(3-(octyloxy)prop-1-ynyl)benzene | 144498-52-2

• 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: (3-(octyloxy)prop-1-ynyl)benzene
• 英文别名: phenylpropargyl octyl ether；3-Octoxyprop-1-ynylbenzene
• CAS: 144498-52-2
• 化学式: C₁₇H₂₄O
• 分子量: 244.377
• InChiKey: VZIGVWNLTBEBNP-UHFFFAOYSA-N

物化性质

• 沸点：
  339.0±25.0 °C(Predicted)
• 密度：
  0.93±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  氯甲基辛基醚 在 4-二甲氨基吡啶 、 三氟化硼乙醚 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 (3-(octyloxy)prop-1-ynyl)benzene
  参考文献：
  名称：

  Expanded Substrate Scope and Improved Reactivity of Ether-Forming Cross-Coupling Reactions of Organotrifluoroborates and Acetals

  摘要：

  Mixed acetals and organotrifluoroborates undergo BF3 center dot OEt2-promoted cross-couplings to give dialkyl ethers under simple, mild conditions. A survey of reaction partners identified a hydroxamate leaving group that improves the regioselectivity and product yield in the BF3 center dot OEt2-promoted coupling reaction of mixed acetals and potassium alkynyl-, alkenyl-, aryl- and heteroaryltrifluoroborates to access substituted dialkyl ethers. This leaving group enables the reaction to proceed rapidly under mild conditions (0 degrees C, 5-60 min) and permits reactions with electron-deficient potassium aryltrifluoroborates that are less reactive with other acetal substrates. A study of the reaction mechanism and characterization of key intermediates by NMR spectroscopy and X-ray crystallography identified a role for the hydroxamate moiety as a reversible leaving group that serves to stabilize the key oxocarbenium intermediate and the need for a slight excess of organodifluoroborane to serve as a catalyst. A secondary role for the boron nucleophile as an activating ligand was also considered. These studies provide the basis for a general class of reagents that lead to dialkyl ethers by a simple, predictable cross-coupling reaction.

  DOI：

  10.1021/ja205174c

文献信息

• Synthesis of Dialkyl Ethers from Organotrifluoroborates and Acetals
  作者：T. Andrew Mitchell、Jeffrey W. Bode

  DOI：10.1021/ja906514s

  日期：2009.12.23

  The formation of ethers by C-O bond formation under harsh basic or acidic conditions is an entrenched synthetic disconnection in organic chemistry. We report a strategic alternative that involves the BF(3).OEt(2)-promoted coupling of stable, easily prepared acetals with widely available potassium aryl-, alkenyl-, and alkynyltrifluoroborates. This fast, operationally simple process offers straightforward

  在苛刻的碱性或酸性条件下通过 CO 键形成形成醚是有机化学中根深蒂固的合成断开。我们报告了一种战略替代方案，涉及 BF(3).OEt(2) 促进的稳定、易于制备的缩醛与广泛可用的芳基-、烯基-和炔基三氟硼酸钾的偶联。这种快速、操作简单的过程提供了直接获得二烷基醚的途径，其中许多使用经典方法难以制备。使用 MOM 保护的醇和缩醛保护的醛可以形成醚，而无需求助于保护基操作或强碱。
• A New Method of Synthesis for Propargylic Amines and Ethers via Benzotriazole Derivatives Using Sodium Dialkynyldiethylaluminates
  作者：Jin Hee Ahn、Meyoung Ju Joung、Nung Min Yoon、Daniela C. Oniciu、Alan R. Katritzky

  DOI：10.1021/jo9814750

  日期：1999.1.1

  1-(alpha-Aminoalkyl)benzotriazoles react with sodium dialkynyldiethylaluminates to give propargylic amines in excellent yields, including unsubstituted N,N-dialkyl propargylamines, which are difficult to obtain from Lithium acetylide. The reaction of alpha-benzotriazolyl alkyl ethers and sodium dialkynyldiethylaluminate in the presence of zinc iodide also gives propargylic ethers in excellent yields. Unsubstituted propargyl ethers are prepared via the desilylation of trimethylsilylpropargyl ethers.
• Palladium catalyzed cross-coupling and tandem cyclization-coupling of α-halo(thio)ethers with organotins
  作者：R.K. Bhatt、Shin Dong-Soo、J.R. Falck、Charles Mioskowski

  DOI：10.1016/s0040-4039(00)61224-8

  日期：1992.8

  Pd(0) mediates the cross-coupling of organotins with a variety of alpha-haloethers/thioethers in moderate-good yields whereas an alpha-chloroacetoxyalkane failed to react. Tandem cyclization-coupling of the alkyl-palladium intermediate affords novel access to heterocycles.