1-((2,2-dimethylhex-5-en-3-yloxy)methyl)benzene | 137438-50-7

• 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-((2,2-dimethylhex-5-en-3-yloxy)methyl)benzene
• 英文别名: 4-benzyloxy-5,5-dimethyl-hex-1-ene；(1-Tert-butyl-but-3-enyloxymethyl)-benzene；2,2-dimethylhex-5-en-3-yloxymethylbenzene
• CAS: 137438-50-7
• 化学式: C₁₅H₂₂O
• 分子量: 218.339
• InChiKey: CYTMRCFVBOCVMW-UHFFFAOYSA-N

物化性质

• 沸点：
  277.4±19.0 °C(Predicted)
• 密度：
  0.910±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2909309090

反应信息

• 作为产物：
  描述：

  苄氧基三甲基硅烷 、 特戊醛 在 trimethylsilyl fluorosulfonate 、 烯丙基三甲基硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以92%的产率得到1-((2,2-dimethylhex-5-en-3-yloxy)methyl)benzene
  参考文献：
  名称：

  Trimethylsilylfluorosulfonate (TMSOFs): An alternative to TMS triflate as a source of Me3Si+

  摘要：

  Generation of trimethylsilylfluorosulfonate in situ provides a useful source of TMS+, the reactivity of which is essentially equivalent to that of TMS triflate. Its precursors, in particular FSO3H, are less costly than those of TMSOTf or the reagent itself

  DOI：

  10.1016/s0040-4039(00)77474-0

文献信息

• 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。
• The silyl modified sakurai (SMS) reaction. An efficient and versatile one-pot synthesis of homoallylic ethers
  作者：Abdelaziz Mekhalfia、István E Markó

  DOI：10.1016/s0040-4039(00)92306-2

  日期：1991.1

  An efficient and versatile preparation of homoallylic ethers from trimethylsilyl ethers, allyltrimethylsilane and carbonyl compounds is described. Some preliminary experiments, aimed at controlling the diastereofacial selection in the SMS reaction, are also reported.

  描述了由三甲基甲硅烷基醚，烯丙基三甲基硅烷和羰基化合物有效和通用地制备均烯丙基醚的方法。还报道了一些旨在控制SMS反应中非对映体选择的初步实验。
• Brønsted Acid-Catalyzed Three-Component Hosomi–Sakurai Reactions
  作者：Daniela Kampen、Arnaud Ladépêche、Gerrit Claßen、Benjamin List

  DOI：10.1002/adsc.200800036

  日期：2008.5.5

  Aldehydes react with silyl ethers or the corresponding alcohols and allylsilanes in the presence of catalytic amounts of 2,4-dinitrobenzenesulfonic acid (DNBA) to provide a wide range of homoallylic ethers in moderate to high yields.

  醛在催化量的2,4-二硝基苯磺酸（DNBA）的存在下与甲硅烷基醚或相应的醇和烯丙基硅烷反应，以中等至高收率提供各种均聚物。
• 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.