(1-甲氧基-3-甲基-3-丁烯)-苯 | 70672-86-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (1-甲氧基-3-甲基-3-丁烯)-苯
• 英文名称: 4-methoxy-2-methyl-4-phenyl-1-butene
• 英文别名: 2-methyl-4-methoxy-4-phenyl-1-butene；(1-Methoxy-3-methyl-but-3-enyl)-benzene；(1-methoxy-3-methylbut-3-enyl)benzene
• CAS: 70672-86-5
• 化学式: C₁₂H₁₆O
• mdl: MFCD09030882
• 分子量: 176.258
• InChiKey: NJORHIXUSNLIQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 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-methyl-1-phenyl-3-butenyl)oxy>methyl>seleno>benzene 生成 (1-甲氧基-3-甲基-3-丁烯)-苯
  参考文献：
  名称：

  Rawal Viresh H., Singh Surendra P., Dufour Claire, Michoud Christophe, J. Org. Chem, 58 (1993) N 27, S 7718-7727

  摘要：

  DOI：

文献信息

• Trimethylsilyl Trifluoromethanesulfonate Catalyzed One-Pot Method for the Conversion of Aldehydes to Homoallyl Ethers in an Ionic Liquid
  作者：Ram Mohan、Peter Anzalone

  DOI：10.1055/s-2005-872112

  日期：——

  A mild method for the trimethylsilyl trifluoromethanesulfonate (TMSOTf) catalyzed one-pot synthesis of homoallyl ethers from aldehydes has been developed in the ionic liquid 1-butyl-3-methylimidazolium trifluoromethanesulfonate ([bmim] [OTf]). The advantages of this method include the use of a recyclable ionic liquid, facile product isolation without employing excess organic solvent, elimination of an aqueous waste stream, and mild reaction conditions.

  在离子液体1-丁基-3-甲基咪唑三氟甲磺酸盐([bmim] [OTf])中，开发了一种温和的方法，用于由醛类通过三甲基硅烷三氟甲磺酸酯(TMSOTf)催化的一锅法合成同烯丙基醚。该方法的优势包括使用可回收的离子液体、便于分离产物而不需要额外使用有机溶剂、消除水性废液流以及温和的反应条件。
• Scope of alkoxymethyl radical cyclizations
  作者：Viresh H. Rawal、Surendra P. Singh、Claire Dufour、Christophe Michoud

  DOI：10.1021/jo00079a016

  日期：1993.12

  We have explored different aspects of the cyclization capability of alkoxymethyl radicals and report here a full account of our investigations. The required radicals were generated from (phenylseleno)methyl ethers (e.g., 6), which were prepared from homoallylic or bis-homoallylic alcohols by a two-step process. The alcohols were alkylated with (iodomethyl)tributylstannane. The stannanes were reacted with n-BuLi, and the resulting alpha-alkoxyanions were trapped with diphenyldiselenide to give the (phenylseleno)methyl ethers, which were stable to chromatography. When treated with tributyltin hydride, in the presence of a radical initiator, these precursors undergo a smooth cyclization to substituted tetrahydrofurans and tetrahydropyrans. Formation of the cyclization product was found to be the primary pathway even at relatively high tin hydride concentration. The diastereoselectivity of this cyclization was comparable to that observed in other radical cyclizations. The cis selectivity in cyclization of 6 increased gradually (up to 11:1) as the reaction temperature was lowered. The cyclization can be used for the synthesis of bicyclic and tricyclic compounds and can be incorporated in systems capable of tandem cyclizations.
• 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.
• Action d'organoaluminiques α-insatures sur les acetals et les cetals
  作者：F. Barbot、Ph. Miginlac

  DOI：10.1016/s0022-328x(00)83185-x

  日期：1979.4
• Cyclization of alkoxymethyl radicals
  作者：Viresh H. Rawal、Surendra P. Singh、Claire Dufour、Christophe Michoud

  DOI：10.1021/jo00018a005

  日期：1991.8

  Alkoxymethyl radicals, generated conveniently from phenylseleno precursors, cyclize to afford substituted tetrahydrofurans and tetrahydropyrans in excellent yield and with good stereoselectivity.