0040-4039(01)93845-6

  日期：1989.1

  2-Substituted tetrahydropyrans were obtained by direct anomeric substitution of tetrahydropyranyl 2,4-dimethoxybenzoate, using Grignard-derived organocopper reagents.

  通过使用格氏试剂衍生的有机铜试剂直接将2，4-二甲氧基苯甲酸四氢吡喃酯进行异头取代，可得到2位取代的四氢吡喃。
• Cyclopropenium-Activated Cyclodehydration of Diols
  作者：Brendan D. Kelly、Tristan H. Lambert

  DOI：10.1021/ol102980t

  日期：2011.2.18

  The dehydrative cyclization of diols to cyclic ethers via cyclopropenium activation is described. Using 2,3-diphenylcyclopropene and methanesulfonic anhydride, a series of 1,4- and 1,5-diols are rapidly cyclized to furnish tetrahydrofurans and tetrahydropyrans in high yield. Eleven total substrates are shown, including a gram scale cyclization of a diterpene derivative.
• On the choice of Lewis acids for the Prins reaction; two total syntheses of (±)-Civet
  作者：Freda K. Chio、Julie Warne、Damien Gough、Mark Penny、Sasa Green (née Martinović)、Simon J. Coles、Mike B. Hursthouse、Peter Jones、Lorraine Hassall、Thomas M. McGuire、Adrian P. Dobbs

  DOI：10.1016/j.tet.2011.05.019

  日期：2011.7

  While developing new variations of the Prins cyclisation reaction, the effect of the choice of Lewis acid on the outcome of the reaction and the product(s) has been investigated, yielding hitherto unseen dihydropyran products in the Prins cyclisation reaction of homoallylic alcohols, and two new modifications of the reaction: the triflate-trapped Prins adduct and the Mukaiyama-Aldol-silyl-Prins reaction. Two of these methods are employed in two complementary total syntheses of the important perfumery compound, (+/-)-Civet. (C) 2011 Elsevier Ltd. All rights reserved.