(+/-)-4-(3,4,5,6-tetrahydro-2H-pyran-2-yloxymethyl)benzaldehyde | 187682-10-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+/-)-4-(3,4,5,6-tetrahydro-2H-pyran-2-yloxymethyl)benzaldehyde
• 英文别名: 4-(perhydro-2H-pyran-2-yloxymethyl)benzaldehyde；4-(Oxan-2-yloxymethyl)benzaldehyde
• CAS: 187682-10-6
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: WFUJQOFADDDNES-UHFFFAOYSA-N

物化性质

• 沸点：
  356.0±37.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-4-(3,4,5,6-tetrahydro-2H-pyran-2-yloxymethyl)benzaldehyde 在 zinc(II) trifluoromethanesulfonate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以95%的产率得到对羟基甲基苯甲醛
  参考文献：
  名称：

  三氟甲磺酸锌：一种温和有效的脱氢四氢吡喃基醚的催化剂

  摘要：

  在甲醇中用三氟甲磺酸锌处理四氢吡喃基（THP）醚为这些醚的脱保护提供了一种简单有效的方法，母体醇的收率极高。

  DOI：

  10.1134/s1070363213120384
• 作为产物：
  描述：

  对苯二甲醛缩二乙醛 在 lithium aluminium tetrahydride 、 4-甲基苯磺酸吡啶 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 50.03h， 生成 (+/-)-4-(3,4,5,6-tetrahydro-2H-pyran-2-yloxymethyl)benzaldehyde
  参考文献：
  名称：

  Dendrimers consisting of stilbene or distyrylbenzene building blocks synthesis and stability

  摘要：

  On the basis of Wittig-Homer reactions and protection group techniques compound 7 for the core and the components 9a-c and 11a-c for the dendrons were prepared and linked in the final step. The convergent synthesis yielded constitutionally and configurationally pure dendrimers (2a-c, 2a'-c') which consist of distyrylbenzene units. Their thermo-oxidative stability in the presence of air was studied by chemiluminescence and compared to the dendrimers 1 consisting of stilbene units, (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00823-6

文献信息

• An Efficient and Versatile Procedure for the Synthesis of Acetals from ­Aldehydes and Ketones Catalyzed by Lithium Tetrafluoroborate
  作者：Tsuneo Sato、Nao Hamada、Kiyoshi Kazahaya、Hisashi Shimizu

  DOI：10.1055/s-2004-820038

  日期：——

  Acetals are obtained in good to excellent yields by treatment of aldehydes and ketones with trialkyl orthoformate and the corresponding alcohol in the presence of a catalytic amount of lithium tetrafluoroborate. Due to the mild reaction conditions, this method is compatible with acid-sensitive substrates.

  在催化量的四氟硼酸锂存在下，用原甲酸三烷基酯和相应的醇处理醛和酮，以良好至极好的收率获得缩醛。由于反应条件温和，该方法适用于对酸敏感的底物。
• Carbene-Catalyzed Reductive Coupling of Nitrobenzyl Bromide and Nitroalkene via the Single-Electron-Transfer (SET) Process and Formal 1,4-Addition
  作者：Yuhuang Wang、Yu Du、Xuan Huang、Xingxing Wu、Yuexia Zhang、Song Yang、Yonggui Robin Chi

  DOI：10.1021/acs.orglett.6b03792

  日期：2017.2.3

  A carbene-catalyzed reductive 1,4-addition of nitrobenzyl bromides to nitroalkenes is disclosed. The reaction proceeds via a carbene-enabled single-electron-transfer process that generates radicals as key intermediates. The present study expands the potentials of carbene catalysis and offers unusual transformations for common substrates in organic synthesis.
• Zinc triflate: A mild and efficient catalyst for deprotection of tetrahydropyranyl ethers
  作者：R. Srinivasulu、P. V. V. Satyanarayana、K. Ravi Kumar

  DOI：10.1134/s1070363213120384

  日期：2013.12

  Treatment of tetrahydropyranyl (THP) ethers with zinc triflate in methanol provides a simple and efficient process for deprotection of these ethers and the parent alcohols are obtained in excellent yields.

  在甲醇中用三氟甲磺酸锌处理四氢吡喃基（THP）醚为这些醚的脱保护提供了一种简单有效的方法，母体醇的收率极高。
• Dendrimers consisting of stilbene or distyrylbenzene building blocks synthesis and stability
  作者：Matthias Lehmann、Bernhard Schartel、Manfred Hennecke、Herbert Meier

  DOI：10.1016/s0040-4020(99)00823-6

  日期：1999.11

  On the basis of Wittig-Homer reactions and protection group techniques compound 7 for the core and the components 9a-c and 11a-c for the dendrons were prepared and linked in the final step. The convergent synthesis yielded constitutionally and configurationally pure dendrimers (2a-c, 2a'-c') which consist of distyrylbenzene units. Their thermo-oxidative stability in the presence of air was studied by chemiluminescence and compared to the dendrimers 1 consisting of stilbene units, (C) 1999 Elsevier Science Ltd. All rights reserved.