(1-ethoxy-but-3-enyl)benzene | 54703-48-9

• 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: (1-ethoxy-but-3-enyl)benzene
• 英文别名: Benzene, (1-ethoxy-3-butenyl)-；1-ethoxybut-3-enylbenzene
• CAS: 54703-48-9
• 化学式: C₁₂H₁₆O
• 分子量: 176.258
• InChiKey: SIZWGEZSKFOIIF-UHFFFAOYSA-N

物化性质

• 沸点：
  89-91 °C(Press: 2 Torr)
• 密度：
  0.9472 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  苯甲醛 在 对甲苯磺酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 2.75h， 生成 (1-ethoxy-but-3-enyl)benzene
  参考文献：
  名称：

  Mesoporous aluminosilicate-catalyzed allylation of carbonyl compounds and acetals

  摘要：

  A mesoporous aluminosilicate (Al-MCM-41) was found to be an effective heterogeneous catalyst for the reaction of both carbonyl compounds and acetals with allylsilanes to afford the corresponding homoallyl silyl ethers and homoallyl alkyl ethers, respectively. Both the mesoporous structure and the presence of aluminum moiety were indispensable for the high catalytic activity of Al-MCM-41. Moreover, Al-MCM-41 could catalyze the reaction of acetals chemoselectively in the presence of the corresponding carbonyl compounds. The solid acid catalyst Al-MCM-41 could be recovered easily by filtration and could be reused three times without a significant loss of catalytic activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.055

文献信息

• Highly efficient indium-catalyzed chemoselective allylation–etherification and reductive etherification of aromatic aldehydes with functional silanes
  作者：Ming-Song Yang、Li-Wen Xu、Hua-Yu Qiu、Guo-Qiao Lai、Jian-Xiong Jiang

  DOI：10.1016/j.tetlet.2007.11.062

  日期：2008.1

  Indium(III) chloride is an effective Lewis acid catalyst for one-pot allylation–etherification and reductive etherification of aromatic aldehydes with functional silanes, allyltriethoxysilane, and triethoxysilane, at room temperature to afford corresponding ethers in excellent yields. Additionally, the InCl3-catalyzed reactions in the presence of TMSCl offer significant advantages in its ease of working-up

  氯化铟（III）是一种有效的路易斯酸催化剂，可在室温下一锅化芳族醛与官能硅烷，烯丙基三乙氧基硅烷和三乙氧基硅烷的烯丙基化—醚化和还原醚化，从而以优异的收率提供相应的醚。另外，在TMSC1存在下，InCl 3催化的反应提供了明显的优点，因为其易于处理以在温和条件下制备不对称醚。
• Catalytic Use of Elemental Gallium for Carbon–Carbon Bond Formation
  作者：Bo Qin、Uwe Schneider

  DOI：10.1021/jacs.6b06767

  日期：2016.10.12

  The first catalytic use of Ga(0) in organic synthesis has been developed by using a Ag(I) cocatalyst, crownether ligation, and ultrasonic activation. Ga(I)-catalyzed C-C bond formations between allyl or allenyl boronic esters and acetals, ketals, or aminals have proceeded in high yields with essentially complete regio- and chemoselectivity. NMR spectroscopic analyses have revealed novel transient Ga(I)

  Ga(0) 在有机合成中的首次催化应用是通过使用 Ag(I) 助催化剂、冠醚连接和超声活化开发的。Ga(I) 催化的烯丙基或丙二烯基硼酸酯与缩醛、缩酮或胺缩醛之间的 CC 键形成以高产率进行，具有基本上完全的区域选择性和化学选择性。核磁共振光谱分析揭示了新的瞬态 Ga(I) 催化物质，分别通过 Ga(0) 和 B-Ga 金属转移的部分氧化原位形成。已经证明了不对称 Ga(I) 催化的可能性。
• Substitution of α-azido ethers with Grignard reagents and its use in combinatorial chemistry
  作者：Mukulesh Baruah、Mikael Bols

  DOI：10.1039/b110428b

  日期：2002.2.6

  α-Azidobenzyl ethers were reacted with alkyl or arylGrignard reagents in toluene to produce α-alkylbenzyl or diarylmethyl ethers in 82–94% yield. α-Azidobenzyl ethers were also reacted with multicomponent Grignard reagents to produce libraries of α-alkylbenzyl ethers.

  在甲苯中，α-叠氮苄基醚与烷基或芳基格氏试剂反应，以82-94%的产率生成α-烷基苄基醚或二芳基甲基醚。α-叠氮苄基醚还可以与多组分格氏试剂反应，生成α-烷基苄基醚的库。
• An Environmentally Friendly Synthesis of Functionalized Indanes Using Electrochemical Cyclization of <i>ortho</i>-Halo-Substituted Homoallyl Ethers and Esters
  作者：Elisabet Duñach、Ram Mohan、Sandra Olivero、Rodolphe Perriot、Ashvin Baru、Eric Bell

  DOI：10.1055/s-2006-948182

  日期：2006.8

  indanes catalyzed by Ni(II) catalyst precursors derived from Ni(cyclam)Br 2 , (cyclam = 1,4,8,11-tetraazacyclotetradecane) and Ni(tmc)Br 2 , (tmc = 1,4,8,11-tetramethyl-1,4,8,11 -tetraazacyclotetradecane) is reported. The starting homoallyl ethers were synthesized using either a one-pot method for allylation of aldehydes or by direct allylation of the corresponding acetals using bismuth triflate as a

  在衍生自 Ni(cyclam)Br 2 、（cyclam = 1,4,8,11-四氮杂环十四烷）的 Ni(II) 催化剂前体催化下，一系列邻卤代高烯丙基醚和酯电化学环化成官能化茚满报道了Ni(tmc)Br 2 ，(tmc = 1,4,8,11-四甲基-1,4,8,11-四氮杂环十四烷)。使用用于醛烯丙基化的一锅法或使用三氟甲磺酸铋作为催化剂通过相应缩醛的直接烯丙基化来合成起始高烯丙基醚。铋盐的显着低毒性、低成本和易于处理，加上电化学过程的温和性质，使得这种茚满合成方法特别环保且具有吸引力。
• Iron(III) Chloride-Catalyzed Convenient One-Pot Synthesis of Homoallyl Benzyl Ethers Starting from Aldehydes
  作者：Tsutomu Watahiki、Yusuke Akabane、Seiji Mori、Takeshi Oriyama

  DOI：10.1021/ol035019w

  日期：2003.8.1

  Iron(III) chloride-catalyzed effective allylation reactions of acetals with allyltrimethylsilane proceeded smoothly in high to excellent yields. In addition, this method could be applied to the one-pot synthesis of homoallyl benzyl ethers by a combination of dibenzyl acetalization of aldehydes and consecutive allylation of dibenzyl acetals.

  [反应：见正文]乙二醛与烯丙基三甲基硅烷的氯化铁催化的有效烯丙基化反应以高收率顺利进行。另外，该方法可以通过醛的二苄基乙缩醛化和二苄基乙缩醛的连续烯丙基化的组合而用于一锅合成高烯丙基苄基醚。