1-bromo-4-(3-phenylpropoxy)benzene | 30752-28-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-bromo-4-(3-phenylpropoxy)benzene
• CAS: 30752-28-4
• 化学式: C₁₅H₁₅BrO
• mdl: MFCD11116249
• 分子量: 291.187
• InChiKey: URUUNCSGZYPTHC-UHFFFAOYSA-N

物化性质

• 沸点：
  385.6±25.0 °C(Predicted)
• 密度：
  1.303±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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-bromo-4-(3-phenylpropoxy)benzene 在 C₈₄H₇₀N₆P₄ 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以83%的产率得到3-phenoxypropylbenzene
  参考文献：
  名称：

  突破中性有机电子给体的极限：四（亚氨基正膦酸酯）取代的双吡啶亚次甲基

  摘要：

  制备了一种新的基态有机电子给体，其在双吡啶亚烷基骨架上具有四个强烈的π-供电子亚氨基膦酸酯取代基。循环伏安法显示，该对夫妇涉及中性有机供体及其指示，相对于饱和甘汞电极（SCE），记录的氧化还原电势为-1.70V。可以通过涉及易于制备的吡啶鎓离子前体的去质子化反应来分离（44％）这种高还原性有机化合物，或者更方便地就地生成。该给体能够还原各种芳基卤化物，并且由于其氧化还原电位，被发现是第一个对热诱导的N，N还原SN键裂解有效的有机给体。-二烷基磺酰胺和丙二醛的还原性加氢脱氰作用。

  DOI：

  10.1002/anie.201505378
• 作为产物：
  描述：

  4-溴苯酚 、 1-溴-3-苯基丙烷 在 sodium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 5.0h， 以75%的产率得到1-bromo-4-(3-phenylpropoxy)benzene
  参考文献：
  名称：

  Accelerated Biphasic Hydroformylation by Vesicle Formation of Amphiphilic Diphosphines

  摘要：

  The synthesis, aggregation behavior, and catalytic activity of rhodium complexes of a series of Xantphos derivatives with surface-active pendant groups, -4-C6H4O(CH2)(n)C6H4(SO3Na)- (n = 0, 3, 6) is described. Electron microscopy experiments show that these ligands and their complexes form vesicles in water if the hydrophobic part of the ligand is large enough (n = 3, 6). The formed aggregates are stable at elevated temperatures (90 degrees C), and their presence lends to a significant enhancement of the solubility of organic substrates in aqueous solution. This enhanced solubility results directly in a higher reaction rate in the rhodium-catalyzed hydroformylation of 1-octene. Furthermore, recycling experiments show that the TOF and the high selectivity toward the more valuable linear aldehyde remains approximately the same in four consecutive runs. This indicates that the aggregates stay intact during the recycling and the active rhodium complex is retained in the water-phase quantitatively.

  DOI：

  10.1021/ja9925610

文献信息

• Base‐Mediated O‐Arylation of Alcohols and Phenols by Triarylsulfonium Triflates
  作者：Xiao‐Xia Ming、Ze‐Yu Tian、Cheng‐Pan Zhang

  DOI：10.1002/asia.201900968

  日期：2019.10

  A mild and efficient protocol for O-arylation of alcohols and phenols (ROH) by triarylsulfonium triflates was developed under transition-metal-free conditions. Various alcohols, including primary, secondary and tertiary, and phenols bearing either electron-donating or electron-withdrawing groups on the aryl rings were smoothly converted to form the corresponding aromatic ethers in moderate to excellent

  在不含过渡金属的条件下，开发了温和有效的三芳基ulf三氟甲磺酸酯进行醇和酚（ROH）芳基化的方案。各种醇，包括在芳基环上带有给电子或吸电子基团的伯，仲和叔醇以及苯酚，可以平稳转化为相应的芳族醚，产率中等至优异。反应在一定的碱存在下于50或80°C进行24小时，并显示出良好的官能团耐受性。不对称的三芳基ulf盐的碱介导的芳基化反应可以选择性地将sulf的芳基转移到ROH上，具体取决于它们固有的电子性质。
• Fe‐Catalyzed Intramolecular Cross‐Dehydrogenative Arylation (CDA), Efficient Synthesis of 1‐Arylnaphthalenes and 4‐Arylcoumarins
  作者：Haiyan Diao、Changcheng Wang、Zhen Zhang、Zhangjie Shi、Feng Liu

