(Z)-(2-butoxyethenyl)benzene | 36586-16-0

• 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: (Z)-(2-butoxyethenyl)benzene
• 英文别名: (Z)-β-Butoxystyrene；butyl-cis-styryl ether；Butyl-cis-styryl-aether；cis-1-Phenyl-2-n-buthoxyethylen；(Z)-(2-Butoxy-vinyl)-benzene；[(Z)-2-butoxyethenyl]benzene
• CAS: 36586-16-0
• 化学式: C₁₂H₁₆O
• 分子量: 176.258
• InChiKey: HXLLCROMVONRRO-LUAWRHEFSA-N

物化性质

• 沸点：
  265.0±9.0 °C(Predicted)
• 密度：
  0.946±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 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：

  乙酸苯汞 生成 (Z)-(2-butoxyethenyl)benzene
  参考文献：
  名称：

  ANDERSSON, CARL-MAGNUS;HALLBERG, ANDERS;DAVES, G. DOYLE JR., J. ORG. CHEM., 52,(1987) N 16, 3529-3636

  摘要：

  DOI：

文献信息

• Rationally Designed Pincer-Type Heck Catalysts Bearing Aminophosphine Substituents: Pd^IVIntermediates and Palladium Nanoparticles
  作者：Jeanne L. Bolliger、Olivier Blacque、Christian M. Frech

  DOI：10.1002/chem.200800441

  日期：2008.9.8

  catalytic cycle of the Heck reaction, their general existence as reactive intermediates (for example, in other reactions) cannot be excluded. On the contrary, they were shown to be thermally accessible. Compounds 1 and 2 show a smooth halide exchange with bromobenzene to yield their bromo derivatives in DMF at 100 degrees C. Experimental observations revealed that the halide exchange most probably proceeded

  氨基膦基钳形配合物[C6H3-2,6-（XP（哌啶基）2）2Pd（Cl）]（X = NH 1; X = O 2）可以很容易地由廉价的起始原料通过依次添加1,1在“一锅”中，在N 2下，将'，1''-膦三基三哌啶和1,3-二氨基苯或间苯二酚制得[Pd（cod）（Cl）2]（cod =环辛二烯）在甲苯中的溶液。事实证明，化合物1和2是出色的Heck催化剂，可以在很短的反应时间和较低的催化剂负载量下，在140℃下将数种电子失活和空间位阻的芳基溴化物与各种烯烃作为偶联伴侣进行定量偶联。升高的反应温度还使得在仅0.01mol％的催化剂存在下，烯烃能够与电子失活的和位阻的芳基氯有效地偶联。进行的机理研究排除了均相的Pd 0配合物是1和2的催化活性形式。另一方面，钯纳米颗粒参与催化循环得到了有力的实验支持。即使衍生自1（和2）的钳型Pd IV中间体不参与Heck反应的催化循环，也不能排除它们作为反应性中
• Aminophosphine Palladium Pincer Complexes for Suzuki and Heck Reactions
  作者：Jeanne L. Bolliger、Christian M. Frech

  DOI：10.2533/chimia.2009.23

  日期：——

  The aminophosphine-based pincer complexes [C6H3-2,6-NHP(piperidinyl)2}2Pd(Cl)] (2) and [C6H3-2,6-OP(piperidinyl)2}2Pd(Cl)] (3) are readily prepared from cheap starting materials by sequential addition of 1,1?,1?-phosphinetriyltripiperidine and 1,3-diaminobenzene or resorcinol to solutions of [Pd(cod)(Cl)2] (cod = cyclooctadiene) in toluene under N2 in 'one pot'. Compounds 2 and 3 proved to be not only excellent catalysts for the Suzuki and the Heck cross-coupling reactions, but they are also very convenient to use: The toluene solutions of the 'one-pot' syntheses can be used directly for the catalytic reactions, thereby saving the time-consuming isolation of the catalysts. The Suzuki cross-coupling reaction catalyzed by 2 and 3 can be performed in air at 100 °C in toluene of technical quality: in the presence of only 0.001mol% of catalyst, several electronically deactivated and sterically hindered aryl bromides are quantitatively coupled with phenylboronic acid within a few minutes of reaction time. Furthermore, complex 2 enables the use of activated and non-activated aryl chlorides as coupling partners in the Suzuki reaction. Compounds 2 and 3 have also been shown to be highly active and reliable Heck catalysts: Very low catalyst loadings and short reaction times are required for the quantitative coupling of several electronically deactivated and sterically hindered aryl bromides with various olefins at 140 °C. At increased temperatures, even electronically deactivated and sterically hindered aryl chlorides can be efficiently coupled with olefins in the presence of only 0.01 mol% of catalyst.

