苯,1-甲氧基-4-[(4-戊炔氧基)甲基]- | 197219-01-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 苯,1-甲氧基-4-[(4-戊炔氧基)甲基]-
• 英文名称: 1-methoxy-4-pent-4-ynyloxymethyl-benzene
• 英文别名: 1-methoxy-4-((pent-4-yn-1-yloxy)methyl)benzene；1-(4-methoxybenzyloxy)pent-4-yne；1-Methoxy-4-(pent-4-ynoxymethyl)benzene
• CAS: 197219-01-5
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: TUPQVADGHLECBL-UHFFFAOYSA-N

物化性质

• 沸点：
  292.5±25.0 °C(Predicted)
• 密度：
  1.009±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  苯,1-甲氧基-4-[(4-戊炔氧基)甲基]- 在 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以91%的产率得到4-戊炔-1-醇
  参考文献：
  名称：

  Mild, selective deprotection of PMB ethers with triflic acid/1,3-dimethoxybenzene

  摘要：

  An efficient method for the cleavage of the p-methoxybenzyl protecting group of several alcohols in the presence of 0.5 equiv of trifluoromethanesulfonic acid and 1,3-dimethoxybenzene in dichloromethane at room temperature is described. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.08.102
• 作为产物：
  描述：

  4-甲氧基苄醇 在 氢溴酸 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 42.17h， 生成 苯,1-甲氧基-4-[(4-戊炔氧基)甲基]-
  参考文献：
  名称：

  Asymmetric Synthesis of (−)-Swainsonine, (+)-1,2-Di-epi-swainsonine, and (+)-1,2,8-Tri-epi-swainsonine

  摘要：

  The asymmetric synthesis of H-swainsonine via a nonchiral pool route that involves the Sharpless epoxidation to induce chirality is reported. The key steps involve vinyl epoxide aminolysis, ring-closing metathesis, and intramolecular N-alkylation to prepare the indolizidine ring and a highly diastereoselective cis-dihydroxylation using AD-mix-cc. This synthetic strategy also allowed for the diastereoselective synthesis of (+)-1,2-di-epi-swainsonine and (+)-1,2,8-tri-epi-swainsonine.

  DOI：

  10.1021/jo025977w

文献信息

• Pd-Catalyzed Difluoromethylation of Vinyl Bromides, Triflates, Tosylates, and Nonaflates
  作者：Dalu Chang、Yang Gu、Qilong Shen

  DOI：10.1002/chem.201500551

  日期：2015.4.13

  Pd‐catalyzed difluoromethylation of di‐, tri‐ or tetra‐substituted vinyl bromides, triflates, tosylates and nonaflates under mild conditions is described. The reaction tolerates a wide range of functional groups, such as bromide, chloride, fluoride, ester, amine, nitrile, and protected carbonyl, thus providing a general route for the preparation of difluoromethylated alkenes.

  描述了在温和条件下二，三或四取代乙烯基溴，三氟甲磺酸酯，甲苯磺酸酯和壬二酸酯的钯催化二氟甲基化。该反应可耐受各种官能团，例如溴化物，氯化物，氟化物，酯，胺，腈和受保护的羰基，因此提供了制备二氟甲基化烯烃的一般途径。
• Benzylation of hydroxy groups with tertiary amine as a base
  作者：Jeremiah W. Gathirwa、Toshihide Maki

  DOI：10.1016/j.tet.2011.10.016

  日期：2012.1

  The benzylation of hydroxy groups in the presence of tertiary amines is described. A mixture of an alcohol and a benzyl halide afforded the corresponding benzyl ether in good to excellent yields in the presence of diisopropylethylamine. The importance of solventless conditions was observed. The reaction showed high tolerance to many functional groups including benzoate, even at a reaction temperature