  DOI：10.1002/hlca.202100056

  日期：2021.7

  Direct cross-dehydrogenative coupling of different inert C−H bonds is the most straightforward and environmentally benign method to construct C−C bonds. In this paper, we developed an iron-catalyzed intramolecular cross-dehydrogenative arylation (CDA) between benzylic C(sp3)H bond and aromatic C(sp2)H bond. From the readily available linear substrates, 1-arylnaphthalenes and 4-arylcoumarins can be

  不同惰性 C-H 键的直接交叉脱氢偶联是构建 C-C 键的最直接和环境友好的方法。在本文中，我们开发了一种铁催化的苄基 C( sp 3 )H 键和芳族 C( sp 2 )H 键之间的分子内交叉脱氢芳基化 (CDA) 。从容易获得的线性底物，可以一步快速构建 1-芳基萘和 4-芳基香豆素，产率中等至良好（18 个例子，产率高达 73%）。具有不同官能团的对称和不对称底物都可以很好地耐受该系统以形成预期的产品。提出了自由基引发的脱氢环化-脱氢串联工艺。
• Structure–activity relationship studies of sphingosine-1-phosphate receptor agonists with N-cinnamyl-β-alanine moiety
  作者：Haruto Kurata、Kazuhiro Otsuki、Kensuke Kusumi、Masakuni Kurono、Masahiko Terakado、Takuya Seko、Hirotaka Mizuno、Takeji Ono、Hiroshi Hagiya、Masashi Minami、Shinji Nakade、Hiromu Habashita

  DOI：10.1016/j.bmcl.2011.01.029

  日期：2011.3

  Structure-activity relationship of sphingosine-1-phosphate receptor agonist was examined. In terms of reducing the flexibility of molecule, hit compound 1 was modified to improve S1P(1) agonistic activity as well as selectivity over S1P(3) agonistic activity. Novel S1P agonists with cinnamyl scaffold or 1,2,5,6-tetrahydropyridine scaffold were identified. (C) 2011 Elsevier Ltd. All rights reserved.
• Pushing the Limits of Neutral Organic Electron Donors: A Tetra(iminophosphorano)-Substituted Bispyridinylidene
  作者：Samuel S. Hanson、Eswararao Doni、Kyle T. Traboulsee、Graeme Coulthard、John A. Murphy、C. Adam Dyker

  DOI：10.1002/anie.201505378

  日期：2015.9.14

  deprotonation reaction involving its readily prepared pyridinium ion precursor. This donor is able to reduce a variety of aryl halides, and, owing to its redox potential, was found to be the first organic donor to be effective in the thermally induced reductive SN bond cleavage of N,N‐dialkylsulfonamides, and reductive hydrodecyanation of malonitriles.

  制备了一种新的基态有机电子给体，其在双吡啶亚烷基骨架上具有四个强烈的π-供电子亚氨基膦酸酯取代基。循环伏安法显示，该对夫妇涉及中性有机供体及其指示，相对于饱和甘汞电极（SCE），记录的氧化还原电势为-1.70V。可以通过涉及易于制备的吡啶鎓离子前体的去质子化反应来分离（44％）这种高还原性有机化合物，或者更方便地就地生成。该给体能够还原各种芳基卤化物，并且由于其氧化还原电位，被发现是第一个对热诱导的N，N还原SN键裂解有效的有机给体。-二烷基磺酰胺和丙二醛的还原性加氢脱氰作用。
• Accelerated Biphasic Hydroformylation by Vesicle Formation of Amphiphilic Diphosphines
  作者：Marcel Schreuder Goedheijt、Brian E. Hanson、Joost N. H. Reek、Paul C. J. Kamer、Piet W. N. M. van Leeuwen

  DOI：10.1021/ja9925610

  日期：2000.3.1

  The synthesis, aggregation behavior, and catalytic activity of rhodium complexes of a series of Xantphos derivatives with surface-active pendant groups, -4-C6H4O(CH2)(n)C6H4(SO3Na)- (n = 0, 3, 6) is described. Electron microscopy experiments show that these ligands and their complexes form vesicles in water if the hydrophobic part of the ligand is large enough (n = 3, 6). The formed aggregates are stable at elevated temperatures (90 degrees C), and their presence lends to a significant enhancement of the solubility of organic substrates in aqueous solution. This enhanced solubility results directly in a higher reaction rate in the rhodium-catalyzed hydroformylation of 1-octene. Furthermore, recycling experiments show that the TOF and the high selectivity toward the more valuable linear aldehyde remains approximately the same in four consecutive runs. This indicates that the aggregates stay intact during the recycling and the active rhodium complex is retained in the water-phase quantitatively.