  基于氨基膦的夹环配合物[C6H3-2,6-NHP(哌啶基)2}2Pd(Cl)]（2）和[C6H3-2,6-OP(哌啶基)2}2Pd(Cl)]（3）可以通过将1,1',1''-膦三哌啶和1,3-二氨基苯或间苯二酚依次加入苯甲醛溶液中[Pd(cod)(Cl)2]（cod = 环辛二烯）在N2气氛下在甲苯中进行'一锅法'合成而得。化合物2和3不仅被证明是苏酞基和赫克交叉偶联反应的优秀催化剂，而且它们也非常方便使用：'一锅法'合成的甲苯溶液可以直接用于催化反应，从而节省了耗时的催化剂分离过程。由2和3催化的苏酞基交叉偶联反应可以在技术质量的甲苯中在空气中以100°C进行：在只有0.001mol%催化剂存在的情况下，几种电子失活和立体位阻的芳基溴化物可以在几分钟内与苯硼酸定量偶联。此外，化合物2使得在苏酞基反应中可以使用活化和非活化的芳基氯化物作为偶联伙伴。化合物2和3也被证明是高活性和可靠的赫克催化剂：在140°C下，对于几种电子失活和立体位阻的芳基溴化物与各种烯烃的定量偶联，需要非常低的催化剂负载和短的反应时间。在提高的温度下，即使是电子失活和立体位阻的芳基氯化物也可以在只有0.01mol%催化剂存在的情况下与烯烃高效偶联。
• Ligand-Free Reusable Palladium-Catalyzed Heck-Type Coupling Reactions of Hypervalent Iodine Reagents under Mild Conditions
  作者：Xiaoming Qu、Peng Sun、Tingyi Li、Jincheng Mao

  DOI：10.1002/adsc.201100008

  日期：2011.5.9

  Highly effective palladium‐catalyzed Heck‐type couplings of hypervalent iodine reagents are reported for the first time. It is noteworthy that such reactions could be carried out in the absence of ligand at 40 °C and the catalytic system could be easily reused for five times.

  首次报道了高价碘试剂的高效钯催化的Heck型偶联。值得注意的是，此类反应可在不存在配体的情况下于40°C进行，催化体系可轻松重复使用五次。
• Nonaqueous Ionic Liquids: Superior Reaction Media for the Catalytic Heck-Vinylation of Chloroarenes
  作者：Volker P. W. Böhm、Wolfgang A. Herrmann

  DOI：10.1002/(sici)1521-3765(20000317)6:6<1017::aid-chem1017>3.0.co;2-8

  日期：2000.3.17

  tetraphenylphosphonium chloride. The scope of the new reaction medium is outlined for the first time for the vinylation of various aryl halides using different mono- and disubstituted olefins as well as a variety of known palladium(0) and palladium(II) catalyst systems. Furthermore, a novel means of catalyst recycling is presented and its scope is evaluated.

  非水离子液体（即熔融盐）构成了所有类型的芳基卤化物的钯催化的Heck乙烯基化的活化和稳定的非纯溶剂。与常规分子溶剂（例如二甲基甲酰胺（DMF），二甲基乙酰胺（DMAc），N-甲基-2-吡咯烷酮（NMP）或二恶烷）相比，尤其是对于氯代芳烃，几乎所有已知催化剂体系的活性和稳定性均得到改善。因此，即使催化量的不含配体的PdCl2，也可以从技术上令人感兴趣的氯苯和苯乙烯以高收率（周转数（TON）= 18）产生二苯乙烯，而无需进一步促进盐添加剂，例如四苯基phosph。首次概述了使用不同的单取代和二取代的烯烃以及各种已知的钯（0）和钯（II）催化剂体系对各种芳基卤化物进行乙烯基化的新反应介质的范围。此外，提出了一种新型的催化剂再循环方法，并对其范围进行了评估。
• Palladium-Catalyzed Regioselective Arylation of an Electron-Rich Olefin by Aryl Halides in Ionic Liquids
  作者：Lijin Xu、Weiping Chen、James Ross、Jianliang Xiao

  DOI：10.1021/ol000362b

  日期：2001.1.1

  [figure: see text] Palladium-catalyzed arylation of the electron-rich olefin butyl vinyl ether has been accomplished in the ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate ([bmim][BF4]), using as the arylating agents aryl iodides and bromides instead of the commonly used, but commercially unavailable and expensive, aryl triflates. The reaction proceeds with high efficiency and remarkable

  [图：见正文]富电子的烯烃丁基乙烯基醚的钯催化芳基化已在离子液体1-丁基-3-甲基咪唑四氟硼酸酯（[bmim] [BF4]）中完成，使用芳基碘化物作为芳基化剂和溴化物代替了芳烃三氟甲磺酸芳烃，而不是常用但市售和昂贵的芳基三氟甲磺酸酯。该反应以高效率和显着的区域选择性进行，几乎完全导致被烯烃碳α上的各种芳基取代为丁基乙烯基醚的杂原子。