  描述了在叔胺存在下羟基的苄基化。在二异丙基乙胺的存在下，醇和苄基卤的混合物以良好或优异的产率提供了相应的苄基醚。观察到无溶剂条件的重要性。该反应即使在150℃的反应温度下也显示出对包括苯甲酸酯在内的许多官能团的高耐受性。发现碘化钠是加速反应的有效催化剂。
• Manganese‐Catalyzed Carbonylative Annulations for Redox‐Neutral Late‐Stage Diversification
  作者：Yu‐Feng Liang、Ralf Steinbock、Annika Münch、Dietmar Stalke、Lutz Ackermann

  DOI：10.1002/anie.201801111

  日期：2018.5.4

  inexpensive, nontoxic manganese catalyst enabled unprecedented redox‐neutral carbonylative annulations under ambient pressure. The manganese catalyst outperformed all other typically used base and precious‐metal catalysts. The outstanding versatility of the manganese catalysis manifold was reflected by ample substrate scope, setting the stage for effective late‐stage manipulations under racemization‐free

  廉价，无毒的锰催化剂可在环境压力下实现前所未有的氧化还原中性羰基环化反应。锰催化剂的性能优于所有其他常用的碱金属和贵金属催化剂。充足的底物范围反映了锰催化歧管出色的多功能性，为在无消旋条件下对许多市售药物和天然产物（包括生物碱，氨基酸，类固醇和碳水化合物）进行有效的后期操作奠定了基础。
• A new strategy for the synthesis of substituted dihydropyrones and tetrahydropyrones via palladium-catalyzed coupling of thioesters
  作者：Haruhiko Fuwa、Kana Mizunuma、Seiji Matsukida、Makoto Sasaki

  DOI：10.1016/j.tet.2011.03.114

  日期：2011.7

  In this paper, we describe a new strategy for the synthesis of substituted dihydropyrones and tetrahydropyrones. By exploiting palladium-catalyzed coupling of thioesters with terminal alkynes or alkenylboronic acids, a variety of β-hydroxy ynones or enones, respectively, could be prepared in an efficient manner under mild conditions. AgOTf-promoted intramolecular oxa-conjugate cyclization of β-hydroxy

  在本文中，我们描述了一种合成取代的二氢吡喃酮和四氢吡喃酮的新策略。通过利用钯催化的硫酯与末端炔烃或烯基硼酸的偶联，可以在温和的条件下以有效的方式分别制备各种β-羟基炔酮或烯酮。AgOTf促进的β-羟基炔酮的分子内氧杂共轭环化反应以极好的收率提供了2,6-取代的二氢吡喃酮。另一方面，β-羟基烯酮的酸催化环化由于其可逆性质而导致产物2,6-取代的四氢吡喃酮的外消旋化。最终，发现取代的二氢吡喃酮的立体选择性加氢是合成2,6-顺式的坚实而有效的方法-取代的四氢吡喃酮衍生物。
• C–F Bond Cleavage Enabled Redox-Neutral [4+1] Annulation via C–H Bond Activation
  作者：Cheng-Qiang Wang、Lu Ye、Chao Feng、Teck-Peng Loh

  DOI：10.1021/jacs.6b12142

  日期：2017.2.8

  α-difluoromethylene alkyne as a nontraditional one-carbon reaction partner, a synthetically novel method for the construction of isoindolin-1-one derivatives via Rh(III)-catalyzed [4+1] annulation reaction is reported. The 2-fold C-F bond cleavage not only enables the generation of desired product under an overall oxidant-free condition but also results in a net migration of carbon-carbon triple bond. In addition

  使用 α,α-二氟亚甲基炔作为非传统的单碳反应伙伴，报道了一种通过 Rh(III) 催化的 [4+1] 环化反应构建异吲哚啉-1-one 衍生物的合成新方法。2 倍 CF 键断裂不仅能够在整体无氧化剂的条件下生成所需的产物，而且还会导致碳-碳三键的净迁移。此外，由于采用了温和的反应条件，本反应方案对广泛的官能团具有耐受性。