1-Methoxy-4-tetradec-1-enylbenzene | 1262791-62-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-Methoxy-4-tetradec-1-enylbenzene
• CAS: 1262791-62-7
• 化学式: C₂₁H₃₄O
• 分子量: 302.5
• InChiKey: INBYXIYMUGBOHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  22
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-Methoxy-4-tetradec-1-enylbenzene 在 potassium permanganate 作用下， 生成 1-(4-methoxyphenyl)-1,2-tetradecanedione
  参考文献：
  名称：

  面包酵母合成新的手性酮醇

  摘要：

  通过面包酵母通过不对称还原相应的二酮1a - 1r，合成了14种手性α-和β-酮醇2a - 2r。此外，通过苯甲酸的相应醛的苯偶姻缩合反应，合成了十种相应的外消旋α-酮醇，它们通过手性HPLC上的手性拆分用于测定ee值。在这15种二酮中，1j和手性α-酮醇2i，2j和手性β-酮醇2r是新型化合物。六种酮醇2b，2c，2d，2f，面包酵母首次合成了2h和2p。文献中有一些研究，其中在与本文报道的条件不同的各种条件下，将面包酵母应用于二酮1a，1g，1e，1k和1n。这些研究的产量和ee值不如我们的结果高。合成的所有酮醇均通过IR，NMR（1 H和13 C）和MS表征。还讨论了二酮的结构与产率，非对映选择性和对映体过量之间的关系。

  DOI：

  10.1016/j.tetasy.2014.01.003
• 作为产物：
  描述：

  1-(4-methoxy-phenyl)-tetradecan-1-one 在 sodium tetrahydroborate 作用下， 生成 1-Methoxy-4-tetradec-1-enylbenzene
  参考文献：
  名称：

  Asymmetric synthesis of new chiral 1,2- and 1,3-diols

  摘要：

  Seven chiral 1,2-diols and six chiral 1,3-diols were synthesized by the asymmetric reduction of the corresponding 1,2-diketones and 1,3-diketones using oxazaborolidine-BH3 catalyst. The 13 corresponding racemic 1,2- and 1,3-diols were synthesized by reducing the diketones with NaBH4 and they were used for determining the ee values through their chiral resolution on HPLC and GC. Five starting diketones, four racemic 1,2-diols, five chiral 1,2-diols, and two chiral 1,3-diols are novel compounds. The new chiral compounds were characterized by IR, H-1 and C-13 NMR, MS, and elemental analysis. The asymmetric reduction method, oxazaborolidine-BH3, was applied to these diketones for the first time in this study. The relationship between the structure of the diketone and the yield, diastereoselectivity, and enantiomeric excess was discussed.

  DOI：

  10.1007/s00706-012-0792-7

文献信息

• Mechanism of Copper-Catalyzed Hydroalkylation of Alkynes: An Unexpected Role of Dinuclear Copper Complexes
  作者：Alison M. Suess、Mycah R. Uehling、Werner Kaminsky、Gojko Lalic

  DOI：10.1021/jacs.5b03086

  日期：2015.6.24

  mechanistic study of copper-catalyzed hydroalkylation of terminal alkynes. Relying on the established chemistry of N-heterocyclic carbene copper hydride (NHCCuH) complexes, we previously proposed that the hydroalkylation reaction proceeds by hydrocupration of an alkyne by NHCCuH followed by alkylation of the resulting alkenylcopper intermediate by an alkyl triflate. NHCCuH is regenerated from NHCCuOTf

  本文介绍了铜催化末端炔烃加氢烷基化的机理研究。依赖于 N-杂环卡宾氢化铜 (NHCCuH) 配合物的既定化学，我们之前提出加氢烷基化反应是通过 NHCCuH 对炔烃的加氢反应进行的，然后通过烷基三氟甲磺酸酯对所得烯基铜中间体进行烷基化。NHCCuH 通过用 CsF 取代然后用硅烷进行金属转移从 NHCCuOTf 再生。根据该提议，NHCCuH 必须比与烷基三氟甲磺酸酯更快地与炔烃反应以避免三氟甲磺酸烷基酯的还原。然而，我们已经确定 NHCCuH 与烷基三氟甲磺酸酯的反应比与末端炔烃的反应速度要快得多，这强烈表明先前提出的机制是不正确的。此外，我们发现 NHCCuOTf 快速捕获 NHCCuX (X = F, H, 烯基) 复合物以产生 (NHCCu)2(μ-X)(OTf) (X = F, H, 烯基) 复合物。在本文中，我们提出了一种新的炔烃加氢烷基化机制，该机制以双核 (NHCCu)2(μ-H)(OTf)（X
• Synthesis of new chiral keto alcohols by baker’s yeast
  作者：Tülay Yıldız、Nurgül Çanta、Ayşe Yusufoğlu

  DOI：10.1016/j.tetasy.2014.01.003

  日期：2014.2

  Fourteen chiral α- and β-keto alcohols 2a–2r were synthesized by the asymmetric reduction of their corresponding diketones 1a–1r via baker’s yeast. In addition, ten corresponding racemic α-keto alcohols were synthesized by the benzoin condensation of their corresponding aldehydes, which were used for the determination of the ee values through their chiral resolution on chiral HPLC. Amongst the 15 diketones

  通过面包酵母通过不对称还原相应的二酮1a - 1r，合成了14种手性α-和β-酮醇2a - 2r。此外，通过苯甲酸的相应醛的苯偶姻缩合反应，合成了十种相应的外消旋α-酮醇，它们通过手性HPLC上的手性拆分用于测定ee值。在这15种二酮中，1j和手性α-酮醇2i，2j和手性β-酮醇2r是新型化合物。六种酮醇2b，2c，2d，2f，面包酵母首次合成了2h和2p。文献中有一些研究，其中在与本文报道的条件不同的各种条件下，将面包酵母应用于二酮1a，1g，1e，1k和1n。这些研究的产量和ee值不如我们的结果高。合成的所有酮醇均通过IR，NMR（1 H和13 C）和MS表征。还讨论了二酮的结构与产率，非对映选择性和对映体过量之间的关系。
• Asymmetric synthesis of new chiral 1,2- and 1,3-diols
  作者：Tülay Yıldız、Ayşe Yusufoğlu

  DOI：10.1007/s00706-012-0792-7

  日期：2013.2

  Seven chiral 1,2-diols and six chiral 1,3-diols were synthesized by the asymmetric reduction of the corresponding 1,2-diketones and 1,3-diketones using oxazaborolidine-BH3 catalyst. The 13 corresponding racemic 1,2- and 1,3-diols were synthesized by reducing the diketones with NaBH4 and they were used for determining the ee values through their chiral resolution on HPLC and GC. Five starting diketones, four racemic 1,2-diols, five chiral 1,2-diols, and two chiral 1,3-diols are novel compounds. The new chiral compounds were characterized by IR, H-1 and C-13 NMR, MS, and elemental analysis. The asymmetric reduction method, oxazaborolidine-BH3, was applied to these diketones for the first time in this study. The relationship between the structure of the diketone and the yield, diastereoselectivity, and enantiomeric excess was discussed.