1-bromo-4-(1-benzyloxy-but-3-enyl)benzene

• 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-bromo-4-(1-benzyloxy-but-3-enyl)benzene
• 英文别名: 1-Bromo-4-(1-phenylmethoxybut-3-enyl)benzene
• 化学式: C₁₇H₁₇BrO
• 分子量: 317.225
• InChiKey: DQQARYUSTMPULG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  对溴苯甲醛 在 三氯化铁 作用下， 以 硝基甲烷 为溶剂， 反应 2.17h， 生成 1-bromo-4-(1-benzyloxy-but-3-enyl)benzene
  参考文献：
  名称：

  氯化铁（III）催化从醛类开始方便地一锅合成高烯丙基苄基醚。

  摘要：

  [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。

  DOI：

  10.1021/ol035019w

文献信息

• Iron(III) p-toluenesulfonate catalyzed synthesis of homoallyl ethers from acetals and aldehydes
  作者：Matthew J. Spafford、Erin D. Anderson、Joshua R. Lacey、Ann C. Palma、Ram S. Mohan

  DOI：10.1016/j.tetlet.2007.10.026

  日期：2007.12

  Iron(III) p-toluenesulfonate, Fe(OTs)3·6H2O, is an inexpensive, versatile and commercially available catalyst for the allylation of acetals using allyltrimethylsilane to yield homoallyl ethers in moderate to good yields. The one-pot conversion of aldehydes to homoallyl ethers using alkoxysilanes has also been accomplished using Fe(OTs)3·6H2O as a catalyst. The use of mild reaction conditions and a

  对甲苯磺酸铁（III）Fe（OTs）3 ·6H 2 O是一种廉价，通用且可商购的催化剂，用于使用烯丙基三甲基硅烷将乙缩醛进行烯丙基化，以中等至良好的产率生成均烯丙基醚。使用Fe（OTs）3 ·6H 2 O作为催化剂，还可以使用烷氧基硅烷将醛单锅转化为均烯丙基醚。使用温和的反应条件和相对无腐蚀性的催化剂使该方法成为合成一系列均烯丙基醚的有吸引力的选择。
• HClO4-supported on silica gel: a mild and efficient catalyst for Hosomi–Sakurai reaction
  作者：Kaliyappan Murugan、Chinpiao Chen

  DOI：10.1016/j.tetlet.2011.08.145

  日期：2011.11

  Perchloric acid supported on silica gel was found to be an efficient catalyst (2 mol %) for the Hosomi–Sakurai allylation of numerous aldehydes with allyltrimethylsilane in the presence of benzyl alcohol. This method was also effective for the allylation of secondary alcohols under mild experimental conditions.

  人们发现，在苄醇存在下，硅胶上负载的高氯酸是将许多醛与烯丙基三甲基硅烷进行Hosomi-Sakurai烯丙基化反应的有效催化剂（2摩尔％）。在温和的实验条件下，该方法对于仲醇的烯丙基化也是有效的。
• Bismuth Compounds in Organic Synthesis. A One-Pot Synthesis of Homoallyl Ethers and Homoallyl Acetates from Aldehydes Catalyzed by Bismuth Triflate
  作者：Peter W. Anzalone、Ashvin R. Baru、Eric M. Danielson、Patrick D. Hayes、Mai P. Nguyen、Ambrose F. Panico、Russell C. Smith、Ram S. Mohan

  DOI：10.1021/jo048475m

  日期：2005.3.1

  [GRAPHICS]Three one-pot methods for the conversion of aldehydes to homoallyl ethers catalyzed by Bi(OTf)(3)center dot xH(2)O (1 < x < 4) have been developed. The one-pot synthesis of homoallyl ethers can be achieved either by in situ generation of the acetal followed by its reaction with allyltrialkylsilane or by a three-component synthesis in which the aldehyde, trimethylorthoformate or an alkoxytrimethylsilane and allyltrimethylsilane are mixed together in the presence of bismuth triflate (0.1-1.0 mol %). In addition, a three-component synthesis of homoallyl acetates, which is achieved by reacting the aldehyde, acetic anhydride, and allyltrimethylsilane in the presence of bismuth triflate (3.0-5.0 mol %), has been developed. The use of a relatively nontoxic, easy to handle, and inexpensive catalyst adds to the versatility of these methods.
• Iodine-catalyzed one-pot three-component synthesis of homoallyl benzyl ethers from aldehydes
  作者：Dolly Kataki、Prodeep Phukan

  DOI：10.1016/j.tetlet.2009.02.052

  日期：2009.4

  Iodine has been found to be an effective catalyst for one-pot synthesis of homoallyl benzyl ethers under mild reaction conditions. Various homoallyl benzyl ethers were synthesized in moderate to high yield by three-component condensation of aldehydes, benzyloxytrimethylsilane, and allyltrimethylsilane in presence of iodine (10 mol %) in dichloromethane at 0 degrees C. (C) 2009 Elsevier Ltd. All rights reserved.
• 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。