1-(1-methoxy-but-3-enyl)-3-methylbenzene

• 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-(1-methoxy-but-3-enyl)-3-methylbenzene
• 英文别名: 1-(1-methoxybut-3-enyl)-3-methylbenzene；1-(1-Methoxybut-3-enyl)-3-methylbenzene
• 化学式: C₁₂H₁₆O
• 分子量: 176.258
• InChiKey: IRLADXXCIPTVSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  4
• 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：

  3-甲基苯甲醛 在 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.75h， 生成 1-(1-methoxy-but-3-enyl)-3-methylbenzene
  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

• 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。
• 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。
• Unexpected Lewis Acid Mediated Reactions of 1-Arylbut-3-en-1-ols with Trimethyl Orthoformate - A New Synthesis of Homoallyl Ethers and Chlorides
  作者：Uwe Beifuss、Elena Merişor、Jürgen Conrad、Chandi Malakar

  DOI：10.1055/s-2008-1042928

  日期：2008.4

  1-Arylbut-3-en-1-ols react with trimethyl orthoformate in the presence of Lewis acids like InCl 3 , BiCl 3 , TiCl 4 , or BF 3 ·OEt 2 providing homoallyl ethers or homoallyl chlorides in high yields.

  1-Arylbut-3-en-1-ols 在路易斯酸如 InCl 3 、BiCl 3 、TiCl 4 或 BF 3 ·OEt 2 存在下与原甲酸三甲酯反应，以高产率提供高烯丙基醚或高烯丙基氯。
• Mesoporous aluminosilicate-catalyzed Sakurai allylation and Mukaiyama aldol reaction of acetals
  作者：Suguru Ito、Akira Hayashi、Hirotomo Komai、Yoshihiro Kubota、Masatoshi Asami

  DOI：10.1016/j.tetlet.2010.06.034

  日期：2010.8

  In the presence of a catalytic amount of mesoporous aluminosilicate (Al-MCM-41), both allyltrimethylsilane and silyl enol ether reacted with various acetals under mild reaction conditions to afford the corresponding homoallyl ethers and beta-alkoxy ketones, respectively. The catalyst was easily recovered from the reaction mixture and could be reused in the same reaction without a significant loss of catalytic activity. Moreover, Al-MCM-41 exhibited high chemoselectivity for acetal over aldehyde in the reactions. (C) 2010 Elsevier Ltd. All rights reserved.
• Baldry, Peter J., Journal of the Chemical Society. Perkin transactions II, 1980, p. 805 - 808
  作者：Baldry, Peter J.

  DOI：——

  日期：——