1-(3-methylphenyl)-1-heptyne | 64146-62-9

• 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-(3-methylphenyl)-1-heptyne
• 英文别名: 1-m-Methylphenyl-1-heptyn；1-Hept-1-ynyl-3-methylbenzene
• CAS: 64146-62-9
• 化学式: C₁₄H₁₈
• 分子量: 186.297
• InChiKey: NEEIGOADGOQPLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-(3-methylphenyl)-1-heptyne 在 氢气 、 C₅₄H₁₀₂Mg₂N₂O₂P₄ 作用下， 以 甲苯 为溶剂， 120.0 ℃ 、500.01 kPa 条件下， 反应 24.0h， 以99%的产率得到
  参考文献：
  名称：

  镁钳配合物及其在炔烃催化半加氢和烯烃加氢中的应用：金属-配体合作的证据

  摘要：

  开发用于环境友好的有机转化的催化剂是一个非常活跃的研究领域。迄今为止报道的大多数催化剂都是基于过渡金属配合物。近年来，已经报道了由主族金属化合物催化的例子。在此，我们报告了一系列镁钳配合物，并通过 NMR 和 X 射线单晶衍射对其进行了表征。研究了通过芳构化/脱芳构化金属-配体合作对 H 2的可逆活化。利用所获得的配合物，在无碱条件下证明了前所未有的均相主族金属催化炔烃的半氢化和烯烃的氢化，得到Z-烯烃和烷烃分别作为产物，具有优异的收率和选择性。对照实验和 DFT 研究揭示了金属-配体合作参与氢化反应。该研究不仅为镁催化的炔烃半加氢和烯烃加氢提供了新途径，而且为主族金属配合物催化的其他化合物加氢提供了机会。

  DOI：

  10.1021/jacs.2c08491
• 作为产物：
  描述：

  间碘甲苯 、 chlorozinc(1+),hept-1-yne 在 bis-triphenylphosphine-palladium(II) chloride 、 二异丁基氢化铝 作用下， 生成 1-(3-methylphenyl)-1-heptyne
  参考文献：
  名称：

  A general synthesis of terminal and internal arylalkynes by the palladium-catalyzed reaction of alkynylzinc reagents with aryl halides

  摘要：

  DOI：

  10.1021/jo00396a046

文献信息

• Palladium-Catalyzed Decarboxylative<i>sp</i>-<i>sp</i>²Cross-Coupling Reactions of Aryl and Vinyl Halides and Triflates with α,β-Ynoic Acids using Silver Oxide
  作者：Hyunseok Kim、Phil Ho Lee

  DOI：10.1002/adsc.200900502

  日期：2009.11

  Palladium-catalyzed decarboxylative sp-sp2 cross-coupling reactions of aryl and vinyl halides and triflates with α,β-ynoic acids using silver oxide have been developed. A variety of α,β-ynoic acids were readily decarboxylated in the presence of silver oxide and then, generated in situ, silver acetylides were coupled with electrophiles in the presence of a palladium(0) catalyst under neutral conditions

  已经开发了使用氧化银的芳族卤化物和乙烯基卤化物以及三氟甲磺酸与钯，α-炔酸的钯催化的脱羧sp-sp 2交叉偶联反应。多种α，β炔酸在氧化银的存在下，容易地脱羧，然后，生成的原位，银乙炔化物加上在中性条件下在钯（0）催化剂的存在下亲电子，产生对称或不对称的二芳基乙炔，芳基烷基乙炔和芳基乙烯基乙炔，收率良好至优异。
• Synthesis of trisubstituted alkenes by Ni-catalyzed hydroalkylation of internal alkynes with cycloketone oxime esters
  作者：Xiao-Yu Lu、Chuang-Chuang Liu、Run-Chuang Jiang、Lu-Yu Yan、Qi-Le liu、Qing-Qing Wang、Jia-Mei Li

  DOI：10.1039/d0cc06517j

  日期：——

  Ni-catalyzed hydroalkylation of internal alkynes with cycloketone oxime esters was developed. The reaction has a broad substrate scope. This hydroalkylation shows excellent regio- and stereo-selectivity. This method enables readily available starting materials to be used to access a range of cyano-substituted single-configuration trisubstituted alkenes. These are valuable feedstock chemicals and are widely

  提出了一种用环酮肟酯对内炔烃进行Ni催化加氢烷基化的方法。该反应具有广泛的底物范围。这种加氢烷基化显示出优异的区域选择性和立体选择性。该方法使得容易获得的起始原料可用于获得一定范围的氰基取代的单构型三取代的烯烃。这些是有价值的原料化学品，并广泛用于合成和药物化学中。
• Copper-catalyzed C(sp²)-C(sp) Sonogashira-type cross-coupling reactions accelerated by polycyclic aromatic hydrocarbons
  作者：Wei Xu、Bo Yu、Huaming Sun、Guofang Zhang、Weiqiang Zhang、Ziwei Gao

  DOI：10.1002/aoc.3298

  日期：2015.6

  Copper‐catalyzed Sonogashira‐type reactions were dramatically accelerated by introducing a catalytic amount of polycyclic aromatic hydrocarbon additive. This novel catalytic system features low copper loading (0.5 mol% < Cu < 5 mol%), broad reaction scope and remarkable substrate tolerance. Both aromatic and aliphatic terminal alkynes as well as diverse aryl iodides were employed in this transformation

  通过引入催化量的多环芳烃添加剂，铜催化的Sonogashira型反应得以显着加速。这种新颖的催化系统具有低铜负载量（0.5 mol％
• Facile Synthesis of Substituted Alkynes by Cyclopalladated Ferrocenylimine Catalyzed Cross-Coupling of Arylboronic Acids/Esters with Terminal Alkynes
  作者：Fan Yang、Yangjie Wu

  DOI：10.1002/ejoc.200700065

  日期：2007.7

  A highly efficient and convenient catalytic system for the cross-coupling reaction of arylboronic reagents with terminal alkynes was described by using cyclopalladated ferrocenylimine (I)/silver oxide as the catalyst at room temperature. This method provides the first examples of a palladacycle-catalyzed cross-coupling reaction of arylboronic acids/esters with terminal alkynes under mild conditions

  通过使用环钯二茂铁亚胺（I）/氧化银作为催化剂，在室温下描述了一种高效、方便的芳基硼试剂与末端炔烃交叉偶联反应的催化体系。该方法提供了钯环催化的芳基硼酸/酯与末端炔烃在温和条件下的交叉偶联反应的第一个例子，也是合成具有 1 mol% 低 Pd 负载的取代炔烃的简便途径。底物可以扩展到缺乏电子的炔烃，而传统的 Sonogashira 反应不会进行。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• Organophosphate-accelerated copper-catalyzed C(sp²)-C(sp) Sonogashira-type cross couplings
  作者：Wei Xu、Bo Yu、Huaming Sun、Guofang Zhang、Weiqiang Zhang、Ziwei Gao

  DOI：10.1002/aoc.3291

  日期：2015.5

  A dramatic acceleration in copper‐catalyzed Sonogashira‐type reactions was observed when an organophosphate was used as additive. The catalyst systems featuring low copper loading (0.5 mol% < Cu < 5 mol%) gave Sonogashira‐type products with a broad scope of aromatic and aliphatic terminal alkynes as well as aryl iodides in good to excellent yields. Among the organophosphate/copper catalytic systems, that of 4 mol% Cu(OTf)2/10 mol% (R)‐(−)‐1,1′‐binaphthyl‐2,2′‐diyl hydrogenphosphate exhibited the highest catalytic activity. Copyright © 2015 John Wiley & Sons, Ltd.