2-heptyl-3,6-dihydro-2H-pyran

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2-heptyl-3,6-dihydro-2H-pyran
• 化学式: C₁₂H₂₂O
• 分子量: 182.306
• InChiKey: RLBZRFYMSFZBRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  在 四丁基高氯酸铵 、 二溴甲烷 作用下， 以82%的产率得到4-bromo-2-heptyloxane
  参考文献：
  名称：

  Anodic cyclization of unsaturated α-stannyl ethers. Termination by bromide derived from dibromomethane

  摘要：

  Bu4NClO4·CH2Br2 中不饱和α-甲锡烷基醚的阳极氧化导致有效环化并将溴化物引入原始烯属碳之一；提出了一种涉及环化碳正离子与 CH2Br2 阴极还原产生的 Br- 之间偶联的机制。

  DOI：

  10.1039/c39940002361

文献信息

• Synthesis of Nitrogen- and Oxygen-Containing Heterocycles by Prins Cyclization in Continuous Flow
  作者：Armando Talavera-Alemán、Guillaume Dagousset、Christine Thomassigny、Jérome Marrot

  DOI：10.1055/s-0040-1705988

  日期：2021.4

  are described for the synthesis of the corresponding tetrahydropyridines and pyran derivatives, respectively. In particular, the use of pyridine-carboxaldehydes for aza-silyl-Prins reaction led to either a symmetrical triarylmethane or two new bicyclic compounds. 4-Fluorinated-2-substituted tetrahydropyran derivatives were also obtained in the oxa-Prins cyclization with good selectivity in favor of

  描述了连续流化学中的氮杂-甲硅烷基-Prins和氧杂-Prins环化反应，分别用于合成相应的四氢吡啶和吡喃衍生物。特别是，将吡啶-甲醛用于氮杂-甲硅烷基-Prins反应可导致对称的三芳基甲烷或两种新的双环化合物。在oxa-Prins环化中还获得了4-氟-2-取代的四氢吡喃衍生物，其具有良好的选择性，有利于抗异构体。
• 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.
• Anodic cyclization of unsaturated α-stannyl ethers. Termination by bromide derived from dibromomethane
  作者：Jun-ichi Yoshida、Kazunori Takada、Yuji Ishichi、Sachihiko Isoe

  DOI：10.1039/c39940002361

  日期：——

  Anodic oxidation of unsaturated α-stannyl ethers in Bu4NClO4–CH2Br2 results in effective cyclization and the introduction of bromide into one of the original olefinic carbons; a mechanism involving the coupling between the cyclized carbocation and Br– generated by cathodic reduction of CH2Br2 is suggested.

  Bu4NClO4·CH2Br2 中不饱和α-甲锡烷基醚的阳极氧化导致有效环化并将溴化物引入原始烯属碳之一；提出了一种涉及环化碳正离子与 CH2Br2 阴极还原产生的 Br- 之间偶联的机制。